[ CAS No. 198-55-0 ] {[proInfo.proName]}

Name: 198-55-0|Perylene|95%
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Quality Control of [ 198-55-0 ]

COA NMR CNMR HPLC LC-MS

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SDS Specification

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Product Details of [ 198-55-0 ]

CAS No. :	198-55-0	MDL No. :	MFCD00004142
Formula :	C₂₀H₁₂	Boiling Point :	-
Linear Structure Formula :	-	InChI Key :	CSHWQDPOILHKBI-UHFFFAOYSA-N
M.W :	252.31	Pubchem ID :	9142
Synonyms :	Peri-dinaphthalene (purified by sublimation)
UV :	410, 436 nm (in THF)
FL :	471 nm (in THF)	Materials Type :	Dopant

Calculated chemistry of [ 198-55-0 ]

Physicochemical Properties

Num. heavy atoms :	20
Num. arom. heavy atoms :	20
Fraction Csp3 :	0.0
Num. rotatable bonds :	0
Num. H-bond acceptors :	0.0
Num. H-bond donors :	0.0
Molar Refractivity :	87.65
TPSA :	0.0 Å²

Pharmacokinetics

GI absorption :	Low
BBB permeant :	No
P-gp substrate :	No
CYP1A2 inhibitor :	Yes
CYP2C19 inhibitor :	No
CYP2C9 inhibitor :	No
CYP2D6 inhibitor :	No
CYP3A4 inhibitor :	No
Log Kp (skin permeation) :	-3.4 cm/s

Lipophilicity

Log Po/w (iLOGP) :	2.78
Log Po/w (XLOGP3) :	6.25
Log Po/w (WLOGP) :	5.74
Log Po/w (MLOGP) :	6.32
Log Po/w (SILICOS-IT) :	5.8
Consensus Log Po/w :	5.38

Druglikeness

Lipinski :	1.0
Ghose :	None
Veber :	0.0
Egan :	0.0
Muegge :	2.0
Bioavailability Score :	0.55

Water Solubility

Log S (ESOL) :	-6.08
Solubility :	0.000209 mg/ml ; 0.000000828 mol/l
Class :	Poorly soluble
Log S (Ali) :	-6.04
Solubility :	0.000232 mg/ml ; 0.000000919 mol/l
Class :	Poorly soluble
Log S (SILICOS-IT) :	-8.26
Solubility :	0.00000138 mg/ml ; 0.0000000055 mol/l
Class :	Poorly soluble

Medicinal Chemistry

PAINS :	0.0 alert
Brenk :	2.0 alert
Leadlikeness :	1.0
Synthetic accessibility :	1.0

Safety of [ 198-55-0 ]

Signal Word:	Danger	Class:	6.1
Precautionary Statements:	P261-P281-P305+P351+P338	UN#:	2811
Hazard Statements:	H315-H319-H335-H336-H350-H373	Packing Group:	Ⅲ
GHS Pictogram:

Application In Synthesis of [ 198-55-0 ]

* All experimental methods are cited from the reference, please refer to the original source for details. We do not guarantee the accuracy of the content in the reference.

Upstream synthesis route of [ 198-55-0 ]
Downstream synthetic route of [ 198-55-0 ]

[ 198-55-0 ] Synthesis Path-Upstream 1~4

1
[ 198-55-0 ]
[ 2050-74-0 ]

Reference： [1] Environmental Science and Technology, 1999, vol. 33, # 7, p. 1038 - 1043

2
[ 198-55-0 ]
[ 71-43-2 ]
[ 188-94-3 ]

Reference： [1] Monatshefte fuer Chemie, 1951, vol. 82, p. 384
[2] Chemische Berichte, 1948, vol. 81, p. 52,55[3] Chemische Berichte, 1949, vol. 82, p. 46,55
[4] Monatshefte fuer Chemie, 1952, vol. 83, p. 1100,1497

3
[ 198-55-0 ]
[ 23683-68-3 ]

Yield	Reaction Conditions	Operation in experiment
90%	With N-Bromosuccinimide In dichloromethane at 20℃; for 0.0833333 h;	BSynthesis of Perylene BromideAfter 3.0 g (11 mmol) of perylene was dissolved in 700 mL of dichloromethane, the solution was stirred for 5 minutes. To the solution, 2.11 g (12 mmol, 1.1 eq) of N-bromosuccinimide was dropwise added slowly at room temperature, followed by stirring overnight. The reaction solution was purified by silica gel column chromatography using a developing solvent adjusted to dichloromethane:hexane=1:1 to remove N-bromosuccinimide. After the solvent was concentrated, yellow crystals (yield 90percent) were obtained. The compound was identified by ¹H-NMR and ESI-MS.¹H-NMR (CDCl₃, 400 MHz) δ 7.46-7.51 (m, 2H), 7.59 (t, J=4.4 Hz, 1H), 7.68-7.72 (m, 2H), 7.78-7.80 (m, 1H), 7.98-8.04 (m, 1H), 8.09-8.14 (m, 1H), 8.17-8.28 (m, 3H).ESI-MS (C₂₀H₁₁Br): Calcd.: 330.00. Found: 331.9.
90%	With N-Bromosuccinimide In N,N-dimethyl-formamide at 20℃; for 24 h; Inert atmosphere	3.2. 3-Bromoperylene 3 A solution of N-bromosuccinimide (706 mg, 3.97 mmol) in dry DMF (20 mL) was added to a solution of perylene (1 g, 3.96 mmol) in dry DMF (250 mL) and stirred at room temperature under nitrogen for 24 h. Addition of water (750 mL) to the mixture gave a suspension which was extracted with dichloromethane (3≍200 mL). The grouped organic phases were then washed with water (5≍100 mL) and dried (MgSO₄). Rotoevaporation of the solvent gave crude 3-bromoperylene, which was recrystallized from toluene. Yield: 90percent; ¹H (300 MHz, CD₂Cl₂): δ 8.16-8.27 (m, 3H), 7.93-8.15 (m, 2H), 7.68-7.79 (m, 3H), 7.46-7.62 (m, 3H);¹³ ¹³C (75 MHz, CD₂Cl₂): δ 150.0, 134.6, 133.1, 131.6, 131.2, 130.7, 130.6, 130.4, 129.8, 128.4, 128.3, 127.9, 127.8, 122.3, 121.1, 120.9, 120.6, 120.5 ppm; MS (CI, CH₄): m/z calcd for C₂₀H₁₁Br: 331.1; found 331.1 [M⁺]. Anal. Calcd for C₂₀H₁₁Br: C, 72.53; H, 3.35. Found : C, 73.12; H, 3.36.
83.2%	With N-Bromosuccinimide In tetrahydrofuran at 20℃; for 24 h; Inert atmosphere	General procedure: Under a nitrogen atmosphere, a solution ofN-bromosuccinimide (213 mg, 1.19 mmol) in dry THF (5 mL) wasadded to a solution of 9 (300 mg, 1.19 mmol) in dry THF (25 mL)and stirred at room temperature for 24 h. The mixture wasconcentrated, and water was added to the residue. The precipitate wascollected by filtration and washed with water. The collectedprecipitate was dried and purified by recrystallization fromchloroform and hexane to give 10 (328 mg, 0.990 mmol, 83.2percent) as ayellow solid. 1H NMR (CDCl3): = 8.27-8.17 (m, 4H), 8.11 (d, J = 8.7 Hz, 1H), 8.02 (d, J = 8.4 Hz,1H), 7.78 (d, J = 8.4 Hz, 1H), 7.73-7.67 (m, 2H), 7.62-7.57 (m, 1H), 7.53-7.47 (m, 2H).IR (KBr): = 1493, 1379, 816, 804, 764 cm-1. Mp: 242-244 °C.

58%

With N-Bromosuccinimide In N,N-dimethyl-formamide at 100℃; for 3 h;

[Synthesis of intermediate B1] [0097] Perylene (5.0g, 20 mmol) was put in anhydrous DMF (200 ml), and the resulting mixture was heated to 100°C to dissolve perylene. Then, an anhydrous DMF solution (10 ml) of N-bromosuccinimide (3.5g, 20 mmol, 1.1 eq.) was added, followed by stirring at 100°C for 3 hours. The resultant was then allowed to stand for overnight. The reaction mixture was washed with methanol, whereby a yellow plate crystal (3.8g, 58percent) was obtained.The resulting crystal was confirmed to be intermediate B1 by NMR. The results are shown below.¹H-NMR (400MHz, CDCl₃, TMS) δ7.45-7.51 (2H,m), 7.58 (1H,t,J=8Hz),7.70 (2H,d,J=8Hz), 7.76 (1H,d,J=8Hz), 7.99 (1H,d,J=8Hz), 8.08 (1H,d,J=8Hz), 8.14-8.24 (3H,m)

Reference： [1] Chemistry - A European Journal, 2018, vol. 24, # 60, p. 16136 - 16148
[2] Journal of Organic Chemistry, 2010, vol. 75, # 8, p. 2752 - 2755
[3] Inorganic Chemistry, 2013, vol. 52, # 7, p. 4113 - 4119
[4] Patent: US2011/15440, 2011, A1, . Location in patent: Page/Page column 12
[5] Tetrahedron, 2012, vol. 68, # 46, p. 9371 - 9375,5
[6] Tetrahedron,
[7] New Journal of Chemistry, 2015, vol. 39, # 8, p. 6498 - 6503
[8] Journal of Organic Chemistry, 2014, vol. 79, # 5, p. 2038 - 2048
[9] Tetrahedron Letters, 2013, vol. 54, # 40, p. 5514 - 5517
[10] Chemical Communications, 2016, vol. 52, # 76, p. 11339 - 11342
[11] Patent: EP2599768, 2013, A1, . Location in patent: Paragraph 0097
[12] Nucleosides, Nucleotides and Nucleic Acids, 2003, vol. 22, # 5-8, p. 1223 - 1225
[13] Journal of Organic Chemistry, 2007, vol. 72, # 23, p. 8990 - 8993
[14] Inorganic Chemistry, 2010, vol. 49, # 20, p. 9169 - 9177
[15] Chemical Physics Letters, 2012, vol. 536, p. 72 - 76
[16] Dyes and Pigments, 2015, vol. 112, p. 298 - 304
[17] Journal of the American Chemical Society, 2016, vol. 138, # 47, p. 15405 - 15412
[18] European Journal of Organic Chemistry, 2017, vol. 2017, # 29, p. 4334 - 4337
[19] Chem, 2018,
[20] Photochemical and Photobiological Sciences, 2018, vol. 17, # 11, p. 1794 - 1803

4
[ 198-55-0 ]
[ 85514-20-1 ]
[ 56752-35-3 ]
[ 23683-68-3 ]

Reference： [1] Recueil des Travaux Chimiques des Pays-Bas, 1993, vol. 112, # 11, p. 584 - 594
[2] Recueil des Travaux Chimiques des Pays-Bas, 1993, vol. 112, # 11, p. 584 - 594

[ 198-55-0 ] Synthesis Path-Downstream 1~87

1
[ 198-55-0 ]
[ 20589-63-3 ]

Yield	Reaction Conditions	Operation in experiment
71%	With sulfuric acid; nitric acid; acetic anhydride at 10℃;
	With 1-nitroethylene; acetic anhydride; nitrobenzene
	With nitric acid; acetic anhydride

	With nitric acid
	With nitric acid
	With nitric acid In 1,4-dioxane at 60℃; for 0.5h;

Reference： [1]Pu, Yong-Jin; Higashidate, Makoto; Nakayama, Ken-Ichi; Kido, Junji [Journal of Materials Chemistry, 2008, vol. 18, # 35, p. 4183 - 4188]
[2]Hopff; Schweizer [Helvetica Chimica Acta, 1959, vol. 42, p. 2315,2323]
[3]Dewar; Mole [Journal of the Chemical Society, 1956, p. 1441]
[4]Looker,J.J. [Journal of Organic Chemistry, 1972, vol. 37, # 21, p. 3379 - 3381]
[5]Grabner, Erich Walter; Hessberger, Harald [Journal of Physical Chemistry, 1987, vol. 91, # 1, p. 226 - 230]
[6]Elmali, Ayhan; Hu, Mengyu; Ji, Shaomin; Karatay, Ahmet; Sukhanov, Andrei A.; Voronkova, Violeta K.; Zhang, Xue; Zhao, Jianzhang [Journal of Physical Chemistry B, 2021, vol. 125, # 16, p. 4187 - 4203]

2
[ 198-55-0 ]
[ 85514-20-1 ]

Yield	Reaction Conditions	Operation in experiment
90%	With N-Bromosuccinimide In dichloromethane at 20℃; for 24h;	2.2.1 Compound 1.2 [3,10-dibromoperylene]: Perylene (4.00 g, 16.00 mmol) and N-bromosuccinimide (7.12 g, 40.0 mmol), were dissolved in 1 L flask containing 400 mL dichloromethane and a magnetic stir bar. The solution was then stirred at room temperature for 24 h. The solution was evaporated to dryness under vacuum resulting in a solid. The solid was extracted with chloroform, continuously, for 8 h to remove any unreacted perylene. A 90% yield of (5.9 g) yellow solid was obtained in, LCMS (APCI+): calculated for C20H20Br2: 407.9; found: 408.
6%	With bromine In benzene at 40 - 70℃; for 1h;
	With bromine

	With bromine In methanol; 5,5-dimethyl-1,3-cyclohexadiene; nitrobenzene	S.1 Synthesis Example 1 Synthesis Example 1 A mixture of 3,9-dibromoperylene and 3,10-dibromoperylene was synthesized. After mixing perylene (product of Aldrich, sublimation purification grade, >99.5%) (25.23 g, 100 mmol) and nitrobenzene (800 ml) in a 1000 ml flask under a nitrogen gas atmosphere, the mixture was heated to 125° C. for dissolution of the total amount of perylene in the nitrobenzene, and then a solution of bromine (32.9 g, 206 mmol) diluted with nitrobenzene (85 ml) was added dropwise over a period of one hour while shielded from light. Upon completion of the dropwise addition, stirring was continued at the same temperature for 5 hours and the mixture was cooled to room temperature. The contents (deposited solid and solution) were transferred to a separately prepared 2000 ml flask, methanol (500 ml) was added while stirring, and the mixture was filtered under reduced pressure, rinsed with methanol (1000 ml) and dried under reduced pressure to obtain yellow crystals (37.9 g). Xylene (1350 ml) was added, and the mixture was stirred for 5 hours while heating to reflux. It was then cooled to room temperature, filtered under reduced pressure, rinsed with methanol (4 times with 100 ml) and dried under reduced pressure to obtain yellow crystals (30.2 g). Xylene (1000 ml) was further added, and the mixture was stirred for 5 hours while heating to reflux. It was then cooled to room temperature, filtered under reduced pressure, rinsed with methanol (4 times with 100 ml) and dried under reduced pressure to obtain yellow crystals (24.6 g). The purity was 99.82% based on the HPLC area percentage value. Analysis by 1H-NMR confirmed the presence of 3,9-dibromoperylene and 3,10-dibromoperylene in a proportion of 50/50. shows a 1H-NMR spectrum (300 MHz, THF-d8) of the yellow crystals obtained in Synthesis Example 1.
	With N-Bromosuccinimide In N,N-dimethyl-formamide

Reference： [1]Current Patent Assignee: NITTO DENKO CORPORATION - WO2020/210761, 2020, A1 Location in patent: Page/Page column 55
[2]Matsumoto, Akinobu; Suzuki, Mitsuharu; Hayashi, Hironobu; Kuzuhara, Daiki; Yuasa, Junpei; Kawai, Tsuyoshi; Aratani, Naoki; Yamada, Hiroko [Chemistry - A European Journal, 2016, vol. 22, # 41, p. 14462 - 14466]
[3]Zinke; Linner; Wolfbauer [Chemische Berichte, 1925, vol. 58, p. 329]
[4]Current Patent Assignee: SUMITOMO CHEMICAL COMPANY LIMITED; Sumitomo Chemical (w/o Dongwoo Fine-Chem) - US2012/217445, 2012, A1
[5]Huang, Ling; Wu, Wenting; Li, Yang; Huang, Kai; Zeng, Le; Lin, Wenhai; Han, Gang [Journal of the American Chemical Society, 2020, vol. 142, # 43, p. 18460 - 18470]

3
[ 198-55-0 ]
[ 85514-20-1 ]
[ 56752-35-3 ]

Yield	Reaction Conditions	Operation in experiment
1: 29% 2: 23%	With bromine In benzene at 40℃; Inert atmosphere;
	With bromine
	With bromine In benzene at 35℃; for 1.16667h; Inert atmosphere; Overall yield = 26 %; Overall yield = 2.1 g;	3,9-dibromoperylene: Following a modified literature procedure, perylene (5.90 g, 23.4 mmol, 1 equiv) was dissolved in 900 mL benzene in a 2 L flask equipped with a base trap at 80 °C. The mixture was allowed to cool to 35 °C (note-some perylene precipitated out of solution) and Br2 (17.3 g, 109 mmol, 4.7 equiv) was added dropwise over 10 min and the reaction was stirred at 35 °C for 1 h then cooled to room temperature. The precipitate was filtered and recrystallized 4× in 5/3 aniline/toluene then washed with acetone affording an orange solid (2.1 g, 26%) 1H NMR (600 MHz, CDCl3) δ 8.24-8.21 (m, 2H), 8.12 (dd, J=8.4, 0.9 Hz, 2H), 8.03 (d, J=8.1 Hz, 2H), 7.78 (d, J=8.1 Hz, 2H), 7.59 (dd, J=8.4, 7.5 Hz, 2H). 13C NMR (151 MHz, CDCl3) δ 133.2, 131.1, 130.9, 130.8, 129.6, 127.9, 127.5, 123.1, 121.4, 121.1. HRMS (CI+) (m/z): calcd for C20H10Br2 407.9149; found 407.9156 IR (film, cm-1): 3047, 1931, 1846, 1777, 1599 characteristic 1H peaks of minor isomer 1H NMR (600 MHz, CDCl3) δ 8.26 (d, J=7.8 Hz, 2H), 7.98 (d, J=8.2 Hz, 2H).

	With bromine; acetic acid at 40℃; for 4h; Overall yield = 100 %; Overall yield = 25.46 g;	1.1 3,9-Dibromoperylene and 3,10-dibromoperylene 3,9-Dibromoperylene and 3,10-dibromoperylene A mixture of 14.9 g (59 mmol) of perylene, 400 ml of acetic acid and 18.9 g (236 mmol) of bromine was stirred at 40° C. for four hours. The excess bromine was subsequently destroyed by adding sodium thiosulfate solution. The precipitate was filtered off, washed with water and dried under reduced pressure. This gave 25.46 g (quant.) of the title compounds as a yellowish precipitate.
	With bromine; acetic acid at 50℃; Overall yield = 89 %; Overall yield = 2.9 g;
	With bromine; acetic acid at 40℃; for 4h; Overall yield = 8 percent;	3,10-Dibromoperylene Perylene (3.00 g, 11.9 mmol) was suspended in 130 mL of acetic acid and stirred at 40° C. A solution of bromine (1.35 mL, 26.2 mmol) in 5.0 mL of acetic acid was slowly added to the suspension of perylene at rapid stirring. The reaction mixture was stirred at 40° C. for four hours. Once cooled to room temperature the reaction was quenched with sodium thiosulfate solution, followed by addition of 300 mL of water. The product mixture was collected by filtration and dried overnight. The isomer mixture was separated by repetitive recrystallization from toluene and THF. The 3,10-dibromoperylene isomer was purified to 90% isomeric purity and taken to the next step. Orange solids. Yield: 8%. 1H NMR (400 MHz, CDCl3, 25° C.): δ=8.25 (d, J=7.6 Hz, 2H), 8.12 (d, J=8.6 Hz, 2H), 7.97 (d, J=8.1 Hz, 2H), 7.77 (d, J=8.1 Hz, 2H), 7.60 (t, J=8.1 Hz, 2H) ppm.

Reference： [1]Hayashi, Koichiro; Inouye, Masahiko [European Journal of Organic Chemistry, 2017, vol. 2017, # 29, p. 4334 - 4337]
[2]Zinke; Troger [Chemische Berichte, 1941, vol. 74, p. 107,112]
[3]Jackson, Evan P.; Sisto, Thomas J.; Darzi, Evan R.; Jasti, Ramesh [Tetrahedron, 2016, vol. 72, # 26, p. 3754 - 3758]
[4]Current Patent Assignee: BASF SE - US2017/183295, 2017, A1 Location in patent: Paragraph 0381
[5]Chen, Zongping; Wang, Hai I.; Bilbao, Nerea; Teyssandier, Joan; Prechtl, Thorsten; Cavani, Nicola; Tries, Alexander; Biagi, Roberto; De Renzi, Valentina; Feng, Xinliang; Kläui, Mathias; De Feyter, Steven; Bonn, Mischa; Narita, Akimitsu; Müllen, Klaus [Journal of the American Chemical Society, 2017, vol. 139, # 28, p. 9483 - 9486]
[6]Current Patent Assignee: BATTELLE MEMORIAL INSTITUTE; MRIGLOBAL - US2020/317855, 2020, A1 Location in patent: Paragraph 0056-0057

4
[ 198-55-0 ]
[ 56752-35-3 ]

Yield	Reaction Conditions	Operation in experiment
94%	With bromine In acetic acid at 50℃; for 5h;
91%	With N-Bromosuccinimide In tetrahydrofuran Inert atmosphere;	1 Preparation of Dibromo-Perylene In a 500mL round bottomed flask with stirring bar was dissolved Perylene (2000mg, 7.94mmol) in THF (320mL). To this was added N- bromosuccinimide (4240mg, 23.8mmol) in one portion and the mixture was allowed to stir overnight. The mixture was slowly poured onto water (1500mL) with stirring. After 30min of stirring, the solids were collected by filtration and dried under vacuum to afford dibromoperylene (2400mg, 91%).
63%	With bromine In tetrachloromethane at 110℃; for 12h;

63%	With bromine In tetrachloromethane at 110℃; for 12h; Darkness;
6%	With bromine In benzene at 40 - 70℃; for 8h;
	With bromine
	With bromine; benzene
	With aluminum tri-bromide; nitrobenzene
	With dihydrogen peroxide; acetic acid; sodium bromide at 90℃;
	With bromine

Reference： [1]Schlichting, Peter; Rohr, Ulrike; Muellen, Klaus [Liebigs Annalen, 1997, # 2, p. 395 - 407]
[2]Current Patent Assignee: SONY CORPORATION - WO2017/197144, 2017, A1 Location in patent: Page/Page column 52
[3]Location in patent: experimental part Kim, Ji-Hoon; Kim, Hee Un; Mi, Dongbo; Jin, Sung-Ho; Shin, Won Suk; Yoon, Sung Cheol; Kang, In-Nam; Hwang, Do-Hoon [Macromolecules, 2012, vol. 45, # 5, p. 2367 - 2376]
[4]Kim, Ji-Hoon; Song, Chang Eun; Kang, In-Nam; Shin, Won Suk; Hwang, Do-Hoon [Chemical Communications, 2013, vol. 49, # 31, p. 3248 - 3250]
[5]Matsumoto, Akinobu; Suzuki, Mitsuharu; Hayashi, Hironobu; Kuzuhara, Daiki; Yuasa, Junpei; Kawai, Tsuyoshi; Aratani, Naoki; Yamada, Hiroko [Chemistry - A European Journal, 2016, vol. 22, # 41, p. 14462 - 14466]
[6]Zinke; Linner; Wolfbauer [Chemische Berichte, 1925, vol. 58, p. 329]
[7]Zinke et al. [Monatshefte fur Chemie, 1928, vol. 50, p. 85]
[8]Zinke; Funke; Lorber [Chemische Berichte, 1927, vol. 60, p. 579,581]
[9]Zinke; Funke; Lorber [Chemische Berichte, 1927, vol. 60, p. 579,581]
[10]Zinke; Troger [Chemische Berichte, 1941, vol. 74, p. 107,112] Zinke; Pongratz [Chemische Berichte, 1936, vol. 69, p. 1591,1593]

5
[ 198-55-0 ]
[ 188-73-8 ]

Yield	Reaction Conditions	Operation in experiment
92%	With trifluorormethanesulfonic acid; 2,3-dicyano-5,6-dichloro-p-benzoquinone In dichloromethane at 20℃; for 24h; Inert atmosphere; Reflux;
83%	With trifluorormethanesulfonic acid; 2,3-dicyano-5,6-dichloro-p-benzoquinone In dichloromethane for 8h; Reflux; Inert atmosphere;	1 Working Example 1 Synthesis of Quaterrylene from Perylene Working Example 1 Synthesis of Quaterrylene from Perylene To a solution of perylene (1.00 g, 3.96 mmol) in dichloromethane (30 mL) was added triflic acid (1.75 ml, 19.8 mmol) over 5 min at room temperature. DDQ (1.80 g, 7.92 mmol) was added and the mixture was refluxed for 8 h under a nitrogen atmosphere. Progress of the reaction was monitored by TLC which showed a rapid loss of starting material. After cooling to ambient temperature, the reaction was quenched with a slight excess of diisopropylethylamine and diluted with methanol (30 ml). The resultant precipitate was filtered and washed with methanol and dichloromethane to give 0.96 g of dark green solid. Successive Soxhlet extraction (8 h each) with methanol, toluene and then chlorobenzene, followed by drying under vacuum, gave 0.83 g (83%) of dark green solid.
	With aluminium trichloride; sodium chloride at 120 - 150℃;

Reference： [1]Thamatam, Rajesh; Skraba, Sarah L.; Johnson, Richard P. [Chemical Communications, 2013, vol. 49, # 80, p. 9122 - 9124]
[2]Current Patent Assignee: UNIVERSITY OF NEW HAMPSHIRE - US2014/378727, 2014, A1 Location in patent: Paragraph 0014; 0018
[3]Clar; Kelly; Laird [Monatshefte fur Chemie, 1957, vol. 87, p. 391,398]

6
[ 198-55-0 ]
[ 856340-79-9 ]

Yield	Reaction Conditions	Operation in experiment
	With hydrogenchloride; dihydrogen peroxide; acetic acid; nitrobenzene at 90℃;
	With manganese(IV) oxide; aluminium trichloride at 150℃;
	With C₆₀F₁₈; iron(III) chloride In 1,2-dichloro-benzene at 90℃;

With hydrogenchloride; dihydrogen peroxide; acetic acid; nitrobenzene at 90℃;

Reference： [1]Zinke; Pongratz; Funke [Chemische Berichte, 1925, vol. 58, p. 332]
[2]Zinke; Funke; Lorber [Chemische Berichte, 1927, vol. 60, p. 579,581]
[3]Darwish, Adam D.; Avent, Anthony G.; Abdul-Sada, Ala'a K.; Gol'dt, Ilya V.; Hitchcock, Peter B.; Kuvytchko, Igor V.; Taylor, Roger [Chemistry - A European Journal, 2004, vol. 10, # 18, p. 4523 - 4531]
[4]Current Patent Assignee: ALOIS ZINKE; CIE NAT MATIERES COLORANTES; ALFRED PONGRATZ; FELICE BENSA - DE498039, 1930, C [Fortschr. Teerfarbenfabr. Verw. Industriezweige, vol. 16, p. 1389][Fortschr. Teerfarbenfabr. Verw. Industriezweige, vol. 16, p. 1389]

7
[ 6364-19-8 ]
[ 198-55-0 ]

Reference： [1]Monatshefte fur Chemie,1930,vol. 56,p. 163,177
[2]Patent: DE486491,
Fortschr. Teerfarbenfabr. Verw. Industriezweige,vol. 16,p. 1396

8
[ 198-55-0 ]
[ 71-43-2 ]
[ 188-94-3 ]

Reference： [1]Monatshefte fur Chemie,1951,vol. 82,p. 384

9
[ 1730-04-7 ]
[ 198-55-0 ]
[ 144694-48-4 ]

Yield	Reaction Conditions	Operation in experiment
1: 39% 2: 42%	With tetrabutylammomium bromide; potassium carbonate In N,N-dimethyl-formamide at 100℃; for 72h;

Reference： [1]Dyker, Gerald [Journal of Organic Chemistry, 1993, vol. 58, # 1, p. 234 - 238]

10
[ 198-55-0 ]
[ 20589-63-3 ]
[ 35337-20-3 ]

Yield	Reaction Conditions	Operation in experiment
1: 20% 2: 63%	With nitric acid In 1,4-dioxane at 60 - 80℃; for 0.5h;	1.1 Example 1The preparation process of the small molecule fluorescent probe of this embodiment mainly includes the following steps: 1,One by one 0.5 g (2 mmol) hydrazine40 mL of 1,4-dioxane was placed in a two-necked flask,Stirring at 80 °C until completely dissolved in a clear yellow solution;Then use a syringe to slowly inject 1 mL of concentrated nitric acid. Concentrated nitric acid is used in a concentration of 65% to 68% of concentrated nitric acid (14.4 to 15.2 mol/L) and stirred at 60°C for 30 minutes.A reaction solution containing Compound 1 and Compound 2 was obtained;The reaction solution was poured into a large amount of ice water while it was hot and filtered under reduced pressure.After drying in vacuum for 12 h, a bright red crude product is obtained; finally,Chromatography of petroleum ether (PE)-dichloromethane (DCM) at a volume ratio of 1.5:1 as eluentTo dark red needle-like solid compound 1 (20% yield) and brick red solid compound 2 (yield 63%).
1: 60% 2: 26%	With pyridine; pyridium nitrate for 0.25h; Heating;
1: 24% 2: 56%	With 4-nitro-4-methyl-2,3,5,6-tetrabromo-2,5-cyclohexadien-1-one In dichloromethane at 20℃; for 2h;

30%	With nitric acid In 1,4-dioxane; water at 60℃; for 0.5h;
1: 15.6% 2: 24.5%	With nitric acid In 1,4-dioxane at 60℃; for 0.5h;	4.3. Synthesis of compound 1-NO, 3-NO The synthetic steps of 1-NO, 3-NO, 1-NH, 3-NH, probe 1 and probe 2 were illustrated in Scheme 1. The routes involves nitration, reduction, and substitution reactions which are classic reactions with high yields, and reaction conditions are easily achieved without complicated instruments and equipment. Some of the synthesis schemes and characterization data for intermediates were described in detail in the Supplementary Information (SI). Compound 1-NO. First, perylene (500.0 mg, 2 mmol) was suspended in 40 mL 1,4-dioxane. Stirred with heating at 60 °C until it completely dissolved and the nitric acid mixture with a concentration of 65-68% solution (1mL, d=7 nitric acid in 10 mL 1,4-dioxane) was injected dropwise. Then the reaction mixture was heated with stirring to reflux for 30 min. After TLC detection, Cool the resulting solution with ice water while hot, the solution precipitated red flocs. Then filtering under reduced pressure and vacuum drying for 12 h, and the crude product was purified by column chromatography (silica gel, PE:DCM=1.5:1). Compound 1-NO was obtained as dark red crystalline solid (15.6 % yield); 1H NMR (400 MHz, CDCl3) δ=8.28 (m, 3H), 7.84 (m, 3H), 7.74 (m, 2H), 7.62 (t, 1H, J=8Hz), 7.57 (m, 2H), 7.44 (t, 1H, J=8Hz). 13C NMR (101 MHz, CDCl3) δ=134.7, 134.1, 132.3, 130.1, 129.7, 129.1, 128.8, 128.4, 128.0, 127.3, 126.7, 126.5, 126.4, 125.6, 124.5, 122.1, 121.9, 121.4, 29.7. Compound 3-NO can be obtained from the same way as 1-NO (24.5% yield). 1H NMR (400 MHz, CDCl3) δ=8.48 (d, 1H,J 8 Hz), 8.26 (m, 4H), 8.10 (d, 1H, J 8 Hz), 7.82 (d, 1H, J 8 Hz),7.76 (d, 1H, J 8Hz), 7.68 (t, 1H, J 8 Hz), 7.53 (m, 2H). 13C NMR (101 MHz, CDCl3) δ=137.5, 134.2, 131.6, 130.3, 130.1, 129.5, 129.4,129.2, 128.8, 127.8, 127.0, 126.7, 125.0, 122.9, 122.6, 121.9, 121.2,118.2, 29.7.
	With dinitrogen tetraoxide In dichloromethane at 20℃; for 0.0833333h; Yield given. Yields of byproduct given;
0.98 mmol	With dinitrogen tetraoxide In dichloromethane
	With dinitrogen tetraoxide In dichloromethane for 0.2h; Ambient temperature; Yield given. Yields of byproduct given;
	With dinitrogen tetraoxide In dichloromethane at 20℃; for 0.0833333h; nitration of polycyclic aromatic hydrocarbons by N₂O₄, selectivity, relative reactivities, effect of acid, base; synthetic and mechanistic study;
	With tetrabutylammonium acetate; dinitrogen tetraoxide In dichloromethane at 20℃; for 0.133333h; various additives, solvents; product isomer ratio; reactions of perylene with silver- or tetrabutylammonium nitrite; reactions of perylene cation radical with nitrite ion and N₂O₄;
1: 0.62 mmol 2: 0.35 mmol	With dinitrogen tetraoxide In tetrachloromethane
	With water; nitric acid In 1,4-dioxane at 60℃; for 0.5h;	1 N-hydro-phenanthro[1,10,9,8-c,d,e,f,g]carbazole:To a hot solution of perylene (25.0 g, 99.1 mmol) in 1,4-dioxane (1000 cm3) was added a mixture of water (20.0 cm3) and nitric acid (12.5 cm3, d = 1.5) dropwise. The resulting solution was heated to 60 0C with vigorous stirring for 25-30 mins, and then cooled and poured into water (4000 cm3). The solid was collected, washed and dried to afford a mixture of 1-nitroperylene (26 %, GC-MS) and 3-nitroperylene (74 % GC-MS) as a brick-red powder (29.1 g). The powder is suspended in triethylphosphite25 (130 cm3) and methanesulfonic acid (6.1 cm3). The mixture is heated to200° C overnight and then the solution is cooled down. The excess of triethylphosphite is removed under vacuum and the product is recovered after column chromatography (silica gel, toluene as eluent). The product is further purified by trituration in hot toluene (125 cm3) to afford the title product (5.12 g, yield 22 % over two steps). NMR (1H, 300 MHz, Acetone- d6) : δ 12.20 (s, 1H); 8.76 (d, J = 7.4 Hz, 2H); 8.18 (d, J = 8.1 Hz, 2H);7.98 (d, J = 8.7 Hz, 2H); 7.95 (d, J = 8.7 Hz, 2H); 7.83 (t, J = 7.8 Hz, 2H).

Reference： [1]Current Patent Assignee: GUANGDONG UNIVERSITY OF TECHNOLOGY - CN107382814, 2017, A Location in patent: Paragraph 0056; 0057; 0058; 0059; 0060; 0061; 0062; 0063
[2]Nefedov [Russian Journal of Organic Chemistry, 1998, vol. 34, # 8, p. 1165 - 1171]
[3]Cerfontain, Hans; Koeberg-Telder, Ankie; Lerch, Ulrike [Recueil des Travaux Chimiques des Pays-Bas, 1993, vol. 112, # 11, p. 584 - 594]
[4]Location in patent: experimental part Jiang, Wei; Qian, Hualei; Li, Yan; Wang, Zhaohui [Journal of Organic Chemistry, 2008, vol. 73, # 18, p. 7369 - 7372]
[5]He, Qin; Dong, Fangdi; Xing, Longjiang; He, Huahong; Chen, Xiaoping; Wang, Huaqian; Ji, Shaomin; Huo, Yanping [Tetrahedron, 2022, vol. 104]
[6]Eberson, Lennart; Radner, Finn [Acta chemica Scandinavica. Series B: Organic chemistry and biochemistry, 1985, vol. 39, # 5, p. 343 - 356]
[7]Eberson, Lennart; Radner, Finn [Acta chemica Scandinavica. Series B: Organic chemistry and biochemistry, 1985, vol. 39, # 5, p. 357 - 374]
[8]Radner, Finn [Acta chemica Scandinavica. Series B: Organic chemistry and biochemistry, 1983, vol. 37, # 1, p. 65 - 68]
[9]Eberson, Lennart; Radner, Finn [Acta chemica Scandinavica. Series B: Organic chemistry and biochemistry, 1985, vol. 39, # 5, p. 343 - 356]
[10]Eberson, Lennart; Radner, Finn [Acta chemica Scandinavica. Series B: Organic chemistry and biochemistry, 1985, vol. 39, # 5, p. 357 - 374]
[11]Eberson, Lennart; Radner, Finn [Acta chemica Scandinavica. Series B: Organic chemistry and biochemistry, 1985, vol. 39, # 5, p. 357 - 374]
[12]Current Patent Assignee: RAYNERGY TEK INCORPORATION - WO2011/18144, 2011, A2 Location in patent: Page/Page column 43

11
[ 198-55-0 ]
[ 85514-20-1 ]
[ 56752-35-3 ]
[ 23683-68-3 ]

Yield	Reaction Conditions	Operation in experiment
90%	With N-Bromosuccinimide In N,N-dimethyl-formamide at 20℃;	Mixture of Brominated Perylenes To a suspension of perylene (25.0 g, 100 mmol, 1 equiv) in DMF (1000 mL) a solution of NBS (23.0 g, 130 mmol, 1.3 equiv) in DMF (400 mL) was added via a syringe pump for 10 h. The obtained mixture was stirred overnight at r.t. and poured into water (2000 mL). The precipitate obtained was filtered off on a glass frit (G3) and was subsequently washed with EtOH (100 mL), Et2O (100 mL), and finally with CH2Cl2 (3 × 100 mL). The obtained solid was dried under vacuum, yielding a mixture of brominated perylenes; yield: 29.8 g (90%); 89% of 3-bromoperylene by GC-MS; yellow solid.
30%	With N-Bromosuccinimide In dichloromethane at 20℃; for 2h;
	With N-Bromosuccinimide In dichloromethane at 20℃; for 2h; Yields of byproduct given. Title compound not separated from byproducts;

Reference： [1]Guzeev, Bogdan A.; Mladentsev, Dmitry Y.; Sharikov, Mikhail I.; Goryunov, Georgy P.; Uborsky, Dmitry V.; Voskoboynikov, Alexander Z. [Synthesis, 2019, vol. 51, # 6, p. 1399 - 1407]
[2]Cerfontain, Hans; Koeberg-Telder, Ankie; Lerch, Ulrike [Recueil des Travaux Chimiques des Pays-Bas, 1993, vol. 112, # 11, p. 584 - 594]
[3]Cerfontain, Hans; Koeberg-Telder, Ankie; Lerch, Ulrike [Recueil des Travaux Chimiques des Pays-Bas, 1993, vol. 112, # 11, p. 584 - 594]

12
[ 198-55-0 ]
C₂₀H₁₆^(2-)*2Li⁽¹⁺⁾ [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	With lithium In ammonia at -60℃; reduced by alkali metal;

Reference： [1]Muellen, Klaus; Huber, Walter; Neumann, Gerd; Schnieders, Christoph; Unterberg, Heinz [Journal of the American Chemical Society, 1985, vol. 107, p. 801 - 807]

13
[ 198-55-0 ]
dodecachloroperylene [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
74%	With disulfur dichloride; aluminium trichloride In sulfuryl dichloride at 64℃; for 4h;

Reference： [1]Sun, Jing; Grützmacher, Hans-Fr.; Lifshitz, Chava [Journal of the American Chemical Society, 1993, vol. 115, # 18, p. 8382 - 8388]

14
[ 128-69-8 ]
[ 198-55-0 ]

Yield	Reaction Conditions	Operation in experiment
84%	With barium dihydroxide In water at 80℃; for 2h;
66%	With potassium hydroxide at 280℃; for 72h;

Reference： [1]Van Dijk, Joost T. M.; Hartwijk, Astrid; Bleeker, Annemarie C.; Lugtenburg, Johan; Cornelisse, Jan [Journal of Organic Chemistry, 1996, vol. 61, # 3, p. 1136 - 1139]
[2]Langhals, Heinz; Grundner, Sabine [Chemische Berichte, 1986, vol. 119, # 7, p. 2373 - 2376]

15
[ 144694-48-4 ]
[ 198-55-0 ]

Yield	Reaction Conditions	Operation in experiment
85%	With tetrabutylammomium bromide; potassium carbonate In N,N-dimethyl-formamide at 100℃; for 168h;

Reference： [1]Dyker, Gerald [Journal of Organic Chemistry, 1993, vol. 58, # 1, p. 234 - 238]

16
[ 198-55-0 ]
[ 1490-25-1 ]
[ 110774-34-0 ]

Yield	Reaction Conditions	Operation in experiment
83.5%	Stage #1: succinic acid monomethylester chloride With aluminium trichloride In dichloromethane at 0℃; for 1h; Stage #2: PERYLENE In dichloromethane at 0 - 20℃;
75%	With aluminum (III) chloride In dichloromethane
62%	Stage #1: succinic acid monomethylester chloride With aluminum (III) chloride In dichloromethane at 0℃; for 1.25h; Inert atmosphere; Stage #2: PERYLENE In dichloromethane at 0 - 20℃; Inert atmosphere;	2.2.8; 2.2.31 Compound 8.1 (Methyl 4-oxo-4-(perylen-3-yl)butanoate): Under protection of nitrogen 20 atmosphere, 1.34 g of AlCl3 (10.00mmol) was added in small portions via a powder dispersion funnel to a mixture of 1.04 mL methyl 4-chloro-4-oxobutanoate (8.45 mmol) in 160 mL DCM anhydrous at 0o C over 15 minutes. The resulting solution was stirred at 0o C for 1 hr. Next, 2.00 g perylene (7.9 mmol) in DCM anhydrous was dropwise to the solution while the temperature was maintained at 0o C. The resulting dark purple solution was stirred overnight at room temperature under nitrogen atmosphere. The next day, the solution was poured into a solution of 75 mL ice water, 5 mL 6N HCl aqueous solution and 150 mL DCM. The organic layer was separated; the water layer was reextracted with ethyl acetate (100 ml). The organic layers were combined, dried with MgSO4 and concentrated. The residue was loaded onto silica gel column. Chromatography was run with DCM, to gain 1.8 g orange color solid product, yield 62%. LCMS (APCI+): calculated for C25H19O3 = 367; found: 367.

56%	Stage #1: PERYLENE; succinic acid monomethylester chloride In dichloromethane at 20℃; for 0.25h; Inert atmosphere; Cooling with ice; Stage #2: With aluminum (III) chloride In dichloromethane at 20℃; for 16h; Cooling with ice; Inert atmosphere;	Step 1: In 1 L two-neck flask equipped with magnetic stirring bar, powder dispenser funnel, a yellow suspension mixture of perylene (5.22 g, 20.68 mmol) in DCM anhydrous (500 mL) was stirred and bubbled with argon 15 minutes in an ice-water bath; methyl 4-chloro-4- oxo butanoate (3.425 g, 22.75 mmol) was added slowly via syringe. The cooling bath was removed to allow the mixture stirring at RT for 15 minutes. The mixture was cooled again with an ice-water bath; AICI3 (3.3 g, 24.74 mmol) was added in small portion via the powder dispenser funnel. The resulting dark purple color mixture was stirred at RT for 16 hours under the protection of Argon. TLC and LCMS shown starting materials were almost consumed. The reaction mixture was diluted with 500 mL DCM then poured to ice-water (150 ml water), the organic layer was separated, dried with MgS04, concentrated to dryness. The residue was triturated with toluene. The solid was filtered, washed with toluene 50 mL. The filtrate and washed were combined and then concentrated to the volume of 50 mL then loaded on to column (330 g), eluting with toluene/ EtOAc (100:0) - (4.1) gained 1.25 g of desired product. The product from column chromatography and the solid product from work up were combined and re-crystallized using hexanes: EtOAc (9:1), gained 4.24 gyellow solid, yield 56%. LCMS (APCI-), calcd (M-) for C25H1803 :366.13; found: 366. 1H NMR (400 MHz, Chloroform- d) d 8.57 (dd, J = 8.6, 1.0 Hz, 1H), 8.30 - 8.17 (m, 4H), 7.97 (d, J = 8.1 Hz, 1H), 7.78 (d, J = 8.1 Hz, 1H), 7.73 (d, J = 8.1 Hz, 1H), 7.64 - 7.48 (m, 3H), 3.75 (s, 3H), 3.41 (t, J = 6.5 Hz, 2H), 2.86 (t, J = 6.5 Hz, 2H).
	With aluminium trichloride; chlorobenzene at 0℃;

Reference： [1]Oskolkova, Olga V.; Saf, Robert; Zenzmaier, Elfriede; Hermetter, Albin [Chemistry and Physics of Lipids, 2003, vol. 125, # 2, p. 103 - 114]
[2]Hart, Lewis R.; Nguyen, Ngoc A.; Harries, Josephine L.; Mackay, Michael E.; Colquhoun, Howard M.; Hayes, Wayne [Polymer, 2015, vol. 69, p. 293 - 300]
[3]Current Patent Assignee: NITTO DENKO CORPORATION - WO2020/210761, 2020, A1 Location in patent: Page/Page column 63; 64; 101; 102
[4]Current Patent Assignee: NITTO DENKO CORPORATION - WO2021/202536, 2021, A1 Location in patent: Page/Page column 25-26
[5]Eichberger, R.; Willig, F.; Storck, W. [Molecular Crystals and Liquid Crystals (1969-1991), 1989, vol. 175, p. 19 - 40]

17
[ 198-55-0 ]
[ 35337-20-3 ]

Yield	Reaction Conditions	Operation in experiment
43.3%	With HNO₃ In 1,4-dioxane; lithium hydroxide monohydrate at 70 - 95℃; for 1h;	1.1 2 mmol of perylene [represented by the formula (S1)] was dissolved in 40 mL of 1,4-dioxane to obtain a starting solution. The starting solution was heated to 70 ° C in a water bath and then 1.3 mL of a nitric acid solution (nitric acid to water ratio of 1: 1.6) was slowly added dropwise to obtain a reaction solution. After the reaction solution was heated to 95 ° C for 60 minutes, water was added to the reaction solution to terminate the reaction. The reaction mixture was filtrated by suction to obtain a crude product. Finally, the reaction mixture was subjected to column chromatography (dichloromethane and hexane (Methylene chloride: hexane = 1: 1) to give the compound of formula (S2) (yield 43.3%) as a bright red solid.
30%	With HNO₃ In 1,4-dioxane; lithium hydroxide monohydrate at 60℃; for 0.666667h;
30%	With HNO₃ In 1,4-dioxane; lithium hydroxide monohydrate at 60℃; for 0.5h;

27%	With HNO₃
27%	With HNO₃
24%	With HNO₃
23.9%	With HNO₃ In 1,4-dioxane at 60℃; for 0.5h;	1.1 (1) Synthesis of Intermediate 1-2 60g of intermediate 1-1 was added to 1.5L of 1,4-dioxane,45ml of 8mol/L concentrated nitric acid was added dropwise at room temperature,After the dropwise addition, the reaction solution was heated to 60°C and stirred for 30min.After the complete reaction of the raw materials, it was lowered to room temperature,The reaction solution was poured into 3L ice water and stirred to precipitate a solid.After filtration, the solid was rinsed with petroleum ether and purified by silica gel column,16.8 g of intermediate 1-2 were obtained with a yield of 23.9%.
7%	With HNO₃ In 1,4-dioxane; lithium hydroxide monohydrate at 60℃; for 0.583333h;
	With HNO₃
	With tetrabutylammonium bromide; HNO₃ In chloroform
	With HNO₃ In 1,4-dioxane; lithium hydroxide monohydrate for 1h; Reflux;
	With HNO₃; glacial acetic acid In dichloromethane at 0℃; for 24h; Inert atmosphere;	Preparation of 1-nitroguanidine Under an argon atmosphere,To the reaction vial was added pyrene (12.0g, 50mmol)A mixture of 25 mL of acetic acid and 25 mL of fuming nitric acid was added dropwise to a solution of 100 mL of dichloromethane at a temperature of 0 ° C for 24 hours.After the reaction was stopped, an aqueous sodium hydroxide solution was added until the pH was greater than 7, washed with water until neutral, extracted with dichloromethane, the organic phase was separated, concentrated, and passed through a silica gel column.Chromatographic purification,A mixed solvent of petroleum ether/dichloromethane (5/1, v/v) was eluted to give a pale yellow solid.
	With lithium hydroxide monohydrate; HNO₃ In 1,4-dioxane at 70℃; for 0.5h;
	With HNO₃ In 1,4-dioxane at 60℃; for 0.5h;

Reference： [1]Current Patent Assignee: FORMOSA PLASTICS CORPORATION - TWI544037, 2016, B Location in patent: Paragraph 0025
[2]Chen, Huajie; Guo, Yunlong; Sun, Xiangnan; Gao, Dong; Liu, Yunqi; Yu, Gui [Journal of Polymer Science, Part A: Polymer Chemistry, 2013, vol. 51, # 10, p. 2208 - 2215]
[3]Madhu, Sheri; Evans, Hayden A.; Doan-Nguyen, Vicky V. T.; Labram, John G.; Wu, Guang; Chabinyc, Michael L.; Seshadri, Ram; Wudl, Fred [Angewandte Chemie - International Edition, 2016, vol. 55, # 28, p. 8032 - 8035][Angew. Chem., 2016, vol. 128, # 28, p. 8164 - 8167,4]
[4]Garcia, Fatima; Buendia, Julia; Ghosh, Samrat; Ajayaghosh, Ayyappanpillai; Sanchez, Luis [Chemical Communications, 2013, vol. 49, # 81, p. 9278 - 9280]
[5]Buendía, Julia; Greciano, Elisa E.; Sánchez, Luis [Journal of Organic Chemistry, 2015, vol. 80, # 24, p. 12444 - 12452]
[6]Greciano, Elisa E.; Sánchez, Luis [Chemistry - A European Journal, 2016, vol. 22, # 38, p. 13724 - 13730]
[7]Current Patent Assignee: XI'AN MANARECO NEW MATERIALS CO LTD - CN113845467, 2021, A Location in patent: Paragraph 0032; 0034-0036
[8]Louillat, Marie-Laure; Biafora, Agostino; Legros, Fabien; Patureau, Frederic W. [Angewandte Chemie - International Edition, 2014, vol. 53, # 13, p. 3505 - 3509][Angew. Chem., 2014, vol. 53, # 13, p. 3573 - 3577,5]
[9]Looker,J.J. [Journal of Organic Chemistry, 1972, vol. 37, # 21, p. 3379 - 3381]
[10]Park, Kwang Hun; Yun, Hui-Jun; Lu, Wanxiang; Chung, Dae Sung; Kwon, Soon-Ki; Kim, Yun-Hi [Dyes and Pigments, 2014, vol. 103, p. 214 - 221]
[11]Santoni, Marie-Pierre; Santoro, Antonio; Salerno, Tania M. G.; Puntoriero, Fausto; Nastasi, Francesco; Di Pietro, M. Letizia; Galletta, Maurilio; Campagna, Sebastiano [ChemPhysChem, 2015, vol. 16, # 15, p. 3147 - 3150]
[12]Current Patent Assignee: SOUTH CHINA UNIVERSITY OF TECHNOLOGY - CN109020978, 2018, A Location in patent: Paragraph 0053-0055
[13]Chintala, Satyanarayana M.; Petroff II, John T.; Barnes, Andrew; McCulla, Ryan D. [Journal of Sulfur Chemistry, 2019, vol. 40, # 5, p. 503 - 515]
[14]Elmali, Ayhan; Hu, Mengyu; Ji, Shaomin; Karatay, Ahmet; Sukhanov, Andrei A.; Voronkova, Violeta K.; Zhang, Xue; Zhao, Jianzhang [Journal of Physical Chemistry B, 2021, vol. 125, # 16, p. 4187 - 4203]

18
[ 198-55-0 ]
[ 7350-92-7 ]

Yield	Reaction Conditions	Operation in experiment
83%	With tetrahydrofuran; methylmagnesium bromide; hydrogen; cobalt acetylacetonate; 1,3-bis[2,6-diisopropylphenyl]imidazolium chloride at 0 - 60℃; for 48h; Autoclave; regioselective reaction;
79%	With hydrogen; magnesium; 1,2-bis(2,6-diisopropylphenylimino)ethane; cobalt(II) bromide In tetrahydrofuran at 60℃; for 48h;
71%	With palladium 10% on activated carbon; hydrogen In ethyl acetate at 60℃; for 5h; Autoclave;	1,2,3,10,11,12-Hexahydroperylene (6). Perylene (3) (20 g, 79.4 mmol) and 10% Pd/C (2.0 g) were suspended in ethyl acetate (750 mL). Hydrogenation was carried out into 1260 mL autoclave at 17 bar and 60oC for 5 h, then heating was off and the shaking was continued overnight. Then resulting suspension was filtered and the catalyst was washed with toluene(3×100 mL). The solvent was evaporated and the residue was purified by column chromatography on alumina eluting with toluene (10→50%, v/v) in n-hexane. Pure1,2,3,10,11,12-hexahydroperylene (14.5 g, 71%) was obtained as light yellowish solid; mp 193-195oC (toluene/iso-propanol), lit.1 mp 193.2-194.1oC, lit.6 mp 190-192oC. 1H NMR (CDCl3) δ =8.55 (d, J 8.3, 2H, H6, H7), 7.48 (t, J 8.4, 2H, H5, H8), 7.35 (d, J 8.3, 2H, H4, H9), 3.13 (t, J 6.1,4H), 3.09 (t, J 6.3, 4H) (H1, H3, H10, H12), 2.11 (pent, J = 6.2, 4H, H2, H11). 13C NMR(CDCl3) δ = 136.68, 129.80, 129.17, 128.97 (internal, not hydrogen-bonded atoms), 125.86,125.07, 121.12 (C4, C5, C6, C7, C8, C9), 31.82, 28.41, 23.27 (C1, C2, C3, C10, C11, C12).

	With copper chromite; hydrogen
	With hydrogen In tetrahydrofuran at 99.99℃; for 0.25h; Autoclave; Green chemistry; chemoselective reaction;
54 %Spectr.	With chromium dichloride; hydrogen; magnesium In tetrahydrofuran at 60℃; for 48h; Autoclave;	27 Example 27 The experimental steps are the same as those in Example 1, and perylene (0.2 mmol) is taken, the bisimine of 2,6-diisopropylbenzene (8 mg, 0.02 mmol) was used as the ligand, the pressure was set to 6 MPa, and the reaction was carried out at 60 °C for 48 h. The product was separated by silica gel column chromatography using an eluent (petroleum ether) to obtain a white solid 2aa with a yield of 54%.

Reference： [1]Han, Bo; Ma, Pengchen; Cong, Xuefeng; Chen, Hui; Zeng, Xiaoming [Journal of the American Chemical Society, 2019, vol. 141, # 22, p. 9018 - 9026]
[2]Han, Bo; Jiao, Hongmei; Ma, Haojie; Wang, Jijiang; Zhang, Miaomiao; Zhang, Yuqi [RSC Advances, 2021, vol. 11, # 63, p. 39934 - 39939]
[3]Chistov, Alexey A.; Kutyakov, Sergey V.; Ustinov, Alexey V.; Aparin, Ilya O.; Glybin, Anton V.; Mikhura, Irina V.; Korshun, Vladimir A. [Tetrahedron Letters, 2016, vol. 57, # 9, p. 1003 - 1005]
[4]Zieger,H.E. [Journal of Organic Chemistry, 1966, vol. 31, p. 2977 - 2981]
[5]Liu, Chengyun; Rong, Zeming; Sun, Zhuohua; Wang, Yong; Du, Wenqiang; Wang, Yue; Lu, Lianhai [RSC Advances, 2013, vol. 3, # 46, p. 23984 - 23988]
[6]Current Patent Assignee: YANAN UNIVERSITY - CN113860984, 2021, A Location in patent: Paragraph 0020

19
[ 198-55-0 ]
[ 75-36-5 ]
[ 7415-79-4 ]

Yield	Reaction Conditions	Operation in experiment
95%	With aluminum (III) chloride In nitromethane; chlorobenzene at 40℃; for 5.83333h; Inert atmosphere;
40%	With aluminium trichloride In dichloromethane for 2h; Heating;
	With aluminium trichloride

	With tin(IV) chloride In 1,2-dichloro-ethane
	With aluminum (III) chloride In dichloromethane at 0 - 20℃;

Reference： [1]Zullo, Valerio; Iuliano, Anna; Pescitelli, Gennaro; Zinna, Francesco [Chemistry - A European Journal, 2022, vol. 28, # 15]
[2]Sarobe, Martin; Kwint, Huibert C.; Fleer, Theun; Havenith, Remco W.A.; Jenneskens, Leonardas W.; Vlietstra, Edward J.; Van Lenthe, Joop H.; Wesseling, Jolanda [European Journal of Organic Chemistry, 1999, # 5, p. 1191 - 1200]
[3]Zieger,H.E. [Journal of Organic Chemistry, 1966, vol. 31, p. 2977 - 2981]
[4]Bag, Subhendu Sekhar; Saito, Yoshio; Hanawa, Kazuo; Kodate, Satoshi; Suzuka, Isamu; Saito, Isao [Bioorganic and Medicinal Chemistry Letters, 2006, vol. 16, # 24, p. 6338 - 6341]
[5]Location in patent: experimental part Brule, Cedric; Sultana, Fatima; Hollenstein, Sandro; Okazaki, Takao; Laali, Kenneth K. [European Journal of Organic Chemistry, 2008, # 21, p. 3700 - 3708]

20
[ 3241-20-1 ]
[ 128-69-8 ]
[ 198-55-0 ]
[ 139260-31-4 ]
N-(1-Octylnonyl)perylene-3,4-dicarboximide [ No CAS ]

Reference： [1]Liebigs Annalen,1995,p. 1229 - 1244

21
[ 198-55-0 ]
[ 126-38-5 ]
[ 174356-23-1 ]
1-(2,2-Dimethoxy-propyl)-perylene [ No CAS ]

Reference： [1]Journal of Organic Chemistry,1996,vol. 61,p. 1136 - 1139

22
[ 198-55-0 ]
[ 2032-35-1 ]
[ 174356-23-1 ]
1-peryleneacetaldehyde diethyl acetal [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	With iodine; sodium 1) THF, sonificated 3 h, <30 deg C; 2) THF, -60 --> 20 deg C, rt, 10 min; 3) THF, -20 deg C --> rt; Yield given. Multistep reaction. Yields of byproduct given;
	With iodine In tetrahydrofuran at -60 - 20℃;	2; 5 The compound was prepared according to the synthetic route 2. Specifically, the perylene prepared in Example 1 was anionized by mixing it with an electrophilic agent in bromoacetaldehyde diethyl acetal and treated with molecular iodine, to give 1-perylene acetaldehyde diethyl acetal and its 3-isomer. The 1- and 3-perylene acetaldehyde diethyl acetals were dissolved in conc. sulfuric acid/methanol mixed solvent and ultrasonicated for 1 hour, to give benzoperylene. Similarly, the benzoperylene obtained was anionized and treated with molecular iodine, to give 5- and 7-benzoperylene acetaldehyde diethyl acetals, and these benzoperylene derivatives were ultrasonicated and purified by recrystallization from toluene, to give coronene. One equivalence of NCS with respect to the coronene was allowed to react with coronene in the presence of CHCl3 in AcOH for chlorination. The product was then allowed to react with n-BuLi and SiCl4 in THF solution, to give trichlorosilylcoronene (yield: 46%).

Reference： [1]Van Dijk, Joost T. M.; Hartwijk, Astrid; Bleeker, Annemarie C.; Lugtenburg, Johan; Cornelisse, Jan [Journal of Organic Chemistry, 1996, vol. 61, # 3, p. 1136 - 1139]
[2]Current Patent Assignee: Sharp (in: Foxconn); HON HAI PRECISION INDUSTRY CO., LTD. - US2008/312463, 2008, A1 Location in patent: Page/Page column 6-7

23
[ 198-55-0 ]
perylene cation radical hexachloroantimonate [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
97%	With triethyloxonium hexachloroantimonate In dichloromethane at 0℃;

Reference： [1]Rathore; Kumar; Lindeman; Kochi [Journal of Organic Chemistry, 1998, vol. 63, # 17, p. 5847 - 5856]

24
[ 198-55-0 ]
[ 2050-74-0 ]

Reference： [1]Environmental Science and Technology,1999,vol. 33,p. 1038 - 1043

25
polyethylene [ No CAS ]
[ 193-39-5 ]
[ 192-97-2 ]
[ 198-55-0 ]
[ 191-24-2 ]

Reference： [1]Chemosphere,1999,vol. 39,p. 1497 - 1512

Yield	Reaction Conditions	Operation in experiment
	With lithium
	With diethyl ether; phenyllithium anschliessende Behandlung mit Eis;
	With diethyl ether; 4-dimethylaminophenyllithium anschliessende Behandlung mit Eis;

	Erhitzen mit einer Schmelze von AlCl₃, NaCl und KCl in Gegenwart von MnO₂, FeCl₃ oder TiCl₄ auf 110grad;
	With palladium on activated charcoal at 490℃;
	With manganese(IV) oxide; hydrogen fluoride at 150℃;
	Erhitzen mit einer Schmelze von AlCl₃, NaCl und KCl in Gegenwart von MnO₂, FeCl₃ oder TiCl₄ auf 110grad;

27
scrap tire [ No CAS ]
[ 822-23-1 ]
[ 198-55-0 ]
[ 191-24-2 ]
[ 203-64-5 ]

Reference： [1]Environmental Science and Technology,2000,vol. 34,p. 2092 - 2099

28
[ 4885-02-3 ]
[ 198-55-0 ]
[ 35438-63-2 ]

Yield	Reaction Conditions	Operation in experiment
92%	With titanium tetrachloride In dichloromethane; 1,2-dichloro-benzene at 0℃; for 1h;
75%	Stage #1: Dichloromethyl methyl ether; PERYLENE With tin(IV) chloride In 1,2-dichloro-ethane for 2h; Heating; Stage #2: at 20℃; for 15h; Stage #3: With water at 20℃; for 3h;
72%	With titanium tetrachloride In 1,2-dichloro-benzene for 1h; cooling;

72.3%	With titanium tetrachloride In 1,2-dichloro-benzene at 0 - 20℃; for 1h; Inert atmosphere;	1 Synthesis of formylperylene (9) To a stirred solution of perylene 8 (1.0 g, 4.0 mmol) in 1,2-dichlorobenzene (25 mL) was added 1,1-dichloromethyl methyl ether (0.68 g, 6.0 mmol) and TiCl4 (1.1 g, 6.0 mmol). The reaction mixture was stirred at 0° C. for 1 hour under nitrogen, and then allowed to warm to room temperature. The reaction mixture was diluted with CH2Cl2 (100 mL) and acidified with aqueous HCl (0.1M, 10 mL). The mixture was washed with water (50 mL*3) and brine (20 mL). The organic phase was dried over Na2SO4, filtered and evaporated to dryness in vacuo. The residue was purified by flash column chromatography on silica gel (hexane/EtOAc, 15:1) to afford 9 (0.81 g, 72.3%). 1H NMR (CDCl3, 400 MHz): δ (ppm) 10.31 (s, 1H, CHO); 9.11 (d, 1H, J=8.8 Hz, aromatic); 8.26-8.15 (m, 4H, aromatic); 7.85 (d, 1H, J=8.0 Hz, aromatic); 7.78 (d, 1H, J=8.0 Hz, aromatic); 7.71 (d, 1H, J=8.0 Hz, aromatic); 7.65 (m, 1H, aromatic); 7.48 (m, 2H, aromatic). 13C NMR (CDCl3, 100 MHz): δ (ppm) 193.3, 137.1, 136.6, 133.8, 131.4, 130.6, 130.0, 129.7, 129.4, 129.3, 129.0, 128.6, 127.9, 127.2, 127.1, 126.9, 123.8, 123.4, 122.0, 121.3, 119.8. HRMS (MALDI) m/z Found: 317.0960, calculated: 317.0937 for C22H14NaO [M+Na]+.
50.9%	With titanium tetrachloride In 1,2-dichloro-benzene for 1h; Inert atmosphere;
	With tin(IV) chloride In water; 1,2-dichloro-ethane

Reference： [1]Location in patent: experimental part Brea, Roberto J.; Perez-Alvite, Maria Jesas; Panciera, Michele; Mosquera, Manuel; Castedo, Luis; Granja, Juan R. [Chemistry - An Asian Journal, 2011, vol. 6, # 1, p. 110 - 121]
[2]Asseline, Ulysse; Cheng, Eric [Tetrahedron Letters, 2001, vol. 42, # 51, p. 9005 - 9010]
[3]Skorobogatyi, Mikhail V.; Pchelintseva, Anna A.; Petrunina, Anna L.; Stepanova, Irina A.; Andronova, Valeriya L.; Galegov, Georgi A.; Malakhov, Andrei D.; Korshun, Vladimir A. [Tetrahedron, 2006, vol. 62, # 6, p. 1279 - 1287]
[4]Current Patent Assignee: EMORY UNIVERSITY; UNIVERSITY SYSTEM OF GEORGIA; GEORGIA INSTITUTE OF TECHNOLOGY - US9821071, 2017, B2 Location in patent: Page/Page column 20
[5]Location in patent: experimental part So, Byoung Min; Chung, Chan Moon; Oh, Se Young [Journal of Nanoscience and Nanotechnology, 2011, vol. 11, # 5, p. 4644 - 4647]
[6]Remon, Patricia; Hammarson, Martin; Li, Shiming; Kahnt, Axel; Pischel, Uwe; Andreasson, Joakim [Chemistry - A European Journal, 2011, vol. 17, # 23, p. 6492 - 6500]

29
[ 198-55-0 ]
[ 23683-68-3 ]

Yield	Reaction Conditions	Operation in experiment
100%	With N-Bromosuccinimide In tetrahydrofuran at 20℃; for 40h; Schlenk technique; Inert atmosphere;
95%	With N-Bromosuccinimide In tetrahydrofuran at 20℃; for 24h;
95%	With N-Bromosuccinimide In tetrahydrofuran at 20℃; Inert atmosphere;

94%	With N-Bromosuccinimide In N,N-dimethyl-formamide at 20℃; Inert atmosphere;
92%	With N-Bromosuccinimide In N,N-dimethyl-formamide at 20℃; for 24h; Inert atmosphere;
90%	With N-Bromosuccinimide In dichloromethane at 20℃; for 0.0833333h;	2 BSynthesis of Perylene BromideAfter 3.0 g (11 mmol) of perylene was dissolved in 700 mL of dichloromethane, the solution was stirred for 5 minutes. To the solution, 2.11 g (12 mmol, 1.1 eq) of N-bromosuccinimide was dropwise added slowly at room temperature, followed by stirring overnight. The reaction solution was purified by silica gel column chromatography using a developing solvent adjusted to dichloromethane:hexane=1:1 to remove N-bromosuccinimide. After the solvent was concentrated, yellow crystals (yield 90%) were obtained. The compound was identified by 1H-NMR and ESI-MS.1H-NMR (CDCl3, 400 MHz) δ 7.46-7.51 (m, 2H), 7.59 (t, J=4.4 Hz, 1H), 7.68-7.72 (m, 2H), 7.78-7.80 (m, 1H), 7.98-8.04 (m, 1H), 8.09-8.14 (m, 1H), 8.17-8.28 (m, 3H).ESI-MS (C20H11Br): Calcd.: 330.00. Found: 331.9.
90%	With N-Bromosuccinimide In N,N-dimethyl-formamide at 20℃; for 24h; Inert atmosphere;	2 3-Bromoperylene 3 3.2. 3-Bromoperylene 3 A solution of N-bromosuccinimide (706 mg, 3.97 mmol) in dry DMF (20 mL) was added to a solution of perylene (1 g, 3.96 mmol) in dry DMF (250 mL) and stirred at room temperature under nitrogen for 24 h. Addition of water (750 mL) to the mixture gave a suspension which was extracted with dichloromethane (3≍200 mL). The grouped organic phases were then washed with water (5≍100 mL) and dried (MgSO4). Rotoevaporation of the solvent gave crude 3-bromoperylene, which was recrystallized from toluene. Yield: 90%; 1H (300 MHz, CD2Cl2): δ 8.16-8.27 (m, 3H), 7.93-8.15 (m, 2H), 7.68-7.79 (m, 3H), 7.46-7.62 (m, 3H);13 13C (75 MHz, CD2Cl2): δ 150.0, 134.6, 133.1, 131.6, 131.2, 130.7, 130.6, 130.4, 129.8, 128.4, 128.3, 127.9, 127.8, 122.3, 121.1, 120.9, 120.6, 120.5 ppm; MS (CI, CH4): m/z calcd for C20H11Br: 331.1; found 331.1 [M+]. Anal. Calcd for C20H11Br: C, 72.53; H, 3.35. Found : C, 73.12; H, 3.36.
87%	With N-Bromosuccinimide In N,N-dimethyl-formamide at 20℃; for 24h;
84%	With N-Bromosuccinimide In N,N-dimethyl-formamide at 20℃; for 24h;
84%	With N-Bromosuccinimide In N,N-dimethyl-formamide at 20℃; Inert atmosphere;
83.2%	With N-Bromosuccinimide In tetrahydrofuran at 20℃; for 24h; Inert atmosphere;	Synthesis of 3-bromoperylene (10) General procedure: Under a nitrogen atmosphere, a solution ofN-bromosuccinimide (213 mg, 1.19 mmol) in dry THF (5 mL) wasadded to a solution of 9 (300 mg, 1.19 mmol) in dry THF (25 mL)and stirred at room temperature for 24 h. The mixture wasconcentrated, and water was added to the residue. The precipitate wascollected by filtration and washed with water. The collectedprecipitate was dried and purified by recrystallization fromchloroform and hexane to give 10 (328 mg, 0.990 mmol, 83.2%) as ayellow solid. 1H NMR (CDCl3): = 8.27-8.17 (m, 4H), 8.11 (d, J = 8.7 Hz, 1H), 8.02 (d, J = 8.4 Hz,1H), 7.78 (d, J = 8.4 Hz, 1H), 7.73-7.67 (m, 2H), 7.62-7.57 (m, 1H), 7.53-7.47 (m, 2H).IR (KBr): = 1493, 1379, 816, 804, 764 cm-1. Mp: 242-244 °C.
82.5%	With N-Bromosuccinimide In N,N-dimethyl-formamide at 25℃; for 48h;	1.1-3.1 Synthesis of compound I Add NBS (N-bromosuccinimide) (40.0g, 158.52mmol) and 350mL of dry DMF (N,N-dimethylformamide) to a 1000mL round-bottom flask in sequence, and stir until all is dissolved; (14.1 g, 79.26 mmol) was dissolved in 350 mL of dry DMF and added to the round bottom flask. The reaction solution was reacted for 48 hours at 25°C. After the reaction, a solid precipitated out. The crude product was obtained by suction filtration and washed with n-hexane to obtain a yellow solid with a yield of 82.5%.
72%	With N-Bromosuccinimide In tetrahydrofuran at 20℃; for 24h; Inert atmosphere;
58%	With N-Bromosuccinimide In N,N-dimethyl-formamide at 100℃; for 3h;	3 [Synthesis of intermediate B1] [Synthesis of intermediate B1] [0097] Perylene (5.0g, 20 mmol) was put in anhydrous DMF (200 ml), and the resulting mixture was heated to 100°C to dissolve perylene. Then, an anhydrous DMF solution (10 ml) of N-bromosuccinimide (3.5g, 20 mmol, 1.1 eq.) was added, followed by stirring at 100°C for 3 hours. The resultant was then allowed to stand for overnight. The reaction mixture was washed with methanol, whereby a yellow plate crystal (3.8g, 58%) was obtained.The resulting crystal was confirmed to be intermediate B1 by NMR. The results are shown below.1H-NMR (400MHz, CDCl3, TMS) δ7.45-7.51 (2H,m), 7.58 (1H,t,J=8Hz),7.70 (2H,d,J=8Hz), 7.76 (1H,d,J=8Hz), 7.99 (1H,d,J=8Hz), 8.08 (1H,d,J=8Hz), 8.14-8.24 (3H,m)
	With N-Bromosuccinimide
	With N-Bromosuccinimide In N,N-dimethyl-formamide at 20℃; for 24h;
	With N-Bromosuccinimide In N,N-dimethyl-formamide
	With N-Bromosuccinimide In N,N-dimethyl-formamide at 20℃; for 24h;
	With N-Bromosuccinimide In tetrahydrofuran at 20℃; for 24h; Inert atmosphere;	1 2.2.1 3-bromoperylene (2) A solution of N-bromosuccinimide (NBS) (70.5 mg, 1.0 mmol) in dry THF (5 mL) was added to a solution of compound 1 (100 mg, 1.0 mmol) in dry THF (5 mL) and stirred at room temperature under nitrogen atmosphere for 24 h. The mixture was poured into water (30 mL) and extracted with dichloromethane (30 mL). The organic layer was dried over anhydrous MgSO4. After filtration, the solvent was removed under reduced pressure to afford compound 2 as a yellow solid (128 mg, 98%). m.p.: 237-240°C; IR νmax (KBr): 2921 (C-H alkyl), 1504, 1493 (C=C aromatic ring), 814, 804 (C-H aromatic ring), 764 (C-Br); 1H RMN δ (400MHz; CDCl3): 7.48 (2H, t, J=8.0Hz), 7.58 (1H, t, J=8.0Hz), 7.70 (2H, d, J=8.0Hz), 7.76 (1H, d, J=8.4Hz), 7.99 (1H, d, J=8.4Hz), 8.08 (1H, d, J=8.4Hz), 8.15 (1H, d, J=7.6Hz), 8.20 (1H, d, J=7.6Hz), 8.23 (1H, d, J=7.2Hz); HRMS (ESI): found [M+H]+ 330.0045; molecular formula C20H11Br requires [M+H]+ 330.0044.
	With N-Bromosuccinimide In N,N-dimethyl-formamide at 20℃;
	With N-Bromosuccinimide In N,N-dimethyl-formamide
	With N-Bromosuccinimide In tetrahydrofuran
	With N-Bromosuccinimide In N,N-dimethyl-formamide at 25℃; for 24h;
	Multi-step reaction with 2 steps 1.1: N-Bromosuccinimide / N,N-dimethyl-formamide / 20 °C 1.2: 1 h / -80 °C 1.3: 20 °C 2.1: N-Bromosuccinimide / dichloromethane / 20 °C
	Multi-step reaction with 2 steps 1.1: N-Bromosuccinimide / N,N-dimethyl-formamide / 20 °C 1.2: 1 h / -80 °C 1.3: 20 °C 2.1: N-Bromosuccinimide / dichloromethane / 20 °C
	With N-Bromosuccinimide In tetrahydrofuran
	With N-Bromosuccinimide In N,N-dimethyl-formamide at 20℃; Inert atmosphere;
	With N-Bromosuccinimide In N,N-dimethyl-formamide
	With N-Bromosuccinimide In tetrahydrofuran at 20℃; for 24h;
	With N-Bromosuccinimide In N,N-dimethyl-formamide for 10h;

Reference： [1]Biesen, Lukas; May, Lars; Nirmalananthan-Budau, Nithiya; Hoffmann, Katrin; Resch-Genger, Ute; Müller, Thomas J. J. [Chemistry - A European Journal, 2021, vol. 27, # 53, p. 13426 - 13434]
[2]Rocard, Lou; Wragg, Darren; Jobbins, Samuel Alexander; Luciani, Lorenzo; Wouters, Johan; Leoni, Stefano; Bonifazi, Davide [Chemistry - A European Journal, 2018, vol. 24, # 60, p. 16136 - 16148]
[3]Börjesson, Karl; Carrod, Andrew J.; Cravcenco, Alexei; Ye, Chen [Journal of Materials Chemistry C, 2022, vol. 10, # 12, p. 4923 - 4928]
[4]Beyer, Christoph; Wagenknecht, Hans-Achim [Journal of Organic Chemistry, 2010, vol. 75, # 8, p. 2752 - 2755]
[5]Raphael Karikachery, Alice; Lee, Han Baek; Masjedi, Mehdi; Ross, Andreas; Moody, Morgan A.; Cai, Xiaochen; Chui, Megan; Hoff, Carl D.; Sharp, Paul R. [Inorganic Chemistry, 2013, vol. 52, # 7, p. 4113 - 4119]
[6]Current Patent Assignee: FUKUOKA UNIVERSITY - US2011/15440, 2011, A1 Location in patent: Page/Page column 12
[7]Nagarajan, Samuthira; Barthes, Cecile; Girdhar, Navdeep K.; Dang, Tung T.; Gourdon, Andre [Tetrahedron, 2012, vol. 68, # 46, p. 9371 - 9375,5] [Tetrahedron]
[8]Markoulides, Marios S.; Venturini, Chiara; Neumeyer, David; Gourdon, André [New Journal of Chemistry, 2015, vol. 39, # 8, p. 6498 - 6503]
[9]Cui, Xiaoneng; Charaf-Eddin, Azzam; Wang, Junsi; Le Guennic, Boris; Zhao, Jianzhang; Jacquemin, Denis [Journal of Organic Chemistry, 2014, vol. 79, # 5, p. 2038 - 2048]
[10]Imran, Muhammad; Taddei, Maria; Sukhanov, Andrey A.; Bussotti, Laura; Ni, Wenjun; Foggi, Paolo; Gurzadyan, Gagik G.; Zhao, Jianzhang; Di Donato, Mariangela; Voronkova, Violeta K. [ChemPhysChem, 2022, vol. 23, # 8]
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[13]Okamoto, Shusuke; Kojiyama, Keita; Tsujioka, Hiroki; Sudo, Atsushi [Chemical Communications, 2016, vol. 52, # 76, p. 11339 - 11342]
[14]Current Patent Assignee: IDEMITSU KOSAN CO LTD - EP2599768, 2013, A1 Location in patent: Paragraph 0097
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[16]Maeda, Hajime; Nanai, Yasuaki; Mizuno, Kazuhiko; Chiba, Junya; Takeshima, Sakiko; Inouye, Masahiko [Journal of Organic Chemistry, 2007, vol. 72, # 23, p. 8990 - 8993]
[17]Location in patent: body text Lentijo, Sergio; Miguel, Jesus A.; Espinet, Pablo [Inorganic Chemistry, 2010, vol. 49, # 20, p. 9169 - 9177]
[18]Location in patent: experimental part Yamaji, Minoru; Maeda, Hajime; Nanai, Yasuaki; Mizuno, Kazuhiko [Chemical Physics Letters, 2012, vol. 536, p. 72 - 76]
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30
[ 928-49-4 ]
1,2-diethylylacenaphthylene [ No CAS ]
[ 198-55-0 ]

Yield	Reaction Conditions	Operation in experiment
1: 67% 2: 22%	In toluene at 130℃;

Reference： [1]Begum, Rowshan Ara; Chanda, Nripen; Ramakrishna; Sharp, Paul R. [Journal of the American Chemical Society, 2005, vol. 127, # 39, p. 13494 - 13495]

31
[ 501-65-5 ]
[ 198-55-0 ]
[ 13638-84-1 ]

Yield	Reaction Conditions	Operation in experiment
1: 64% 2: 18%	In toluene at 120℃;

Reference： [1]Begum, Rowshan Ara; Chanda, Nripen; Ramakrishna; Sharp, Paul R. [Journal of the American Chemical Society, 2005, vol. 127, # 39, p. 13494 - 13495]

32
[ 762-42-5 ]
[ 198-55-0 ]
[ 22187-10-6 ]

Yield	Reaction Conditions	Operation in experiment
1: 74% 2: 22.5%	In toluene at 120℃;

Reference： [1]Begum, Rowshan Ara; Chanda, Nripen; Ramakrishna; Sharp, Paul R. [Journal of the American Chemical Society, 2005, vol. 127, # 39, p. 13494 - 13495]

33
[ 762-21-0 ]
[ 198-55-0 ]
diethyl acenaphthylene-1,2-dicarboxylate [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
1: 66% 2: 33%	In toluene at 120℃;

Reference： [1]Begum, Rowshan Ara; Chanda, Nripen; Ramakrishna; Sharp, Paul R. [Journal of the American Chemical Society, 2005, vol. 127, # 39, p. 13494 - 13495]

34
[ 198-55-0 ]
[ 73183-34-3 ]
2-[5,8,11-tetrakis(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)perylen-2-yl]-1,3,2-dioxaborolane [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
95%	With (1,5-cyclooctadiene)(methoxy)iridium(I) dimer; 4,4'-di-tert-butyl-2,2'-bipyridine In cyclohexane at 80℃; for 40h; Inert atmosphere;
95%	With (1,5-cyclooctadiene)(methoxy)iridium(l) dimer; 4,4'-di-tert-butyl-2,2'-bipyridine In tetrahydrofuran at 80℃; for 18h; Schlenk technique; Inert atmosphere;
90%	With (1,5-cyclooctadiene)(methoxy)iridium(I) dimer; 4,4'-di-tert-butyl-2,2'-bipyridine In tetrahydrofuran at 85℃; for 40h; Inert atmosphere; Glovebox;

85%	With (1,5-cyclooctadiene)(methoxy)iridium(I) dimer; 4,4'-di-tert-butyl-2,2'-bipyridine In cyclohexane at 80℃; for 72h; Inert atmosphere;
83%	With dtbpy In cyclohexane at 80℃; for 16h;
83%	With catalyst:[Ir(OMe)COD]2/dtbpy In cyclohexane perylene (1.98 mmol) reacted (16 h) with 4.4 molar equiv. of B2pin2, (Ir(OMe)COD)2 (5 mol%), 4,4'-di-tert-butyl-2,2'-bipyridine (5 mol%); Kugelrohr distn. (300°C, vac.); recrystd. by layering Et2O over CH2Cl2;
75%	With (1,5-cyclooctadiene)(methoxy)iridium(I) dimer; 3,4,7,8-Tetramethyl-o-phenanthrolin In tetrahydrofuran at 80℃; for 24h; Schlenk technique; Inert atmosphere;
	With catalyst:[Ir(OMe)COD]2/dtbpy In cyclohexane byproducts: (C20H11)(Bpin), (C20H10)(Bpin)2, (C20H9)(Bpin)3; perylene, 2.2 molar equiv of B2pin2, (Ir(OMe)COD)2 (5 mol%), 4,4'-di-tert-butyl-2,2'-bipyridine (10 mol%) reacted in cyclohexane (16 h); HPLC;
	With (1,5-cyclooctadiene)(methoxy)iridium(I) dimer; 4,4'-di-tert-butyl-2,2'-bipyridine In Cyclopentane at 80℃; for 72h; Inert atmosphere;	FIG. 3A is a chemical reaction diagram illustrating a process 300 of forming a first sidechain-modified molecular annihilator, according to some embodiments of the present disclosure. A solution of perylene, (1,5-cycloocta- diene)(methoxy)iridium(I) dimer ([Ir(OMe)(1 ,5-cod)]2]), 4,4’-di-tert-butyl-2,2’-dipyridyl (dtbppy), and bis(pinacolato)diboron (R2pin2) in anhydrous cyclopentane is prepared. Oxygen can be removed from the solution (e.g., by freeze drying at least twice under vacuum). The solution can be stirred at approximately 80° C. under an inert atmosphere (e.g., N2 gas) for about 72 hours. The mixture can then be passed through a silica plug with a chloroform eluent. The solvent can then be removed under reduced pressure. Purification of the resulting residue (e.g., by column chromotography) yields 2,5,8,11-tetrakis(4,4,5,5-tetramethyl-1,3,2- dioxaborolan-2-yl) perylene (“perylene-Bpin4”).

Reference： [1]Ascherl, Laura; Evans, Emrys W.; Gorman, Jeffrey; Orsborne, Sarah; Bessinger, Derya; Bein, Thomas; Friend, Richard H.; Auras, Florian [Journal of the American Chemical Society, 2019, vol. 141, # 39, p. 15693 - 15699]
[2]Alves-Favaro, Marcelo; Canivet, Jérôme; Duguet, Mathis; Farrusseng, David; Ghosh, Ashta C.; Lorentz, Chantal; Mellot-Draznieks, Caroline; Mohr, Yorck; Palkovits, Regina; Perrinet, Quentin; Quadrelli, Elsje Alessandra; Wisser, Florian M.; de Waele, Vincent [Angewandte Chemie - International Edition, 2020, vol. 59, # 13, p. 5116 - 5122][Angew. Chem., 2020, vol. 132, # 13, p. 5154 - 5160,7]
[3]Merz, Julia; Steffen, Andreas; Nitsch, Jörn; Fink, Julian; Schürger, Claudia B.; Friedrich, Alexandra; Krummenacher, Ivo; Braunschweig, Holger; Moos, Michael; Mims, David; Lambert, Christoph; Marder, Todd B. [Chemical Science, 2019, vol. 10, # 32, p. 7516 - 7534]
[4]Bhunia, Subhajit; Dey, Nilanjan; Pradhan, Anirban; Bhattacharya, Santanu [Chemical Communications, 2018, vol. 54, # 54, p. 7495 - 7498]
[5]Coventry, David N.; Batsanov, Andrei S.; Goeta, Andres E.; Howard, Judith A. K.; Marder, Todd B.; Perutz, Robin N. [Chemical Communications, 2005, # 16, p. 2172 - 2174]
[6]Coventry, David N.; Batsanov, Andrei S.; Goeta, Andres E.; Howard, Judith A. K.; Marder, Todd B.; Perutz, Robin N. [Chemical Communications, 2005, # 16, p. 2172 - 2174]
[7]Tran, Ly D.; Ma, Jialiu; Wong-Foy, Antek G.; Matzger, Adam J. [Chemistry - A European Journal, 2016, vol. 22, # 16, p. 5509 - 5513]
[8]Coventry, David N.; Batsanov, Andrei S.; Goeta, Andres E.; Howard, Judith A. K.; Marder, Todd B.; Perutz, Robin N. [Chemical Communications, 2005, # 16, p. 2172 - 2174]
[9]Current Patent Assignee: INTERNATIONAL BUSINESS MACHINES CORP - US2022/41925, 2022, A1 Location in patent: Paragraph 0040

35
[ 108-31-6 ]
[ 198-55-0 ]
[ 6245-10-9 ]

Yield	Reaction Conditions	Operation in experiment
100%	With 2,3,5,6-tetrachlorocyclohexa-2,5-diene-1,4-dione at 240℃; for 0.166667h;
99%	With 2,3,5,6-tetrachlorocyclohexa-2,5-diene-1,4-dione at 240℃; for 0.166667h;
98%	With 2,3,5,6-tetrachlorocyclohexa-2,5-diene-1,4-dione In 5,5-dimethyl-1,3-cyclohexadiene for 0.166667h; Reflux;

95%	With 2,3,5,6-tetrachlorocyclohexa-2,5-diene-1,4-dione at 240℃; for 0.216667h; Microwave irradiation;
91%	With 2,3,5,6-tetrachlorocyclohexa-2,5-diene-1,4-dione at 240℃; for 0.166667h;
85%	With 2,3,5,6-tetrachlorocyclohexa-2,5-diene-1,4-dione at 240℃; Reflux;
	In 2,3,5,6-tetrachlorocyclohexa-2,5-diene-1,4-dione at 240℃; for 0.166667h; Inert atmosphere;
	With 2,3,5,6-tetrachlorocyclohexa-2,5-diene-1,4-dione In dichloromethane at 140℃; for 4h;
	With 2,3,5,6-tetrachlorocyclohexa-2,5-diene-1,4-dione at 240℃;
	Stage #1: maleic anhydride; PERYLENE at 240℃; Stage #2: With 2,3,5,6-tetrachlorocyclohexa-2,5-diene-1,4-dione for 0.166667h; Reflux;

Reference： [1]Alibert-Fouet, Sonia; Seguy, Isabelle; Bobo, Jean-Francois; Destruel, Pierre; Bock, Harald [Chemistry - A European Journal, 2007, vol. 13, # 6, p. 1746 - 1753]
[2]Location in patent: scheme or table Rao, K. Venkata; George, Subi J. [Organic Letters, 2010, vol. 12, # 11, p. 2656 - 2659]
[3]Yang, Meiding; Zhou, Huipeng; Li, Yongxin; Zhang, Qingfeng; Li, Juanmin; Zhang, Cuiyun; Zhou, Chuibei; Yu, Cong [Journal of Materials Chemistry B, 2017, vol. 5, # 32, p. 6572 - 6578]
[4]Srideep, Dasari; Sriram, Kasilingam; Kotha, Srinu; Babu, Deepu J.; Singh, Saurabh Kumar; Rao, Kotagiri Venkata [Chemistry - An Asian Journal, 2022, vol. 17, # 8]
[5]Kotha, Srinu; Mabesoone, Mathijs F. J.; Srideep, Dasari; Sahu, Rahul; Reddy, Sandeep K.; Rao, Kotagiri Venkata [Angewandte Chemie - International Edition, 2021, vol. 60, # 10, p. 5459 - 5466][Angew. Chem., 2021, vol. 133, # 10, p. 5519 - 5526,8]
[6]Location in patent: experimental part Manning, Steven J.; Bogen, William; Kelly, Lisa A. [Journal of Organic Chemistry, 2011, vol. 76, # 15, p. 6007 - 6013]
[7]Jain, Ankit; Rao, K. Venkata; Kulkarni, Chidambar; George, Anjana; George, Subi J. [Chemical Communications, 2012, vol. 48, # 10, p. 1467 - 1469]
[8]Hirayama, Sunao; Sakai, Hayato; Araki, Yasuyuki; Tanaka, Minako; Imakawa, Masaki; Wada, Takehiko; Takenobu, Taishi; Hasobe, Taku [Chemistry - A European Journal, 2014, vol. 20, # 29, p. 9081 - 9093]
[9]Keshri, Sudhir Kumar; Asthana, Deepak; Chorol, Sonam; Kumar, Yogendra; Mukhopadhyay, Pritam [Chemistry - A European Journal, 2018, vol. 24, # 8, p. 1821 - 1832]
[10]Cole, Justin P.; Chen, Dian-Feng; Kudisch, Max; Pearson, Ryan M.; Lim, Chern-Hooi; Miyake, Garret M. [Journal of the American Chemical Society, 2020, vol. 142, # 31, p. 13573 - 13581]

36
[ 198-55-0 ]
[ 110774-34-0 ]

Yield	Reaction Conditions	Operation in experiment
83.5%	Stage #1: succinic acid monomethylester chloride With aluminum (III) chloride In dichloromethane at 0℃; for 1h; Stage #2: PERYLENE In dichloromethane at 0 - 20℃; Stage #3: With hydrogenchloride; water In dichloromethane	3- (3-PERYLENOYL) PROPANSäUREMETHYLESTER Zu einer Lösung von 3-Carbomethoxypropionylchlorid (51, 8 1, 0,415 mmol) in 10 ml Dichlormethan wurden unter Rühren bei 0°C 64,7 mg (0,476 mmol) Aluminiumchlorid portionsweise hinzugefügt. Die Reaktion wurde 1 Stunde lang bei dieser Temperatur gehalten, und danach wurden portionsweise 100, 0 MG (09396 RRLMOL) PERYLEN HINZUGERIGT. Die Mischung wurde 1 Stunde lang bei 0°C und danach über Nacht bei Raumtemperatur gehalten, auf etwa 10 g Eis gegossen und mit 1-3 Tropfen konzentrierter Salzsäure angesäuert. Das Produkt wurde mit Dichlormethan (6x 50 ml) extrahiert und mit Wasser (2x 10 ml) gewaschen. Die organischen Schichten wurden über Natriumsulfat getrocknet. Nach dem Abdampfen wurde der Rest durch eine Säulenchromatographie auf Kieselgel gereinigt, wobei mit Chloroform eluiert wurde, um das reine Produkt Perylenoylpropansäure- methylester (121,2 mg, 83, 5%) zu erhalten. RF0, 16 (System L). LH-NMR (CDC13) (6, PPM) : 2,87 (t, 2H, Ja, b=J2,3 6,52 Hz, 2-CH2-COO-), 3,40 (t, 2H, JA, B=J2, 3 6,51 Hz, 3-CH2-CO-Ar), 3,77 (s, 3H, CH3-OCO-), 7, 47-7,65 (M, 3H, Ar), 7,74 (t, 2H, J 8, 63 Hz, Ar), 7,95 (d, 1H, J 8,01 Hz, Ar), 8,14-8, 31 (M, 3H, Ar), 8, 56 (d, 1H, J 8, 57 Hz, Ar).
	Multi-step reaction with 2 steps 1: 1.1 g / AlCl₃ / CH₂Cl₂ / 4 h / 20 °C 2: HCl
	Multi-step reaction with 2 steps 1: 1.) AlCl₃, 2.) HCl, -6 to -4 deg C, 30 min / nitromethane 2: CH₂Cl₂

Multi-step reaction with 2 steps 1: aluminium chloride; carbon disulfide 2: hydrogen chloride

Reference： [1]Current Patent Assignee: AUSTRIA WIRTSCHAFTSSERVICE GMBH - WO2004/83220, 2004, A1 Location in patent: Page 5
[2]Grechishnikova, I. V.; Mikhalev, I. I.; Molotkovskii, Jul. G. [Russian Journal of Bioorganic Chemistry, 1995, vol. 21, # 1, p. 62 - 67][Bioorganicheskaya Khimiya, 1995, vol. 21, # 1, p. 70 - 76]
[3]Johansson, Lennart B.-A.; Molotkovsky, Julian G.; Bergelson, Lev D. [Journal of the American Chemical Society, 1987, vol. 109, # 24, p. 7374 - 7381]
[4]Zinke; Troger; Ziegler [Chemische Berichte, 1940, vol. 73, p. 1042,1046]

37
[ 69022-30-6 ]
[ 198-55-0 ]
[ 594-09-2 ]
{Fe(cp)(PMe₃)3}(PF₆) [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
83%	In tetrahydrofuran inert atmosphere; stirring (-20°C, 30 min); evapn. of solvent (vac.), recrystn. (acetone/ether);

Reference： [1]Ruiz, Jaime; Lacoste, Marc; Astruc, Didier [Journal of the American Chemical Society, 1990, vol. 112, # 14, p. 5471 - 5483]

38
[ 604-53-5 ]
[ 198-55-0 ]

Yield	Reaction Conditions	Operation in experiment
100%	Stage #1: 1,1'-bisnaphthalene With potassium In tetrahydrofuran at 85℃; for 12h; sealed tube; Stage #2: With iodine In tetrahydrofuran at 20℃; for 0.25h;
	Stage #1: 1,1'-bisnaphthalene With lithium In tetrahydrofuran Stage #2: With oxygen In tetrahydrofuran	1; 4 The compound was prepared according to the synthetic route 1. Specifically, naphthalene (Sigma-Aldrich Corporation) was allowed to react in NaNO2-TfOH (Tf=CF3SO2) solution, to give binaphthyl from naphthalene. Binaphthyl was allowed to react in the presence of LiTHF under oxygen bubbling, to give perylene. SbF5 purchased from Sigma-Aldrich Corporation was diluted twice under dry argon atmosphere. SO2ClF was prepared from SO2Cl2 previously prepared in halogen exchange reaction between NH4F and TFA. Perylene was allowed to react with SbF5-SO2ClF, and the product was purified by HPLC, to give dibenzoperylene. One equivalence of NCS with respect to dibenzoperylene was allowed to react with dibenzoperylene in AcOH in the presence of CHCl3 for chlorination. The product was then allowed to react with n-BuLi and Si(OC2H5)4 in THF solution, to give triethoxylsilyldibenzoperylene (yield: 8%).

Reference： [1]Location in patent: experimental part Rickhaus, Michel; Belanger, Anthony P.; Wegner, Hermann A.; Scott, Lawrence T. [Journal of Organic Chemistry, 2010, vol. 75, # 21, p. 7358 - 7364]
[2]Current Patent Assignee: Sharp (in: Foxconn); HON HAI PRECISION INDUSTRY CO., LTD. - US2008/312463, 2008, A1 Location in patent: Page/Page column 5-6

39
[ 198-55-0 ]
[ 33513-42-7 ]
[ 35438-63-2 ]

Yield	Reaction Conditions	Operation in experiment
85%	With trichlorophosphate In chlorobenzene at 100℃;
82.3%	With phosphorus trichloride In 1,2-dichloro-benzene at 100℃; for 6h; Inert atmosphere;	Synthesis of 3-formylperylene (18) Under a nitrogen atmosphere, phosphorictrichloride (500 μL, 5.36 mmol) was added dropwise over 30 min to a solution of 9(300 mg, 1.19 mmol) and dry DMF (600 μL, 7.74 mmol) in dry o-dichlorobenzene (5mL) at 100 °C. After stirring at 100 °C for 6 h, the reaction mixture was cooled to room temperature, and sat. aqueous sodium acetate solution was addeduntil the mixture became pH 4, and extracted with chloroform (50 mL× 3). The combined organic layer was washed with water (50 mL × 3),dried over anhydrous Na2SO4, and concentrated. The residue waspurified by silica gel column chromatography with chloroform /hexane (v/v, 3/1) to give 18 (274 mg, 0.980 mmol, 82.3%) as anorange solid. 1H NMR (CDCl3): = 10.35 (s, 1H), 9.20 (d, J = 8.4 Hz, 1H), 8.37-8.30 (m, 4H), 7.99(d, J = 7.8 Hz, 1H), 7.85-7.70 (m, 3H), 7.61-7.54 (m, 2H). IR (KBr): = 1682, 1588,1567, 1520, 1503, 1212, 1159, 1087, 897, 810, 769, 742 cm-1. Mp: 233-236 °C.
72.2%	With trichlorophosphate In 1,2-dichloro-benzene at 100℃;	2.2.6 Compound 6.1 (perylene-3-carbaldehyde): 0.75 mL of POCl3 was added to a suspension of 5 perylene (1.0 g, 3.96 mmol) in 2mL anhydrous DMF and 2mL anhydrous o-dichlorobenzene. The resulting solution was then heated at 100 C overnight. The net morning, the solution was cooled in an ice-bath for 1 hr. Next, the solution was neutralized with 5 mL of 10% NaOAc aqueous solution. Once neutralized the solution was filtered. After filtration, the solid was collected and dried in a vacuum oven for 3 hours. After drying, the solid is re-dissolved in 250 20 mL dichloromethane, loaded on silica gel and purified by flash chromatography using dichloromethane/hexanes (10% 50%) for the eluents. The desired fractions were collected and dried under reduced pressure to give an orange solid (0.80 g, in 72.2% yield). 1H NMR (400 MHz, Chloroform-d) d 10.34 (s, 1H), 9.20 (d, J = 8.5 Hz, 1H), 8.38- 8.27 (m, 4H), 7.97 (d, J = 7.9 Hz, 1H), 7.83 (d, J = 8.1Hz, 1H), 7.80- 7.68 (m, 2H), 7.56 (td, J = 7.8, 4.2 Hz, 2H).

64%	With trichlorophosphate In 1,2-dichloro-benzene at 100℃; for 4h; Inert atmosphere;
62.8%	With trichlorophosphate In 1,2-dichloro-benzene at 100℃; for 2.5h;
62.8%	With trichlorophosphate In 1,2-dichloro-benzene at 100℃; for 4.5h;
62%	With trichlorophosphate In 1,2-dichloro-benzene at 100℃; for 4h;
50%	With trichlorophosphate In 1,2-dichloro-benzene for 2h; Reflux;
44%	With phosphorus trichloride In 1,2-dichloro-benzene at 100℃; for 3.5h;	2.1.1. 3-Formylperylene [2] 2.1.1. 3-Formylperylene [2] Perylene (981 mg, 3.89 mmol) was dissolved in 1,2-dichlorobenzene (2 mL). Then DMF(1.85 g, 25.3 mmol) was added and the solution was heated to 100 °C. Over a period of 10min phosphorus trichloride (1.19 g, 7.78 mmol) was added dropwise and the reaction mixturewas heated to 100 °C for 3.5 h. Thereafter the solution was poured into 150 mL of anaqueous sodium acetate solution and cooled to 0 °C for 3 h. The precipitate was filtered off,adsorbed to Celite and purified by chromatography on silica gel (CHCl3) to give 3-formylperylene (480 mg, 1.71 mmol, 44%) as an orange solid
44.7%	With trichlorophosphate In 1,2-dichloro-benzene at 100℃;

Reference： [1]Markovic, Vesna; Villamaina, Diego; Barabanov, Igor; Lawson Daku, Latevi Max; Vauthey, Eric [Angewandte Chemie - International Edition, 2011, vol. 50, # 33, p. 7596 - 7598]
[2]Kodama, Koichi; Kobayashi, Akinori; Hirose, Takuji [Tetrahedron Letters, 2013, vol. 54, # 40, p. 5514 - 5517]
[3]Current Patent Assignee: NITTO DENKO CORPORATION - WO2020/210761, 2020, A1 Location in patent: Page/Page column 60; 61
[4]Imran, Muhammad; Taddei, Maria; Sukhanov, Andrey A.; Bussotti, Laura; Ni, Wenjun; Foggi, Paolo; Gurzadyan, Gagik G.; Zhao, Jianzhang; Di Donato, Mariangela; Voronkova, Violeta K. [ChemPhysChem, 2022, vol. 23, # 8]
[5]Location in patent: experimental part Qiu, Haixiao; Wang, Chengyun; Xu, Jinfeng; Lai, Guoqiao; Shen, Yongjia [Monatshefte fur Chemie, 2008, vol. 139, # 11, p. 1357 - 1362]
[6]Mahmood, Zafar; Zhao, Jianzhang [Journal of Organic Chemistry, 2016, vol. 81, # 2, p. 587 - 594]
[7]Bussotti, Laura; Di Donato, Mariangela; Dick, Bernhard; Fedin, Matvey; Foggi, Paolo; Gao, Yuting; Ivanov, Mikhail; Luo, Liang; Mazzone, Gloria; Russo, Nino; Wang, Zhijia; Zhang, Huimin; Zhao, Jianzhang [Chemistry - A European Journal, 2020]
[8]Bocklitz, Thomas; Dietzek, Benjamin; Görls, Helmar; Hager, Martin D.; Schmidt, Benny; Sittig, Maria; Wächtler, Maria; Zechel, Stefan [Physical Chemistry Chemical Physics, 2020, vol. 22, # 7, p. 4072 - 4079]
[9]Börgardts, Markus; Müller, Thomas J. J. [Beilstein Journal of Organic Chemistry, 2017, vol. 13, p. 768 - 778]
[10]Peng, Yuan-Zhao; Guo, Guang-Chen; Guo, Song; Kong, Li-Hui; Lu, Tong-Bu; Zhang, Zhi-Ming [Angewandte Chemie - International Edition, 2021, vol. 60, # 40, p. 22062 - 22069][Angew. Chem., 2021, vol. 133, # 40, p. 22233 - 22240]

40
[ 507-63-1 ]
[ 198-55-0 ]
[ 1227002-92-7 ]

Yield	Reaction Conditions	Operation in experiment
65%	With copper In dimethyl sulfoxide at 120℃; for 24h; Inert atmosphere; regioselective reaction;

Reference： [1]Li, Yan; Li, Cheng; Yue, Wan; Jiang, Wei; Kopecek, Ralf; Qu, Jianqiang; Wang, Zhaohui [Organic Letters, 2010, vol. 12, # 10, p. 2374 - 2377]

41
[ 625-48-9 ]
[ 198-55-0 ]
[ 191-24-2 ]

Yield	Reaction Conditions	Operation in experiment
	With phthalic anhydride; In 1,2-dichloro-benzene; at 200℃; for 20h;Inert atmosphere; Microwave irradiation;	7, Benzo[ghi]perylene, perylene (25 mg, 0.099 mmol, 1 equiv) and phthalic anhydride (367 mg, 2.5 mmol, 25 equiv) were charged to a microwave vial. The vial was evacuated and refilled with N2 3 times. 2-nitroethan-1-ol (225 mg, 0.29 mmol, 25 equiv) was and the mixture was dissolved in 4 mL 1,2-dichlorobenzne. The vial was heated to 200 °C for 20 h and the mixture was diluted with toluene and solvent was removed in vacuo. The crude residue was purified by flash chromatography (10percent CH2Cl2/hexanes) affording a mixture of product and starting material (25 mg, ratio 1.39:1, 55percent yield). Spectral data matched as previously reported.

Reference： [1]Angewandte Chemie - International Edition,2010,vol. 49,p. 6626 - 6628
[2]Tetrahedron,2016,vol. 72,p. 3754 - 3758

42
[ 198-55-0 ]
[ 20451-53-0 ]
[ 191-24-2 ]

Reference： [1]Angewandte Chemie - International Edition,2010,vol. 49,p. 6626 - 6628

43
perylenetetracarboxylic dianhydride [ No CAS ]
[ 461-82-5 ]
[ 111-42-2 ]
[ 108-95-2 ]
[ 198-55-0 ]

Yield	Reaction Conditions	Operation in experiment
95%	In methanol; sulfuric acid; water	1.a a) a) Synthesis At 80° C., 200 g of phenol were introduced. Added thereto was 0.1 mol of perylenetetracarboxylic dianhydride (per acid) and 0.3 mol of diethanolamine, and the batch was heated to 120° C. in 30 minutes. It was admixed with 0.225 mol of p-trifluoromethoxyaniline and then heated at 150° C. for 5 hours with distillative removal of phenol/water. Subsequently the batch was cooled indirectly to 90° C. and 280 g of methanol were added dropwise. This was followed by cooling to 40° C. and isolation. The product was washed with 500 g of methanol and then with 500 g of water. The moist presscake was introduced into 800 ml of 5% strength KOH solution, this system was heated to 80° C. and stirred for 1 hour, and the product was isolated, washed to neutrality with water and dried. The product was dissolved in 1500 g of sulphuric acid at 20° C. and discharged slowly at about 60° C. onto 2000 ml of methanol. The mixture was diluted with water and the product was isolated by filtration, washed and dried. Yield: 95% of perylene of the formula (II)

Reference： [1]Current Patent Assignee: LANXESS AG - US2010/264382, 2010, A1

44
[ 198-55-0 ]
[ 35337-22-5 ]

Yield	Reaction Conditions	Operation in experiment
22%	Stage #1: PERYLENE With water; nitric acid In 1,4-dioxane at 60℃; for 0.5h; Stage #2: With methanesulfonic acid; triethyl phosphite at 200℃;	1 N-hydro-phenanthro[1,10,9,8-c,d,e,f,g]carbazole:To a hot solution of perylene (25.0 g, 99.1 mmol) in 1,4-dioxane (1000 cm3) was added a mixture of water (20.0 cm3) and nitric acid (12.5 cm3, d = 1.5) dropwise. The resulting solution was heated to 60 0C with vigorous stirring for 25-30 mins, and then cooled and poured into water (4000 cm3). The solid was collected, washed and dried to afford a mixture of 1-nitroperylene (26 %, GC-MS) and 3-nitroperylene (74 % GC-MS) as a brick-red powder (29.1 g). The powder is suspended in triethylphosphite25 (130 cm3) and methanesulfonic acid (6.1 cm3). The mixture is heated to200° C overnight and then the solution is cooled down. The excess of triethylphosphite is removed under vacuum and the product is recovered after column chromatography (silica gel, toluene as eluent). The product is further purified by trituration in hot toluene (125 cm3) to afford the title product (5.12 g, yield 22 % over two steps). NMR (1H, 300 MHz, Acetone- d6) : δ 12.20 (s, 1H); 8.76 (d, J = 7.4 Hz, 2H); 8.18 (d, J = 8.1 Hz, 2H);7.98 (d, J = 8.7 Hz, 2H); 7.95 (d, J = 8.7 Hz, 2H); 7.83 (t, J = 7.8 Hz, 2H).

Reference： [1]Current Patent Assignee: RAYNERGY TEK INCORPORATION - WO2011/18144, 2011, A2 Location in patent: Page/Page column 43

45
[ 85-44-9 ]
[ 198-55-0 ]
[ 190-84-1 ]

Yield	Reaction Conditions	Operation in experiment
4.8%	at 1000℃; Pyrolysis;	Naphtho[1,2,3,4-ghi]perylene (1), in the gas phase A solid mixture of 200 mg (0.79 mmol) of perylene and 1.18 g (8.0 mmol) of phthalic anhydride was divided into two portions. The portions were homogenized individually by ball-milling for 5 min each and were then recombined in a quartz boat, which was inserted into the capped end of the quartz pyrolysis tube. The system was pumped down to 0.5 mmHg. The sublimation oven was then turned on and allowed to equilibrate to 500 °C, while the reaction oven was turned on and allowed to equilibrate to 1000 °C. The boat was then quickly moved to the middle of the sublimation oven.15 The temperature of the reaction oven temporarily dropped by approximately 10 °C, and the pressure shot off-scale as the material sublimed rapidly, but the pressure returned to below 1.0 mmHg within approximately 90 s. Once the starting materials had fully sublimed, the ovens were switched off, and the apparatus was allowed to cool. The crude pyrolysate was taken up in DCM and filtered to remove insoluble carbonaceous material. Column chromatography on silica gel with 10% DCM in hexanes gave 12.6 mg (4.8%) of clean 1 in the third fraction. The spectral properties matched those of a sample prepared as described above.

Reference： [1]Location in patent: experimental part Fort, Eric H.; Scott, Lawrence T. [Tetrahedron Letters, 2011, vol. 52, # 17, p. 2051 - 2053]

46
[ 198-55-0 ]
[ 88284-48-4 ]
[ 190-84-1 ]

Yield	Reaction Conditions	Operation in experiment
45%	With tetrabutyl ammonium fluoride In toluene for 1.5h; Reflux; Inert atmosphere;	Naphtho[1,2,3,4-ghi]perylene (1), in solution To a 50 mL two-necked round bottomed flask equipped with a reflux condenser and under nitrogen, 50 mg (0.20 mmol) of perylene and 1.24 g (4.0 mmol) of tetrabutylammonium fluoride trihydrate (TBAF) were added. To this was added 1 mL of dry toluene, and the reaction mixture was heated to reflux. To this reaction mixture was added, dropwise from a syringe at a rate of approximately 8 mL/h, a solution of 0.96 μL (4.0 mmol) of 2-(trimethylsilyl)phenyl trifluoromethanesulfonate in 8 mL of toluene. After completion of the addition, the reaction mixture was maintained at reflux for an additional 1.5 h and was then allowed to cool to room temperature. The mixture was diluted with dichloromethane (DCM); the solution was washed with 3 × 300 mL of H2O, and the organic solvent was then removed under reduced pressure. The resulting solid was digested in ethanol and filtered to yield 28.8 mg (45%) of 1 as a yellow solid. The spectroscopic properties of 1 matched those of a sample prepared previously by an independent synthesis.5c

Reference： [1]Location in patent: experimental part Fort, Eric H.; Scott, Lawrence T. [Tetrahedron Letters, 2011, vol. 52, # 17, p. 2051 - 2053]

47
[ 3262-89-3 ]
[ 198-55-0 ]
[ 1415803-83-6 ]
[ 1256556-19-0 ]
3,4,9,10-tetraphenylperylene [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
1: 17% 2: 11% 3: 0.7%	With o-tetrachloroquinone; palladium diacetate In 1,2-dichloro-ethane at 80℃; for 2h; Inert atmosphere;	2 4.2 Procedure for direct C-H phenylation of perylene A solution of Pd(OAc)2 (11.2 mg, 50 μmol, 5.0 mol %), o-chloranil (490 mg, 2.0 mmol, 2.0 equiv), perylene (252 mg, 1.0 mmol, 1.0 equiv), and phenylboroxin (311 mg 1.0 mmol, 1.0 equiv) in dry 1,2-dichloroethane (20 mL) was stirred at 80 °C for 2 h. After cooling the reaction mixture to room temperature, the mixture was passed through a short pad of silica gel (CH2Cl2, 100 mL). The filtrate was then evaporated and the residue was purified by silica gel column chromatography (hexane/CH2Cl2=100:0 to 85:15) to obtain 3-phenylperylene (1) (56.2 mg 17%), mixture of diphenylperylene isomers (2) (97.5 mg, 24%), 3,4,9-triphenylperylene (3) (54.2 mg, 11%), and 3,4,9,10-tetraphenylperylene (4) (3.7 mg, 0.7%).
1: 17% 2: 11% 3: 0.7%	With o-tetrachloroquinone; palladium diacetate In 1,2-dichloro-ethane at 80℃; for 2h;	53 Similiar to Examples 37 to 52, perylene was used as a substrate in place of fluoranthene. By the reaction shown below, phenylperylene, di-phenylperylene, triphenylperylene, and tetraphenylperylene were obtained. The details are described below. A Pd(OAc)2 solution (11.2 mg, 50 mmol, 5.0 mmol%), o-chloranil (490 mg, 2.0 mmol, 2.0 equivalents), perylene(252 mg, 1.0 mmol, 1.0 equivalent) represented by the formula below: and a boron compound (311 mg, 1.0 mmol, 1.0 equivalent) represented by the formula below: were introduced into dry 1,2-dichloroethane (1,2-DCE, 20 mL). The mixture was stirred for 2 hours at 80°C. After coolingto room temperature, the reaction product was filtered using a silica gel (eluent: CH2Cl2, 100 mL). After the filtrate was evaporated, the residue was purified by silica gel column chromatography (eluent: hexane/CH2Cl2 = 7.00/0 to 85/15) to obtain 56.2 mg of 3-phenylperylene at a yield of 17%, 97.5 mg of di-phenylperylene at a yield of 24%, 54.2 mg of 3,4,9-triphenylperylene at a yield of 11%, and 3.7 mg of tetraphenylperylene at a yield of 0.7%. 3,4,9-Triphenylperylene: 1H NMR (600 MHz, CDCl3/CS2 = 1/1) δ 8.24 (d, J = 7.8 Hz, 1H), 8.23 (d, J = 7.8 Hz, 1H), 8.21 (d, J = 7.8 Hz, 1H),8.19 (d, J = 7.8 Hz, 1H), 7.74 (d, J = 7.8 Hz, 1H), 7.49-7.45 (m, 4H), 7.42-7.37 (m, 5H), 6.96 (d, J = 7.2 Hz, 4H),6.89 (t, J = 7.2 Hz, 4H), 6.84 (d, J = 7.2 Hz, 2H); 13C NMR (150 MHz, CDCl3/CS2 = 1/1) δ142.9, 140.4, 140.01,139.98, 139.6, 132.5, 131.5, 131.3, 130.61, 130.59, 130.56, 130.5, 130.4, 129.8, 129.4, 128.4, 128.2, 127.8, 127.2,126.6, 125.8, 125.7, 120.4, 120.3, 120.1, 120.0. HRMS (DART, ESI+) m/z calcd for C38H25 [M+H]+: 481.1956, found:481.1955. 3,4,9,10-Tetraphenylperylene: 1H NMR (600 MHz, CDCl3/CS2 = 1/1) δ 8.32 (d, J = 7.8 Hz 4H), 7.45 (d, J = 7.8 Hz 4H), 7.02 (d, J = 6.6 Hz, 8H),6.93 (t, J = 7.2 Hz, 8H), 6.89 (t, J = 7.4 Hz, 4H); 13C NMR (150 MHz, CDCl3/CS2 = 1/1) δ142.8, 140.0, 131.7, 130.7,130.4, 130.1, 129.4, 127.2, 125.7, 120.4. HRMS (DART, ESI+) m/z calcd for C44H29O [M+H]+: 557.2269, found: 557.2243.

Reference： [1]Kawasumi, Katsuaki; Mochida, Kenji; Segawa, Yasutomo; Itami, Kenichiro [Tetrahedron, 2013, vol. 69, # 22, p. 4371 - 4374]
[2]Current Patent Assignee: TOKAI NATIONAL HIGHER EDUCATION AND RESEARCH SYSTEM - EP2730554, 2014, A1 Location in patent: Paragraph 0306; 0307; 0308

48
[ 198-55-0 ]
[ 4755-77-5 ]
[ 1449412-40-1 ]

Yield	Reaction Conditions	Operation in experiment
94%	With aluminum (III) chloride In 1,2-dichloro-ethane at 20℃; for 2h; Inert atmosphere;	2.2.48 stir bar and flushed with argon. To this flask was added AlCl3 (15.0 mmol, 2.00 g, followed by anhydrous dichloroethane (150 mL). The solution was stirred at room temperature and ethyl 2-chloro-2-oxoacetate (12.0 mmol, 1.34 mL) was added, followed by perylene (10.0 mmol, 2.523 g). More anhydrous dichloroethane was added (50 mL) and the reaction was stirred at room temperature under argon for two hours. The reaction was quenched by the addition of water (100 mL) and aqueous 6N HCl (50 mL) with vigorous stirring. The layers were separated and the water layer extracted with DCM (3 X 25 mL). The organic layers were dried with 10 MgSO4, filtered, and evaporated to dryness. The product was purified by flash chromatography on silica gel (60% DCM/hexane (2 CV) 100% DCM (8 CV) 100% DCM). Fractions containing product were evaporated to dryness to give 3.323 g (94% yield). MS (APCI): calculated for C24H16O3 (M + H) = 353; found: 353.
79%	With zirconium(IV) chloride In dichloromethane at 0 - 25℃; for 16h;

Reference： [1]Current Patent Assignee: NITTO DENKO CORPORATION - WO2020/210761, 2020, A1 Location in patent: Page/Page column 135; 136
[2]Sarkar, Parantap; Durola, Fabien; Bock, Harald [Chemical Communications, 2013, vol. 49, # 68, p. 7552 - 7554]

49
[ 198-55-0 ]
[ 955121-20-7 ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 2 steps 1.1: N-Bromosuccinimide / tetrahydrofuran / 24 h / 20 °C / Inert atmosphere 2.1: n-butyllithium / hexane / 1 h / -78 °C / Inert atmosphere 2.2: 4 h / -78 - 20 °C / Inert atmosphere

Reference： [1]Kodama, Koichi; Kobayashi, Akinori; Hirose, Takuji [Tetrahedron Letters, 2013, vol. 54, # 40, p. 5514 - 5517]

50
[ 91-20-3 ]
[ 198-55-0 ]
benzo[4,5]indeno[1,2,3-cd]perylene [ No CAS ]
[ 49644-36-2 ]

Yield	Reaction Conditions	Operation in experiment
31%	Stage #1: PERYLENE With trifluorormethanesulfonic acid In 1,2-dichloro-ethane at 20℃; for 0.0833333h; Stage #2: With 2,3-dicyano-5,6-dichloro-p-benzoquinone In 1,2-dichloro-ethane for 0.0833333h; Inert atmosphere; Stage #3: naphthalene In 1,2-dichloro-ethane at 0 - 20℃; for 14h;	3 Working Example 3 Synthesis of Terrylene from Perylene Working Example 3Synthesis of Terrylene from PeryleneTo a solution of Perylene (1.00 g, 3.96 mmol) in dichloroethane (30 mL) at 0° C. was added triflic acid (0.7 ml, 7.93 mmol) and the mixture stirred for 5 minutes at room temperature. Then the mixture was treated with DDQ (1.8 g, 7.93 mmol, 1 equivalent per C-C bond formation) and stirred for 5 minutes under a nitrogen atmosphere. Naphthalene (0.53 g, 4.15 mmol) dissolved in dichloroethane (10 ml) was added slowly to the reaction mixture at 0° C. and the mixture was stirred for 2 hours at 0° C. before being warmed to room temperature. After stirring for 12 h at room temperature, the reaction was quenched with diisopropylethylamine and diluted with methanol (30 ml). The resultant precipitate was filtered and washed with methanol and dichloromethane to give 0.91 g of dark orange solid. The solid was then transferred to a thimble and extracted in a Soxhlet apparatus first with dichloromethane (50 ml) for 24 h and later with toluene (50 ml) for 2-3 days. The toluene extract was cooled to room temperature and centrifuged to give 0.46 g of dark violet solid. Yield 31%. This substance was characterized as primarily terrylene by its UV/VIS (in N-methylpyrrolidone as solvent) and MALDI mass spectra.

Reference： [1]Current Patent Assignee: UNIVERSITY OF NEW HAMPSHIRE - US2014/378727, 2014, A1 Location in patent: Paragraph 0023; 0024

51
[ 198-55-0 ]
[ 58601-32-4 ]
C₃₂H₂₀O₂ [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	With aluminum (III) chloride In 1,2-dichloro-ethane at 20℃; for 5h;	12.1 First Step: Friedel-Craft Acylation Reaction SYNTHESIS EXAMPLE 12 First Step: Friedel-Craft Acylation Reaction 15 g (0.0595 mol) of perylene, 13.12 g (0.0595 mol) of 6-methoxynaphthalene-2-carbonyl chloride, and 144.18 g of 1,2-dichloroethane were put into a flask to prepare a solution. Subsequently, 7.93 g (0.0595 mol) of aluminum chloride was slowly added to the solution, and the resultant was agitated at room temperature for 5 hours. When the reaction was complete, methanol was added thereto, and a precipitate obtained therefrom was filtered and dried.

Reference： [1]Current Patent Assignee: SAMSUNG C&T CORPORATION - US2015/274622, 2015, A1 Location in patent: Paragraph 0155-0156

52
[ 198-55-0 ]
[ 100-07-2 ]
C₂₈H₁₈O₂ [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	With aluminum (III) chloride In 1,2-dichloro-ethane at 20℃; for 12h;	8.1 First Step: Friedel-Craft Acylation Reaction SYNTHESIS EXAMPLE 8 First Step: Friedel-Craft Acylation Reaction 18.5 g (0.07330 mol) of perylene, 12.5 g (0.07330 mol) of 4-methoxybenzoylchloride, and 367 g of 1,2-dichloroethane were put into a flask to prepare a solution. 9.77 g (0.07330 mol) of aluminum chloride was slowly added to the solution, and the resultant was agitated at room temperature for 12 hours. When the reaction was complete, methanol was added thereto, and a precipitate obtained therefrom and filtered and dried, obtaining a compound.

Reference： [1]Current Patent Assignee: SAMSUNG C&T CORPORATION - US2015/274622, 2015, A1 Location in patent: Paragraph 0129-0130

53
[ 198-55-0 ]
[ 7415-79-4 ]

Yield	Reaction Conditions	Operation in experiment
91%	With aluminum (III) chloride; nitromethane In chlorobenzene at 40℃;	3-Acetylperylene (4). Perylene 3 (25.2 g, 100 mmol) was suspended in dry chlorobenzene (1.5 L) and heated with stirring until dissolved (at 40oC). To the resulting solution acetyl chloride(10.7 mL, 150 mmol) was added at once. Then anhydrous aluminium chloride (20.0 g, 150mmol) was dissolved in nitromethane (100 mL) and added dropwise to the reaction mixture. Theheating was removed and the reaction was vigorously stirred for 3 h, until almost completedis appearance of starting perylene (monitoring by TLC on silica gel eluted with toluene). The reaction mixture was poured onto aqueous HCl (40 mL of 36% HCl with 500 mL of water and ~200 g of cracked ice). The resulting suspension was filtered and the precipitate was washed withwater (5×200 mL). The solid was dried in vacuum over P2O5. The organic layer of the filtratewas separated, washed with water (3×1 L), dried over CaCl2 and evaporated in vacuum. Theresidue was combined with the dried solid and purified by flash chromatography on silica gel (10×40 cm). The unreacted traces of starting perylene were eluted with chlorobenzene and discarded. The column was washed with n-hexane (500 mL) and then eluted with CHCl3 to give pure 3-acetylperylene (26.9 g, 91%) as orange solid; mp 245-247oC (CHCl3), lit.1 mp 245.5-247.0oC. 1H NMR (CDCl3): δ = 8.72 (d, 1H, J 7.8, H2); 8.29-8.24 (m, 3H, H6, H7, H12); 8.19(d, 1H, J 7.8, H1); 7.96 (d, 1H, J 7.8, H4); 7.78 (d, 1H, J 7.8, H9); 7.76 (d, 1H, J 7.8, H10); 7.63(t, 1H, J 8.3, H5); 7.54 (t, 2H, J 7.8, H8, H11); 2.77 (s, 3H, CH3). 13C NMR (CDCl3): δ = 201.11(C=O); 135.62, 134.43, 134.06, 131.92, 131.11, 130.99, 130.20, 129.69, 129.28 (2C), 128.38,128.24, 128.12, 126.88, 126.60, 126.01, 121.85, 121.10, 120.82, 118.74 (perylene); 29.86 (CH3).

Reference： [1]Chistov, Alexey A.; Kutyakov, Sergey V.; Ustinov, Alexey V.; Aparin, Ilya O.; Glybin, Anton V.; Mikhura, Irina V.; Korshun, Vladimir A. [Tetrahedron Letters, 2016, vol. 57, # 9, p. 1003 - 1005]

54
[ 198-55-0 ]
[ 29261-33-4 ]
C₂₀H₁₂*C₁₂F₄N₄ [ No CAS ]

Reference： [1]Crystal Growth and Design,2016,vol. 16,p. 3019 - 3027

55
[ 198-55-0 ]
1,1-dichlorooxymethyl ether [ No CAS ]
[ 35438-63-2 ]

Yield	Reaction Conditions	Operation in experiment
60.3%	Stage #1: PERYLENE; 1,1-dichlorooxymethyl ether With tin(IV) chloride In 1,2-dichloro-ethane at 0℃; for 19h; Reflux; Stage #2: In water at 20℃; for 3h;

Reference： [1]Wang, Zhixuan; Pei, Xiaojing; Li, Na; Tang, Xinjing [Journal of Materials Chemistry B, 2016, vol. 4, # 24, p. 4330 - 4336]

56
[ 198-55-0 ]
[ 73183-34-3 ]
3,9-bis(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)perylene [ No CAS ]
3,10-bis(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)perylene [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
370 mg	Stage #1: PERYLENE With bromine In benzene at 35℃; for 1.16667h; Inert atmosphere; Stage #2: bis(pinacol)diborane With (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; potassium acetate In toluene at 80℃; Inert atmosphere;	3,9-dibromoperylene: Following a modified literature procedure, perylene (5.90 g, 23.4 mmol, 1 equiv) was dissolved in 900 mL benzene in a 2 L flask equipped with a base trap at 80 °C. The mixture was allowed to cool to 35 °C (note-some perylene precipitated out of solution) and Br2 (17.3 g, 109 mmol, 4.7 equiv) was added dropwise over 10 min and the reaction was stirred at 35 °C for 1 h then cooled to room temperature. The precipitate was filtered and recrystallized 4× in 5/3 aniline/toluene then washed with acetone affording an orange solid (2.1 g, 26%) 1H NMR (600 MHz, CDCl3) δ 8.24-8.21 (m, 2H), 8.12 (dd, J=8.4, 0.9 Hz, 2H), 8.03 (d, J=8.1 Hz, 2H), 7.78 (d, J=8.1 Hz, 2H), 7.59 (dd, J=8.4, 7.5 Hz, 2H). 13C NMR (151 MHz, CDCl3) δ 133.2, 131.1, 130.9, 130.8, 129.6, 127.9, 127.5, 123.1, 121.4, 121.1. HRMS (CI+) (m/z): calcd for C20H10Br2 407.9149; found 407.9156 IR (film, cm-1): 3047, 1931, 1846, 1777, 1599 characteristic 1H peaks of minor isomer 1H NMR (600 MHz, CDCl3) δ 8.26 (d, J=7.8 Hz, 2H), 7.98 (d, J=8.2 Hz, 2H). 4.1. 3,9-bis(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)perylene. 3,9-dibromoperylene (1.00 g, 2.44 mmol, 1 equiv), B2Pin2 (1.54 g, 6.06 mmol, 2.5 equiv), Pd(dppf)Cl2 (175 mg, 0.239 mmol, 0.1 equiv), and finely ground KOAc (1.41 g, 14.4 mmol, 6 equiv) were combined in a dry flask. The flask was then evacuated and backfilled with N2 3 times. 25 mL of toluene was added to the mixture and the flask was heated to 80 °C and allowed to stir overnight. The mixture was cooled to room temperature then filtered through a pad a Celite eluting with ethyl acetate. Solvent was removed in vacuo and the crude residue was purified via flash chromatography (5% EtOAc/Hexanes) affording a yellow solid (370 mg, 31%) 1H NMR (600 MHz, CDCl3) δ 8.67 (dd, J=8.4, 1.0 Hz, 2H), 8.25 (m, 2H), 8.18 (d, J=7.6 Hz, 2H), 8.06 (d, J=7.6 Hz, 2H), 7.53 (dd, J=8.4, 7.5 Hz, 2H), 1.42 (s, 24H). 13C NMR (151 MHz, CDCl3) δ 138.3, 136.3, 134.4, 131.0, 129.1, 128.4, 126.8, 120.8, 119.5, 83.7, 25.0. HRMS (ES+) (m/z): [M+Na]+ calcd for C32H34B2O4Na 527.2552 found 527.2568 IR (film, cm-1): 2974, 1588, 1506, 1370. 1H peaks of minor isomer 1H NMR (600 MHz, CDCl3) δ 8.64 (d, J=8.3 Hz, 2H), 8.22-8.20 (m, 4H).

Reference： [1]Jackson, Evan P.; Sisto, Thomas J.; Darzi, Evan R.; Jasti, Ramesh [Tetrahedron, 2016, vol. 72, # 26, p. 3754 - 3758]

57
[ 140-10-3 ]
[ 198-55-0 ]
(E)-1-(perylen-3-yl)-3-phenylprop-2-en-1-one [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
81%	With trifluorormethanesulfonic acid; trifluoroacetic anhydride In dichloromethane at 0℃; for 4h;

Reference： [1]Głodek, Marta; Makal, Anna; Kłys, Arkadiusz; Zakrzewski, Janusz; Plażuk, Damian [European Journal of Organic Chemistry, 2016, vol. 2016, # 24, p. 4215 - 4223]

58
[ 541-47-9 ]
[ 198-55-0 ]
3-methyl-1-(perylen-3-yl)but-2-en-1-one [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
84%	With trifluorormethanesulfonic acid; trifluoroacetic anhydride In dichloromethane at 0℃; for 4h;

Reference： [1]Głodek, Marta; Makal, Anna; Kłys, Arkadiusz; Zakrzewski, Janusz; Plażuk, Damian [European Journal of Organic Chemistry, 2016, vol. 2016, # 24, p. 4215 - 4223]

59
[ 198-55-0 ]
[ 66634-97-7 ]
cis-6-isopropyl-5-methyl-5,6-dihydro-4H-cyclopenta[b]perylen-4-one [ No CAS ]
C₂₇H₂₂O [ No CAS ]

Reference： [1]European Journal of Organic Chemistry,2016,vol. 2016,p. 4215 - 4223

60
[ 60065-21-6 ]
[ 198-55-0 ]
6-(tert-butyl)-5-methyl-5,6-dihydro-4H-cyclopenta[b]perylen-4-one [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
96%	With trifluorormethanesulfonic acid; trifluoroacetic anhydride In dichloromethane at 20℃; for 2h;

Reference： [1]Głodek, Marta; Makal, Anna; Kłys, Arkadiusz; Zakrzewski, Janusz; Plażuk, Damian [European Journal of Organic Chemistry, 2016, vol. 2016, # 24, p. 4215 - 4223]

61
[ 198-55-0 ]
copper(l) cyanide [ No CAS ]
[ 98-80-6 ]
C₃₄H₁₈N₂ [ No CAS ]
C₃₄H₁₈N₂ [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	Stage #1: PERYLENE With bromine; acetic acid at 40℃; for 4h; Stage #2: phenylboronic acid With tetrakis(triphenylphosphine) palladium⁽⁰⁾; potassium carbonate In water; toluene at 90℃; for 60h; Stage #3: copper(l) cyanide Further stages;	1.1; 1.2; 1.3; 1.4 Mixture of Compounds of the Formulae (1.4a) and (1.4b) A mixture of 14.9 g (59 mmol) of perylene, 400 ml of acetic acid and 18.9 g (236 mmol) of bromine was stirred at 40° C. for four hours. The excess bromine was subsequently destroyed by adding sodium thiosulfate solution. The precipitate was filtered off, washed with water and dried under reduced pressure. This gave 25.46 g (quant.) of the title compounds as a yellowish precipitate. 3,9-Diphenylperylene and 3,10-diphenylperylene A mixture of 1.23 g (3 mmol) of 3,9-dibromoperylene and 3,10-dibromoperylene from example 1.1, 30 ml of toluene, 1.46 g (12 mmol) of phenylboronic acid, 2.49 g (18 mmol) of potassium carbonate, 8 ml of water, 0.24 g (0.2 mmol) of tetrakistriphenylphosphinepalladium was heated to 90° C. for 60 hours. After the reaction mixture had been cooled, it was diluted with toluene, the phases were separated and the toluene phase was purified by means of column filtration with silica gel. This gave 1.1 g (92%) of the title compound as a yellow solid. Rf (petroleum ether:toluene 5:1)=0.31 , at least two of the R1, R2, R3, R4, R5, R6, R7 and R8 substituents are bromine, and the other R1, R2, R3, R4, R5, R6, R7 and R8 substituents are hydrogen. To a mixture of 202 mg (0.5 mmol) of 3,9-diphenylperylene and 3,10-diphenylperylene from example 1.2 and 25 ml of chlorobenzene were added 5 ml of water, 10 ml of chlorobenzene and 800 mg (10 mmol) of bromine, and the mixture was heated at reflux for 22 hours. The reaction mixture was cooled. Thereafter, 200 ml of dilute sodium thiosutfate solution were added at room temperature, the mixture was admixed with ethyl acetate, and the phases were separated and concentrated to obtain the title compounds with an Rf (petroleum ether:toluene 5:1)=0.61. 280 mg (0.5 mmol) of the mixture obtained in 1.3, 896 mg (10 mmol) of copper cyanide and 30 ml of NMP (N-methylpyrrolidone) were stirred at 100° C. for 6 h and at 150° C. for a further 16 h. After cooling to room temperature, the mixture was precipitated with dilute HCl, and the precipitate was filtered off with suction, washed with water and dried at 60° C. under reduced pressure. The residue was chromatographed on silica gel (eluent:toluene:ethyl acetate 100:1). This gave 17 mg of the title compounds. Absorption: λmax (CH2Cl2): 497 nm; Emission: λmax=(CH2Cl2): 563 nm

Reference： [1]Current Patent Assignee: BASF SE - US2017/183295, 2017, A1 Location in patent: Paragraph 0377- 0389

62
[ 198-55-0 ]
[ 98-80-6 ]
3,9-diphenylperylene [ No CAS ]
[ 143076-97-5 ]

Yield	Reaction Conditions	Operation in experiment
	Stage #1: PERYLENE With bromine; acetic acid at 40℃; for 4h; Stage #2: phenylboronic acid With tetrakis(triphenylphosphine) palladium⁽⁰⁾; potassium carbonate In water; toluene at 90℃; for 60h; Overall yield = 92 %; Overall yield = 1.1 g;	1.1; 1.2 3,9-diphenylperylene and 3,10-diphenylperylene A mixture of 14.9 g (59 mmol) of perylene, 400 ml of acetic acid and 18.9 g (236 mmol) of bromine was stirred at 40° C. for four hours. The excess bromine was subsequently destroyed by adding sodium thiosulfate solution. The precipitate was filtered off, washed with water and dried under reduced pressure. This gave 25.46 g (quant.) of the title compounds as a yellowish precipitate. 3,9-Diphenylperylene and 3,10-diphenylperylene A mixture of 1.23 g (3 mmol) of 3,9-dibromoperylene and 3,10-dibromoperylene from example 1.1, 30 ml of toluene, 1.46 g (12 mmol) of phenylboronic acid, 2.49 g (18 mmol) of potassium carbonate, 8 ml of water, 0.24 g (0.2 mmol) of tetrakistriphenylphosphinepalladium was heated to 90° C. for 60 hours. After the reaction mixture had been cooled, it was diluted with toluene, the phases were separated and the toluene phase was purified by means of column filtration with silica gel. This gave 1.1 g (92%) of the title compound as a yellow solid. Rf (petroleum ether:toluene 5:1)=0.31.

Reference： [1]Current Patent Assignee: BASF SE - US2017/183295, 2017, A1 Location in patent: Paragraph 0381; 0382

63
[ 198-55-0 ]
[ 98-80-6 ]
C₃₂H₁₈Br₂ [ No CAS ]
C₃₂H₁₈Br₂ [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	Stage #1: PERYLENE With bromine; acetic acid at 40℃; for 4h; Stage #2: phenylboronic acid With tetrakis(triphenylphosphine) palladium⁽⁰⁾; potassium carbonate In water; toluene at 90℃; for 60h; Stage #3: With bromine In water; chlorobenzene for 22h; Reflux;	1.1; 1.2; 1.3 Mixture of Compounds of the Formulae (1.3a) and (1.3b) A mixture of 14.9 g (59 mmol) of perylene, 400 ml of acetic acid and 18.9 g (236 mmol) of bromine was stirred at 40° C. for four hours. The excess bromine was subsequently destroyed by adding sodium thiosulfate solution. The precipitate was filtered off, washed with water and dried under reduced pressure. This gave 25.46 g (quant.) of the title compounds as a yellowish precipitate. 3,9-Diphenylperylene and 3,10-diphenylperylene A mixture of 1.23 g (3 mmol) of 3,9-dibromoperylene and 3,10-dibromoperylene from example 1.1, 30 ml of toluene, 1.46 g (12 mmol) of phenylboronic acid, 2.49 g (18 mmol) of potassium carbonate, 8 ml of water, 0.24 g (0.2 mmol) of tetrakistriphenylphosphinepalladium was heated to 90° C. for 60 hours. After the reaction mixture had been cooled, it was diluted with toluene, the phases were separated and the toluene phase was purified by means of column filtration with silica gel. This gave 1.1 g (92%) of the title compound as a yellow solid. Rf (petroleum ether:toluene 5:1)=0.31 , at least two of the R1, R2, R3, R4, R5, R6, R7 and R8 substituents are bromine, and the other R1, R2, R3, R4, R5, R6, R7 and R8 substituents are hydrogen. To a mixture of 202 mg (0.5 mmol) of 3,9-diphenylperylene and 3,10-diphenylperylene from example 1.2 and 25 ml of chlorobenzene were added 5 ml of water, 10 ml of chlorobenzene and 800 mg (10 mmol) of bromine, and the mixture was heated at reflux for 22 hours. The reaction mixture was cooled. Thereafter, 200 ml of dilute sodium thiosutfate solution were added at room temperature, the mixture was admixed with ethyl acetate, and the phases were separated and concentrated to obtain the title compounds with an Rf (petroleum ether:toluene 5:1)=0.61.

Reference： [1]Current Patent Assignee: BASF SE - US2017/183295, 2017, A1 Location in patent: Paragraph 0381; 0382; 0383; 0384; 0385; 0386

64
[ 198-55-0 ]
[ 16419-60-6 ]
3,9-bis(o-tolyl)perylene [ No CAS ]
3,10-bis(o-tolyl)perylene [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	Stage #1: PERYLENE With bromine; acetic acid at 40℃; for 4h; Stage #2: 2-Methylphenylboronic acid With tetrakis(triphenylphosphine) palladium⁽⁰⁾; potassium carbonate In water; toluene at 90℃; for 34h; Overall yield = 5.54 g;	1.1; 2.1 3,9-bis(o-tolyl)perylene and 3,10-bis(o-tolyl)perylene 3,9-Dibromoperylene and 3,10-dibromoperylene A mixture of 14.9 g (59 mmol) of perylene, 400 ml of acetic acid and 18.9 g (236 mmol) of bromine was stirred at 40° C. for four hours. The excess bromine was subsequently destroyed by adding sodium thiosulfate solution. The precipitate was filtered off, washed with water and dried under reduced pressure. This gave 25.46 g (quant.) of the title compounds as a yellowish precipitate. A mixture of 4.10 g (10 mmol) of 3,9-dibromoperylene and 3,10-dibromoperylene from example 1.1, 100 ml of toluene, 5.44 g (40 mmol) of 2-methylphenylboronic acid, 8.3 g (60 mmol) of potassium carbonate, 15 ml of water, 2.32 g (2 mmol) of tetrakistriphenylphosphinepalladium was heated to 90° C. for 34 hours. After the reaction mixture had been cooled, it was diluted with toluene, the phases were separated and the toluene phase was purified by means of column filtration with silica gel. This gave 5.54 g of the title compound as a yellow solid, Rf (petroleum ether:toluene 5:1)=0.33, and a by-product with Rf (petroleum ether:toluene 5:1)=0.09.

Reference： [1]Current Patent Assignee: BASF SE - US2017/183295, 2017, A1 Location in patent: Paragraph 0381; 0396

65
[ 67-56-1 ]
[ 198-55-0 ]
[ 24471-30-5 ]

Yield	Reaction Conditions	Operation in experiment
49%	Stage #1: PERYLENE With trichlorophosphate In N,N-dimethyl-formamide; 1,2-dichloro-benzene at 100℃; for 16h; Stage #2: methanol With sodium tetrahydroborate; sodium acetate; sodium hydroxide In tetrahydrofuran at 20℃; for 4h;	Synthesis of perylen-3-ylmethanol To a suspension of perylene (1.01 g; 4.00 mmol) ino-dichlorobenzene (2.0 mL), DMF (1.90 g; 26.0 mmol) and phosphoryl chloride (0.72 mL; 8.0mmol) were added. The reaction mixture was stirred at 100 °C for 16 h, and then neutralized by adding 5M sodium hydroxide (2.0 mL). The resulting mixture was poured into 5% sodiumacetate (200 mL), and filtered with suction to obtain a brown solid. The solid was dissolved inTHF (226 mL). To the solution, methanol (17 mL) and sodium borohydride (252 mg; 6.63mmol) were added successively. The mixture was stirred at room temperature for 4 h, and thenconcentrated under reduced pressure. The resulting residue was chromatographed on silica gel(eluent: CHCl3) to obtain perylen-3-ylmethanol (553 mg; 1.97 mmol; 49 %)

Reference： [1]Okamoto, Shusuke; Tsujioka, Hiroki; Sudo, Atsushi [Chemistry Letters, 2018, vol. 47, # 3, p. 369 - 372]

66
[ 198-55-0 ]
[ 191-24-2 ]

Reference： [1]Patent: KR2018/43221,2018,A

67
[ 198-55-0 ]
[ 2032-35-1 ]
1-peryleneacetaldehyde diethyl acetal [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	Stage #1: PERYLENE With sodium In tetrahydrofuran at 30℃; for 3h; Inert atmosphere; Stage #2: Bromoacetaldehyde diethyl acetal With iodine; sodium thiosulfate at -60℃; Inert atmosphere;	3A-1 3A-1. Preparation of 1- (2,2-diethoxyethyl) perylene (2) Perylene (4.00 g, 15.9 mmol), tetrahydrofuran (THF) (250 mL), and sodium (0.80 g) were added to the reactor substituted with argon.Was added and the mixture was sonicated at 30 ° C for 3 hours, then cooled to -60 ° C and bromoacetaldehyde diethyl acetal (3.13 g, 15.9 mmol) was added together with stirring. Then, iodine (6.05 g, 23.8 mmol) was added and sodium thiosulfate (100 ml) was added to obtain 1- (2,2-diethoxyethyl) perylene (2).
	Stage #1: PERYLENE; Bromoacetaldehyde diethyl acetal With sodium In tetrahydrofuran at 30℃; for 3h; Inert atmosphere; Sonication; Stage #2: Bromoacetaldehyde diethyl acetal With iodine; sodium thiosulfate In tetrahydrofuran at -60℃;	3A-1 3A-1. Preparation of 1-(2,2-diethoxyethyl)perylene (2) Perylene (4.00 g, 15.9 mmol), tetrahydrofuran (THF) (250 ml) and sodium (0.80 g) were placed in a reactor substituted with argon and ultrasonicated at 30° C. for 3 hours, cooled to -60° C., and bromoacetaldehyde diethyl acetal (3.13 g, 15.9 mmol) was added with stirring. Then, iodine (6.05 g, 23.8 mmol) was added and sodium thiosulfate (100 ml) was added to obtain 1-(2,2-diethoxyethyl) perylene (2).10358] 1 -(2,2-diethoxyethyl) perylene: ‘H NMR (600MHz, CDC13) ö 7.91 (s, 3H), 7.39 (s, 6H), 7.26 (s, 1H), 7.17(s, 1H), 4.58 (t, 1H), 3.50 (m, 4H), 3.28 (d, 2H), 1.10 (t, 6H)

Reference： [1]Current Patent Assignee: HANYANG UNIVERSITY - KR2018/43221, 2018, A Location in patent: Paragraph 0321; 0322; 0323
[2]Current Patent Assignee: HANYANG UNIVERSITY - US2019/31586, 2019, A1 Location in patent: Paragraph 0356; 0357; 0358

68
[ 198-55-0 ]
C₁₇H₁₄O₂ [ No CAS ]
C₃₇H₂₄O₂ [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
54%	In chloroform Inert atmosphere; Sealed tube; Heating;	General protocol for performing domino HDDA reactions General procedure: The headspace of a threaded vial containing the polyyne precursor in an organic solvent (initial concentration typically 0.02 M, often in ethanol-free CHCl3) and the indicated number of equivalents of the trapping reactant was flushed with nitrogen immediately before being sealed with a teflon-lined cap. The reaction solution washeated at 80-130 °C for ~5-16 h. The product(s) was (were) separated/purified bysilica gel chromatography.

Reference： [1]Xiao, Xiao; Hoye, Thomas R. [Nature Chemistry, 2018, vol. 10, # 8, p. 838 - 844]

69
[ 198-55-0 ]
[ 1066-54-2 ]
[ 132196-66-8 ]

Yield	Reaction Conditions	Operation in experiment
28.9 mg	Stage #1: PERYLENE With N-Bromosuccinimide In N,N-dimethyl-formamide for 24h; Stage #2: trimethylsilylacetylene With copper(l) iodide; tetrakis(triphenylphosphine) palladium⁽⁰⁾; triethylamine In N,N-dimethyl-formamide at 90℃; for 24h; Inert atmosphere; Stage #3: With tetrabutyl ammonium fluoride In tetrahydrofuran at 20℃; for 4h;	4.1 (1) Synthesis of Compound II-2 To a round bottom flask was added hydrazine (1.02 g) and N,N-dimethylformamide (180.0 mL), and stirred at room temperature until completely dissolved. Then, a solution of NBS (712.0 mg) in N,N-dimethylformamide (20.0 mL) was slowly added dropwise, and the mixture was stirred for 24 h under test conditions. After completion of the reaction, an appropriate amount of water was added to the reaction mixture to precipitate a solid, and the mixture was filtered to give a solid yellow solid. The obtained golden yellow solid (337.0 mg), trimethylethynyl silicon (1 mL), cuprous iodide (11..0), tetrakistriphenylphosphine palladium (40.0 mg), triethylamine (40.0 mL) N,N-dimethylformamide (10.0 mL) was added to a round bottom flask, which was distilled to a nitrogen atmosphere and refluxed at 90 ° C for 24 h. After the reaction is completed, the pH is adjusted to neutral with an appropriate amount of dilute hydrochloric acid. Then, 25 mL of chloroform was added to the reaction mixture, followed by washing with a saturated aqueous solution of ammonium chloride (1×50 mL), and the aqueous phase was extracted with chloroform (2×25 mL). The solvent was evaporated to dryness, and the obtained crude product was purified by silica gel column chromatography (chloroform). The yellow solid obtained in this step (100.0 mg), tetrabutylammonium fluoride (0.3 mL) was added to a tetrahydrofuran solution (11 mL)Stir at room temperature for 4 h.After the reaction is completed, it is evaporated to dryness by a rotary evaporator.The obtained crude product was purified by silica gel column chromatography (chloroform).It was then recrystallized from hexane and chloroform to give the product 28.9mg.

Reference： [1]Current Patent Assignee: TIANJIN UNIVERSITY - CN107641141, 2018, A Location in patent: Paragraph 0093; 0095; 0096

70
[ 1953-99-7 ]
[ 198-55-0 ]
C₂₀H₁₂*C₈Cl₄N₂ [ No CAS ]

Reference： [1]Crystal Growth and Design,2019,vol. 19,p. 291 - 299

71
[ 18162-84-0 ]
[ 198-55-0 ]
C₃₀H₃₄Si [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
12.2 g	Stage #1: PERYLENE With N-Bromosuccinimide In N,N-dimethyl-formamide at 20℃; Stage #2: With n-butyllithium In tetrahydrofuran; hexane at -80℃; for 1h; Stage #3: dimethyl-n-octylchlorosilane In tetrahydrofuran; hexane at 20℃;	Mixture of Brominated Perylenes To a suspension of perylene (25.0 g, 100 mmol, 1 equiv) in DMF (1000 mL) a solution of NBS (23.0 g, 130 mmol, 1.3 equiv) in DMF (400 mL) was added via a syringe pump for 10 h. The obtained mixture was stirred overnight at r.t. and poured into water (2000 mL). The precipitate obtained was filtered off on a glass frit (G3) and was subsequently washed with EtOH (100 mL), Et2O (100 mL), and finally with CH2Cl2 (3 × 100 mL). The obtained solid was dried under vacuum, yielding a mixture of brominated perylenes; yield: 29.8 g (90%); 89% of 3-bromoperylene by GC-MS; yellow solid. Bromoperylene (PerBr) via OctMe2SiPer; Method A. OctMe2SiPer. To a suspension of the brominated perylenes (12.4 g, 36.7 mmol, 1 equiv) in anhyd THF (500 mL), 2.5 M nBuLi in hexanes (17.6 mL, 44.1 mmol, 1.2 equiv) was added dropwise at -80 °C. The reaction mixture was stirred for 1 h at this temperature, and then dimethyl(n-octyl)silylchloride (9.87 g, 47.7 mmol, 1.3 equiv) was added and the obtained suspension was stirred overnight at r.t. Thereafter the resulting mixture was carefully poured into water (1000 mL) and the obtained two-phase mixture was extracted with CH2Cl2 (3 × 200 mL). The combined organic extract was dried over Na2SO4 and then evaporated to dryness. The residue was purified by flash chromatography (silica gel, n-hexane/CH2Cl2, 4:1). This procedure gave OctMe2SiPer; yield: 12.2 g (78%); yellow solid; mp 100.5-100.9 °C. IR (neat): 3048w, 2955w, 2919m, 2851w, 1590w, 1457w, 1383w, 1246m, 1063w, 1002m, 846m, 809s, 763s, 682m cm-1. 1H NMR (400 MHz, CDCl3): δ = 8.15-8.19 (m, 3 H), 8.12 (d, J = 7.5 Hz, 1H), 7.95 (d, J = 8.3 Hz, 1 H), 7.64-7.69 (m, 3 H), 7.48-7.52 (m, 1 H), 7.45 (t, J = 7.8 Hz, 2 H), 1.22-1.42 (m, 12 H), 0.99-1.03 (m, 2 H), 0.88 (t, J = 6.9 Hz, 3 H), 0.50 (s, 6 H). 13C NMR (100 MHz, CDCl3): δ = 138.5, 137.5, 134.5, 134.1, 132.2, 131.8, 131.4, 131.2, 128.7, 128.5, 127.9, 127.6, 126.51, 126.49, 126.0, 120.3, 120.1, 119.9, 119.3, 33.6, 31.9, 29.3, 24.1, 22.7, 16.5, 14.1, -1.5. HRMS: m/z calcd for C30H34Si: 422.2430; found: 422.2448.

72
[ 75-77-4 ]
[ 198-55-0 ]
C₂₃H₂₀Si [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
0.78 g	Stage #1: PERYLENE With N-Bromosuccinimide In N,N-dimethyl-formamide at 20℃; Stage #2: With n-butyllithium In tetrahydrofuran; hexane at -80℃; for 1h; Stage #3: chloro-trimethyl-silane In tetrahydrofuran; hexane at 20℃;	Mixture of Brominated Perylenes To a suspension of perylene (25.0 g, 100 mmol, 1 equiv) in DMF (1000 mL) a solution of NBS (23.0 g, 130 mmol, 1.3 equiv) in DMF (400 mL) was added via a syringe pump for 10 h. The obtained mixture was stirred overnight at r.t. and poured into water (2000 mL). The precipitate obtained was filtered off on a glass frit (G3) and was subsequently washed with EtOH (100 mL), Et2O (100 mL), and finally with CH2Cl2 (3 × 100 mL). The obtained solid was dried under vacuum, yielding a mixture of brominated perylenes; yield: 29.8 g (90%); 89% of 3-bromoperylene by GC-MS; yellow solid. Bromoperylene (PerBr) via TMSPer; Method B. TMSPer. To a suspension of the brominated perylenes (1.36 g, 4.43 mmol, 1 equiv) in anhyd THF (50 mL), 2.5 M nBuLi in hexanes (1.95 mL, 4.87 mmol, 1.1 equiv) was added dropwise at -80 °C. The reaction mixture was stirred for 1 h at this temperature; then TMSCl (0.62 mL, 4.87 mmol, 1.1 equiv) was added, and the obtained suspension was stirred overnight at r.t. Thereafter the resulting mixture was carefully poured into water (100 mL) and the obtained two-phase mixture was extracted with CH2Cl2 (3 × 50 mL). The combined organic extract was dried over Na2SO4 and then evaporated to dryness. The residue was purified by flash chromatography (silica gel, n-hexane/THF, 4:1). This procedure gave TMSPer; yield: 0.78 g (54%); yellow solid; mp 181.2-181.7 °C. IR (neat): 3047w, 2952w, 2895w, 1497w, 1247w, 1062w, 1002w, 857m, 824s, 808s, 763s, 666m cm-1. 1H NMR (400 MHz, CDCl3): δ = 8.15-8.19 (m, 3 H), 8.11 (d, J = 7.4 Hz, 1H), 7.95 (d, J = 8.2 Hz, 1 H), 7.65-7.69 (m, 3 H), 7.43-7.52 (m, 3 H),0.51 (s, 9 H). 13C NMR (100 MHz, CDCl3): δ = 138.4, 138.1, 134.6, 133.9, 132.3, 131.9, 131.4, 131.2, 128.7, 128.6, 128.2, 128.0, 127.7, 128.6 (overlapping resonances), 126.1, 120.4, 120.2, 120.0, 119.4, 0.2. HRMS: m/z calcd for C23H20Si: 324.1334; found: 324.1346.

73
[ 198-55-0 ]
3,7,10-tris(trimethylsilyl)-2,6,11-tris(trifluoromethanesulfonate)triphenylene [ No CAS ]
C₇₈H₃₆ [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
66%	With cesium fluoride In dichloromethane; acetonitrile at 90℃; for 50h; Sealed tube; Green chemistry;	2 Synthetic method steps: 3,7,10-tris(trimethylsilyl)-2,6,11-tris(trifluoromethanesulfonate) triphenylene(100 mg, 0.113 mmol), compound 7 (85 mg, 0.339 mmol) and anhydrous CsF (52 mg, 0.339 mmol) were added to a 40 mL screw bottle.Then add 8 mL of acetonitrile and 4 mL of dichloromethane, bubble for 3 min, and tighten the stopper.After heating at 90 ° C for 50 h, the solution after the reaction was filtered, washed with water (2 x 5 mL),Wash with methanol (2x5mL), wash with ether (2x5 mL) and wash with chloroform (2x5mL).After drying in a vacuum drying oven, 62 mg of an off-white solid was obtained, yield: 66%.

Reference： [1]Current Patent Assignee: HARBIN INSTITUTE OF TECHNOLOGY - CN110105160, 2019, A Location in patent: Paragraph 0064; 0083-0084

74
[ 198-55-0 ]
[ 79865-03-5 ]
3-(perfluorobenzyl)perylene [ No CAS ]
1-(perfluorobenzyl)perylene [ No CAS ]
3,10-bis(perfluorobenzyl)perylene [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
1: 16% 2: 10.8%	With copper In dimethyl sulfoxide at 145℃; for 48h; Inert atmosphere; Schlenk technique;	Reaction 1a (schlenk tube without stir bar) A Schlenk tube equipped with a No.9 O-ring sidearm was charged with PERY (10 mg, 40 μmol) and Cu powder (15 mg, 240 μmol, 6 equiv) and subsequently dried overnight in a 120 °C oven. The reaction tube was taken from the oven and attached to a schlenk line to cool under dynamic vacuum. BnFI (13.4 μL, 80 μmol, 2 equiv) and DMSO (5.0 mL) were added via syringe with the tube open under a flow of N2. The reaction tube was degassed by using the freeze-pump-thaw (FPT) technique three times. The reaction flask was closed under vacuum and allowed to warm to room temperature before placing in a heated oil bath (145±5°C) for 24 hours. Note: the reaction should be refluxing shortly after placing the flask in the oil bath due to the reduced pressure. After 24 hours, the flask was cooled to room temperature and opened under a positive pressure of N2 to add more BnFI (13.4 μL, 80 μmol, 2 equiv) to the reaction, for a total of 4 equiv. of BnFI added. This was FPTx3 as before and placed back into the heated oil bath (145±5°C) for an additional 24 hours. Note that the reaction does not reflux as vigorously the second time it is placed in the oil bath compared to the first. Upon completion (48 h total), the reaction was cooled to room temperature and the contents poured into a separatory funnel containing dd-H2O (20 mL). The mixture was extracted with diethyl ether (3x20 mL); the organic layers were combined and washed with dd-H2O (3x20 mL), NaCl brine (20 mL), and dried over MgSO4. The solvent was removed by rotary evaporation and the products were separated by HPLC. PERY-1-1. Isolated yield of 3.0 mg (reaction 1a) (16 % yield); 1H NMR (400 MHz, CHLOROFORM-d) δ ppm 8.19 - 8.29 (m, 4 H), 7.93 (d, J=8.2 Hz, 1 H), 7.74 (d, J=8.2 Hz, 2 H), 7.77 (d, J=8.2 Hz, 1 H), 7.49 - 7.58 (m, 3 H). 19F NMR (376 MHz, CHLOROFORM-d) δ ppm -86.28 (t, J=23.2 Hz, 2 F), -141.51- -141.22 (m, 2 F), -152.92 (t, J=21.8 Hz, 1 F), -163.40 - -163.18 (m, 2 F) PERY-1-2. 1H NMR (400 MHz, CHLOROFORM-d) δ ppm 8.25 (d, J=7.4 Hz, 2 H), 8.02 (d, J=8.6 Hz, 1 H), 7.97 (d, J=7.0 Hz, 1 H), 7.86 (d, J=9.0 Hz, 1 H), 7.82 (d, J=8.2 Hz, 1 H), 7.76 (d, J=8.2 Hz, 1 H), 7.70 (d, J=7.8 Hz, 1 H), 7.66 (t, J=7.4 Hz, 1 H), 7.58 (t, J=7.8 Hz, 1 H), 7.40 (t, J=7.8 Hz, 1 H). 19F NMR (376 MHz, CHLOROFORM-d) δ ppm -72.85 (t, J=23.2 Hz, 2 F), -141.18 (q, J=21.8 Hz, 2 F), -153.95 (t, J=20.4 Hz, 1 F), -164.64 (tsxt, J=16.4, 16.4, 5.5, 5.5, 5.5, 5.5, 5.5 Hz, 2 F) PERY-2-1. Isolated yield of 2.9 mg (reaction 1a) and 11.6 mg (reaction 1b) (10.8 and 8.5 % yield, respectively); 1H NMR (400MHz, CHLOROFORM-d) δ = 8.29 (d, J = 7.8 Hz, 4 H), 7.99 (d, J = 8.6 Hz, 2 H), 7.84 (d, J = 7.8 Hz, 2 H), 7.58 (t, J = 8.0 Hz, 2 H). 19F NMR (376 MHz, CHLOROFORM-d) δ ppm -86.31 (t, J=23.2 Hz, 4 F), -141.42 (td, J=23.2, 19.1 Hz, 4 F), -152.63 (t, J=21.8 Hz, 2 F), -163.27 - -163.05 (m, 4 F).

Reference： [1]Brook, Colin P.; DeWeerd, Nicholas; Strauss, Steven H.; Boltalina, Olga V. [Journal of Fluorine Chemistry, 2020, vol. 231]

75
[ 198-55-0 ]
[ 1313497-83-4 ]
C₄₂H₅₈Au₂I₂N₄ [ No CAS ]
C₂₀H₁₂*C₁₃₂H₁₆₂Au₄N₁₀ [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
91%	Stage #1: 3,6‐di‐tert‐butyl‐1,8‐diethynylcarbazole With sodium hydroxide In methanol at 80℃; for 1h; Stage #2: PERYLENE; C₄₂H₅₈Au₂I₂N₄ In methanol at 80℃; for 4h;

Reference： [1]Ibáñez, Susana; Peris, Eduardo [Angewandte Chemie - International Edition, 2020, vol. 59, # 17, p. 6860 - 6865][Angew. Chem., 2020, vol. 132, p. 6927 - 6932,6]

76
[ 507-20-0 ]
[ 198-55-0 ]
[ 108318-07-6 ]

Yield	Reaction Conditions	Operation in experiment
	With aluminum (III) chloride In 1,2-dichloro-benzene at 0 - 20℃;	2.2.4 Compound 4.1: 2.0 g of perylene (7.94 mmol) was added to 100 mL o-dichlorobenzene. The solution was stirred at 70 °C for 20 min until the perylene was fully dissolved. The solution was then cooled to 0 °C and 1.05 g of anhydrous AlCl3 (7.94 mmol) was added. Next, 11 mL of tert-butylchloride was slowly added to the solution. The resulted mixture was warmed up to room temperature and stirred overnight. The whole was poured into dichloromethane (400 mL), washed with water, brine, and dried over Na2SO4, concentrated to 100 mL and passed through a silica column with hexanes/dichloromethane (1:1 v/v) used as the eluents. 15 The major fractions were collected and concentrated to 100 mL.

Reference： [1]Current Patent Assignee: NITTO DENKO CORPORATION - WO2020/210761, 2020, A1 Location in patent: Page/Page column 58

77
[ 507-20-0 ]
[ 198-55-0 ]
[ 369612-06-6 ]

Yield	Reaction Conditions	Operation in experiment
52%	With aluminum (III) chloride In 1,2-dichloro-benzene at 0 - 20℃; for 24h; Inert atmosphere;	2.2.10; 2.2.34 Compound 10.1 (2,5-di-tert-butylperylene): Under protection of Nitrogen atmosphere, 5 g of perylene (19.81 mmol) was dissolved in 300 ml ortho-dichlorobenzene anhydrous in a three neck round bottle flask. The resulting yellow solution was cooled to 0o C.2.64 g of AlCl3 (19.81 mmol) was added in small portions via a powder dispensing funnel over 45 minutes following by dropwise addition of 50 mL of tert-butylchloride (458 mmol). The resulting green color solution was stirred 24 hrs. at room temperature. The reaction mixture was poured into 100 mL of ice- water. The organic layer was separated, concentrated to dryness using a rotary evaporator with its water bath set at 70o C. The residue was re-dispersed into 450 mL of hot 0 hexanes. The yellow solution was cooled and stood at room temperature overnight. The insoluble material was filtered and detected by LCMS as tetra butyl analog (M+H= 477), the filtrate was a mixture of di and tri t-butyl perylene which was loaded onto silica gel column. Chromatography was run with Hexanes: EtOAc (9:1) to gain 3.75 g pale yellow color solid product of 2,5-di-tert-butylperylene, yield 52%. LCMS (APCI+) calculated for C28H29 (M+H) 25 =365; found 365.1H NMR (400 MHz, Chloroform-d) d 8.30- 8.21 (m, 4H), 7.72- 7.63 (m, 4H), 7.50 (t, J = 7.8 Hz, 2H), 1.50 (s, 18H).
52%	Stage #1: PERYLENE With aluminum (III) chloride In 1,2-dichloro-benzene at 0℃; for 0.75h; Inert atmosphere; Stage #2: tertiary butyl chloride In 1,2-dichloro-benzene at 20℃; for 24h; Inert atmosphere;	Compound 10.1 (2,5-di-tert-butylperylene): Under protection of nitrogen atmosphere, 5 g of perylene (19.81 mmol) was dissolved in 300 ml ortho-dichlorobenzene anhydrous in a three neck round bottle flask. The resulting yellow solution was cooled to 0 °C. 2.64 g of AICI3 (19.81 mmol) was added in small portions via a powder dispensing funnel over 45 minutes following by dropwise addition of 50 mL of tert- butylchloride (458 mmol). The resulting green color solution was stirred 24 hrs. at room temperature. The reaction mixture was poured into 100 mL of ice- water. The organic layer was separated, concentrated to dryness with a rotavapor with its water bath was set at 70 °C. The residue was re-dispersed into 450 mL of hot hexanes. The yellow solution was cooled and stood at room temperature overnight. The insoluble material was filtered and detected by LCMS as the tetra-tert-butyl analog (M+H= 477), while the filtrate was a mixture of di- and tri- tert-butyl perylene which was loaded onto silica gel column. Chromatography was run with Hexanes: EtOAc (9:1) to gain 3.75 g pale yellow color solid product of compound 10.1, 2,5-di- tert-butylperylene, yield 52%. LCMS (APCI+) calculated for C28H29 (M+H) =365; found 365. 1H NMR (400 MHz, Chloroform-d) d 8.30 - 8.21 (m, 4H), 7.72 - 7.63 (m, 4H), 7.50 (t, J = 7.8 Hz, 2H), 1.50 (s, 18H).

Reference： [1]Current Patent Assignee: NITTO DENKO CORPORATION - WO2020/210761, 2020, A1 Location in patent: Page/Page column 67; 106; 107
[2]Current Patent Assignee: NITTO DENKO CORPORATION - WO2021/202536, 2021, A1 Location in patent: Page/Page column 21-22

78
[ 1501-26-4 ]
[ 198-55-0 ]
methyl 5-oxo-5-(perylen-3-yl)pentanoate [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
35%	Stage #1: methyl 4-(chlorocarbonyl)butyrate With aluminum (III) chloride In dichloromethane at 0℃; for 1h; Inert atmosphere; Stage #2: PERYLENE In dichloromethane at 0 - 45℃;	2.2.40 nec roun o ome flask was charged with a stir bar and flushed thoroughly with argon. AlCl3 (34.7 mmol, 4.624 g) was added to the flask, followed by anhydrous dichloromethane (600 mL). The reaction mixture was cooled to 0 °C with an ice-water bath and methyl 5-chloro-5-oxopentanoate (30.4 mmol, 5.00 g) was added via syringe with stirring under argon. This mixture was stirred 15 at 0 °C for one hour, then perylene (28.9 mmol, 7.300 g) was added with stirring. The cooling bath was removed, and the reaction mixture was stirred at room temperature for two hours. The flask was fitted with a finned air condenser and heated in a heating block set at 45 °C with stirring overnight under argon. The reaction mixture was cooled to room temperature and quenched with the addition of crushed ice (600 mL, loosely packed). To this mixture was added aqueous 6N HCl (100 mL). Stirring was continued until all ice had melted. The layers were separated, and the aqueous layer was extracted with DCM (2 X 200 mL). The combined organic layers were dried over MgSO4, filtered, and concentrated in vacuo. The crude reaction was purified by flash chromatography on silica gel (100% DCM (3 CV) 5% EtOAc/DCM (10 CV)). The fractions containing product were collected and concentrated in vacuo to give 3.810 g, 35% yield. MS (APCI): calculated for C26H20O3 (M + H) = 381; found: 381.
35%	Stage #1: methyl 4-(chlorocarbonyl)butyrate With aluminum (III) chloride In dichloromethane at 0℃; for 1h; Inert atmosphere; Stage #2: PERYLENE In dichloromethane at 20 - 45℃; Inert atmosphere;	2.1 Compound 1.3 (5-oxo-5-(perylen-3-yl)pentanoic acid): A 3L 2 neck round bottomed flask was charged with a stir bar and flushed thoroughly with argon. AICI3 (34.7 mmol, 4.624 g) was added to the flask, followed by anhydrous dichloromethane (600 mL). The reaction mixture was cooled to 0 °C with an ice-water bath and methyl 5-chloro-5-oxopentanoate (30.4 mmol, 5.00 g) was added via syringe with stirring under argon. This mixture was stirred at 0 °C for one hour, then perylene (28.9 mmol, 7.300 g) was added with stirring. The cooling bath was removed, and the reaction mixture was stirred at room temperature for two hours. The flask was fitted with a finned air condenser and heated in a heating block set at 45 °C with stirring overnight under argon. The reaction mixture was cooled to room temperature and quenched with the addition of crushed ice (600 mL, loosely packed). To this mixture was added aqueous 6N HCI (100 mL). Stirring was continued until all ice had melted. The layers were separated, and the aqueous layer was extracted with DCM (2 X 200 mL). The combined organic layers were dried over MgSCU, filtered, and concentrated in vacuo. The crude reaction was purified by flash chromatography on silica gel (100% DCM (3 CV) -> 5% EtOAc/DCM (10 CV)). The fractions containing product were collected and concentrated in vacuo to give 3.810 g, 35% yield. MS (APCI): calculated for C26H20O3(M + H) = 381; found: 381.

Reference： [1]Current Patent Assignee: NITTO DENKO CORPORATION - WO2020/210761, 2020, A1 Location in patent: Page/Page column 115; 116
[2]Current Patent Assignee: NITTO DENKO CORPORATION - WO2021/146380, 2021, A1 Location in patent: Page/Page column 39; 40; 41; 42

79
[ 37517-81-0 ]
[ 198-55-0 ]
methyl 3-oxo-3-(perylen-3-yl)propanoate [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
68%	With aluminum (III) chloride In dichloromethane at 20 - 45℃; Inert atmosphere;	2.2.42 Compound 42.1 (methyl 3-oxo-3-(perylen-3-yl)propanoate): A 500 mL 3 nec round bottom flask was charged with a stir bar and flushed with argon. To this flask was added AlCl3 (9.52 mmol, 1.27 g, followed by anhydrous dichloromethane (160 mL). The solution was stirred at room temperature and methyl 3-chloro-3-oxopropanoate (8.30 mmol, 0.890 mL) was added, followed by perylene (7.92 mmol, 1.99 g). The reaction was stirred at room temperature under argon overnight. The following morning, the flask was fitted with a finned air condenser and heated with a heat block to 45 °C and stirred at this temperature over the weekend under argon. Added another portion of methyl 3-chloro-3-oxopropanoate (8.30 mmol, 0.890 mL) and continued stirring at 45 °C under argon overnight. The reaction was quenched by the addition of water (100 mL) and aqueous 6N HCl (100 mL) and diluted with dichloromethane (100 mL). The layers were separated (emulsion) and the water layer extracted with DCM (2 X 200 mL, emulsion), then DCM (4 X 100 mL). The organic layers were dried with MgSO4, filtered, and concentrated in vacuo. The product was purified by flash chromatography on silica gel (100% DCM (3 CV) 1% EtOAc/DCM (0 CV) 1% EtOAc/DCM (3 CV) 10% EtOAc/DCM (8 CV)) to give product, 1.905 g (68% yield). MS (APCI): calculated for C24H16O3 (M + H) = 353; found: 353.
68%	With aluminum (III) chloride In dichloromethane at 0 - 45℃; Inert atmosphere;	RLE-16 Compound 15.4A (methyl 3-oxo-3-(perylen-3-yl)propanoate): A 500 mL 3 neck round bottom flask was charged with a stir bar and flushed with argon. To this flask was added AICI3(9.52 mmol, 1.27 g, followed by anhydrous dichloromethane (160 mL). The solution was stirred at room temperature and methyl 3-chloro-3-oxopropanoate (8.30 mmol, 0.890 mL) was added, followed by perylene (7.92 mmol, 1.99 g). The reaction was stirred at room temperature under argon overnight. The following morning, the flask was fitted with a finned air condenser and heated with a heat block to 450C and stirred at this temperature over the weekend under argon. Added another portion of methyl 3-chloro-3-oxopropanoate (8.30 mmol, 0.890 mL) and continued stirring at 450C under argon overnight. The reaction was quenched by the addition of water (100 mL) and aqueous 6N HCI (100 mL) and diluted with dichloromethane (100 mL). The layers were separated (emulsion) and the water layer extracted with DCM (2 X 200 mL, emulsion), then DCM (4 X 100 mL). The organic layers were dried with MgSO4, filtered, and concentrated in vacuo. The product was purified by flash chromatography on silica gel (100% DCM (3 CV) → 1% EtOAc/DCM (0 CV) · 1% EtOAc/DCM (3 CV) · 10% EtOAc/DCM (8 CV)) to give product, 1.905 g (68% yield).MS (APCI): calculated for C24H16O3(M + H) = 353; found: 353

Reference： [1]Current Patent Assignee: NITTO DENKO CORPORATION - WO2020/210761, 2020, A1 Location in patent: Page/Page column 118; 119
[2]Current Patent Assignee: NITTO DENKO CORPORATION - WO2021/146380, 2021, A1 Location in patent: Page/Page column 76; 77

80
[ 198-55-0 ]
[ 1066-54-2 ]
3,9-bis(trimethylsilylethynyl)perylene [ No CAS ]
3,10-bis(trimethylsilylethynyl)perylene [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	Stage #1: PERYLENE With bromine; acetic acid at 40℃; for 4h; Stage #2: With copper(l) iodide; tetrakis(triphenylphosphine) palladium⁽⁰⁾ In tetrahydrofuran at 60℃; for 0.116667h; Inert atmosphere; Stage #3: trimethylsilylacetylene With triethylamine In tetrahydrofuran at 60 - 100℃; Inert atmosphere; Darkness; Overall yield = 63 percent; Overall yield = 0.212 g;	3,10-Dibromoperylene Perylene (3.00 g, 11.9 mmol) was suspended in 130 mL of acetic acid and stirred at 40° C. A solution of bromine (1.35 mL, 26.2 mmol) in 5.0 mL of acetic acid was slowly added to the suspension of perylene at rapid stirring. The reaction mixture was stirred at 40° C. for four hours. Once cooled to room temperature the reaction was quenched with sodium thiosulfate solution, followed by addition of 300 mL of water. The product mixture was collected by filtration and dried overnight. The isomer mixture was separated by repetitive recrystallization from toluene and THF. The 3,10-dibromoperylene isomer was purified to 90% isomeric purity and taken to the next step. Orange solids. Yield: 8%. 1H NMR (400 MHz, CDCl3, 25° C.): δ=8.25 (d, J=7.6 Hz, 2H), 8.12 (d, J=8.6 Hz, 2H), 7.97 (d, J=8.1 Hz, 2H), 7.77 (d, J=8.1 Hz, 2H), 7.60 (t, J=8.1 Hz, 2H) ppm.3,10-bis(TMS-alkynyl)perylene3,10-Dibromoperylene (90% isomer mixture) (0.310 g, 0.76 mmol) was dissolved in 20 mL of THF at 60° C. and the solution was sparged with N2for 10 minutes. Pd(PPh3)4(88 mg, 0.076 mmol), and CuI (15 mg, 0.079 mmol) were added to the reaction flask against the positive flow of N2and the mixture was sparged with N2for additional 7 minutes. In another flask a solution of TMS-acetylene (0.50 mL, 3.6 mmol) in triethylamine (5 mL) was sparged with N2for 10 minutes. The solution of TMS-acetylene was added dropwise to the reaction mixture at 100° C. The reaction was stirred overnight, in the dark, under an atmosphere of N2at 60° C. The mixture was then cooled to room temperature and poured into a saturated aqueous solution of ammonium chloride; the product was extracted with dichloromethane. The combined organic layer was dried with MgSO4and the product was purified by column chromatography on silica gel using hexanes at the eluent. The product was subsequently recrystallized from dichloromethane and hexanes. Orange solids, 0.212 g Yield: 63%. 1H NMR (400 MHz, CDCl3, 25° C.): δ=8.25 (d, J=7.2 Hz, 2H), 8.21 (d, J=8.5 Hz, 2H), 8.10 (d, J=7.8 Hz, 2H), 7.69 (d, J=7.8 Hz, 2H), 7.59 (t, J=8.3 Hz, 2H), 0.35 (s, 18H) ppm.

Reference： [1]Current Patent Assignee: BATTELLE MEMORIAL INSTITUTE; MRIGLOBAL - US2020/317855, 2020, A1 Location in patent: Paragraph 0056-0058

81
[ 67-56-1 ]
[ 957014-38-9 ]
oxovanadium(IV) sulfate [ No CAS ]
[ 198-55-0 ]
[ 33513-42-7 ]
9O₄S^(2-)*72CH₃O^(1-)*18C₂H₇N*18H⁽¹⁺⁾*6C₁₈H₆O₈^(4-)*3C₂₀H₁₂*48OV⁽²⁺⁾ [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
63%	at 160℃; for 48h; Autoclave;

Reference： [1]Gong, Yaru; Pan, Qinhe; Qin, Chao; Su, Zhongmin; Sun, Chunyi; Wang, Xinlong; Zhang, Yuteng [Angewandte Chemie - International Edition, 2020, vol. 59, # 49, p. 22034 - 22038][Angew. Chem., 2020, vol. 132, # 49, p. 22218 - 22222,5]

82
[ 198-55-0 ]
[ 620-05-3 ]
2-benzylperylene [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
41%	With tetra-n-butylphosphonium chloride In tetrahydrofuran at 200℃; for 3h;	2.23 Example 2-23 Example 2-23 Synthesis of 2-benzylperylene 50 g (0.2 mol) of perylene, 86.4 g (0.4 mol) of 1-(iodomethyl)benzene, 11.7 g (0.04 mol) of tetrabutylphosphonium chloride, and 100 ml of THF were reacted at 200° C. for 3 hours in the same manner as in Example 2-11 to obtain 27.8 g (0.08 mol, yield 41%) of 2-benzylperylene. As a result of 300 MHz hydrogen nuclear magnetic resonance analysis of the obtained product, Ph-CH2-Ph. and Ph-H and perylene-H were confirmed at 3.9 ppm (s, 2H) and 7.0 to 9.0 ppm (m, 16H), respectively.

Reference： [1]Current Patent Assignee: JSI SILICONE - US2021/188739, 2021, A1 Location in patent: Paragraph 0095

83
[ 18157-21-6 ]
[ 198-55-0 ]
3-(2-(trimethoxysilyl)ethyl)perylene [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
49%	With tetra-n-butylphosphonium chloride In decane at 230℃; for 6h;	3.19 Example 3-19 Example 3-19 Synthesis of 3-(2-(trimethoxysilyl)ethyl)perylene 50 g (0.198 mol) of perylene, 18.3 g (0.099 mol) of 2-chloroethyl trimethoxysilane, 2.9 g (0.0099 mol) of tetrabutylphosphonium chloride, and 50 ml of decane were reacted at 230° C. for 6 hours in the same manner as in Example 3-17 to obtain 19.6 g (0.049 mol, yield 49%) of a product. As a result of 300 MHz hydrogen nuclear magnetic resonance analysis of the obtained product, Si-CH2-C, C-CH2-C, Si-OCH3, and Perylene-H were confirmed at 0.93 ppm (t, 2H), 3.0 ppm (t, 2H), 3.6 ppm (s, 9H), and 7.2 to 8.2 ppm (m, 11H), respectively.

Reference： [1]Current Patent Assignee: JSI SILICONE - US2021/188739, 2021, A1 Location in patent: Paragraph 0128

84
[ 198-55-0 ]
C₅H₇ClO₄ [ No CAS ]
[ 110774-34-0 ]

Yield	Reaction Conditions	Operation in experiment
56%	With aluminum (III) chloride In dichloromethane at 20℃; for 16.25h; Cooling with ice; Inert atmosphere;	2.8.1 Step 1: In 1 L two neck flash equipped with magnetic stirring bar, powder dispenser funnel, a yellow suspension mixture of perylene (5.22 g, 20.68 mmol) in DCM anhydrous (500 mL) was stirred and bubbled with Argon 15 minutes on a cooling ice + water bath; methyl 4-{4,12b- dihydroperyien-3-yl) butanoate (3.425 g, 22.75 mmol) was added slowly via syringe and needle. Cooling bath was removed to allow the mixture stirring at RT for 15 minutes. The mixture was cooled again with ice+ water bath; AICI3 (3.3 g, 24.74 mmol) was added in small portion via the powder dispenser funnel. The resulting dark purple color mixture was stirred at RT for 16 hours under the protection of Argon. TIC and LCMS shown starting materials were almost consumed. The reaction mixture was diluted with 500 ml DCM then poured to ice+ water 150 ml water, organic layer was separated, dried with MgSO4 , concentrated, to the volume of 100 ml; SiO? (100 g) was added to THE solution mixture to absorb the product then load on to column (330 g), eluting withl Hexanes/ DCM (100:0) (0:100) gained 1.25 g of desired product. The product from column chromatography and the solid product from filtering were combined and re- crystallize by Hexanes: EtAco (9:1), gained 4.24 g yellow solid, yield 56%. LCMS (APCI+), calcd for Formula: C25H18O3; found: 366,: 1H NMR (400 MHz, Chloroform-d) δ 8.57 (dd, J = 8.6, 1.0 Hz, 1H), 8.30 - 8.17 (m, 4H), 7.97 (d, J = 8.1 Hz, 1H), 7.78 (d, J = 8.1 Hz, 1H), 7.73 (d, J = 8.1 Hz, 1H), 7.64 - 7.48 (m, 3H), 3.75 (s, 3H), 3.41 (t, J = 6.5 Hz, 2H), 2.86 (t, J = 6.5 Hz, 2H).

Reference： [1]Current Patent Assignee: NITTO DENKO CORPORATION - WO2021/146380, 2021, A1 Location in patent: Page/Page column 56; 57

85
[ 198-55-0 ]
[ 73183-34-3 ]
4,4,5,5-tetramethyl-2-(perylene-2-yl)-1,3,2-dioxaborolane [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
62%	With bis(η⁴-1,5-cyclooctadiene)-di-μ-methoxy-diiridium(I); 4,4'-di-tert-butyl-2,2'-bipyridine In tetrahydrofuran at 80℃; for 24h; Glovebox; Schlenk technique; Microwave irradiation; Inert atmosphere;

Reference： [1]Börjesson, Karl; Carrod, Andrew J.; Cravcenco, Alexei; Ye, Chen [Journal of Materials Chemistry C, 2022, vol. 10, # 12, p. 4923 - 4928]

86
[ 198-55-0 ]
C₁₀₄H₉₂N₄O₈Rh₄⁽⁴⁺⁾*4CF₃O₃S^(1-) [ No CAS ]
C₁₀₄H₉₂N₄O₈Rh₄⁽⁴⁺⁾*4CF₃O₃S^(1-)*2C₂₀H₁₂ [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
92%	for 2h;	4.4. Preparation of host-guest systems with PAHs General procedure: The metalla-rectangle 1 (5 mg, 0.002 mmol) was dissolved in 1 mL acetonitrile or methanol. The corresponding PAH guest molecules (2 equiv., 0.004 mmol) were added. The mixture was stirred for 2 h and centrifugated to remove any insoluble matter. 7 mL diethyl ether was layered on the resulting dark green so- lution. Dark green solids precipitated within 3 days. The products were then collected and dried in air.

Reference： [1]Jin, Guo-Xin; Lin, Yue-Jian; Liu, Dong [Journal of Organometallic Chemistry, 2022, vol. 967]

87
cesium 3,3-commo-bis[η5-1,2-dicarba-(3)-cobalt(III)-closo-dodecaborate] [ No CAS ]
[ 198-55-0 ]
[ 75-57-0 ]
C₂₄H₃₀B₁₈Co^(1-)*C₄H₁₂N⁽¹⁺⁾ [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
69%	Stage #1: cesium 3,3-commo-bis[η5-1,2-dicarba-(3)-cobalt(III)-closo-dodecaborate]; PERYLENE With Aluminum Chloride at 160℃; for 2h; Stage #2: anhydrous tetramethylammonium chloride In ethanol

Reference： [1]Olid, David; Poater, Jordi; Solà, Miquel; Teixidor, Francesc; Viñas, Clara [Angewandte Chemie - International Edition, 2022, vol. 61, # 22][Angew. Chem., 2022, vol. 134, # 22]

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[ 198-55-0 ] Synthesis Path-Upstream 1~4

[ 198-55-0 ] Synthesis Path-Downstream 1~87

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P302 + P334	IF ON SKIN: Immerse in cool water/wrap in wet bandages.
P302 + P350	IF ON SKIN: Gently wash with plenty of soap and water.
P303 + P361 + P353	IF ON SKIN (or hair): Remove/Take off Immediately all contaminated clothing. Rinse SKIN with water/shower.
P304 + P312	IF INHALED: Call a POISON CENTER or doctor/physician if you feel unwell.
P304 + P340	IF INHALED: Remove victim to fresh air and Keep at rest in a position comfortable for breathing.
P304 + P341	IF INHALED: If breathing is difficult, remove victim to fresh air and keep at rest in a position comfortable for breathing.
P305 + P351 + P338	IF IN EYES: Rinse cautiously with water for several minutes. Remove contact lenses, if present and easy to do. Continue rinsing.
P306 + P360	IF ON CLOTHING: Rinse Immediately contaminated CLOTHING and SKIN with plenty of water before removing clothes.
P307 + P311	IF exposed: call a POISON CENTER or doctor/physician.
P308 + P313	IF exposed or concerned: Get medical advice/attention.
P309 + P311	IF exposed or if you feel unwell: call a POISON CENTER or doctor/physician.
P332 + P313	IF SKIN irritation occurs: Get medical advice/attention.
P333 + P313	IF SKIN irritation or rash occurs: Get medical advice/attention.
P335 + P334	Brush off loose particles from skin. Immerse in cool water/wrap in wet bandages.
P337 + P313	IF eye irritation persists: Get medical advice/attention.
P342 + P311	IF experiencing respiratory symptoms: call a POISON CENTER or doctor/physician.
P370 + P376	In case of fire: Stop leak if safe to Do so.
P370 + P378	In case of fire:
P370 + P380	In case of fire: Evacuate area.
P370 + P380 + P375	In case of fire: Evacuate area. Fight fire remotely due to the risk of explosion.
P371 + P380 + P375	In case of major fire and large quantities: Evacuate area. Fight fire remotely due to the risk of explosion.
Storage
Code	Phrase
P401
P402	Store in a dry place.
P403	Store in a well-ventilated place.
P404	Store in a closed container.
P405	Store locked up.
P406	Store in corrosive resistant/ container with a resistant inner liner.
P407	Maintain air gap between stacks/pallets.
P410	Protect from sunlight.
P411
P412	Do not expose to temperatures exceeding 50 oC/ 122 oF.
P413
P420	Store away from other materials.
P422
P402 + P404	Store in a dry place. Store in a closed container.
P403 + P233	Store in a well-ventilated place. Keep container tightly closed.
P403 + P235	Store in a well-ventilated place. Keep cool.
P410 + P403	Protect from sunlight. Store in a well-ventilated place.
P410 + P412	Protect from sunlight. Do not expose to temperatures exceeding 50 oC/122oF.
P411 + P235	Keep cool.
Disposal
Code	Phrase
P501	Dispose of contents/container to ...
P502	Refer to manufacturer/supplier for information on recovery/recycling