Name: 110677-45-7|4-(9H-Carbazol-9-yl)benzaldehyde|95%
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1
[ 104-88-1 ]
[ 86-74-8 ]
[ 110677-45-7 ]

Reference： [1]Tetrahedron Letters,2000,vol. 41,p. 481 - 483

2
[ 110677-45-7 ]
4-(3,6-dibromo-9H-carbazol-9-yl)benzaldehyde [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
Ca. 92%	With N-Bromosuccinimide; In N,N-dimethyl-formamide; toluene; at 0℃; for 0.5h;	Compound 3 (1.60 g, 5.9 mmol) was dissolved intoluene (10 mL) and cooled to 0C in an ice bath. Thena solution of NBS (2.60 g, 13.2 mmol) in DMF (15 mL)was added dropwise to the dissolved compound 3 andstirred for 30 min. The reaction mixture was pouredin ice-cold water and the obtained precipitate wasfiltered, washed with cold methanol for several times,and dried under reduced pressure. Yield ∼92%.
82%	With bromine; In dichloromethane; for 6h;Cooling with ice;	3,6-dibromo-9- (4-formylphenyl) carbazole: in 250mL one-neck flask, 9- (4-formylphenyl) carbazole (5.00g, 18.428mmoL) and 145mL of methylene chloride were dissolved with stirring, cooled with ice bath, was slowly added dropwise thereto and mixed 8mLDCM the liquid bromine (1.45mL, 56.115mmoL), after the completion of the dropwise addition, the reaction was 6h.After completion of the reaction, with a sufficient amount of saturated aqueous NaOH quenched, extracted with methylene chloride, dried over anhydrous Na2SO4And dried under reduced pressure the reaction was removed by rotary evaporation the solvent, the residue was recrystallized from ethanol to give a dark yellow solid 6.48g, yield% 82.0

Reference： [1]Tetrahedron Letters,2000,vol. 41,p. 8573 - 8576
[2]Journal of Chemical Sciences,2015,vol. 127,p. 383 - 394
[3]Macromolecules,2014,vol. 47,p. 7397 - 7406
[4]Patent: CN105646502,2016,A .Location in patent: Paragraph 0017; 0030; 0031
[5]New Journal of Chemistry,2021,vol. 45,p. 2141 - 2146
[6]Journal of Organometallic Chemistry,2016,vol. 817,p. 43 - 49

3
[ 459-57-4 ]
[ 86-74-8 ]
[ 110677-45-7 ]

Yield	Reaction Conditions	Operation in experiment
79.08%	With sodium hydroxide; In N,N-dimethyl-formamide; at 130℃; for 6h;	A mixture of 9H-Carbazole(5 g, 0.03 mol), and sodium hydroxide (1.2 g, 0.03 mol) in drydimethylformamide (DMF) was heated with stirring. Then 4-fluorobenzaldehyde (3.72 g, 0.03 mol) was added, and the reactionmixture was stirred at 130 C for 6 h. After cooling to roomtemperature, the mixture was poured into distilled water andextracted with ethyl acetate. The organic layer was dried withanhydrous magnesium sulfate and concentrated by vacuum evaporation.The crude product was purified by column chromatographyusing the mixture of petroleum and dichloromethane (vol.ratio 3:1) as an eluent to get the desired compound as a yellow solid(6.43 g) with a yield of 79.08%.
74%	With potassium carbonate; In dimethyl sulfoxide; at 150℃;	The intermediate 4-(9H-carbazol-9-yl)benzaldehyde wassynthesized according to the reported procedure [33]. Asolution of 4-fluorobenzaldehyde (0.222 g, 1.79 mmol),carbazole (0. 30 g, 1.79 mmol), K2CO3(500 mg) and DMSO(10 mL) was heated at 150 C overnight. After completionof the reaction as confirmed by thin layer chromatographicanalysis (TLC), the solution was cooled to room temperatureand water was added to the reaction mixture. The mixturewas extracted thrice with DCM (3 X 10 mL) and the organiclayer was separated and dried over anhydrous Na2SO4.Afterthe solvent was evaporated a yellow solid was obtained,which is followed by recrystallization from EtOH yieldingintermediate compound 4-(9H-carbazol-9-yl)benzaldehydewith 74% yield.
68%		In a 250 mL two-necked flask, anhydrous DMF (100 mL) was addedto a mixture of 9H-carbazole (8.40 g, 50 mmol) and potassium tertbutoxide(5.52 g, 50 mmol). The mixture was stirred at 110 C for30 min under nitrogen atmosphere. Then, 4-fluorobenzaldehyde(1.24 g, 10 mmol) was added and stirred for 36 h. Then, the reactionmixture was cooled to room temperature and the reaction solvent wasremoved by distillation under reduced pressure. The residue was extractedwith ethyl acetate and water. Further purification was carriedout by silica gel chromatography to afford Cz9PhCHO as a light yellowsolid (9.30 g, 68%). 1H NMR (300 MHz, CDCl3, δ/ppm): 10.11 (s, 1H),8.12-8.16 (m, 4H), 7.79 (d, J=8.4Hz, 2H), 7.51 (d, J=7.5 Hz, 2H),7.44 (t, J=7.2 Hz, 2H), 7.33 (t, J=7.8 Hz, 2H); 13C NMR (75 MHz,CDCl3, δ/ppm): 191.03, 143.39, 140.07, 134.64, 131.42, 126.82,126.34, 124.00, 120.88, 120.56, 109.81. HRMS (m/z): calcd forC19H13NO: 271.0997. Found: 271.0996.

67.5%		9- (4-formylphenyl) carbazole: in 250mL three-necked flask, carbazole (3.345g, 20mmoL), potassium t-butylate (2.245g, 20mmoL) and purified 80mL of DMF.Under nitrogen conditions, the mixed solution was magnetically stirred reaction at 110 0.5h, then slowly added dropwise thereto in dissolved 20mLDMF fluorobenzaldehyde (2.483g, 20mmoL), After dropping the reaction was stirred at this temperature for 36h.After completion of the reaction, cooled to room temperature, the mixture was poured into cold water, the reaction mixture was stirred 0.5h, filtered and the filter residue recrystallized from absolute ethanol to give a yellow solid 3.66g, yield 67.5%.
Ca. 60%	With potassium tert-butylate; In N,N-dimethyl-formamide; at 110℃; for 37h;Inert atmosphere;	Compound 3 was synthesized as per the reported procedure.26 In 50mL RB flask, carbazole (2.0 g,11.9 mmol) and t-BuOK (1.33 g, 11.9 mmol) were dissolvedtogether in DMF (10 mL) and heated at 110Cunder stirring for 30 min. 4-Fluorobenzaldehyde (1.5 g,11.9 mmol) was taken in 5mL of DMF and addeddropwise to the reaction mixture over 30 min. Then thereaction mixture refluxed for another 36 h at the sametemperature under nitrogen atmosphere. After completionof the reaction, the reaction mixture was cooledto room temperature and poured in excess amount ofice-cold water (700 mL), from which solid precipitated.Then the solid was filtered under reduced pressure anddried. Finally, the crude compound was purified bycolumn chromatography employing silica gel as stationaryphase and CHCl3: Hexane (1:1) as mobilephase. Yield ∼60%
60%		To a stirred solution of carbazole 3 (6.30 g, 37.7 mmol) in anhydrousDMF (150 mL) was added potassium tert-butoxide (4.23 g, 37.7 mmol) atroom temperature under nitrogen atmosphere. The reaction mixture washeated to 110 C and then a solution of 4-fluorobenzaldehyde 4 (4.04mL g, 37.7 mmol) in anhydrous DMF (10 mL) was added dropwise intothe mixture over 50 min. The mixture was kept at 110 C for 36 h. Thenthe mixture was cooled to room temperature and poured into 500 mL icewater. The precipitate obtained was filtered, dried and recrystallized byusing acetone/water (v/v = 9:1) system to afford compound 5 as a paleyellow solid (6.15 g, 60%).mp 156-158 C; 1H NMR (500 MHz, CDCl3): δ = 7.33 (t, J = 7.0 Hz, 2H), 7.44 (t, J = 8.0, 7.0 Hz, 2H), 7.51 (d, J = 8.0 Hz, 2H), 7.80 (d, J =7.5 Hz, 2H), 8.15 (t, J = 7.5, 7.0 Hz, 4H), 10.12 (s, 1H); 13C NMR (125MHz, CDCl3): δ = 109.75, 120.49, 120.80, 123.97, 126.27, 126.84,131.37, 134.65, 140.07, 143.41, 190.95; ESI-MS: m/z 272.03 [M + H]+.
43%	With potassium carbonate; In N,N-dimethyl-formamide; at 140℃; for 18h;Schlenk technique; Inert atmosphere;	Add 4-fluorobenzaldehyde (1.27mL, 12mmol), carbazole (1670mg, 10mmol) and K2CO3 (4150mg, 30mmol) were added to a 50mL Schlenk tube, 20mL DMF was added, and heated to reflux for 18h under nitrogen protection. Dilute the cooled reaction solution with 20mL saturated sodium chloride solution, extract with 3*25mL ethyl acetate, combine the organic phases, add anhydrous MgSO4 to dry, filter to remove anhydrous magnesium sulfate, evaporate the solvent under reduced pressure,Petroleum ether: dichloromethane (6:1) column chromatography to obtain the target product with a yield of 43%.

Reference： [1]Patent: CN107721905,2018,A .Location in patent: Paragraph 0026
[2]Luminescence,2014,vol. 29,p. 540 - 548
[3]Chemistry - A European Journal,2019,vol. 25,p. 3325 - 3336
[4]Dyes and Pigments,2014,vol. 100,p. 127 - 134
[5]RSC Advances,2015,vol. 5,p. 86191 - 86198
[6]Journal of Fluorescence,2021,vol. 31,p. 1645 - 1664
[7]New Journal of Chemistry,2014,vol. 38,p. 5736 - 5746
[8]RSC Advances,2017,vol. 7,p. 30229 - 30241
[9]Dyes and Pigments,2018,vol. 157,p. 101 - 108
[10]New Journal of Chemistry,2021,vol. 45,p. 2141 - 2146
[11]Patent: CN105646502,2016,A .Location in patent: Paragraph 0014; 0028; 0029
[12]Journal of Materials Chemistry,2012,vol. 22,p. 520 - 526
[13]Journal of Chemical Sciences,2015,vol. 127,p. 383 - 394
[14]Organic electronics,2021,vol. 92
[15]Chemical Papers,2013,vol. 67,p. 110 - 116,7
[16]Journal of Materials Chemistry,2000,vol. 10,p. 2698 - 2703
[17]Patent: CN113429394,2021,A .Location in patent: Paragraph 0111-0115
[18]Molecular Crystals and Liquid Crystals,2012,vol. 563,p. 257 - 271
[19]Journal of Organic Chemistry,2010,vol. 75,p. 2578 - 2588
[20]European Journal of Inorganic Chemistry,2006,p. 430 - 436
[21]Journal of Coordination Chemistry,2012,vol. 65,p. 2127 - 2134
[22]Journal of Organic Chemistry,2013,vol. 78,p. 3222 - 3234
[23]Dyes and Pigments,2014,vol. 106,p. 51 - 57
[24]Australian Journal of Chemistry,2013,vol. 66,p. 1406 - 1414
[25]Synthesis and Reactivity in Inorganic, Metal-Organic, and Nano-Metal Chemistry,2015,vol. 45,p. 639 - 647
[26]Dyes and Pigments,2015,vol. 122,p. 31 - 39
[27]Journal of Organometallic Chemistry,2016,vol. 817,p. 43 - 49
[28]RSC Advances,2016,vol. 6,p. 114143 - 114158
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[30]Patent: CN106632262,2017,A .Location in patent: Paragraph 0020; 0021; 0022
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[33]Journal of Materials Chemistry C,2021,vol. 9,p. 12681 - 12693
[34]Journal of Alloys and Compounds,2022,vol. 902

4
[ 51044-13-4 ]
[ 110677-45-7 ]
[ 1019779-50-0 ]

Reference： [1]Bulletin of the Chemical Society of Japan,2005,vol. 78,p. 300 - 306
[2]Chemistry - A European Journal,2003,vol. 9,p. 5074 - 5084

5
[ 86-74-8 ]
[ 1122-91-4 ]
[ 110677-45-7 ]

Yield	Reaction Conditions	Operation in experiment
95%	With copper(l) iodide; potassium carbonate; In N,N-dimethyl-formamide; at 140℃; for 12h;Inert atmosphere;	Scheme 4A mixture of 9H-carbazole (9.53 g, 57 mmol), 4-bromobenzaldehyde (21.1 g, 114 mmol), Copper(I) iodide (1.80 g, 9.4 mmol), K2C03 (11.8 g, 86 mmol), in 60 mL dry DMF, was heated to 140C, under nitrogen atmosphere for 12 hours. After cooling to room temperature, the inorganic solid was filtered, and the residue was poured into ice water to precipitate the product.The so-formed solid was collected, and washed by water, ethanol several times, then crystallized from CH2C12 and ethanol, to give light-yellow solid (yield: 95%). MS (ESI): 272.10 [M+H].
87%	With copper; potassium carbonate; In nitrobenzene; at 180℃; for 24h;Inert atmosphere;	(2) carbazole (1.0 g, 6 mmol, 6.0 eq), 4-bromobenzaldehyde (2.2 g, 12 mmol, 12.0 eq), copper powder (64 mg,1 mmol, 1.0 eq), K2CO3 (1.24 g, 9 mmol, 9.0 eq) was dissolved in 10 mL of nitrobenzene, protected with nitrogen, heated at 180 C.Should be 24h The reaction was detected by TCL plate. After the reaction was complete, the mixture was cooled to room temperature and separated on a silica gel column. The silica gel particle size was200-300 mesh, eluent ratio of ethyl acetate / petroleum ether = 1: 50, the product 2-1, the yield of 87%.
85%	With copper(l) iodide; 18-crown-6 ether; potassium carbonate; In dimethyl sulfoxide; at 130℃; for 24h;	(1) 10 g of carbazole was added to a 250 mL three-necked flask.13.2g 4-bromobenzaldehyde,5g potassium carbonate,2.5 g of cuprous iodide and 2 g of 18-[crown]-6 ether,Add 150 mL of dimethyl sulfoxide as solvent.The oil bath is reacted at 130 C for 24 hours;After the reaction is over,After the reaction solution is cooled to room temperature,Filtering,Then, the filtrate was mixed with a 20 wt% NaCl aqueous solution to precipitate a solid.Recover solids and dry,Recrystallization 3 times with acetonitrile,The intermediate (4-(9H-carbazol-9-yl)benzaldehyde is obtained,The yield is 85%;

84%	With 18-crown-6 ether; copper; potassium carbonate; In 1,2-dichloro-benzene; at 200℃;Inert atmosphere;	Example 1.1.1 4-(9H-carbazol-9-yl)benzaldehyde (1) 9H-carbazole (30.0 g, 179.4 mmol), 4-bromobenzaldehyde (36.5 g, 197.4 mmol), potassium carbonate (109.1 g, 789.5 mmol), and 18-crown-6 (4.7 g 17.9 mmol) were dissolved in 1,2-dicholorobenzene. The reaction mixture was degassed with argon and then copper (29.9 g, 466.5 mmol) was added. The reaction was heated to about 200 C. under argon for about 36-40 hours. The copper, potassium carbonate, and 18-crown-6 were then filtered off. The solvent was removed and the resulting residue was purified by a silica chromatography, employing 1:1 dichloromethane:hexanes as an eluent. A recrystallization was performed in tetrahydrofuran (THF)/methanol to yield the product 1 as tan solid (84% yield). 1H NMR (400 MHz, DMSO-d): δ 10.13 (s, 1H), 8.27 (d, J=7.7 Hz, 2H), 8.20 (d, J=8.4 Hz, 2H), 7.90 (d, J=8.4 Hz, 2H), 7.52 (d, J=8.1 Hz, 2H), 7.48-7.44 (m, 2H), 7.33 (t, J=7.0 Hz, 2H)
81.7%	With tri-tert-butyl phosphine; palladium diacetate; potassium carbonate; In toluene; at 115℃; for 24h;	0.090 g (3.7 mol%) of P(t-Bu)3 and 0.035 g (1.3 mol%) Pd(OAC)2 were added to 80 mL degassed toluene, followed by 2.5 g (0.0135 mol) of 4-bromobenzaldehyde and 2.000 g (0.0120 mol) of 9H-carbazole and 4.150 g (0.0300 mol) anhydrous K2CO3. The reaction mixture was heated to 115 C for 24 h. The solvent was removed under vacuum, and 150 mL CH2Cl2 was added. The material was washed with 2 * 50 mL 20% NaOH, washed with 1 * 50 mL brine, and dried with anhydrous MgSO4. The solvent was removed under vacuum, and the residue was purified by column chromatography on silica gel using ethyl acetate/petroleum ether (1:20, v/v) as the eluent to give 4-(9H-carbazol-9-yl)benzaldehyde as white powder (2.65 g, 81.7%). m.p.: 156-158 C. 1H NMR (CDCl3, δ, ppm): 10.13 (s, 1H, -CHO), 8.16 (dd, J = 8.5 Hz, 4H), 7.81 (d, J = 8.0 Hz, 2H), 7.52 (d, J = 8.0 Hz, 2H), 7.45 (t, J = 7.6 Hz, 2H), 7.34 (t, J = 8.0 Hz, 2H).
80%	With tri-tert-butyl phosphine; palladium diacetate; potassium carbonate; In toluene; for 24h;Inert atmosphere; Reflux;	According to the literature,4 9H-carbazole (1.67 g, 10.00 mmol), 4-bromobenzaldehyde (2.08 g, 11.25 mmol), K2CO3 (3.46 g, 25.00 mmol), Pd(OAc)2 (0.17 g, 0.83 mmol) and P(t-Bu)3 (10%, 2.5 mL, 1.00 mmol) in anhydrous toluene (17 mL) were refluxed under N2 atmosphere for 24 h. After cooled to room temperature, the reaction mixture was filtered to remove precipitate and the solution was evaporated under vacuum. Finally, the residue was purified by silica gel column chromatography with petroleum ether/dichloromethane as the eluent (4/1, v/v). The white solid was obtained. Yield: 80%.
80%	With copper(l) iodide; 18-crown-6 ether; potassium carbonate; In 1,2-dichloro-benzene; at 180℃; for 48h;Inert atmosphere;	3g carbazole, 3.3g p-bromobenzaldehyde, 3.7g potassium carbonate 0.33g 18-crown-6, 0.4g cuprous iodide and18ml of o-dichlorobenzene was added to a 100ml round-bottomed flask, vacuum was evacuated under nitrogen three times after freezing, and it was stirred and refluxed at 180 C for 48 hours. After completion of the reaction, the reaction system was washed repeatedly with 5% hydrochloric acid solution, extracted three times with dichloromethane, dried with anhydrous magnesium sulfate, and then the solvent was removed, and the pure product was separated by column chromatography to obtain 3.9g, with a yield of 80%.
76.6%	With tri-tert-butyl phosphine; potassium carbonate;palladium diacetate; In toluene; at 115℃; for 36h;	0.9 g (3.7 mol %) of P(t-Bu)3 and 0.35 g (1.3 mol %) Pd(OAc)2 were added to 800 ml degassed toluene, followed by 25 g (1.1 eq., 0.1316 mol) of 4-bromobenzaldehyde and 20 g (0.1196 mol) of 9H-carbazole and 41.5 g (2.5 eq., 0.2990 mol) anhydrous K2CO3. The reaction mixture was heated to 115 C. for 24 hours. Most of the solvent was removed and the reaction stirred for another 12 hours at 115 C. Solvent was removed under vacuum, and 300 ml CH2Cl2 was added. The material was washed with 2×50 ml H2O and 2×50 ml 20% NaOH, washed with 1×50 ml brine, and dried with MgSO4. The solvent was removed, leaving the intermediate, 4-(9H-carbazol-9-yl)benzaldehyde, an orange-brown solid. 125 ml of 80% hexanes/20% EtOAc were added. The mixture was stirred, cooled and vacuum filtered, leaving an off-white solid. After washing with more hexanes/EtOAc, the white solid was recrystallized from ethanol/toluene to give 20.53 g fine white needle crystals. A second crop of crystals provided 4.34 additional grams of the intermediate, 4-(9H-carbazol-9-yl)benzaldehyde. Total yield was 24.87 g or 76.6%.; 0.9 g (3.7 mol %) of P(t-Bu)3 and 0.35 g (1.3 mol %) Pd(OAc)2 were added to 800 ml degassed toluene, followed by 25 g (1.1 eq., 0.1316 mol) of 4-bromobenzaldehyde, 20 g (0.1196 mol) of 9H-carbazole, and 41.5 g (2.5 eq., 0.2990 mol) anhydrous K2CO3. The reaction mixture was heated to 115 C. for 24 hours. Most of the solvent was removed under vacuum and the reaction stirred for another 12 hours at 115 C. The remaining solvent was removed under vacuum, and 300 ml CH2Cl2 was added to the reaction mixture. The material was washed with 2×50 ml H2O and 2×50 ml 20% NaOH, then with 1×50 ml brine, and then dried with MgSO4. The solvent was removed, leaving an orange-brown solid. 125 ml of 80% hexanes/20% EtOAc was added to the mixture, which was stirred, cooled and vacuum filtered, leaving an off-white solid. After washing with more hexanes/EtOAc, the white solid was recrystallized from ethanol/toluene to give 20.53 g fine white needle crystals of 4-(9H-carbazol-9-yl)benzaldehyde intermediate product. A second crop of crystals provided 4.34 additional grams of the 4-(9H-carbazol-9-yl)benzaldehyde intermediate product. The total yield was 24.87 g or 76.6%.1H NMR (500 MHz, CDCl3), δ 10.10 (s, 1H), 8.13 (dd, J=8.5 Hz), 7.78 (d, J=8.5 Hz, 2H), 7.49 (d, J=8 Hz, 2H), 7.43 (dd, J=8.5 Hz, 2H), 7.32 (dd, J=8.5 Hz, 2H)
74%	With copper(l) iodide; potassium carbonate; In N,N-dimethyl-formamide; at 140℃; for 19h;	A mixture of 9.53 g (57 mmol) carbazole, 21.31 g (114 mmol) 4-bromobenzaldehyde, 11.89 g K2CO3 (86 mmol), 1.80 g (9.4 mmol) Cul in 60 ml of DMF was reacted for 19 hours at 140C. The reaction mixture was cooled to room temperature, filtered, washed with DMF and the filtrate diluted with ice. The residue was filtered and washed with water and ethanol. 1 1.36 g (74%) of a beige solid were obtained.
73%	With tris-(dibenzylideneacetone)dipalladium(0); tri-tert-butyl phosphine; sodium t-butanolate; In toluene; for 18h;Reflux; Inert atmosphere;	9H-Carbazole 1eq (30.8g), 4-Bromo-Aldehyde 1eq (34.1g), sodium-t-butoxide 2eq (35.4g), Pd2 (dba)3 0.05eq (5.3g) toluene (750ml ), and then tri-tertiary butylphosphine was stirred under reflux for 18 hours under a nitrogen flow of 0.15eq. After completion of the reaction, extraction was performed with toluene and distilled water, and the organic layer was dried over magnesium sulfate (MgSO4), filtered, and the filtrate was concentrated under reduced pressure. The organic solution was removed, followed by silica gel column with hexane:dichloromethane=7:3 (v/v), and the product solid was recrystallized from dichloromethane and acetone to obtain an intermediate a-1 (36.5g, Y=73%).
71%	With tri-tert-butyl phosphine; palladium diacetate; potassium carbonate; In toluene; for 48h;Inert atmosphere; Reflux;	Add carbazole (2.0g, 12mmol), 4-bromobenzaldehyde(2.5g, 13.5mmol), potassium carbonate (4.15 g, 30mmol), palladium acetate (0.2g, 1.0mmol),And tri-tert-butyl phosphine (0.3 mL) in a nitrogen atmosphere,Dissolved in 20 mL of anhydrous toluene and refluxed for 48 hours.After the reaction, it was cooled to room temperature, filtered, and the filtrate was taken.The filtrate was extracted with water and dichloromethane, and the organic phase was taken.After using a rotary evaporator to remove the solvent,Purify the residue by column chromatography(Petroleum ether/CH2Cl2, V/V=1:1),2.3 g of a white solid was obtained (71% yield).
63.4%	With 18-crown-6 ether; copper; potassium carbonate; In 1,2-dichloro-benzene; at 170℃; for 12h;Inert atmosphere;	A mixture of 4-bromobenzaldehyde (0.231 g, 1.25 mmol), 9H-carbazole(0.167 g, 1.00 mmol), copper powder (0.095 g, 1.50 mmol),potassium carbonate (0.207 g, 1.50 mmol) and 18-crown-6(0.013 g, 0.05 mmol) in 1,2-dichlorobenzene was stirred at170 oC for 12 hours under the nitrogen atmosphere. After thereaction mixture was cooled down to room temperature,excess of K2CO3 and Cu is removed by the filtration. Aportion of 100 mL of water was added into the filtrate andthen extracted three times of with a portion of 100 mL ofMC. The combined organic layer was dried over anhydrousMgSO4 then the solvent was removed using a rotary evaporator.The yield of the colorless solid was 0.172 g (63.4%).mp 160.3 oC. 1H-NMR (400 MHz, CDCl3) 10.10 (s, 1H),8.16-8.11 (m, 4H), 7.79-7.77 (d, J = 8.08 Hz, 2H), 7.52-7.49(d, J = 8.08 Hz, 2H), 7.46-7.42 (t, J = 6.96 Hz, 2H), 7.36-7.32 (t, J = 7.72 Hz, 2H), 13C-NMR (100 MHz, CDCl3) 190.92, 143.32, 139.99, 134.56, 131.32, 126.74, 126.23,123.91, 120.77, 120.45, 109.71. Anal. Calcd. For C19H13NO:C, 84.11; H, 4.83; N, 5.16; O, 5.90. Found: C, 84.10; H, 4.79; N, 5.97.
58%	With copper; potassium carbonate; In nitrobenzene; for 6h;Inert atmosphere;	The 3.34g (20mmol) carbazole, 3.70g (20mmol) of bromobenzaldehyde, 5.0g (36mmol) and anhydrous potassium carbonate320mg (5mmol) of copper powder placed 200mL single jar, add 40mL nitrobenzene was heated under nitrogen backFlow 6h, the reaction was stopped, cooled, filtered, and evaporated under reduced pressure nitrobenzene, was added 30mL recrystallized from ethanol to give a brownBulk solids 3.12g, yield = 58%
49%	With copper(l) iodide; 18-crown-6 ether; potassium carbonate; In 1,2-dichloro-benzene; for 48h;Inert atmosphere; Reflux;	Carbazole (5.00 g, 29.90 mol),4-bromobenzaldehyde (5.55 g, 29.9 mmol), K2CO3 (6.20 g,44.86 mmol), 18-crown-6 (550.00 mg, 2.08 mmol), CuI (680.00 mg, 3.57 mmol) wereadded to 1,2-dichlorobenzene (30 mL), then refluxed under nitrogen for 48 h.After cooling, the reaction mixture was quenched with (NH4)2CO3solution and extracted with CH2Cl2, then dried overanhydrous MgSO4. After removal of the solvent, the residue waspurified by column chromatography on silica gel using CH2Cl2/petroleum(1:1, v/v) as eluent followed by recrystallization from mixture of CH2Cl2and ethanol to give the product as white powder. Yield: 49%. 1H NMR(500 MHz, DMSO, δ): 10.14 (s, 1H), 8.29 (d, J= 7.77 Hz, 2H), 8.22 (d, J = 7.77 Hz,2H), 7.93 (d, J = 7.77 Hz, 2H), 7.54(d, J = 8.44 Hz, 2H), 7.49 (t, J = 7.77 Hz, 7.77 Hz, 2H), 7.36 (t, J = 7.77 Hz, 7.26 Hz, 2H).
	With copper; potassium carbonate; In nitrobenzene; for 24h;Reflux; Inert atmosphere;	A mixture of carbazole (1.67 g, 10 mmol), 4-bromobenzaldehyde (2.00 g, 10.8 mmol), K2CO3 (5.52 g, 40 mmol) and Cu (0.45 g, 7 mmol) in anhydrous nitrobenzene was refluxed and stirred for 24 h under nitrogen gas protection. After reaction, the mixture was cooled down to room temperature and the solvent was evaporated under reduced pressure. The residue was purified by silica gel column chromatography to yield pure product. 1H NMR (400 MHz, CDCl3) δ=10.09 (s, 1H), 8.20 (d, J = 8.0 Hz, 2H), 8.10 (d, J = 8.4 Hz, 2H), 7.75 (d, J = 8.4 Hz, 2H), 7.55 (d, J = 8.4 Hz, 2H), 7.49 (t, J = 8.4 Hz, 2H), 7.40 (t, J = 7.6 Hz, 2H). 13C NMR (100 MHz, CDCl3) δ= 191.06, 143.32, 140.08, 134.63, 131.42, 126.74, 126.42, 124.06, 120.97, 120.63, 109.90.
900 mg	With copper(l) iodide; caesium carbonate; In N,N-dimethyl-d6-formamide; at 110℃; for 1h;Inert atmosphere; Microwave irradiation;	Weigh 1.67g of carbazole and 2.035g of p-bromobenzaldehyde in a 30ml microwave reaction tube, and then weigh 1.93g of cesium carbonate as an acid binding agent. 190mg of cuprous iodide was used as a catalyst, oxygen was passed through argon to ensure that the system was in an anaerobic environment, and finally 10ml of anhydrous DMF was added as a solvent. Put the microwave reaction tube into a microwave reactor and react at 110 C for 1 hour. Extraction was continued, and after column chromatography, 900 mg of p-aldehyde phenylcarbazole was obtained as a white powder.

Reference： [1]Photochemical and Photobiological Sciences,2013,vol. 12,p. 284 - 297
[2]Patent: WO2016/28902,2016,A1 .Location in patent: Page/Page column 24
[3]Advanced Synthesis and Catalysis,2017,vol. 359,p. 2259 - 2268
[4]Patent: CN107089937,2017,A .Location in patent: Paragraph 0020; 0022
[5]Patent: CN108484478,2018,A .Location in patent: Paragraph 0028; 0029; 0030
[6]Patent: US2013/87772,2013,A1 .Location in patent: Paragraph 0076; 0077
[7]Spectrochimica Acta Part A: Molecular and Biomolecular Spectroscopy,2013,vol. 109,p. 179 - 185
[8]Chemistry Letters,2020,vol. 49,p. 64 - 67
[9]Patent: CN104312576,2020,B .Location in patent: Paragraph 0007; 0009
[10]Patent: US2009/43109,2009,A1 .Location in patent: Page/Page column sheet 3; 10; sheet 6; 12
[11]Patent: WO2019/238532,2019,A1 .Location in patent: Page/Page column 49-50
[12]Patent: KR102129510,2020,B1 .Location in patent: Paragraph 0263-0265
[13]Chemical Communications,2015,vol. 51,p. 10381 - 10384
[14]Patent: CN111205271,2020,A .Location in patent: Paragraph 0063; 0067-0068
[15]Journal of Materials Chemistry C,2014,vol. 2,p. 5709 - 5716
[16]Macromolecules,2014,vol. 47,p. 7397 - 7406
[17]Bulletin of the Korean Chemical Society,2014,vol. 35,p. 569 - 574
[18]Journal of Materials Chemistry,2007,vol. 17,p. 2088 - 2094
[19]Patent: CN102382037,2016,B .Location in patent: Paragraph 0207; 0208
[20]Research on Chemical Intermediates,2019,vol. 45,p. 2429 - 2439
[21]Chemistry Letters,2008,vol. 37,p. 570 - 571
[22]Chemistry - A European Journal,2013,vol. 19,p. 2602 - 2605
[23]Organic electronics,2014,vol. 15,p. 2667 - 2676
[24]Organic electronics,2014,vol. 15,p. 2667 - 2676
[25]Organic Letters,2009,vol. 11,p. 5542 - 5545
[26]Angewandte Chemie - International Edition,2019,vol. 58,p. 16018 - 16022
Angew. Chem.,2019,vol. 131,p. 16164 - 16168,5
[27]Chemistry Letters,2007,vol. 36,p. 264 - 265
[28]ChemMedChem,2014,vol. 9,p. 918 - 921
[29]Dyes and Pigments,2016,vol. 129,p. 1 - 8
[30]Chemistry - A European Journal,2017,vol. 23,p. 15783 - 15789
[31]Tetrahedron Letters,2018,vol. 59,p. 2704 - 2707
[32]Physical Chemistry Chemical Physics,2018,vol. 20,p. 27418 - 27428
[33]Chemistry - A European Journal,2019,vol. 25,p. 1010 - 1017
[34]Journal of Porphyrins and Phthalocyanines,2020,vol. 24,p. 693 - 704
[35]Patent: CN110437133,2019,A .Location in patent: Paragraph 0073-0076
[36]Journal of Photochemistry and Photobiology A: Chemistry,2020,vol. 401
[37]Organic electronics,2021,vol. 92

6
[ 110677-45-7 ]
[ 71935-22-3 ]

Yield	Reaction Conditions	Operation in experiment
91%	With methanol; sodium tetrahydroborate; In tetrahydrofuran; at 20℃; for 1.5h;	Example 1.1.2 4-(9H-carbazol-9-yl)phenyl)methanol (2) <strong>[110677-45-7]4-(9H-carbazol-9-yl)benzaldehyde</strong> (1) (8.0 g, 29.5 mmol) was dissolved in a (2:1) mixture of tetrahydrofuran/methanol. Sodium borohydride (1.4 g, 38.3 mmol) was added portion wise to the reaction mixture. The reaction mixture was stirred for about 1.5 hours at room temperature and the solvents were then removed. Deionized water was then added to the crude material, and 1M HCl was added dropwise until the solution was neutral. The material was then extracted with ethyl acetate and washed with water. The ethyl acetate was then removed and the product 2 was precipitated out of dichloromethane/hexanes to yield white solid 2 (91% yield). 1H NMR (400 MHz, DMSO-d): δ 8.25 (d, J=7.7 Hz, 2H), 7.60 (dd, J1=8.4 Hz, J2=20.2 Hz, 4H), 7.45-7.41 (m, 2H), 7.35 (d, J=8.4 Hz, 2H), 7.28 (t, J=7.0 Hz, 2H), 5.42-5.40 (m, 1H), 4.65 (d, J=5.5 Hz, 2H)
83%	With sodium hydroxide; sodium tetrahydroborate; In tetrahydrofuran; methanol; water; at 20℃; for 16h;	4.3 g (0.1585 mol) of the intermediate, <strong>[110677-45-7]4-(9H-carbazol-9-yl)benzaldehyde</strong>, 0.3 g (0.5 equivalents, 0.007925 mol) NaBH4, and 2.3 ml 20% NaOH were added to a mixture of 75 ml THF and 75 ml MeOH. The solution was stirred for 16 hours at 20 C. Most of the solvent was removed under vacuum and the remainder poured into 200 ml H2O. The mixture was neutralized with 3M HCl, extracted with 3×50 ml CH2Cl2, and washed with 2×40 ml H2O and 1×40 ml brine. The solvent was removed under vacuum, and the residue was taken up in 20 ml hot CH2Cl2. Hexanes were added drop-wise until the desired intermediate, (4-(9H-carbazol-9-yl)phenyl)methanol, precipitated out. 3.58 g of fine needles of the alcohol product were obtained. The total yield of intermediate, (4-(9H-carbazol-9-yl)phenyl)methanol, was 3 was 3.58 g or 83%.
82.57%	With sodium tetrahydroborate; sodium hydroxide; In tetrahydrofuran; methanol; at 20℃; for 16h;	2.200 g (0.008 mol) of <strong>[110677-45-7]4-(9H-carbazol-9-yl)benzaldehyde</strong>, 0.153 g (0.5 eq, 0.004 mol) of NaBH4, and 1.2 mL 20% NaOH were added to a mixture of 37 mL THF and 37 mL MeOH. The solution was stirred for 16 h at room temperature. The reaction mixture was poured into 100 mL H2O, and then neutralized with 3 M HCl. The solution was extracted with CH2Cl2 (3 × 50 mL) and then dried over anhydrous MgSO4. After filtering, the solvent was removed under vacuum, and the residue was taken up in 10 mL hot CH2Cl2. Hexanes were added dropwise until (4-(9H-carbazol-9-yl)phenyl)methanol precipitated out. 1.83 g of fine needles of the alcohol product was obtained. The total yield of (4-(9H-carbazol-9-yl)phenyl)methanol was 1.83 g (82.57%). m.p.: 120-122 C. 1H NMR (CDCl3, δ, ppm): 8.15 (d, J = 7.4 Hz, 2H), 7.63 (d, J = 8.8 Hz, 2H), 7.58 (d, J = 8.4 Hz, 2H), 7.42 (t, J = 7.4 Hz, 2H), 7.32 (d, J = 8.2 Hz, 2H), 7.29 (t, J = 7.4 Hz, 2H), 4.85 (d, J = 5.6 Hz, 2H), 1.81 (t, J = 5.6 Hz, 1H).

Reference： [1]Patent: US2013/87772,2013,A1 .Location in patent: Paragraph 0078; 0079
[2]RSC Advances,2019,vol. 9,p. 460 - 465
[3]Patent: US2009/43109,2009,A1 .Location in patent: Page/Page column sheet 3; 10
[4]Spectrochimica Acta Part A: Molecular and Biomolecular Spectroscopy,2013,vol. 109,p. 179 - 185
[5]Journal of Materials Chemistry,2012,vol. 22,p. 520 - 526
[6]Chemistry Letters,2007,vol. 36,p. 264 - 265

7
[ 1779-49-3 ]
[ 110677-45-7 ]
[ 52913-19-6 ]

Yield	Reaction Conditions	Operation in experiment
90.34%	With potassium tert-butylate; In tetrahydrofuran; for 24h;Inert atmosphere;	A mixture of 2 (2.71 g,10 mmol), potassium tert-butylate (1.68 g, 15 mmol), andCH3PPh3Br (4.28 g, 12 mmol) in dry THF (100 mL) under nitrogenwas stirred for 24 h the mixturewas poured into distilled water and extracted with ethyl acetate. The organic layer was dried withanhydrous magnesium sulfate and concentrated by vacuum evaporation.The crude product was purified by column chromatographyusing the mixture of petroleum and dichloromethane (vol.ratio 5:1) as an eluent to get the desired compound as a white solid(2.43 g) with a yield of 90.34%.
67%		Experimental procedure: In a 100ml three-necked flask, add methyltriphenylphosphonium bromide (1.7g, 11.2mmol) in sequence,Potassium tert-butoxide (0.33 g, 13.4 mmol) and 30 mL THF. After reacting for 30 minutes, the color of the solution was light yellow. 1 g (7.5 mmol) of 9-phenyl-9H-carbazole-3-carbaldehyde was dissolved in an appropriate amount of THF and added dropwise to the above mixture.The color of the solution immediately became dark yellow. N2 protection,Reaction at room temperature for 15-16h. The color of the solution is dark yellow,Pour the reaction solution into 100ml ice water, Extract the organic phase with dichloromethane, separate the organic phase,Dry the organic phase with anhydrous sodium sulfate, filter,Rotary evaporation to remove the solvent, column chromatography to separate the target product,The eluent is petroleum ether: dichloromethane = 10:1,0.67 g of light yellow target product was obtained, and the yield was 67%.
44%	With potassium tert-butylate; In tetrahydrofuran; at 0 - 20℃;	Example 1.3.2 9-(4-vinylphenyl)-9H-carbazole (8) <strong>[110677-45-7]4-(9H-carbazol-9-yl)benzaldehyde</strong> (1) (13.38 g, 49.37 mmol) was dissolved in tetrahydrofuran (200 mL) and then methyltriphenylphosphonium bromide (19.38 g, 54.31 mmol) was added. The reaction mixture was cooled to about 0 C. Potassium t-butoxide was then added. The reaction mixture was stirred at about 0 C. for about 5 minutes, then allowed to warm to room temperature and then stirred overnight. The reaction was then concentrated in vacuo, poured into water, and then extracted with ethyl acetate. The ethyl acetate layer was then dried down and the crude product was run through a silica plug using 1:4 dichloromethane:hexanes to yield an off white solid 8 (44% yield). 1H NMR (400 MHz, CDCl3): δ 8.16 (d, J=8.8 Hz, 2H), 7.65 (d, J=8.4 Hz, 2H), 7.54 (d, J=8.4 Hz, 2H), 7.45-7.40 (m, 4H), 7.32-7.29 (m, 2H), 6.84 (dd, J1=17.6 Hz, 32=10.6 Hz, 1H), 5.87 (d, J=17.2 Hz, 1H), 5.38 (d, J=11.0 Hz, 1H).

Reference： [1]Dyes and Pigments,2014,vol. 100,p. 127 - 134
[2]Journal of Materials Chemistry,2007,vol. 17,p. 2088 - 2094
[3]Patent: CN111434651,2020,A .Location in patent: Paragraph 0154-0156; 0160-0161
[4]Patent: US2013/87772,2013,A1 .Location in patent: Paragraph 0092; 0093
[5]Chemistry - A European Journal,2017,vol. 23,p. 15783 - 15789

8
[ 109-77-3 ]
[ 110677-45-7 ]
[ 1044509-91-2 ]

Yield	Reaction Conditions	Operation in experiment
83%	With pyridine; In acetonitrile; for 4h;Reflux;	(2) To 100 ml of a three-necked flask equipped with electromagnetic stirring, 7.5 g of (<strong>[110677-45-7]4-(9H-carbazol-9-yl)benzaldehyde</strong> was added.Completely dissolved with 20 mL of anhydrous acetonitrile,2mL anhydrous pyridine as a catalyst,Then add 2.8 g of malononitrile,Heating and refluxing for 4 h,After the reaction is over,The reaction solution was mixed with a 15 wt% NaCl aqueous solution to precipitate a solid.Recover solids and dry,Recrystallization 3 times with acetonitrile,The target product (4-(9H-carbazol-9-yl)benzylidene)malononitrile was obtained.The yield was 83%.

Reference： [1]Chemistry Letters,2008,vol. 37,p. 570 - 571
[2]Patent: CN108484478,2018,A .Location in patent: Paragraph 0028; 0029; 0031
[3]Molecular Crystals and Liquid Crystals,2012,vol. 563,p. 257 - 271

9
C₃₄H₆₆O₂P₂⁽²⁺⁾*2Cl^(1-) [ No CAS ]
[ 110677-45-7 ]
C₄₁H₅₁NO₂P⁽¹⁺⁾*Cl^(1-) [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
62%	With potassium tert-butylate; In tetrahydrofuran; isopropyl alcohol; at 0 - 20℃; for 6h;	4.0 g (0.01474 mol) of the 4(9H-carbazole-9-yl)benzaldehyde and 14.1 g (1.5 eq., 0.02211 mol) of Wittig Salt VI [5] were added to a mixture of 150 ml dry THF and 250 ml IPA under N2. The solution was cooled to 0 C., and 16.5 ml (1.1 eq., 0.01621 mol) of 1 M t-Bu3O-K+ were added drop-wise. The temperature was allowed to rise slowly to 20 C., and the reaction was stirred for 6 hours. After removing most of the solvent, 250 ml CH2Cl2 were added. The solution was washed with 3×50 ml H2O and 1×50 ml brine, dried with MgSO4, and evaporated, leaving a thick, yellow slurry that was purified through a short silica gel column eluting with CH2Cl2 followed by 85% CH2Cl2/15% MeOH. The total yield of the intermediate product, Wittig Salt VII, was 6.25 g or 62%.1H NMR (500 MHz, CDCl3), δ 8.13 (d, J=7.5 Hz, 2H), 7.76 (d, J=7.5 Hz, 2H), 7.55-7.04 (m, 12H), 4.10 (d, J=24 Hz, 2H), 3.90 (s, 6H), 2.40 (t, J=11 Hz, 6H), 1.44 (m, 12H), 0.90 (t, J=11 Hz, 9H)

Reference： [1]Patent: US2009/43109,2009,A1 .Location in patent: Page/Page column sheet 6; 12-13

10
[ 86-74-8 ]
[ 15164-44-0 ]
[ 110677-45-7 ]

Yield	Reaction Conditions	Operation in experiment
25%	With copper(I) oxide; In N,N-dimethyl acetamide; at 190℃; for 72h;	A DMAc solution (60 mL) of 4-iodobenzaldehyde (3.48 g,15.00 mmol), carbazole (3.01 g, 18.00 mmol), and copper(I) oxide (2.57 g, 18.00 mmol) was stirred at 190 Cfor 3 days. After cooling to room temperature, the productmixture was washed with water. After removal ofthe organic solvent, the residue was purified by columnchromatography on silica gel using methylene chlorideand n-hexane (1:5, v/v) as an eluent. Further purificationwas performed by precipitation in n-hexane to obtain1 as a light yellow solid. Yield (1.02 g, 25%). mp160-162 C. 1H NMR (400 MHz, DMSO-d6) 7.33(t, 2 H, -Ph-carbazole), 7.46 (t, 3 H, -Ph-carbazole),7.52 (d, 2 H, -Ph-carbazole), 7.91 (d, 2 H, -carbazole-Ph), 8.20 (d, 2 H, -carbazole-Ph), 8.27 (d, 2 H, -Ph-carbazole), 10.12 (s, 1 H, -Ph-CHO); 13C NMR(100.64 MHz, DMSO-d6) 100.86, 120.67, 120.78,123.24, 126.53, 126.72, 131.41, 134.58, 139.45, 142.20,192.23.

Reference： [1]European Journal of Organic Chemistry,2008,p. 1065 - 1071
[2]Chemical Communications,2010,vol. 46,p. 1088 - 1090
[3]New Journal of Chemistry,2013,vol. 37,p. 3252 - 3260
[4]RSC Advances,2015,vol. 5,p. 41193 - 41202
[5]Journal of Nanoscience and Nanotechnology,2015,vol. 15,p. 1434 - 1442
[6]Dalton Transactions,2009,p. 10592 - 10600
[7]Journal of Materials Chemistry C,2020,vol. 8,p. 9916 - 9922

11
[ 110677-45-7 ]
[ 601454-30-2 ]

Reference： [1]Chemistry - A European Journal,2010,vol. 16,p. 13127 - 13138
[2]New Journal of Chemistry,2021,vol. 45,p. 2141 - 2146
[3]European Journal of Organic Chemistry,2008,p. 1065 - 1071
[4]Chemical Communications,2010,vol. 46,p. 1088 - 1090
[5]Journal of Organic Chemistry,2010,vol. 75,p. 2578 - 2588

12
[ 372-09-8 ]
[ 110677-45-7 ]
[ 1199945-09-9 ]

Yield	Reaction Conditions	Operation in experiment
58%	With piperidine; In acetonitrile; at 80℃; for 6h;Inert atmosphere;	Compound 1 (271 mg, 1.0 mmol), 2-cyanoaceticacid (126 mg, 1.50 mmol), piperidine (0.1 mL, 1.0 mmol) werestirred in dry acetronitrile (20 mL) and the solution was heated at80 C for 6 h under N2. After cooling to room temperature, solventswere removed by rotary evaporation, and the residue was purifiedby silica gel column chromatography with CH2Cl2: CH3OH (v: v, 10:1) as eluent to afford D1 as yellow solids (196 mg, 58%). M.p.207e208 C. 1H NMR (500 MHz, DMSO-d6, ppm): d 8.49 (s, 1H),8.36 (d, J 8.6 Hz, 2H), 8.28 (d, J 7.7 Hz, 2H), 7.92 (d, J 8.6 Hz,2H), 7.56 (d, J 8.3 Hz, 2H), 7.48 (t, J 7.1 Hz, 2H), 7.34 (t, J 7.0 Hz,2H). 13C NMR (126 MHz, DMSO-d6, ppm): d 140.08,139.34,138.47,131.59, 130.39, 126.11, 125.79, 123.01, 120.83, 120.18, 119.87, 116.78,109.32, 107.32, 109.72, 96.08, 85.46. Anal. Calcd. for C22H14N2O2: C78.09, H 4.17, N 8.28. Found: C 78.26, H 4.29, N 8.45. HRMS (ESI, m/z): [MH] calcd. for C22H13N2O2, 337.0983; found, 339.1036.

Reference： [1]Organic Letters,2009,vol. 11,p. 5542 - 5545
[2]RSC Advances,2015,vol. 5,p. 86191 - 86198
[3]Dyes and Pigments,2016,vol. 134,p. 498 - 505

13
[ 51044-13-4 ]
[ 110677-45-7 ]
[ 916060-59-8 ]
[ 1019779-50-0 ]

Yield	Reaction Conditions	Operation in experiment
	With potassium tert-butylate; In tetrahydrofuran; at 20℃;Inert atmosphere;	[Step 2; Synthesis of (E)-4-bromo-4'-(9H-carbazol-9-yl)stilbene] Next, 9.44 g (18.4 mmol) of 4-bromobenzyl triphenylphosphonium bromide obtained in Step 1 and 5.00 g (18.4 mmol) of <strong>[110677-45-7]4-(9H-carbazol-9-yl)benzaldehyde</strong> were placed into a 300 mL three-neck flask, and nitrogen substitution was carried out in the three-neck flask. Then, 50 mL of tetrahydrofuran (THF) was added thereto. A suspension in which 2.07 g (18.4 mmol) of potassium tert-butoxide was mixed in 50 mL of THF was dropped into this mixture. After the completion of the dropping, the reaction mixture was stirred at room temperature for 24 hours. After the completion of the reaction, water was added to the reaction mixture, and the precipitate was collected by suction filtration. 4.41 g of a yellow powdered solid, (E)-4-bromo-4'-(9H-carbazol-9-yl)stilbene, which was the target substance, was obtained in a yield of 56.4%. It was confirmed that (Z)-4-bromo-4'-(9H-carbazol-9-yl)stilbene which is an isomer of the target substance was included in the obtained filtrate. A synthetic scheme (a-2) of (E)-4-bromo-4'-(9H-carbazol-9-yl)stilbene is shown below.

Reference： [1]Patent: US7732619,2010,B2 .Location in patent: Page/Page column 80

14
[ 57102-42-8 ]
[ 33513-42-7 ]
[ 110677-45-7 ]

Yield	Reaction Conditions	Operation in experiment
72.58%		Preparation of compound 2-2 [95] The compound 2-1(18 g, 55.86 mmol) was dissolved in THF (200 mL) and n-buLi (24.58 mL, 61.45 mmol, 2.5 M in Hexane) was slowly added thereto at -78C. 1 hours later, DMF (5.6 mL, 72.65 mmol) was added and the mixture was stirred for 12 hours at room temperature. Distilled water was added thereto and the product was extracted with EA. After drying with MgSO4 and distilling under reduced pressure, a compound 2-2 (11 g, 40.54 mmol, 72.58 %) was given by column separation.
51%		To a solution of 0.90 g 9-(4-bromo-phenyl)-9H-carbazole (1) (2.8 mmol) in 30 ml anhydrous Et2O was added 1.34 ml of 2.5 M n-BuLi in hexane (3.4 mmol) at -78 C under nitrogen atmosphere. After the reaction mixture was warmed to 0 C, 0.26 ml DMF(3.4 mmol) was added at -78 C. The resulting mixture was allowed to warm to room temperature and stirred at room temperature overnight. Then the mixture was poured into ice water and 5% HCl (aq.) (5 ml) was added and the two layers were separated. The aqueous layer was extracted with Et2O (3 × 20 ml) and the combined organic layer was washed with brine (15 ml), dried with MgSO4 and evaporated under reduced pressure, a yellow power was obtained by crystallized from ethanol (0.39 g, yield:51%). m.p. 148-150 C refPreviewPlaceHolder[31]. 1H NMR (300 MHz, CDCl3) δppm 10.12-10.20 (s, 1H), 8.12-8.16 (m, 4H), 7.78-7.86 (d, 2H), 7.49-7.63 (d, 2H), 7.32-7.44 (t, 2H), 7.19-7.30 (t, 2H). MS(M+) 271.0997. Anal. Calc. for C19H13ON: C, 84.13%; H, 4.80%; N, 5.17%. Found: C, 84.40%; H, 4.77%; N, 5.12%.

Reference： [1]Patent: WO2011/55911,2011,A1 .Location in patent: Page/Page column 15
[2]Spectrochimica Acta Part A: Molecular and Biomolecular Spectroscopy,2011,vol. 81,p. 730 - 738

15
[ 86-74-8 ]
[ 110677-45-7 ]

Yield	Reaction Conditions	Operation in experiment
69%	With copper(l) iodide; 18-crown-6 ether; potassium carbonate; In 1,2-dichloro-benzene; at 180℃; for 48h;Schlenk technique; Inert atmosphere;	The compound 8 was synthesized as described inliterature.24 In a typical reaction, 249.4 mg (1.5 mmol) of 9H-carbazole, 283.2 mg (1.5 mmol) of 4-bromobenzaldehyde,58.0 mg (0.22 mmol) of 18-crown-6, 303.9 mg (2.2 mmol)of K2CO3, 42.3 mg (15 mmol%) CuI and 1.5 mL of o-dichlorobenzene were added to a 10 mL Schlenk tube. The mixture was refluxed under nitrogen atmosphere at 180 C for 48 h. After, the reaction was quenched with aqueous 20% HCl and extracted with chloroform. The organic phase was dried with anhydrous Na2SO4 and concentrated under vacuum. The product was purified by silica flash column chromatography(mobile phase: ethyl acetate/hexane 5%). The compound 8 was obtained as a white solid in 69% yield. 1H NMR (400 MHz,DMSO-d6) δ 10.14 (s, 1H), 8.28 (d, J 7.67 Hz, 2H), 8.21 (d,J 8.35 Hz, 2H), 7.92 (d, J 8.32 Hz, 2H), 7.53 (d, J 8.32 Hz,2H), 7.47 (t, J 7.63 Hz, 2H), 7.34 (t, J 7.38 Hz, 2H); 13C NMR(100 MHz, DMSO-d6) δ 193.1, 143.1, 140.4, 135.5, 132.3,127.6, 127.4, 124.2, 121.7, 121.6, 110.8; infrared (IR)(attenuated total reflectance, ATR) ν / cm-1 3050, 2824, 2743,1702, 1595, 1510, 1479, 1450, 1361, 1336, 1198, 1161, 1123,1103, 916, 830, 749, 720, 633, 620, 567, 529, 502.

Reference： [1]Journal of the Brazilian Chemical Society,2019,vol. 30,p. 81 - 89
[2]Patent: WO2011/55911,2011,A1
[3]Spectrochimica Acta Part A: Molecular and Biomolecular Spectroscopy,2011,vol. 81,p. 730 - 738
[4]Dalton Transactions,2014,vol. 43,p. 11305 - 11308

16
[ 38875-53-5 ]
[ 110677-45-7 ]
[ 1301187-38-1 ]

Yield	Reaction Conditions	Operation in experiment
28.07%	In dimethyl sulfoxide; at 200℃; for 12h;	Preparation of compound 2-3 [97] After the compound 2-2(11 g, 40.54 mmol), and 5-bromopyridine-2,3-diamine (7.6 g, 40.54 mmol) were dissolved in DMSO (200 mL),the mixture was heated at 200C for 12 hours. After cooling to room temperature, the product was washed with distilled water and extracted with EA. After drying with MgSO4 and distilling under reduced pressure, acompound 2-3 (5 g, 11.38 mmol, 28.07 %) was given by column separation.

Reference： [1]Patent: WO2011/55911,2011,A1 .Location in patent: Page/Page column 15

17
[ 120-75-2 ]
[ 110677-45-7 ]
[ 1338711-70-8 ]

Yield	Reaction Conditions	Operation in experiment
75%		Under nitrogen, to a solution of 0.16 ml (1.2 mmol) of 2-methylbenzothiazole in 10 ml of anhydrous THF at -78 C was added dropwise, 0.56 ml (1.4 mmol) of 2.5 M n-BuLi in hexane. The mixture was stirred at -78 C for 30 min, then 0.27 g (1.0 mmol) of <strong>[110677-45-7]4-(9H-carbazol-9-yl)benzaldehyde</strong> in 5 ml of anhydrous THF was added dropwise. The reaction was stirred at -78 C for 1 h, then allowed to warm to ambient temperature and stirred overnight. Next, 0.20 ml of acetic acid was added, and the mixture was diluted with 50 ml of CH2Cl2. The solution was dried over MgSO4, filtered, and concentrated in vacuo. A yellow power was obtained by recyrstallized from ethanol. (0.38 g, yield: 75%). m.p. 176.5-178 C. 1H NMR (300 MHz, CDCl3) δppm 7.88-7.94 (d, 2H), 7.70-7.72 (d, 1H), 7.52-7.59 (d, 1H), 7.50-7.51 (d, 2H), 7.40-7.43 (m, 2H), 7.27-7.30 (m, 6H), 7.26 (m, 2H), 5.44-5.46 (m, 1H), 3.55-3.57 (m, 2H), 2.84-2.85 (s, 1H). MS(M+) 420.1356. Anal. Calc. for C27H20N2OS: C, 77.12%; H, 4.79%; N, 6.66%. Found: C, 77.20%; H, 4.84%; N, 6.72%.

Reference： [1]Spectrochimica Acta Part A: Molecular and Biomolecular Spectroscopy,2011,vol. 81,p. 730 - 738

18
[ 137-07-5 ]
[ 110677-45-7 ]
[ 664995-52-2 ]

Yield	Reaction Conditions	Operation in experiment
86%	In dimethyl sulfoxide; at 120℃; for 12h;	A mixture of the corresponding 0.41 g <strong>[110677-45-7]4-(9H-carbazol-9-yl)benzaldehyde</strong> (2) (1.50 mmol), 0.20 ml 2-aminothiophenol (1.87 mmol), and 30 ml DMSO was heated in an oil bath to 120 C, held at that temperature for 12 h, then poured into water and extracted with CH2Cl2 (3 × 10 ml). The combined organic layer was dried with anhydrous Na2SO4 and evaporated to dryness. The crude compound was stirred for 15 min in 30 ml of boiling ethanol, then the solution was cooled, and the pure product was isolated by filtration. (0.48 g, yield: 86%). m.p. 190-193 C. 1H NMR (300 MHz, CDCl3) δppm 8.11-8.17 (m, 2H), 7.82-7.97 (m, 4H), 7.72-7.75 (d, 2H), 7.50-7.59 (d, 2H), 7.41-7.46 (d, 2H), 7.25-7.34 (m, 4H). MS(M+) 376.1382. Anal. Calc. for C25H16N2S: C, 79.78%; H, 4.26%; N, 7.45%. Found: C, 80.02%; H, 4.12%; N, 7.27%.
80%	In 1-methyl-pyrrolidin-2-one; at 110℃; for 48h;Inert atmosphere;	Compound 1b (1.37 g, 5 mmol), 2-aminothiophenol (0.55 mL, 5 mmol)And NMP (10 mL) were heated in an oil bath at 110 C for 48 hours,It was then poured into 1: 1 ethanol / water.The precipitate was collected and recrystallized from ethanol to obtain compound 2b in a yield of 80%.
65.6%	In dimethyl sulfoxide; at 150 - 160℃; for 3.5h;	A mixture of <strong>[110677-45-7]4-(9H-carbazol-9-yl)benzaldehyde</strong> (1.626g, 6mmol), 2-aminothiophenol (0.825g, 6.6mmol) and DMSO (24mL) was heated to 150-160C in oil bath for 3.5h. The mixture was cooled to RT and poured into sodium chloride aqueous solution and then the resulting precipitate was filtered. The light-yellow crystal was obtained after recrystallization with ethyl acetate as solvent. Yield: 65.6%. Mp: 223.3-223.6C. MS (ESI): m/z 377.3 [M+H+]. 1H NMR (500MHz, CD2Cl2, TMS):δ 8.39 (d, J=8.5Hz, 2H), 8.20 (d, J=7.5Hz, 2H), 8.14 (d, J=8.5Hz, 1H), 8.01 (d, J=8.0Hz, 1H), 7.78 (d, J=8.5Hz, 2H), 7.59-7.55 (t, 3H), 7.49-7.46 (m, 3H), 7.36-7.33 (t, 2H); 13C NMR (125MHz, CD2Cl2, TMS): 166.91, 154.04, 140.48, 140.22, 135.15, 132.22, 129.05, 127.19, 126.52, 126.15, 125.45, 123.67, 123.15, 121.77, 120.38, 120.30, 109.83.

Reference： [1]Journal of Materials Chemistry C,2014,vol. 2,p. 5709 - 5716
[2]Spectrochimica Acta Part A: Molecular and Biomolecular Spectroscopy,2011,vol. 81,p. 730 - 738
[3]Patent: CN110845489,2020,A .Location in patent: Paragraph 0042; 0046-0047; 0056; 0060-0061
[4]Dyes and Pigments,2014,vol. 106,p. 51 - 57

19
[ 110677-45-7 ]
4-(2-benzothiazolyl)-benzyl triphenyl phosphonium bromide [ No CAS ]
[ 1338711-69-5 ]

Yield	Reaction Conditions	Operation in experiment
24%		Under nitrogen atmosphere, a stirred slurry of 1.00 g 4-(2-benzothiazolyl)-benzyl triphenyl phosphonium bromide (1.77 mmol) in 30 ml anhydrous THF was cooled to -78 C, 0.70 ml of 2.5 M n-BuLi in hexane (1.77 mmol) was added and the mixture was warmed to room temperature over 2 h. Then a solution of 0.48 g <strong>[110677-45-7]4-(9H-carbazol-9-yl)benzaldehyde</strong> (2) (1.77 mmol) in 10 ml THF was added dropwise with vigorous stirring at -78 C. The reaction was warmed to room temperature and stirred for 12 h. Then the THF was evaporated at reduced pressure and the residue was separated by column chromatography (petroleum ether/methylene chloride 1:3) to give a yellow power.(0.20 g, yield: 24%). m.p. 263-265 C. 1H NMR (300 MHz, CDCl3): δppm 8.11-8.13 (m, 1H), 7.94-7.82 (m, 1H), 7.69-7.71 (m, 2H), 7.60-7.62 (m, 4H), 7.51-7.53 (d, 2H), 7.42-7.45 (d, 2H), 7.38-7.40 (m, 2H), 7.26-7.36 (d, 2H), 7.21-7.24 (m, 4H), 7.15-7.18 (m, 2H). MS(M+): 478.1528. Anal. Calc. for C33H22N2S: C, 82.85%; H, 4.60%; N, 5.86%. Found: C, 82.91%; H, 4.58%; N, 5.77%.

Reference： [1]Spectrochimica Acta Part A: Molecular and Biomolecular Spectroscopy,2011,vol. 81,p. 730 - 738

20
[ 110677-45-7 ]
[ 173443-43-1 ]
[ 1395880-55-3 ]

Reference： [1]Chemical Communications,2012,vol. 48,p. 9011 - 9013,3

21
[ 62-53-3 ]
[ 84-11-7 ]
[ 110677-45-7 ]
[ 1335137-46-6 ]

Yield	Reaction Conditions	Operation in experiment
75%	With ammonium acetate; acetic acid; for 2h;Inert atmosphere; Reflux;	Synthesis of (2-(4-(9H-carbazol-9-yl)phenyl)-1-phenyl-1H-phenanthro[9,10-d]imidazole (M1): a mixture of <strong>[110677-45-7]4-(9H-carbazol-9-yl)benzaldehyde</strong> (1.00 g, 3.70 mmol), phenanthrene-9,10-dione (767.50 mg, 3.70 mmol), aniline (0.85 g, 18.50 mmol), ammonium acetate (1.14 g, 14.80 mmol), and acetic acid (10 mL) were refluxed under nitrogen in an oil bath. After 2 h, the mixture was cooled and filtered. The solid product was washed with an acetic acid/water mixture (1:1, 150 mL) and water. It was then purified by chromatography using CH2Cl2/petroleum ether (1:1) as eluent to obtain the product as white powder. Yield: 75%. 1H NMR (500 MHz, DMSO, δ): 8.96 (d, J = 8.30 Hz, 1H), 8.91 (d, J = 8.45 Hz, 1H), 8.74 (d, J = 7.36 Hz, 1H), 8.26 (d, J = 7.83 Hz, 2H), 7.89 (d, J = 8.22 Hz, 2H), 7.84-7.76 (m, 6H), 7.73 (t, J = 7.50 Hz, 6.43 Hz, 1H), 7.66 (d, J = 7.94 Hz, 2H), 7.59 (t, J = 6.97 Hz, 7.68 Hz, 1H), 7.46 (t, J = 7.50 Hz, 7.14 Hz, 2H), 7.40 (d, J = 8.61 Hz, 2H), 7.38 (t, J = 7.68 Hz, 7.68 Hz, 1H), 7.32 (t, J = 7.68 Hz, 7.68 Hz, 2H), 7.11 (d, J = 8.47 Hz, 1H); 13C NMR (500 MHz, CDCl3, Hz): 140.53, 130.80, 130.40, 130.14, 129.15, 128.39, 127.42, 126.61, 126.39, 126.02, 124.19, 123.57, 123.18, 120.91, 120.35, 120.20, 109.78; FTIR (KBr, ν, cm-1) 3058, 1625, 1532, 1475, 1451, 1429, 1378, 1358, 1241, 1225, 1174, 1147, 1111, 1018, 1004, 929, 844, 750, 724, 667, 620, 563, 535; MALDI-TOF (m/z): [M+] calcd for C39H25N3: 535.64; Found: 535.90. Anal. calcd for C39H25N3: C 87.45, H 4.70, N 7.84; Found: C 87.45, H 4.66, N 8.03.
75%	With ammonium acetate; acetic acid; at 120℃; for 2h;Inert atmosphere;	A mixture of<strong>[110677-45-7]4-(9H-carbazol-9-yl)benzaldehyde</strong> (1.00 g,3.70 mmol),phenanthrene-9,10-dione (767.50 mg,3.70 mmol), aniline(0.85 g,18.50 mmol), ammonium acetate (1.14 g,14.80 mmol), and acetic acid (10 mL) were refluxed undernitrogen in an oil bath. After 2 h, the mixture was cooledand filtered. The solid product was washed with an aceticacid/water mixture (1:1,150 mL) and water. It was thenpurified by chromatography using CH2Cl2/petroleum ether(1:1) as eluent to obtain the product as white powder.Yield: 75%. 1H NMR (500 MHz, DMSO, d): 8.96 (d, J =8.30 Hz, 1H), 8.91 (d, J = 8.45 Hz, 1H), 8.74 (d, J = 7.36 Hz,1H), 8.26 (d, J = 7.83 Hz, 2H), 7.89 (d, J = 8.22 Hz, 2H),7.84-7.76 (m,6H), 7.73 (t, J = 7.50 Hz, 6.43 Hz, 1H), 7.66(d, J = 7.94 Hz, 2H), 7.59 (t, J = 6.97 Hz, 7.68 Hz, 1H), 7.46(t, J = 7.50 Hz, 7.14 Hz, 2H), 7.40 (d, J = 8.61 Hz, 2H), 7.38(t, J = 7.68 Hz, 7.68 Hz, 1H), 7.32 (t, J = 7.68 Hz, 7.68 Hz,2H), 7.11 (d, J = 8.47 Hz, 1H); 13C NMR (500 MHz, CDCl3,Hz): 140.53, 130.80, 130.40, 130.14, 129.15, 128.39,127.42, 126.61, 126.39, 126.02, 124.19, 123.57, 123.18,120.91, 120.35, 120.20, 109.78; FTIR (KBr, m, cm1) 3058,1625, 1532, 1475, 1451, 1429, 1378, 1358, 1241, 1225,1174, 1147, 1111, 1018, 1004, 929, 844, 750, 724, 667,620, 563, 535; MALDI-TOF (m/z): [M+] calcd for C39H25N3:535.64; Found: 535.90. Anal. calcd for C39H25N3: C 87.45,H 4.70, N 7.84; Found: C 87.45, H 4.66, N 8.03.

Reference： [1]Chemistry - A European Journal,2013,vol. 19,p. 2602 - 2605
[2]Organic electronics,2014,vol. 15,p. 2667 - 2676
[3]Organic electronics,2014,vol. 15,p. 2667 - 2676

22
[ 98-86-2 ]
[ 110677-45-7 ]
C₂₇H₁₉NO [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
65%	With sodium hydroxide; In ethanol; at 20℃; for 12h;	The a (217mg, 0.8mmol), acetophenone (0.8mmol), NaOH (40mg, 1mmol) placed in a single neck flask 25mL, 10mL of absolute ethanol was added, stirred at room temperature 12h, TLC monitoring, the majority of starting material spot disappeared, stop reaction. The solvent was evaporated, the remaining solid was washed with water until neutral, dried and separated by column chromatography to give B as a yellow solid, yield 65%.

Reference： [1]Patent: CN102382037,2016,B .Location in patent: Paragraph 0082; 0083
[2]Chemistry - An Asian Journal,2016,vol. 11,p. 1572 - 1587
[3]Bioorganic and Medicinal Chemistry Letters,2013,vol. 23,p. 6217 - 6222

23
[ 14727-71-0 ]
[ 62-53-3 ]
[ 110677-45-7 ]
5,11-bis(4-(9H-carbazol-9-yl)phenyl)-4,10-diphenyl-4,10-dihydropyreno[4,5-d:9,10-d']diimidazole [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
45%	With ammonium acetate; acetic acid for 2h; Inert atmosphere; Reflux;

Reference： [1]Liu, Yulong; Gao, Zhao; Wang, Zhiming; Feng, Cunfang; Shen, Fangzhong; Lu, Ping; Ma, Yuguang [European Journal of Organic Chemistry, 2013, # 32, p. 7267 - 7271]

24
[ 110677-45-7 ]
[ 71935-21-2 ]

Yield	Reaction Conditions	Operation in experiment
53.7%	With dihydrogen peroxide; sodium hydroxide; In 1,4-dioxane; at 0 - 100℃; for 14h;	A portionof compound 2 (0.061 g, 0.220 mmol), hydrogen peroxide(0.5 mL, 0.220 mmol) and sodium hydroxide (0.009 g, 0.220mmol) was dissolved in 1 mL of dioxane and the mixturewas stirred for 2 h at 0 oC. Then the reaction mixture washeated up to 100 oC and stirred for 12 h. The reactionmixture was cooled down the room temperature and filtered.The filtrate was adjusted to pH 2 with HCl solution, andfiltered again. The crude residue was purified by recrystallizationusing n-hexane. The yield of the yellowish white solidwas 0.034 g (53.7%). mp 213.0 oC. 1H-NMR (400 MHz,MeOH-d3) 8.31-8.28 (d, J = 8.80 Hz, 2H), 8.15-8.13 (d, J= 7.68 Hz, 2H), 7.72-7.69 (d, J = 8.44 Hz, 2H), 7.47-7.38(m, 4H), 7.29-7.26 (t, J = 7.68 Hz, 2H). Anal. Calcd. ForC19H13NO2: C, 79.43; H, 4.56; N, 4.88; O, 11.14. Found: C,79.82; H, 4.47; N, 4.79.

Reference： [1]Bulletin of the Korean Chemical Society,2014,vol. 35,p. 569 - 574

25
[ 100-06-1 ]
[ 110677-45-7 ]
[ 1367364-35-9 ]

Yield	Reaction Conditions	Operation in experiment
51%	With sodium hydroxide; In ethanol; at 20℃; for 12h;	The 4- (9- (9H- carbazol-yl)) benzaldehyde (217mg, 0.8mmol), 1- (4- methoxyphenyl) ethanone (0.8mmol),NaOH (40mg, 1mmol) placed in a single neck flask 25mL, 10mL of absolute ethanol was added, stirred at room temperature 12h,Monitored by TLC the disappearance of most of the spot of the material, the reaction was stopped. The solvent was evaporated, the remaining solid was washed with water until neutral,Drying, column chromatography, a yellow solid a, yield 51%

Reference： [1]Patent: CN102382037,2016,B .Location in patent: Paragraph 0097; 0098
[2]ChemMedChem,2014,vol. 9,p. 918 - 921

26
[ 122-00-9 ]
[ 110677-45-7 ]
[ 1367364-37-1 ]

Yield	Reaction Conditions	Operation in experiment
57%	With sodium hydroxide; In ethanol; at 20℃; for 12h;	The 4-(9-(9H-carbazolyl)) benzaldehyde (217 mg, 0 . 8mmol), 1-(4-methyl phenyl) ethanone (0.8mmol), NaOH (40 mg, 1mmol) in 25 ml single-port the bottle, by adding 10 ml anhydrous ethanol, stirring the mixture at room temperature for 12h, TLC monitoring, most of the point of disappearance of the raw materials, to stop the reaction. Evaporate the solvent, the remaining solid washing with water to neutral, drying, column chromatography separation, a to get the yellow solid, yield 57%.

Reference： [1]Patent: CN102382037,2016,B .Location in patent: Paragraph 0117; 0118
[2]ChemMedChem,2014,vol. 9,p. 918 - 921

27
[ 403-42-9 ]
[ 110677-45-7 ]
[ 1367364-39-3 ]

Yield	Reaction Conditions	Operation in experiment
54%	With sodium hydroxide; In ethanol; at 20℃; for 12h;	The 4-(9-(9H-carbazolyl)) benzaldehyde (217 mg, 0 . 8mmol), 1-(4-fluoro-phenyl) ethanone (0.8mmol), NaOH (40 mg, 1mmol) in 25 ml single-port the bottle, by adding 10 ml anhydrous ethanol, stirring the mixture at room temperature for 12h, TLC monitoring, most of the point of disappearance of the raw materials, to stop the reaction. Evaporate the solvent, the remaining solid washing with water to neutral, drying, column chromatography separation, a to get the yellow solid, yield 54%.

Reference： [1]Patent: CN102382037,2016,B .Location in patent: Paragraph 0129; 0130
[2]ChemMedChem,2014,vol. 9,p. 918 - 921

28
[ 92-91-1 ]
[ 110677-45-7 ]
[ 1367364-41-7 ]

Yield	Reaction Conditions	Operation in experiment
73%	With sodium hydroxide; In methanol; at 20℃; for 12h;	The 4- (9- (9Η-P P sat specifically yl)) benzoic acid (217mg, 0 8mmol.), 4,4 '- phenethyl-linked pay (0 · 8mmol), Na0H (40mg, lmmol) placed in 25mL single neck flask was added 10mL of anhydrous ethanol, stirred at room temperature 12h, TLC monitoring, the majority of starting material spot disappeared, the reaction was stopped. The solvent was evaporated, the remaining solid was washed with water until neutral, dried and separated by column chromatography to give a yellow solid a, yield 73%

Reference： [1]Patent: CN102382037,2016,B .Location in patent: Paragraph 0141; 0142
[2]ChemMedChem,2014,vol. 9,p. 918 - 921

29
[ 941-98-0 ]
[ 110677-45-7 ]
[ 1367364-45-1 ]

Yield	Reaction Conditions	Operation in experiment
68%	With sodium hydroxide; In ethanol; chloroform; at 20℃;	The 816 mg (4.8mmol) α- acetonaphthone , 240 mg (6mmol) sodium hydroxide in 100 ml of water, adding 6 ml ethanol, 12 drip enable its dissolution. The 1302 mg (4.8mmol) 4-(9-(9H-carbazolyl)) benzaldehyde dissolved in 18 ml in chloroform, in the above-mentioned is dripped into the ethanol solution, stirring the mixture at room temperature for overnight, to stop the reaction. Overhanging organic solvent, water and dilute, dichloromethane extraction, drying, recrystallized (petroleum ether: ethyl acetate = 15 the [...] 1), to get the yellow cluster crystal a1.37g, yield = 68%.

Reference： [1]Patent: CN102382037,2016,B .Location in patent: Paragraph 0174; 0175
[2]ChemMedChem,2014,vol. 9,p. 918 - 921

30
[ 38861-78-8 ]
[ 110677-45-7 ]
[ 1367364-56-4 ]

Yield	Reaction Conditions	Operation in experiment
66%	With sodium hydroxide; In ethanol; dichloromethane; water; at 20℃;	The 528mg (3mmol) 4- isobutyl acetophenone, 160mg (4mmol) sodium hydroxide was placed in 100mL single jarWas added 10 drops of water, 20 mL of ethanol and dissolved; the 813mg (3mmol) 4- (9- (9H- carbazolyl)) benzoateAldehyde was dissolved in 10mL of dichloromethane, ethanol and added dropwise to the mixture, stirred at room temperature overnight, filtered, ethanol, washed with petroleum ether, and dried to give a pale yellow solid (LJZ-5-13) 851mg, Yield = 66% .

Reference： [1]Patent: CN102382037,2016,B .Location in patent: Paragraph 0239; 0240
[2]ChemMedChem,2014,vol. 9,p. 918 - 921

31
[ 30492-50-3 ]
[ 110677-45-7 ]
[ 1367364-64-4 ]

Yield	Reaction Conditions	Operation in experiment
58%	With sodium hydroxide; In ethanol; dichloromethane; water; at 20℃; for 6h;	The 786mg (3mmol) 3,5- di-tert-butyl-4-methoxyacetophenone, 160mg (4mmol) of sodium hydroxide is placed100mL single-mouth bottle, add 10 drops of water, 20mL ethanol and dissolved; the 813mg (3mmol) 4- (9- (9H-Carbazol-yl)) benzaldehyde was dissolved in 10mL of dichloromethane, ethanol and added dropwise to the mixture, stirred at room temperature 6h,Filtered, ethanol, washed with petroleum ether, and dried to give a khaki solid (LJZ-5-1) 890mg, yield = 58%.

Reference： [1]Patent: CN102382037,2016,B .Location in patent: Paragraph 0263; 0264
[2]ChemMedChem,2014,vol. 9,p. 918 - 921

32
[ 5731-01-1 ]
[ 110677-45-7 ]
[ 1610365-57-5 ]

Reference： [1]ChemMedChem,2014,vol. 9,p. 918 - 921

33
[ 30071-93-3 ]
[ 110677-45-7 ]
[ 1367364-65-5 ]

Yield	Reaction Conditions	Operation in experiment
63%	With potassium hydroxide; In ethanol; dichloromethane; water; at 20℃;	The 768mg (3mmol) 3,5- two trifluoromethyl acetophenone, 160mg (4mmol) sodium hydroxide was placed in 100mLSingle neck flask was added 10 drops of water, 20 mL of ethanol and dissolved; the 813mg (3mmol) 4- (9- (9H- carbazoleYl)) benzaldehyde was dissolved in 10mL of dichloromethane, ethanol and added dropwise to the mixture, stirred overnight at room temperature, overFiltered, ethanol, washed with petroleum ether, and dried to give a yellow solid (LJZ-5-31) 956mg, Yield = 63%.

Reference： [1]Patent: CN102382037,2016,B .Location in patent: Paragraph 0287; 0288
[2]ChemMedChem,2014,vol. 9,p. 918 - 921

34
[ 54916-28-8 ]
[ 110677-45-7 ]
[ 1367364-67-7 ]

Yield	Reaction Conditions	Operation in experiment
92%	With sodium hydroxide; In ethanol; dichloromethane; water; at 20℃;	The 726mg (3mmol) 4- methoxy-4'-diphenyl ether, 160mg (4mmol) of sodium hydroxide in 100mL single-neck flask, add 10 drops of water, 20mL ethanol and dissolved; the 813mg (3mmol) 4- (9- (9H-Carbazol-yl)) benzaldehyde was dissolved in 10mL of dichloromethane, ethanol and added dropwise to the mixture, stirred at room temperature overnight, filtered, ethanol, washed with petroleum ether, and dried to give a yellow solid (LJZ-5-47) 1.45g , yield = 92%.

Reference： [1]Patent: CN102382037,2016,B .Location in patent: Paragraph 0311; 0312
[2]ChemMedChem,2014,vol. 9,p. 918 - 921

35
[ 2879-20-1 ]
[ 110677-45-7 ]
[ 1367364-66-6 ]

Yield	Reaction Conditions	Operation in experiment
65%	With sodium hydroxide; In ethanol; dichloromethane; water; at 20℃;	The 534mg (3mmol) 6- acetyl-1,4-benzo-dioxane, 160mg (4mmol) of sodium hydroxide in 100mL single-neck flask, add 10 drops of water, 20mL ethanol and dissolved; the 813mg (3mmol) 4- (9- (9H-Carbazol-yl)) benzaldehyde was dissolved in 10mL of dichloromethane, ethanol and added dropwise to the mixture, stirred at room temperature overnight, filtered, ethanol, washed with petroleum ether, and dried to give a pale yellow solid (LJZ-5-32) 842mg the yield was 65%.

Reference： [1]Patent: CN102382037,2016,B .Location in patent: Paragraph 0299; 0300
[2]ChemMedChem,2014,vol. 9,p. 918 - 921

36
[ 54696-05-8 ]
[ 110677-45-7 ]
[ 1367364-71-3 ]

Yield	Reaction Conditions	Operation in experiment
91%	With sodium hydroxide; In ethanol; dichloromethane; water; at 20℃; for 6h;	The 678mg (3mmol) 4- benzyloxy acetophenone, 160mg (4mmol) sodium hydroxide was placed in 100mL single jarWas added 10 drops of water, 10 mL of ethanol and dissolved; the 813mg (3mmol) 4- (9- (9H- carbazolyl)) benzoateAldehyde was dissolved in 10mL of dichloromethane, ethanol and added dropwise to the mixture, stirred at room temperature 6h, filtered, ethanol,Washed with petroleum ether and dried to give a pale yellow powder (LJZ-6-23) 1.31g, yield 91%.

Reference： [1]Patent: CN102382037,2016,B .Location in patent: Paragraph 0349; 0350
[2]ChemMedChem,2014,vol. 9,p. 918 - 921

37
[ 13679-74-8 ]
[ 110677-45-7 ]
[ 1367364-61-1 ]

Yield	Reaction Conditions	Operation in experiment
821 mg	With sodium hydroxide; In ethanol; dichloromethane; water; at 20℃;	The 420mg (3mmol) 2- methyl-5-acetyl-thiophene, 160mg (4mmol) sodium hydroxide was placed in 100mL singleNeck flask was added 10 drops of water, 20 mL of ethanol and dissolved; the 813mg (3mmol) 4- (9- (9H- carbazol-yl))Benzaldehyde was dissolved in 10mL of dichloromethane, ethanol and added dropwise to the mixture, stirred at room temperature overnight, filtered,Ethanol, washed with petroleum ether and dried to give a yellow solid (LJZ-5-14) 821mg.

Reference： [1]ChemMedChem,2014,vol. 9,p. 918 - 921
[2]Patent: CN102382037,2016,B .Location in patent: Paragraph 0251; 0252

38
[ 1150-62-5 ]
[ 33513-42-7 ]
[ 110677-45-7 ]

Yield	Reaction Conditions	Operation in experiment
55%	With trichlorophosphate; at 0 - 85℃; for 2h;Inert atmosphere;	In an ice-water bath at 0 C, 9-phenyl-9H-carbazole (2.43 g, 10 mmol),Dissolved in 25ml of anhydrous DMF solution, and slowly added 25mL of POCl3.And slowly heated the mixture to 85 C under nitrogen protection for 2h,After cooling to room temperature, the reaction mixture was poured into an ice bath and neutralized with NaOH,It was then extracted with chloroform and dried over anhydrous sodium sulfate.It was separated and purified by silica gel column chromatography, and finally the target product 1b was obtained.1.778 g of a yellow solid with a reaction yield of 55%.

Reference： [1]Dalton Transactions,2014,vol. 43,p. 11305 - 11308
[2]Patent: CN110845489,2020,A .Location in patent: Paragraph 0042-0045; 0056-0059
[3]Spectrochimica Acta Part A: Molecular and Biomolecular Spectroscopy,2018,vol. 199,p. 441 - 447

39
[ 109-97-7 ]
[ 110677-45-7 ]
[ 1621528-51-5 ]

Yield	Reaction Conditions	Operation in experiment
82%	With trifluoroacetic acid; In dichloromethane; for 1h;Inert atmosphere;	5- (4- (9-carbazolyl) phenyl) - dipyrromethane (a): To a 250mL three-necked flask, 100mL of dried methylene chloride, freshly distilled pyrrole 50mL (704 mmol) .After argon atmosphere to drain the reaction flask, was added trifluoroacetic acid (0.205mL, 0.275mmoL), magnetic stirring, trifluoroacetic acid be completely dissolved in the solution, and then dissolved in 10mL of dichloromethane was slowly added dropwise 4 - (9H- carbazole) benzaldehyde (0.500g, 1.84mmoL) solution, then stirring was continued until complete solution of the reaction 1h, after completion of the reaction, sufficient amount of saturated NaOH solution was quenched and extracted with dichloromethane, separated the organic layer was dried over anhydrous Na2SO4Dried, and then methylene chloride were evaporated under reduced pressure and excess pyrrole, the residue using silica gel column chromatography using dichloromethane as eluent, flash column chromatography, of 0.585 g of a yellow solid, yield 82.0%
52%		General procedure: Aldehyde (3 mmol) and pyrrole (30 mmol, 10 equiv) werestirred for 5 min at room temperature under N2atmosphere.After 5 min, added 0.1 equiv of TFA and allowed the reactionmixture to stir for half an hour. Completion of the reactionwas confirmed by checking TLC. Removed excess pyrroleby vacuum distillation and purified the compound bysilica gel column chromatography (DCM/hexane).
13%	With trifluoroacetic acid; In dichloromethane; for 1h;Inert atmosphere; Darkness;	<strong>[110677-45-7]4-(9H-carbazol-9-yl)benzaldehyde</strong> (0.54 g, 2 mmol) and pyrrole (0.69 mL, 10 mmol) was dissolved in 100mL of dry dichloromethane under nitrogen atmosphere. Then 65μL of trifluoroacetic acid was added in dropwise. The reaction was shielded from light and stirred for 60 min. The mixture was washed with saturated NaHCO3, water, brines and then dried over Na2SO4. The solvent was evaporated and the residue was purified by silica gel column chromatography using a mixture of dichloromethane/petroleum ether (1:1) to obtain a pale white solid 1c, 13%. 1H NMR (400 MHz, CDCl3) δ 8.15 (d, J=7.7Hz, 2H), 8.06 (s, 2H), 7.51 (t, J=10.0Hz, 2H), 7.48-7.37 (m, 6H), 7.35-7.26 (m, 2H), 6.78 (d, J=1.5Hz, 2H), 6.28-6.18 (m, 2H), 6.01 (s, 2H), 5.61 (s, 1H) ppm. 13C NMR (101 MHz, CDCl3) δ = 141.42, 140.81, 136.41, 132.17, 129.80, 127.11, 125.93, 123.37, 120.33, 119.95, 117.58, 109.80, 108.63, 107.52, 43.75ppm

Reference： [1]Patent: CN105622584,2016,A .Location in patent: Paragraph 0027; 0028
[2]New Journal of Chemistry,2021,vol. 45,p. 2141 - 2146
[3]RSC Advances,2013,vol. 3,p. 14780 - 14790
[4]Journal of Fluorescence,2017,vol. 27,p. 2131 - 2144
[5]Polyhedron,2017,vol. 127,p. 287 - 292

40
[ 95-54-5 ]
[ 110677-45-7 ]
[ 1332836-95-9 ]

Yield	Reaction Conditions	Operation in experiment
46%	With sodium dithionite; In water; N,N-dimethyl-formamide; at 20℃;Inert atmosphere;	Dissolve 1 eq (36.5 g) of intermediate a-1 and 1 eq (15.3 g) of 1,2-diaminobenzene in 300 ml of dimethylformamide (DMF), and then 1.2 eq (30.7 g) of sodium metabisulfate in 300 ml of distilled water. After dissolving, slowly drop it at room temperature under nitrogen stream. When the reaction was completed, the organic layer was dissolved in dichloromethane, and then recrystallized from acetone to obtain an intermediate a-2 (22.3g, Y=46%).

Reference： [1]Patent: KR102129510,2020,B1 .Location in patent: Paragraph 0263-0264; 0266
[2]Luminescence,2014,vol. 29,p. 540 - 548

41
[ 140-29-4 ]
[ 110677-45-7 ]
(Z)-3-(-4-(9H-carbazol-9-yl)phenyl)-2-phenylacrylonitrile [ No CAS ]

Reference： [1]CrystEngComm,2019,vol. 21,p. 6604 - 6612
[2]New Journal of Chemistry,2014,vol. 38,p. 5736 - 5746
[3]Journal of Materials Chemistry C,2021,vol. 9,p. 12681 - 12693

42
[ 2065-66-9 ]
[ 110677-45-7 ]
[ 52913-19-6 ]

Yield	Reaction Conditions	Operation in experiment
78%	With potassium tert-butylate; In tetrahydrofuran; at 20℃;Inert atmosphere;	A THF solution (40 mL) of 1 (0.81 g, 3.00 mmol)was added to a THF solution of potassium tert-butoxide(3.60 mL, 3.60 mmol) and methyl triphenyl phosphoniumiodide (1.46 g, 3.60 mmol). The solution was then stirredat room temperature for 4 h under nitrogen. The solutionwas poured into methylene chloride and washed withdistilled water. The organic layer was purified by columnchromatography on silica gel using n-hexane as an eluent.After removal of the solvent, the residue was precipitatedin methanol to give 2 as a white solid. Yield (630 mg,78%). mp 120-122 C. 1H NMR (400 MHz, DMSO-d6) 5.38 (d, 1 H, -CH CH2), 5.96 (d, 1 H, -CH CH2),6.88 (dd, 1 H, -CH CH2), 7.28 (t, 2 H, -Ph-carbazole),7.42 (m, 4 H, -Ph-carbazole), 7.60 (d, 2 H, -carbazole-Ph), 7.76 (d, 2 H, -carbazole-Ph), 8.24 (d, 2 H, -Ph-carbazole); 13C NMR (100.64 MHz, DMSO-d6) 115.08,120.67, 125.51, 125.82, 126.06, 128.16, 131.68, 132.18,133.23, 141.26, 141.78, 145.44.

Reference： [1]Journal of Nanoscience and Nanotechnology,2015,vol. 15,p. 1434 - 1442
[2]Advanced Synthesis and Catalysis,2017,vol. 359,p. 2259 - 2268

43
[ 4041-21-8 ]
[ 110677-45-7 ]
9-{4-[bis(9-hexylcarbazol-3-yl)methyl]phenyl}carbazole [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
30%	With hydrogenchloride; acetic acid; In water; for 3h;Reflux;	9-hexylcarbazole (1.2 g, 4.6 mmol) hydrochloric acid (10 ml, 35 %) was slowly added to an acetic acid (16 ml) solution of <strong>[110677-45-7]4-(9-carbazolyl)benzaldehyde</strong> (0.5 g, 1.85 mmol) under stirring and the mixture was refluxed for 3 h. The resulting solution was poured into H2O and filtered. The deposit was dissolved in methylene chloride and washed with H2O three times. The separated organic layer was dried over anhydrous Na2SO4. The crude product was purified by silica gel column chromatography using a mixture of ethyl acetate and hexane (vol. ratio 1:25) as an eluent, yielding 0.23 g. (30 %) of a white amorphous solid. 1H NMR spectrum (400 MHz, CDCl3, δ, ppm): 8.13 (d, 2H, J = 8.0 Hz, Ar); 8.02 (d, 2H, J = 7.6 Hz, Ar); 7.96 (s, 2H, Ar); 7.51 -7.36 (m, 16H, Ar); 7.27 (t, 2H, J = 7.4 Hz, Ar); 7.17 (t, 2H, J = 7.4 Hz, Ar); 6.09 (s, 1H, CH); 4.29 (t, 4H, J = 7.4 Hz, NCH2); 1.91-1.84 (m, 4H, NCH2CH2); 1.44-1.37 (m, 4H, NCH2CH2CH2); 1.36-1.24 (m, 8H, CH2CH2CH3); 0.86 (t, 6H, J = 7.0 Hz, CH3). 13C NMR spectrum (400 MHz, CDCl3, δ, ppm): 14.1 (CH3(2C)), 22.5 (CH2CH3(2C)), 27.1 (CH2CH2CH3(2C)), 29.1 (CH2CH2 CH2CH3(2C)), 31.6 (CH2CH2N(2C)), 43.3 (CH2N(2C)), 56.7 (CH); 108.7 (2C); 108.8 (2C); 110.0 (2C), 118,7 (2C), 119.9 (2C), 120.3 (2C), 120.5 (2C), 121.2 (2C), 122.7 (2C), 122.8 (2C), 123.4 (2C), 125.7 (2C), 125.9 (2C), 126.8 (2C), 127.6 (2C), 131.0 (2C), 134.0 (2C), 135.6 (C), 139.7 (2C), 140.2 (2C), 141.0 (2C), 145.0 (C). Elemental analysis for C55H53N3 % Calc.: C 87.38, H 7.07, N 5.56; % Found: C 87.36, H 7.11, N 5.54. IR (KBr, cm-1): 3048 (C-H, Ar); 2953, 2926, 2853 (C-H); 1626, 1598 (C=C Ar); 1483, 1479, 1467 (C=C, Ar and C-H); 1348, 1332, 1316 (C-N, Ar); 1230 (C-N); 798, 770, 747, 724, 627 (C-H Ar).

Reference： [1]Dyes and Pigments,2015,vol. 122,p. 257 - 263

44
[ 102331-54-4 ]
[ 110677-45-7 ]
2-(4-(8a,9a-dihydro-9H-carbazol-9-yl)-phenyl)-6,9-dimethyl-1H-imidazo[4,5-f][1,10]phenanthroline [ No CAS ]

Reference： [1]Inorganic Chemistry,2020,vol. 59,p. 12994 - 12999
[2]RSC Advances,2015,vol. 5,p. 69430 - 69440

45
[ 134-81-6 ]
[ 110677-45-7 ]
9-[4-(4,5-diphenyl-1H-imidazol-2-yl)phenyl]-9H-carbazole [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
85.6%	With aluminum oxide; ammonium acetate; at 110℃; for 10h;Green chemistry;	General procedure: Benzil (0.21 g, 1 mmol), 3a (0.23 g, 1 mmol), acidic alumina (1.02 g, 10 mmol), and ammonium acetate (0.39 g, 5 mmol) were ground into powder in a mortar, and then heated in a thermostatic reactor at 110 C for 10 h. After completion of the reaction confirmed by TLC, the reaction mixture was treated with water to furnish the crude products. Further purification was done by silica gel column chromatography to provide M1 as yellow needle crystals (0.34 g). Yield: 81.4%;

Reference： [1]Tetrahedron,2016,vol. 72,p. 2988 - 2996

46
[ 5447-87-0 ]
[ 110677-45-7 ]
2-(3-(4-(9H-carbazol-9-yl)phenyl)-1-phenylallylidene)malononitrile [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
61%	With piperidine; In ethanol; for 4h;Reflux;	General procedure: The carbaldehyde (4, 4a and 4b 1 eq.) and different active methylene compound (5 and 7; 1.2 eq.) were dissolved in absolute ethanol (10 mL). Piperidine was added in catalytic amount (0.1 mL) and the reaction mixture was refluxed for 4 h. The corresponding extended styryls (6, 8, 9, 10, 11 and 12) were obtained, filtered and recrystallized from methanol.

Reference： [1]Dyes and Pigments,2016,vol. 129,p. 1 - 8

47
ethyl 2-cyano-3-phenylbut-2-enoate [ No CAS ]
[ 110677-45-7 ]
ethyl 5-(4-(9H-carbazol-9-yl)phenyl)-2-cyano-3-phenylpenta-2,4-dienoate [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
71%	With piperidine; In ethanol; for 4h;Reflux;	General procedure: The carbaldehyde (4, 4a and 4b 1 eq.) and different active methylene compound (5 and 7; 1.2 eq.) were dissolved in absolute ethanol (10 mL). Piperidine was added in catalytic amount (0.1 mL) and the reaction mixture was refluxed for 4 h. The corresponding extended styryls (6, 8, 9, 10, 11 and 12) were obtained, filtered and recrystallized from methanol.

Reference： [1]Dyes and Pigments,2016,vol. 129,p. 1 - 8

48
[ 110677-45-7 ]
4-(3-bromo-9H-carbazol-9-yl)benzaldehyde [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	With N-Bromosuccinimide; In N,N-dimethyl-formamide; at 20℃; for 12.5h;	To a solution of <strong>[110677-45-7]4-(9H-carbazol-9-yl)benzaldehyde</strong> (26.6 g, 98 mmol) in 100 mL DMF, NBS (17.4 g, 98 mmol), in 100 mL DMF, was added dropwise in 30 minutes. After addition, the mixture was stirred at room temperature for 12 hours. The solution was poured into ice water to precipitate the product. After filtration, the solid was collected, and washed by water, ethanolseveral times, then dried under vacuum, and used for the next step without further purification (yield: 96%). MS (ESI): 350.01 [M+Hf’.

Reference： [1]Patent: WO2016/28902,2016,A1 .Location in patent: Page/Page column 24

49
[ 5731-01-1 ]
[ 110677-45-7 ]
C₃₅H₂₅NO₂ [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	With sodium hydroxide; In ethanol; dichloromethane; water; at 20℃;	The 550 mg (2mmol) 4-(4-bromophenyl) acetophenone, 120 mg (3mmol) sodium hydroxide in 100 ml of water, adding 10 drip, 20 ml of ethanol and make the; will 542 mg (2mmol) 4-(9-(9H-carbazolyl)) benzaldehyde dissolved in 10 ml methylene chloride, ethanol are added in the above-mentioned drop in the liquid mixture, stirring the mixture at room temperature for overnight, filtering, ethanol, petroleum ether washing, to get the yellow powder (LJZ-5-3), not the drying process, one-step reaction is directly cast.

Reference： [1]Patent: CN102382037,2016,B .Location in patent: Paragraph 0275; 0276

50
[ 5653-09-8 ]
[ 110677-45-7 ]
C₃₃H₂₉NO [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
89%	With water; sodium hydroxide; In ethanol;	The 606mg (3mmol) 4- cyclohexyl acetophenone, 160 (4mmol) sodium hydroxide was placed in 100mL flasks single port,Add 10 drops of water, 20mL ethanol and dissolved; the 813mg (3mmol) 4- (9- (9H- card oxazolyl)) - benzene, formaldehyde solutionIn 10mL of dichloromethane was added dropwise to the above mixture of ethanol, stirred at room temperature overnight, filtered, ethanol, stoneWashed with petroleum ether and dried to give a pale yellow solid 1.22g, yield = 89%.

Reference： [1]Patent: CN102382037,2016,B .Location in patent: Paragraph 0209; 0210

51
[ 108-78-1 ]
[ 110677-45-7 ]
C₄₁H₂₈N₈ [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	With formic acid; In N,N-dimethyl-formamide; at 20℃; for 8h;Reflux;	1) 1mol melamine was weighed and dissolved in 60ml of DMF. The system was raised to 120C to completely dissolve under stirring. 2) 2mol <strong>[110677-45-7]4-(carbazol-9-yl)benzaldehyde</strong> was weighed and dissolved in 20ml of DMF at room temperature with stirring. 3) The solution obtained in step 2 was added dropwise to the step 1 solution. 0.01mol formic acid was added and refluxed for 8h. The reaction was completed. The final reaction product was removed of solvent by rotary evaporation and purified by column chromatography to isolate pure melamine polycondensated with carbazolbenzaldehyde double Schiff base.

Reference： [1]Patent: CN105669656,2016,A .Location in patent: Paragraph 0016; 0017; 0018; 0019

52
[ 1034-49-7 ]
[ 110677-45-7 ]
[ 262861-81-4 ]

Yield	Reaction Conditions	Operation in experiment
41%		t-BuOK (4 equiv) was allowed to dissolve in dried THF (2 ml/mmol) under argon and the solution was cooled to 78 C. After 20 min, 1.6 equiv of (bromomethyl)triphenylphosphonium bromide was added portionwise and stirring under argon continued for 2 h. Then a solution of aldehyde 8 (2.47 mmol) or 9 (0.74 mmol) in dried THF (2 ml/mmol) was slowly added dropwise and stirring continued for 1 h at 78 C and 20 h at rt. The solution was mixed with the same volume of NH4Cl (aq), acidified with 2 M HCl (aq) and extracted with ethyl acetate (350 ml). The organic layer was dried over Na2SO4, filtered and the solvent was evaporated in vacuo. Purification of the residue by chromatography on a SiO2 column (20% CHCl3 in hexanes) gave the title compound 7a (510 mg), 77%, (yellow solid) or 7b (80 mg, 41%, light-yellow crystalline solid; after chromatography the semi-solid oil was dissolved in hot hexanes, the solution was allowed to reach RT, filtered and concentrated under vacuum).

Reference： [1]Tetrahedron,2016,vol. 72,p. 7081 - 7092

53
[ 108-78-1 ]
[ 110677-45-7 ]
C₂₂H₁₇N₇ [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	With acetic acid; In dimethyl sulfoxide; at 20℃; for 1h;Reflux;	1), weighing 1mol melamine dissolved in 60 ml of in DMSO, make the system heating to 100 C, completely dissolved under agitation;2) weighing 0.8mol P of formaldehyde, the dissolved in 20 ml of in DMSO, at room temperature, stirring is dissolved;3) step 2 the resulting solution, is added dropwise to the step 1) in the preparation of the solution; and adding 0.01mol acetic acid, so that the system return 1h, reaction finishes; the final product of the reaction, to remove the solvent by the spin vaporization; and by column chromatography, separation to obtain pure melamine-formaldehyde shan Xifu P-alkali.

Reference： [1]Patent: CN105712980,2016,A .Location in patent: Paragraph 0017; 0018; 0019; 0020

54
[ 108-78-1 ]
[ 110677-45-7 ]
C₆₀H₃₉N₉ [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	With acetic acid; In dimethyl sulfoxide; at 20 - 100℃; for 20h;	1), weighed 1mol melamine dissolved in 60ml of dimethyl sulfoxide, making the system temperature to 100 , completely dissolved in the stirring;2) 5 mol of carbazole benzaldehyde was weighed out, dissolved in 60 ml of dimethylsulfoxide, and dissolved by stirring at room temperature.3) adding the solution obtained in the step 2 to the solution prepared in the step 1); and adding 0.01 mol of acetic acid to make the system reflux for 20 hours, and the reaction is finished; the final product is evaporated to remove the solvent; Chromatography, separation of pure melamine tricarbazole benzaldehyde three Schiff base.

Reference： [1]Patent: CN105541809,2016,A .Location in patent: Paragraph 0016; 0017; 0018; 0019

55
[ 948-65-2 ]
[ 110677-45-7 ]
9-{4-[bis(2-phenyl-1H-indol-3-yl)methyl]phenyl}-9H-carbazole [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
74%	With hydrogenchloride; In tetrahydrofuran; methanol; at 20℃; for 2h;	General procedure: 5-Methoxyindole (I) (1.42 g, 9.6 mmol) and concentrated hydrochloricacid (2 ml) were slowly added to tetrahydrofuran(1.1 ml) and methanol (11 ml) solution of <strong>[110677-45-7]4-(9H-carbazol-9-yl)benzaldehyde</strong> (1) (0.99 g, 3.6 mmol), and the mixture was stirredfor 2 h at room temperature. The resulting solutionwas poured intowater and filtered. The precipitate was dissolved in ethylacetateand washed with 10% NaOH solution. The separated organic layerwas dried over anhydrous Na2SO4. The crude product was purifiedby crystallization from diethyl ether to afford the product as brightyellow crystals.

Reference： [1]Dyes and Pigments,2017,vol. 139,p. 487 - 497

56
[ 110677-45-7 ]
[ 666201-15-6 ]
9-{4-[bis(1-(4-methoxyphenyl)-2-methyl-1H-indol-3-yl)methyl]phenyl}-9H-carbazole [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
30%	With hydrogenchloride; In tetrahydrofuran; methanol; at 20℃; for 2h;	General procedure: 5-Methoxyindole (I) (1.42 g, 9.6 mmol) and concentrated hydrochloricacid (2 ml) were slowly added to tetrahydrofuran(1.1 ml) and methanol (11 ml) solution of <strong>[110677-45-7]4-(9H-carbazol-9-yl)benzaldehyde</strong> (1) (0.99 g, 3.6 mmol), and the mixture was stirredfor 2 h at room temperature. The resulting solutionwas poured intowater and filtered. The precipitate was dissolved in ethylacetateand washed with 10% NaOH solution. The separated organic layerwas dried over anhydrous Na2SO4. The crude product was purifiedby crystallization from diethyl ether to afford the product as brightyellow crystals.

Reference： [1]Dyes and Pigments,2017,vol. 139,p. 487 - 497

57
[ 1006-94-6 ]
[ 110677-45-7 ]
9-{4-[bis(5-methoxy-1H-indol-3-yl)methyl]phenyl}-9H-carbazole [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
76%	With hydrogenchloride; In tetrahydrofuran; methanol; at 20℃; for 2h;	5-Methoxyindole (I) (1.42 g, 9.6 mmol) and concentrated hydrochloricacid (2 ml) were slowly added to tetrahydrofuran(1.1 ml) and methanol (11 ml) solution of <strong>[110677-45-7]4-(9H-carbazol-9-yl)benzaldehyde</strong> (1) (0.99 g, 3.6 mmol), and the mixture was stirredfor 2 h at room temperature. The resulting solutionwas poured intowater and filtered. The precipitate was dissolved in ethylacetateand washed with 10% NaOH solution. The separated organic layerwas dried over anhydrous Na2SO4. The crude product was purifiedby crystallization from diethyl ether to afford the product as brightyellow crystals. Yield 1.52 g, 76%. 1H NMR spectrum (300 MHz,DMSO, δ, ppm): 10.76 (s, 2H, NH), 8.23 (d, J 7.7 Hz, 2H, Ar), 7.67 (d,J 8.3 Hz, 4H), 7.53 (d, J 8.3 Hz, 2H, Ar) 7.44-7.22 (m, 8H, Ar), 6.99(d, J 2.3 Hz, 2H, Ar), 6.86 (d, J 2.3 Hz, 2H, Ar), 6.74 (dd, J1 8.3 HzJ2 2.3 Hz, 2H, Ar), 5.94 (s, 1H, CH), 3.64 (s, 6H, CH3). 13C NMRspectrum (75.4 MHz, DMSO, δ, ppm): 153.8,140.7,131.4,130.1,127.4,126.6, 125.7, 124.4, 123.3, 120.2, 119.5, 118.7, 112.2, 111.6, 109.7, 101.9,55.8, 40.1. IR (KBr, cm-1): 3416 (NH); 3052 (C-H, Ar); 2993, 2936,2829 (C-H); 1624, 1582 (C]C Ar); 1512, 1482 (C]C, Ar and CH);1452, 1439 (OCH3); 1360, 1335, 1315 (C-N, Ar); 1211 (C-N); 797,773, 751, 715, 625 (C-H Ar). MS (APCI+, 20 V), m/z: 549 ([MH]).Anal. Calcd. for C37H29N3O2: C, 81.15; H, 5.34, N, 7.67; O, 5.84%;found C 81.22, H 5.33, N 7.62%.

Reference： [1]Dyes and Pigments,2017,vol. 139,p. 487 - 497

58
[ 34289-60-6 ]
[ 110677-45-7 ]
4-{2-[4-(9H-carbazol-9-yl)phenyl]ethenyl}-2-hydroxy-6-methylpyrimidine hydrochloride [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	With hydrogenchloride; In ethanol; water;Reflux;	General procedure: An equimolar mixture (0.0125 mol) of 2-hydroxypyrimidines 1-2 and a corresponding arylcarboxaldehyde in 80 ml of ethanol was stirred for about 15min and then treated with 2.5 mL of HCl (cc). The obtained reaction mixture was heated under reflux for 6 h togive the corresponding hydrochlorides as red solids, which were then neutralized by 10% aqueous-alcoholic solution of carbonate of potassium. The resulting products (yellow solids) were filtered off, washed by hotethanol and dried in the air.

Reference： [1]Arkivoc,2017,vol. 2017,p. 105 - 120

59
[ 38186-51-5 ]
[ 110677-45-7 ]
[ 1019779-50-0 ]

Yield	Reaction Conditions	Operation in experiment
93%	With potassium tert-butylate; In tetrahydrofuran; at 0℃; for 24h;Inert atmosphere;	Potassium t-butoxide (t-BuOK) (0.22 g, 2 mmol) was placed in a two-necked flask, evacuated and nitrogen was introduced, and 3 mL of anhydrous tetrahydrofuran (THF) was added. A mixture of 4- (9H-carbazol-9-yl) benzaldehyde (0.27 g, 1 mmol) and diethyl 4-bromobenzylphosphate (diethyl Bromobenzyl phosphonate (0.34 g, 1.1 mmol) was placed in a single neck flask and 3 mL of anhydrous tetrahydrofuran was added under a nitrogen atmosphere. The solution in the flask was slowly added to the two-necked flask under ice-cooling and mixed and reacted at 0 C for 1 day. The reaction solution was poured into water to precipitate a yellow solid. The precipitated yellow solid was filtered and the intermediate product I-5 ((E) -9- (4- (4-bromostyryl) phenyl) -9H-carbazole was obtained by repeatedly washing with methanol to obtain a pale yellow powder. (0.39 g, yield 93%).
93%	With potassium tert-butylate; In tetrahydrofuran; at 0℃; for 0.25h;Inert atmosphere;	Potassium t-butoxide (t-BuOK) (0.22 g, 2 mmol) was placed in a two-necked flask, evacuated and nitrogen was introduced, and 3 mL of anhydrous tetrahydrofuran (THF) was added. A mixture of 4-(9H-carbazol-9-yl)benzaldehyde (0.27 g, 1 mmol) and diethyl 4-bromobenzyl phosphonate (0.34 g, 1.1 mmol) placed in a single neck flask, in the nitrogen environment by adding 3mL of anhydrous tetrahydrofuran. The solution in the flask was slowly added to the flask and mixed under ice bath and reacted at 0 C for 1 day. The reaction solution was poured into water to precipitate a yellow solid. The precipitated yellow solid was evacuated and filtered, and repeatedly washed with methanol to obtain the intermediate product of the pale yellow powder I-5 ((E)-9-(4-(4-bromostyryl)phenyl)-9H-carbazole (0.39 g, yield 93%).

Reference： [1]Patent: TWI571454,2017,B .Location in patent: Paragraph 0071-0073
[2]Patent: CN107098818,2017,A .Location in patent: Paragraph 0116-0119

60
[ 1558838-01-9 ]
[ 110677-45-7 ]
C₄₃H₃₀N₂ [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	With sodium ethanolate; In N,N-dimethyl-formamide; at 20℃; for 5h;	General procedure: In a round bottom flask equipped with compound 10 (5 mmol) was added a solution of 4- (9H-carbazol-9-yl) benzaldehyde 3(5 mmol) in DMF solution (5 mL), and then slowly dropwise with 10 mL of DMF containing sodium ethoxide (5 mmol), reacted at room temperature for 5 h, filtered,The crude product was washed with absolute ethanol and the crude product was purified by column chromatography (eluent petroleum ether: ethyl acetate = 20: 1)Compound 11.

Reference： [1]Patent: CN106632262,2017,A .Location in patent: Paragraph 0023; 0024; 0025; 0026; 0027

61
C₃₄H₄₁NO₆P₂ [ No CAS ]
[ 110677-45-7 ]
C₆₃H₄₃N₃ [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	With sodium ethanolate; In N,N-dimethyl-formamide; at 20℃; for 5h;	General procedure: In a round bottom flask equipped with compound 10 (5 mmol) was added a solution of 4- (9H-carbazol-9-yl) benzaldehyde 3(5 mmol) in DMF solution (5 mL), and then slowly dropwise with 10 mL of DMF containing sodium ethoxide (5 mmol), reacted at room temperature for 5 h, filtered,The crude product was washed with absolute ethanol and the crude product was purified by column chromatography (eluent petroleum ether: ethyl acetate = 20: 1)Compound 11.

Reference： [1]Patent: CN106632262,2017,A .Location in patent: Paragraph 1

62
C₃₉H₅₂NO₉P₃ [ No CAS ]
[ 110677-45-7 ]
C₈₃H₅₆N₄ [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	With sodium ethanolate; In N,N-dimethyl-formamide; at 20℃; for 5h;	General procedure: In a round bottom flask equipped with compound 10 (5 mmol) was added a solution of 4- (9H-carbazol-9-yl) benzaldehyde 3(5 mmol) in DMF solution (5 mL), and then slowly dropwise with 10 mL of DMF containing sodium ethoxide (5 mmol), reacted at room temperature for 5 h, filtered,The crude product was washed with absolute ethanol and the crude product was purified by column chromatography (eluent petroleum ether: ethyl acetate = 20: 1)Compound 11.

Reference： [1]Patent: CN106632262,2017,A .Location in patent: Paragraph 0023; 0024; 0025; 0026; 0027

63
1-ethyl-2,3,3-trimethyl-3H-indol-1-ium bromide [ No CAS ]
[ 110677-45-7 ]
C₃₂H₂₉N₂⁽¹⁺⁾*Br^(1-) [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
47%	In N,N-dimethyl-formamide; at 90℃; for 6h;Inert atmosphere;	(3) Compound 2-1 (500 mg, 1.84 mmol, 1.0 eq), compound 1 (540 mg, 2 mmol, 1.1 eq) was dissolved in6mL DMF, nitrogen protection, 90 heating reflux reaction 6h, with TCL plate detection reaction, the reaction is complete, the dichloromethane extraction2 times, saturated salt water washing 2-3 times, anhydrous sodium sulfate drying. The solvent was dried under reduced pressure to give a crude product which was chromatographed on a silica gel columnThe silica gel particle size was 200-300 mesh and the eluent ratio was methanol / dichloromethane = 1: 20 to give the product CIV1 in a yield of47%

Reference： [1]Patent: CN107089937,2017,A .Location in patent: Paragraph 0020; 0023

64
[ 95-21-6 ]
[ 110677-45-7 ]
C₂₇H₁₈N₂O [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
45%		Under nitrogen protection conditions,2.2 g (19.6 mmol) of potassium tert-butoxide was added to 20 mL of anhydrous tetrahydrofuran,Then stirred under ice-cooling for 10 minutes,The suspension was added dropwise1.3 mL (10.8 mmol) of 2-methylbenzoxazole,Under this condition, stirring was continued for 10 min,A solution containing N- (4-formylphenyl) carbazole (9.8 mmol) in dry tetrahydrofuran was slowly added to the above solution,After stirring for 2 hours,The mixture was poured into 200 mL of water,Extracted three times with dichloromethane (50 mL x 3)Combined organic layer,Washed with water, dried Na2SO4,Vacuum distillation, remove the organic solvent,The residue was purified by silica gel column chromatography,The eluent is dichloromethane,And recrystallized from n-Hexane-CH2Cl2 to give pure pale yellow product. Yield: 45%.

Reference： [1]Patent: CN107056765,2017,A .Location in patent: Paragraph 0029; 0030

65
[ 54-85-3 ]
[ 110677-45-7 ]
(E)-N′-(4-(9H-carbazol-9-yl)benzylidene)isonicotinohydrazide [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
87%	With acetic acid; In ethanol; for 6h;Reflux;	General procedure: To an equimolar ethanolic solution of acid hydrazide(0.1 mol) and carbazole aldehyde (1 and/or 4) (0.1 mol), afew drops of glacial acetic acid were added. The mixturewas then refluxed for 6 h. It was then allowed to cool andfiltered. The crude product was recrystallised from methanolto yield carbazole carbohydrazides (2a, 2b, 5a, 5b).

Reference： [1]Journal of Fluorescence,2017,vol. 27,p. 2095 - 2100

66
[ 636-97-5 ]
[ 110677-45-7 ]
(E)-N′-(4-(9H-carbazol-9-yl)benzylidene)-4-nitrobenzohydrazide [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
90%	With acetic acid; In ethanol; for 6h;Reflux;	General procedure: To an equimolar ethanolic solution of acid hydrazide(0.1 mol) and carbazole aldehyde (1 and/or 4) (0.1 mol), afew drops of glacial acetic acid were added. The mixturewas then refluxed for 6 h. It was then allowed to cool andfiltered. The crude product was recrystallised from methanolto yield carbazole carbohydrazides (2a, 2b, 5a, 5b).

Reference： [1]Journal of Fluorescence,2017,vol. 27,p. 2095 - 2100

67
[ 1014-25-1 ]
[ 110677-45-7 ]
C₂₈H₂₀N₄OS [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
80.43%	In ethanol; at 70℃; for 12h;	T1 (0.271 g, 1 mmol) and compound 1 (0.248 g, 1.2 mmol) weredissolved in 15 mL of anhydrous alcohol, the reaction mixture wasrefluxed at 70 C for 12 h. After the reaction finished, the solutionwas cooled to room temperature, the solid was filtered and washedtwo times with anhydrous ethanol to give 0.37 g green solid, yield:80.43%. Melting point: 217.4-218.5 C. FT- IR (KBr, Disc, cm1):1601.19 (s, nu CN), 1582.00 (m), 1558.11 (m), 1514.46 (s, nubenzene),1445.05 (s), 1417.20 (m), 1360.58 (m), 1337.06 (m), 1312.98 (w),1252.84 (m), 1224.75 (m, nuOCH3), 1178.97 (m, nu OCH3), 1159.28 (m,nu OCH3), 825.46 (m), 737.66 (m), 718.23 (m). 1H NMR (DMSO-d6,400 MHz, ppm) delta: 9.20 (s, 1H, CHN), 8.38-8.36 (d, J = 8.0 Hz, 2H),8.30-8.28 (d, J =8.0 Hz, 2H), 7.98-7.91 (q, 4H), 7.58-7.56 (d,J =8.0 Hz, 2H), 7.51-7.48 (t, 2H), 7.37-7.34 (t, 2H), 7.16-7.14 (d,J = 8.0 Hz, 2H), 3.85 (s, 3H, OCH3). 13C NMR (100 MHz, CDCl3)delta 172.83,167.39,165.10,162.03,142.39,140.16,133.11,131.72,129.25,126.89, 126.27, 123.95, 123.25, 120.74, 120.49, 114.59, 109.86, 55.50.MS (ESI) m/z: found, [M+H]+, 461.1427; molecular formulaC28H20N4OS requires [M+H]+, 461.1436.

Reference： [1]Dyes and Pigments,2017,vol. 145,p. 152 - 159

68
[ 16532-79-9 ]
[ 110677-45-7 ]
(Z)-3-(4-(9H-carbazol-9-yl)phenyl)-2-(4-bromophenyl)acrylonitrile [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
98%	With potassium hydroxide; In ethanol; water; acetonitrile; at 50℃;	General procedure: Ten mmol of the acetonitrile derivate and 10 mmol of N-(4-formylphenyl) carbazole are placed ina 50-mL flask, 25 mL of ethanol are added. Then the mixture is stirred for 5 min, after that, 3 dropsof an aqueous solution 10% of potassium hydroxide is added to the mixture, the reaction is stirredand heat up to 50 C, and was monitored by thin layer chromatography until was completed, then themixture is cool down to 0 C. The formation of a crystalline precipitate is observed, it is filtered andwashed using cold EtOH. The solid is recovered and purified by recrystallization process using assolvent a mixture of acetone/EtOH 40:60.

Reference： [1]Molecules,2018,vol. 23

69
[ 20893-30-5 ]
[ 110677-45-7 ]
(E)-3-(4-(9H-carbazol-9-yl)phenyl)-2-(thiophen-2-yl)acrylonitrile [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
90%	With potassium hydroxide; In ethanol; water; acetonitrile; at 50℃;	General procedure: Ten mmol of the acetonitrile derivate and 10 mmol of N-(4-formylphenyl) carbazole are placed ina 50-mL flask, 25 mL of ethanol are added. Then the mixture is stirred for 5 min, after that, 3 dropsof an aqueous solution 10% of potassium hydroxide is added to the mixture, the reaction is stirredand heat up to 50 C, and was monitored by thin layer chromatography until was completed, then themixture is cool down to 0 C. The formation of a crystalline precipitate is observed, it is filtered andwashed using cold EtOH. The solid is recovered and purified by recrystallization process using assolvent a mixture of acetone/EtOH 40:60.(E)-3-(4-(9H-carbazol-9-yl)phenyl)-2-(thiophen-2-yl)acrylonitrile (CZ-2): Yellow solid, Yield: 90%, m.p.159-161 C. FTIR (ATR, cm-1) 2214 (CN), 1487 (CS). 1H NMR (500 MHz, THF-d6) λ (ppm): 8.07-8.21(4H, m), 7.62-7.77 (3H, m), 7.32-7.52 (6H, m), 7.16-7.26 (2H, m), 7.04-7.13 (1H, m); 13C NMR (125 MHz,THF-d6) λ (ppm): 140.2, 139.4, 139.2, 132.4, 130.6, 127.9, 127.1, 126.8, 126.7, 125.9, 123.8, 120.2, 120.1,116.4, 109.6, 106.1; HRMS-TOF (ESI, m/z): [M + H]+ Found: 377.11064 for C25H16N2S; [M + H]+ Calcd:377.11069; Error 0.1987 ppm.

Reference： [1]Molecules,2018,vol. 23

70
[ 62532-99-4 ]
[ 110677-45-7 ]
C₂₉H₁₈N₂S [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
54%	With trifluoroacetic acid; In toluene; at 130℃; for 72h;	2-(2-thienyl)aniline (5.3 g, 30 mmol), 4-(carbazol-9-yl)carbaldehyde (11.9 g, 50 mmol), 10 mL of trifluoroacetic acid and 100 mL of toluene were added to a 250 mL round bottom flask. The mixture was heated and stirred at 130C for three days. Cool to room temperature, quench with aqueous sodium hydroxide, extract with dichloromethane, and remove the solvent on a rotary evaporator. Purification by column chromatography. A white solid (13.5 g, 54%) was obtained.

Reference： [1]Patent: CN107501336,2017,A .Location in patent: Paragraph 0184; 0185; 0186

71
[ 876-87-9 ]
[ 110677-45-7 ]
2‑[4‑(9H‑carbazol‑9‑yl)styryl]‑1‑methylquinolinuum iodide [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
53.8%	With piperidine; In ethanol; for 12h;Reflux; Inert atmosphere;	General procedure: A solution of intermediate <strong>[110677-45-7]4-(9H-carbazol-9-yl)benzaldehyde</strong> 3 (0.27 g, 1.0 mmol), 1-methyl-2-picoliniuiodide (0.2 g, 0.85 mmol) and 5 drops piperidine in anhydrous ethanol (50 mL) was refluxed for 12 h under nitrogen with stirring. After cooling to room temperature, a precipitate was formed during the process of reaction. The reaction mixture was filtered, and washed thoroughly with anhydrous ethanol. The residue was purified by column chromatography on silica gel eluting with CH2Cl2/CH3OH (10:1, v/v) to afford 1a (0.24 g, 57.9%) as a yellow solid.

Reference： [1]Spectrochimica Acta Part A: Molecular and Biomolecular Spectroscopy,2018,vol. 199,p. 441 - 447

72
[ 872-73-1 ]
[ 110677-45-7 ]
2‑[4‑(9H‑carbazol‑9‑yl)styryl]‑1‑methylpyridinium iodide [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
57.9%	With piperidine; In ethanol; for 12h;Reflux; Inert atmosphere;	A solution of intermediate <strong>[110677-45-7]4-(9H-carbazol-9-yl)benzaldehyde</strong> 3 (0.27 g, 1.0 mmol), 1-methyl-2-picoliniuiodide (0.2 g, 0.85 mmol) and 5 drops piperidine in anhydrous ethanol (50 mL) was refluxed for 12 h under nitrogen with stirring. After cooling to room temperature, a precipitate was formed during the process of reaction. The reaction mixture was filtered, and washed thoroughly with anhydrous ethanol. The residue was purified by column chromatography on silica gel eluting with CH2Cl2/CH3OH (10:1, v/v) to afford 1a (0.24 g, 57.9%) as a yellow solid. 1H NMR (400 MHz, DMSO-d6) δ: 8.84-8.82 (m, 2H), 8.53 (d, J = 7.68 Hz, 1H), 8.43 (t, J = 7.76 Hz, 1H), 8.31 (d, J = 7.64 Hz, 1H), 8.15-8.11 (br, 1H), 7.91-7.89 (m, 1H), 7.81-7.77 (m, 1H), 7.69-7.65 (m, 2H), 7.63-7.59 (br, 3H), 7.56-7.52 (m, 1H), 7.47-7.43 (m, 1H), 7.40-7.38 (br, 1H), 7.35-7.31 (br, 2H), 4.38 (s, 3H); 13C NMR (100 MHz, DMSO-d6) δ: 150.30, 146.22, 144.60, 144.32, 142.01, 141.38, 136.73, 130.80, 128.63, 127.77, 127.20, 121.99, 121.35, 115.05, 110.62, 46.67; LC-MS: (positive mode, m/z) calculated 361.1699, found 361.1687 for [M-I]+.

Reference： [1]Spectrochimica Acta Part A: Molecular and Biomolecular Spectroscopy,2018,vol. 199,p. 441 - 447

73
[ 555-21-5 ]
[ 110677-45-7 ]
(Z)-3-(4-(9H-carbazol-9-yl)phenyl)-2-(4-nitrophenyl)acrylonitrile [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
56%	With piperidine; In acetonitrile; at 40℃; for 18h;	General procedure: Aldehyde (1 equiv.) and acceptor compound (1 equiv.) were dissolved in acetonitrile (100 mL for 14 mmol). Piperidine (0.01 equiv.)was added and the solution was stirred at the temperature indicated forthe time indicated in each protocol. The solution was then concentratedunder vacuum and the product purified by column chromatography onsilica gel.