4877-80-9|Triphenylene-2,3,6,7,10,11-hexaol| Ambeed

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Quality Control of [ 4877-80-9 ] Purity: 97% SDS Specification

COA

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NMR

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CNMR

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HPLC

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Product Citations Show More

Scalable templated fabrication of Cu-based MOF on textiles for simultaneous sensing, filtration, and detoxification of SO2

Zhong, Zhuoran ; Damacet, Patrick ; Sánchez-González, Elí ; Eagleton, Aileen M ; Vereshchuk, Nataliia ; Wongratanaphisan, Ravint , et al.

DOI: 10.1016/j.chempr.2025.102580 Chem,2025,102580.

Abstract: As smart electronic textiles (e-textiles) rapidly emerge as a transformative technology in advanced functional materials, a significant gap remains in developing multifunctional devices for air quality management and monitoring. This study addresses this challenge by demonstrating the first example of simultaneous sulfur dioxide (SO₂) sensing and filtration using a copper-based hexahydroxytriphenylene (Cu₃(HHTP)₂) metal-organic framework (MOF) incorporated into polyester textiles via a scalable templated fabrication method. First, the prepared MOF/textile composites meet the Occupational Safety and Health Administration’s (OSHA) permissible exposure limit (PEL) with sub-ppm sensing capabilities, while offering high SO₂ adsorption capacity and device regenerability. Second, this work provides valuable fundamental insights into the interactions between MOF and SO₂ through a combination of experimental and computational studies, revealing the pathway by which SO₂ is converted into less-toxic sulfate species. This understanding will contribute to future research on MOF-based air pollutant remediation. Third, the scalable fabrication method up to 100 cm² dimension lays the groundwork for the production of largearea MOF/textile devices. The scalability enhances the potential for widespread use of MOF materials in wearable sensors and personal protective equipment (PPE), where timely detection and filtration of harmful gases are crucial. Ultimately, this research establishes the scientific basis for the integration of functional MOFs into next-generation smart textiles, with promising applications in environmental monitoring, health protection, and air remediation.

Purchased from AmBeed: 4877-80-9 ; 20427-59-2

Smart Textile: Electrohydrodynamic Jet Printing of Ionic Liquid-Functionalized Cu3 (HHTP) 2 Metal–Organic Frameworks for Gas-Sensing Applications

Ahmadipour, Maedeh ; Damacet, Patrick ; Xiang, Chunhui ; Mirica, Katherine A ; Montazami, Reza ;

DOI: 10.1021/acsami.4c20696 PubMed ID: 39961630 ACS Appl. Mater. Interfaces,2025,17(8):12425-12439.

Abstract: This study presents the development and characterization of a smart textile gas sensor based on the integration of ionic liquid (IL)-functionalized Cu₃(HHTP)₂ metal−organic frameworks (MOFs), using electrohydrodynamic jet (e-jet) printing. The sensor was designed for the detection of nitric oxide (NO) gas, a critical target in various environmental and safety applications. Cu₃(HHTP)₂ MOFs were synthesized and subsequently functionalized with 1-Ethyl-3-methylimidazolium trifluoromethanesulfonate (EMIM⁺ Otf⁻) ionic liquid to enhance their chemiresistive performance toward NO gas. The functionalized MOF was then e-jet printed onto electrospun polylactic acid (PLA) substrates to fabricate smart textile sensors. The IL-functionalized Cu₃(HHTP)₂ sensors demonstrated a 582× increase in conductivity compared to previously reported MOF-based sensors. Additionally, IL functionalization enhanced sensor sensitivity, with a response increasing from less than 5% in pristine MOF@PLA sensors to approximately 570% at 100 ppm of NO gas. Performance was systematically evaluated across NO concentrations ranging from 5 to 300 ppm, achieving a theoretical limit of detection of 3.7 ppm. The sensors exhibited partial reversibility and retained functionality over extended periods and under humid conditions. Comprehensive analyses using SEM, EDX, FTIR, and XRD were performed to assess the crystallinity of MOF deposits and elucidate the sensing mechanism. These findings highlight the potential of e-jet printing of IL-functionalized MOFs for the development of advanced, flexible gas sensors with applications in both civilian and military settings and implications for personal protective wearable technologies.

Keywords: Cu₃(HHTP)₂ MOF ; ionic liquid functionalization ; E-jet printing ; smart textile ; chemiresistive NO detection

Purchased from AmBeed: 4877-80-9

Dioxin-Linked Covalent Organic Framework-Supported Palladium Complex for Rapid Room-Temperature Suzuki-Miyaura Coupling Reaction

Campbell, Allea ; Alsudairy, Ziad ; Dun, Chaochao ; Akram, Fazli ; Smith-Petty, Kayla ; Ambus, Abrianna , et al.

DOI: 10.3390/cryst13081268 Crystals,2023,13(8):1268.

Abstract: Covalent organic framework (COF)-supported palladium catalysts have garnered enormous attention for cross-coupling reactions. However, the limited linkage types in COF hosts and their suboptimal catalytic performance have hindered their widespread implementation. Herein, we present the first study immobilizing palladium acetate onto a dioxin-linked COF (Pd/COF-318) through a facile solution impregnation approach. By virtue of its permanent porosity, accessible Pd sites arranged in periodic skeletons, and framework robustness, the resultant Pd/COF-318 exhibits exceptionally high activity and broad substrate scope for the Suzuki-Miyaura coupling reaction between aryl bromides and arylboronic acids at room temperature within an hour, rendering it among the most effective Pd/COF catalysts for Suzuki-Miyaura coupling reactions to date. Moreover, Pd/COF-318 demonstrates excellent recyclability, retaining high activity over five cycles without significant deactivation. The leaching test confirms the heterogeneity of the catalyst. This work uncovers the vast potential of dioxin-linked COFs as catalyst supports for highly active, selective, and durable organometallic catalysis.

Keywords: covalent organic framework (COF) ; dioxin-linked COF ; Pd(II) immobilization ; Suzuki-Miyaura coupling

Purchased from AmBeed: 24067-17-2 ; 98-80-6 ; 3375-31-3 ; 71597-85-8 ; 4877-80-9 ; 99768-12-4

Product Details of [ 4877-80-9 ]

CAS No. :	4877-80-9
Formula :	C₁₈H₁₂O₆
M.W :	324.28
SMILES Code :	OC1=C(O)C=C2C3=CC(O)=C(O)C=C3C4=CC(O)=C(O)C=C4C2=C1
MDL No. :	MFCD01321170
InChI Key :	QMLILIIMKSKLES-UHFFFAOYSA-N
Pubchem ID :	11088610

Safety of [ 4877-80-9 ]

GHS Pictogram:
Signal Word:	Warning
Hazard Statements:	H302-H315-H319
Precautionary Statements:	P261-P305+P351+P338

Computational Chemistry of [ 4877-80-9 ] Show Less

Physicochemical Properties

Num. heavy atoms	24
Num. arom. heavy atoms	18
Fraction Csp3	0.0
Num. rotatable bonds	0
Num. H-bond acceptors	6.0
Num. H-bond donors	6.0
Molar Refractivity	91.1
TPSA ? Topological Polar Surface Area: Calculated from Ertl P. et al. 2000 J. Med. Chem.	121.38 Å²

Lipophilicity

Log P_o/w (iLOGP)? iLOGP: in-house physics-based method implemented from Daina A et al. 2014 J. Chem. Inf. Model.	1.19
Log P_o/w (XLOGP3)? XLOGP3: Atomistic and knowledge-based method calculated by XLOGP program, version 3.2.2, courtesy of CCBG, Shanghai Institute of Organic Chemistry	2.75
Log P_o/w (WLOGP)? WLOGP: Atomistic method implemented from Wildman SA and Crippen GM. 1999 J. Chem. Inf. Model.	3.38
Log P_o/w (MLOGP)? MLOGP: Topological method implemented from Moriguchi I. et al. 1992 Chem. Pharm. Bull. Moriguchi I. et al. 1994 Chem. Pharm. Bull. Lipinski PA. et al. 2001 Adv. Drug. Deliv. Rev.	1.29
Log P_o/w (SILICOS-IT)? SILICOS-IT: Hybrid fragmental/topological method calculated by FILTER-IT program, version 1.0.2, courtesy of SILICOS-IT, http://www.silicos-it.com	2.08
Consensus Log P_o/w? Consensus Log P_o/w: Average of all five predictions	2.14

Water Solubility

Log S (ESOL):? ESOL: Topological method implemented from Delaney JS. 2004 J. Chem. Inf. Model.	-4.14
Solubility	0.0236 mg/ml ; 0.0000728 mol/l
Class? Solubility class: Log S scale Insoluble < -10 < Poorly < -6 < Moderately < -4 < Soluble < -2 Very < 0 < Highly	Moderately soluble
Log S (Ali)? Ali: Topological method implemented from Ali J. et al. 2012 J. Chem. Inf. Model.	-4.95
Solubility	0.00361 mg/ml ; 0.0000111 mol/l
Class? Solubility class: Log S scale Insoluble < -10 < Poorly < -6 < Moderately < -4 < Soluble < -2 Very < 0 < Highly	Moderately soluble
Log S (SILICOS-IT)? SILICOS-IT: Fragmental method calculated by FILTER-IT program, version 1.0.2, courtesy of SILICOS-IT, http://www.silicos-it.com	-3.95
Solubility	0.0362 mg/ml ; 0.000112 mol/l
Class? Solubility class: Log S scale Insoluble < -10 < Poorly < -6 < Moderately < -4 < Soluble < -2 Very < 0 < Highly	Soluble

Pharmacokinetics

GI absorption? Gatrointestinal absorption: according to the white of the BOILED-Egg	High
BBB permeant? BBB permeation: according to the yolk of the BOILED-Egg	No
P-gp substrate? P-glycoprotein substrate: SVM model built on 1033 molecules (training set) and tested on 415 molecules (test set) 10-fold CV: ACC=0.72 / AUC=0.77 External: ACC=0.88 / AUC=0.94	No
CYP1A2 inhibitor? Cytochrome P450 1A2 inhibitor: SVM model built on 9145 molecules (training set) and tested on 3000 molecules (test set) 10-fold CV: ACC=0.83 / AUC=0.90 External: ACC=0.84 / AUC=0.91	Yes
CYP2C19 inhibitor? Cytochrome P450 2C19 inhibitor: SVM model built on 9272 molecules (training set) and tested on 3000 molecules (test set) 10-fold CV: ACC=0.80 / AUC=0.86 External: ACC=0.80 / AUC=0.87	No
CYP2C9 inhibitor? Cytochrome P450 2C9 inhibitor: SVM model built on 5940 molecules (training set) and tested on 2075 molecules (test set) 10-fold CV: ACC=0.78 / AUC=0.85 External: ACC=0.71 / AUC=0.81	Yes
CYP2D6 inhibitor? Cytochrome P450 2D6 inhibitor: SVM model built on 3664 molecules (training set) and tested on 1068 molecules (test set) 10-fold CV: ACC=0.79 / AUC=0.85 External: ACC=0.81 / AUC=0.87	No
CYP3A4 inhibitor? Cytochrome P450 3A4 inhibitor: SVM model built on 7518 molecules (training set) and tested on 2579 molecules (test set) 10-fold CV: ACC=0.77 / AUC=0.85 External: ACC=0.78 / AUC=0.86	Yes
Log Kp (skin permeation)? Skin permeation: QSPR model implemented from Potts RO and Guy RH. 1992 Pharm. Res.	-6.33 cm/s

Druglikeness

Lipinski? Lipinski (Pfizer) filter: implemented from Lipinski CA. et al. 2001 Adv. Drug Deliv. Rev. MW ≤ 500 MLOGP ≤ 4.15 N or O ≤ 10 NH or OH ≤ 5	1.0
Ghose? Ghose filter: implemented from Ghose AK. et al. 1999 J. Comb. Chem. 160 ≤ MW ≤ 480 -0.4 ≤ WLOGP ≤ 5.6 40 ≤ MR ≤ 130 20 ≤ atoms ≤ 70	None
Veber? Veber (GSK) filter: implemented from Veber DF. et al. 2002 J. Med. Chem. Rotatable bonds ≤ 10 TPSA ≤ 140	0.0
Egan? Egan (Pharmacia) filter: implemented from Egan WJ. et al. 2000 J. Med. Chem. WLOGP ≤ 5.88 TPSA ≤ 131.6	0.0
Muegge? Muegge (Bayer) filter: implemented from Muegge I. et al. 2001 J. Med. Chem. 200 ≤ MW ≤ 600 -2 ≤ XLOGP ≤ 5 TPSA ≤ 150 Num. rings ≤ 7 Num. carbon > 4 Num. heteroatoms > 1 Num. rotatable bonds ≤ 15 H-bond acc. ≤ 10 H-bond don. ≤ 5	1.0
Bioavailability Score? Abbott Bioavailability Score: Probability of F > 10% in rat implemented from Martin YC. 2005 J. Med. Chem.	0.55

Medicinal Chemistry

PAINS? Pan Assay Interference Structures: implemented from Baell JB. & Holloway GA. 2010 J. Med. Chem.	1.0 alert
Brenk? Structural Alert: implemented from Brenk R. et al. 2008 ChemMedChem	2.0 alert: heavy_metal
Leadlikeness? Leadlikeness: implemented from Teague SJ. 1999 Angew. Chem. Int. Ed. 250 ≤ MW ≤ 350 XLOGP ≤ 3.5 Num. rotatable bonds ≤ 7	No; 1 violation:MW<0.0
Synthetic accessibility? Synthetic accessibility score: from 1 (very easy) to 10 (very difficult) based on 1024 fragmental contributions (FP2) modulated by size and complexity penaties, trained on 12'782'590 molecules and tested on 40 external molecules (r² = 0.94)	1.27

Application In Synthesis of [ 4877-80-9 ]

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

Downstream synthetic route of [ 4877-80-9 ]

[ 4877-80-9 ] Synthesis Path-Downstream 1~35

1
[ 764-85-2 ]
[ 4877-80-9 ]
[ 70351-95-0 ]

References: [1]Molecular Crystals and Liquid Crystals (1969-1991),1986,vol. 137,p. 381 - 390.

2
[ 38870-89-2 ]
[ 4877-80-9 ]
[ 110344-75-7 ]

References: [1]Tetrahedron Letters,1987,vol. 28,p. 2269 - 2272.

3
[ 56680-69-4 ]
[ 4877-80-9 ]
[ 110344-76-8 ]

References: [1]Tetrahedron Letters,1987,vol. 28,p. 2269 - 2272.

4
[ 22809-37-6 ]
[ 4877-80-9 ]
[ 129090-61-5 ]

References: [1]Molecular Crystals and Liquid Crystals (1969-1991),1990,vol. 182,p. 201 - 207.

5
[ 108345-45-5 ]
[ 4877-80-9 ]
[ 110344-77-9 ]

References: [1]Tetrahedron Letters,1987,vol. 28,p. 2269 - 2272.

6
[ 4244-62-6 ]
[ 4877-80-9 ]
3-Butoxy-propionic acid 3,6,7,10,11-pentakis-(3-butoxy-propionyloxy)-triphenylen-2-yl ester [ No CAS ]

References: [1]Journal of Organic Chemistry,1991,vol. 56,p. 6064 - 6066.

7
[ 89693-15-2 ]
[ 4877-80-9 ]
4-Propylsulfanyl-butyric acid 3,6,7,10,11-pentakis-(4-propylsulfanyl-butyryloxy)-triphenylen-2-yl ester [ No CAS ]

References: [1]Journal of Organic Chemistry,1991,vol. 56,p. 6064 - 6066.

8
[ 860580-85-4 ]
[ 4877-80-9 ]
[ 110344-78-0 ]

References: [1]Tetrahedron Letters,1987,vol. 28,p. 2269 - 2272.

9
[ 4877-80-9 ]
[ 50586-80-6 ]
2,3,6,7,10,11-hexa(2-(2-methoxyethoxy)ethoxy)triphenylene [ No CAS ]

References: [1]Chemistry - A European Journal,2005,vol. 11,p. 2519 - 2524.

10
[ 875440-61-2 ]
[ 4877-80-9 ]
C₈₄H₉₆O₂₄ [ No CAS ]

References: [1]Journal of the American Chemical Society,2006,vol. 128,p. 1489 - 1499.

11
[ 20769-85-1 ]
[ 4877-80-9 ]
2,3,6,7,10,11-hexakis(2-bromoisobutyryloxy)triphenylene [ No CAS ]

References: [1]Chemistry Letters,2013,vol. 42,p. 609 - 611.
[2]Macromolecules,2005,vol. 38,p. 2093 - 2100.

12
[ 4877-80-9 ]
[ 76071-00-6 ]
2,3,6,7,10,11-hexakis(4-butoxy-2,3,5,6-tetrafluorobenzoyloxy)triphenylene [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	With dmap; dicyclohexyl-carbodiimide; In dichloromethane; at 0 - 20℃;	Third StepA solution of 3.26 g of the compound (3), 0.44 g of <strong>[4877-80-9]2,3,6,7,10,11-hexahydroxytriphenylene</strong>, and 1.50 g of 4-dimethylaminopyridine (DMAP) dissolved in 60 mL of dichloromethane was stirred at room temperature for 1 hour, then thereto was added, under ice cooling, 2.53 g of N,N-dicyclohexylcarbodiimide (DCC) dissolved in 20 mL of dichloromethane, followed by stirring under ice cooling for 5 minutes, and stirring overnight at room temperature. The precipitated dicyclohexylurea was filtered off, and the filtrate washed with 3-N hydrochloric acid, a saturated aqueous solution of sodium hydrogen carbonate, and saturated brine, followed by drying over anhydrous sodium sulfate. After evaporating the solvent, the product was purified by silica gel column chromatography and was recrystallized from hexane/ethanol to yield 2.10 g (1.15 mmol) of white solid 2,3,6,7,10,11-hexakis(4-butoxy-2,3,5,6-tetrafluorobenzoyloxy)triphenylene (A).Phase transition temperature (° C.)Cry 191 X1 232 X2 272 X3 311 X4 337 Iso1H-NMR (CDCl3: delta ppm) 7.87 (S, 6H), 4.33 (t, 12H), 1.82 (m, 12H), 1.57 (m, 12H), 1.04 (t, 18H).

References: [1]Patent: US2008/58544,2008,A1 .Location in patent: Page/Page column 11.

13
[ 4877-80-9 ]
[ 76071-02-8 ]
2,3,6,7,10,11-hexakis(4-heptyloxy-2,3,5,6-tetrafluorobenzoyloxy)triphenylene [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	With dmap; dicyclohexyl-carbodiimide; In dichloromethane; at 0 - 20℃;	Third StepA solution of 7.76 g of the compound (7), 0.44 g of <strong>[4877-80-9]2,3,6,7,10,11-hexahydroxytriphenylene</strong>, and 1.50 g of DMAP dissolved in 60 mL of dichloromethane was stirred at room temperature for 1 hour, then thereto was added, under ice cooling, 2.53 g of DCC dissolved in 20 mL of dichloromethane, followed by stirring under ice cooling for 5 minutes, and stirring overnight at room temperature. The precipitated dicyclohexylurea was filtered off, and the filtrate washed with 3-N hydrochloric acid, a saturated aqueous solution of sodium hydrogen carbonate, and saturated brine, followed by drying over anhydrous sodium sulfate. After evaporating the solvent, the product was purified by silica gel column chromatography and was recrystallized from hexane/ethanol to yield 2.02 g (0.98 mmol) of white solid 2,3,6,7,10,11-hexakis(4-heptyloxy-2,3,5,6-tetrafluorobenzoyloxy)triphenylene (C).Phase transition temperature (° C.): Cry 142 Colh 307 Iso1H-NMR (CDCl3: delta ppm) 8.01 (S, 6H), 4.34 (t, 12H), 1.85 (m, 12H), 1.51 (m, 12H), 1.44-1.36 (m, 36H), 0.94 (t, 18H).

References: [1]Patent: US2008/58544,2008,A1 .Location in patent: Page/Page column 13.
[2]Molecular Crystals and Liquid Crystals,2009,vol. 509,p. 186 - 194.

14
[ 4877-80-9 ]
[ 76071-03-9 ]
2,3,6,7,10,11-hexakis(4-octyloxy-2,3,5,6-tetrafluorobenzoyloxy)triphenylene [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	With dmap; dicyclohexyl-carbodiimide; In dichloromethane; at 0 - 20℃;	Third StepA solution of 3.94 g of the compound (9), 0.44 g of <strong>[4877-80-9]2,3,6,7,10,11-hexahydroxytriphenylene</strong>, and 1.50 g of DMAP dissolved in 60 mL of dichloromethane was stirred at room temperature for 1 hour, then thereto was added, under ice cooling, 2.53 g of DCC dissolved in 20 mL of dichloromethane, followed by stirring under ice cooling for 5 minutes, and stirring overnight at room temperature. The precipitated dicyclohexylurea was filtered off, and the filtrate washed with 3-N hydrochloric acid, a saturated aqueous solution of sodium hydrogen carbonate, and saturated brine, followed by drying over anhydrous sodium sulfate. After evaporating the solvent, the product was purified by silica gel column chromatography and was recrystallized from hexane/ethanol to yield 1.44 g (0.67 mmol) of white solid 2,3,6,7,10,11-hexakis(4-octyloxy-2,3,5,6-tetrafluorobenzoyl oxy)triphenylene (D).Phase transition temperature (° C.): Cry 133 Colh 308 Iso1H-NMR (CDCl3: delta ppm) 8.00 (S, 6H), 4.34 (t, 12H), 1.85 (m, 12H), 1.53 (m, 12H), 1.39-1.35 (m, 48H), 0.94 (t, 18H).

References: [1]Patent: US2008/58544,2008,A1 .Location in patent: Page/Page column 14.
[2]Molecular Crystals and Liquid Crystals,2009,vol. 509,p. 186 - 194.

15
[ 4877-80-9 ]
[ 97206-29-6 ]
2,3,6,7,10,11-hexakis(4-dodecyloxy-2,3,5,6-tetrafluorobenzoyloxy)triphenylene [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	With dmap; dicyclohexyl-carbodiimide; In dichloromethane; at 0 - 20℃;	Third StepA solution of 4.63 g of the compound (13), 0.44 g of <strong>[4877-80-9]2,3,6,7,10,11-hexahydroxytriphenylene</strong>, and 1.50 g of DMAP dissolved in 60 mL of dichloromethane was stirred at room temperature for 1 hour, then thereto was added, under ice cooling, 2.53 g of DCC dissolved in 20 mL of dichloromethane, followed by stirring under ice cooling for 5 minutes, and stirring overnight at room temperature. The precipitated dicyclohexylurea was filtered off, and the filtrate washed with 3-N hydrochloric acid, a saturated aqueous solution of sodium hydrogen carbonate, and saturated brine, followed by drying over anhydrous sodium sulfate. After evaporating the solvent, the product was purified by silica gel column chromatography and was recrystallized from hexane/ethanol to yield 1.63 g (0.66 mmol) of white solid 2,3,6,7,10,11-hexakis(4-dodecyloxy-2,3,5,6-tetrafluorobenzoyloxy)triphenylene (F).Phase transition temperature (° C.): Cry 79 Colh 288 Iso1H-NMR (CDCl3: delta ppm) 8.06 (S, 6H), 4.34 (t, 12H), 1.84 (m, 12H), 1.51 (m, 12H), 1.40-1.30 (m, 96H), 0.90 (t, 18H).

References: [1]Patent: US2008/58544,2008,A1 .Location in patent: Page/Page column 16.
[2]Molecular Crystals and Liquid Crystals,2009,vol. 509,p. 186 - 194.

16
[ 4877-80-9 ]
[ 128895-76-1 ]
2,3,6,7,10,11-hexakis(4-octyloxy-3-fluorobenzoyloxy)triphenylene [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	With dmap; dicyclohexyl-carbodiimide; In dichloromethane; at 0 - 20℃;	Third StepA solution of 4.38 g of the compound (16), 0.44 g of <strong>[4877-80-9]2,3,6,7,10,11-hexahydroxytriphenylene</strong>, and 1.50 g of DMAP dissolved in 60 mL of dichloromethane was stirred at room temperature for 1 hour, then thereto was added, under ice cooling, 2.53 g of DCC dissolved in 20 mL of dichloromethane, followed by stirring under ice cooling for 5 minutes, and stirring overnight at room temperature. The precipitated dicyclohexylurea was filtered off, and the filtrate washed with 3-N hydrochloric acid, a saturated aqueous solution of sodium hydrogen carbonate, and saturated brine, followed by drying over anhydrous sodium sulfate. After evaporating the solvent, the product was purified by silica gel column chromatography and was recrystallized from hexane/ethanol to yield 1.41 g (0.77 mmol) of white solid 2,3,6,7,10,11-hexakis(4-octyloxy-3-fluorobenzoyloxy)triphenylene (G).Phase transition temperature (° C.): Cry 56.4 M1 196.9 M2 210.2 M3 235.5 M4>350 Dec.1H-NMR (CDCl3: delta ppm) 8.01 (S, 6H), 7.64 (d, 6H), 7.48 (dd, 6H), 6.65 (t, 6H), 3.96 (t, 12H), 1.81 (m, 12H), 1.45 (m, 12H), 1.34-1.30 (m, 48H), 0.89 (t, 18H).

References: [1]Patent: US2008/58544,2008,A1 .Location in patent: Page/Page column 17.

17
[ 1010184-72-1 ]
[ 4877-80-9 ]
2,3,6,7,10,11-hexakis(4-octyloxy-2,6-difluorobenzoyloxy)triphenylene [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	With dmap; dicyclohexyl-carbodiimide; In dichloromethane; at 0 - 20℃;	Third StepA solution of 4.67 g of the compound (19), 0.44 g of <strong>[4877-80-9]2,3,6,7,10,11-hexahydroxytriphenylene</strong>, and 1.50 g of DMAP dissolved in 60 mL of dichloromethane was stirred at room temperature for 1 hour, then thereto was added, under ice cooling, 2.53 g of DCC dissolved in 20 mL of dichloromethane, followed by stirring under ice cooling for 5 minutes, and stirring overnight at room temperature. The precipitated dicyclohexylurea was filtered off, and the filtrate washed with 3-N hydrochloric acid, a saturated aqueous solution of sodium hydrogen carbonate, and saturated brine, followed by drying over anhydrous sodium sulfate. After evaporating the solvent, the product was purified by silica gel column chromatography and was recrystallized from hexane/ethanol to yield 1.50 g (0.78 mmol) of white solid 2,3,6,7,10,11-hexakis(4-octyloxy-2,6-difluorobenzoyloxy)tri phenylene (H).Phase transition temperature (° C.): Cry1 53.2 Cry2 115.5 Colh 176.2 Iso1H-NMR (CDCl3: delta ppm) 8.51 (S, 6H), 6.49 (d, 6H), 3.98 (t, 12H), 1.80 (m, 12H), 1.45 (m, 12H), 1.35-1.30 (m, 48H), 0.90 (t, 18H).

References: [1]Chemical Communications,2008,p. 1452 - 1454.
[2]Patent: US2008/58544,2008,A1 .Location in patent: Page/Page column 18.

18
[ 189135-66-8 ]
[ 4877-80-9 ]
2,3,6,7,10,11-hexakis(4-octyloxy-3,5-difluorobenzoyloxy)triphenylene [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	With dmap; dicyclohexyl-carbodiimide; In dichloromethane; at 0 - 20℃;	Third StepA solution of 4.67 g of the compound (22), 0.44 g of <strong>[4877-80-9]2,3,6,7,10,11-hexahydroxytriphenylene</strong>, and 1.50 g of DMAP dissolved in 60 mL of dichloromethane was stirred at room temperature for 1 hour, then thereto was added, under ice cooling, 2.53 g of DCC dissolved in 20 mL of dichloromethane, followed by stirring under ice cooling for 5 minutes, and stirring overnight at room temperature. The precipitated dicyclohexylurea was filtered off, and the filtrate washed with 3-N hydrochloric acid, a saturated aqueous solution of sodium hydrogen carbonate, and saturated brine, followed by drying over anhydrous sodium sulfate. After evaporating the solvent, the product was purified by silica gel column chromatography and was recrystallized from hexane/ethanol to yield 1.75 g (0.91 mmol) of white solid 2,3,6,7,10,11-hexakis(4-octyloxy-2,5-difluorobenzoyloxy)tri phenylene (I).Phase transition temperature (° C.): Cry1 14.8 Cry2 139.8 Colh>350 Dec.1H-NMR (CDCl3: delta ppm) 8.06 (S, 6H), 7.38 (d, 6H), 4.19 (t, 12H), 1.76 (m, 12H), 1.45 (m, 12H), 1.34-1.30 (m, 48H), 0.90 (t, 18H).

References: [1]Chemical Communications,2008,p. 1452 - 1454.
[2]Patent: US2008/58544,2008,A1 .Location in patent: Page/Page column 19.

19
[ 4877-80-9 ]
[ 76070-96-7 ]
2,3,6,7,10,11-tetrakis(4-hexyloxy-2,3,5,6-tetrafluorobenzoyloxy)triphenylene [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	With dmap; dicyclohexyl-carbodiimide; In dichloromethane; at 0 - 20℃;	Third StepA solution of 2.35 g of the compound (5), 0.44 g of <strong>[4877-80-9]2,3,6,7,10,11-hexahydroxytriphenylene</strong>, and 1.50 g of DMAP dissolved in 60 mL of dichloromethane was stirred at room temperature for 1 hour, then thereto was added, under ice cooling, 2.53 g of DCC dissolved in 20 mL of dichloromethane, followed by stirring under ice cooling for 5 minutes, and stirring overnight at room temperature. The precipitated dicyclohexylurea was filtered off, and the filtrate washed with 3-N hydrochloric acid, a saturated aqueous solution of sodium hydrogen carbonate, and saturated brine, followed by drying over anhydrous sodium sulfate. After evaporating the solvent, the product was purified by silica gel column chromatography and was recrystallized from hexane/ethanol to yield 1.40 g (0.71 mmol) of white solid 2,3,6,7,10,11-hexakis(4-hexyloxy-2,3,5,6-tetrafluorobenzoyl oxy)triphenylene (B).Phase transition temperature (° C.): Cry1 130 Cry2 157 Colh 301 Iso1H-NMR (CDCl3: delta ppm) 7.97 (S, 6H), 4.34 (t, 12H), 1.84 (m, 12H), 1.52 (m, 12H), 1.41-1.38 (m, 24H), 0.97 (t, 18H).

References: [1]Chemistry Letters,2007,vol. 36,p. 584 - 585.
[2]Patent: US2008/58544,2008,A1 .Location in patent: Page/Page column 12.
[3]Molecular Crystals and Liquid Crystals,2009,vol. 509,p. 186 - 194.

20
[ 4877-80-9 ]
[ 97206-27-4 ]
2,3,6,7,10,11-tetrakis(4-decyloxy-2,3,5,6-tetrafluorobenzoyloxy)triphenylene [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	With dmap; dicyclohexyl-carbodiimide; In dichloromethane; at 0 - 20℃;	Third StepA solution of 4.29 g of the compound (11), 0.44 g of <strong>[4877-80-9]2,3,6,7,10,11-hexahydroxytriphenylene</strong>, and 1.50 g of DMAP dissolved in 60 mL of dichloromethane was stirred at room temperature for 1 hour, then thereto was added, under ice cooling, 2.53 g of DCC dissolved in 20 mL of dichloromethane, followed by stirring under ice cooling for 5 minutes, and stirring overnight at room temperature. The precipitated dicyclohexylurea was filtered off, and the filtrate washed with 3-N hydrochloric acid, a saturated aqueous solution of sodium hydrogen carbonate, and saturated brine, followed by drying over anhydrous sodium sulfate. After evaporating the solvent, the product was purified by silica gel column chromatography and was recrystallized from hexane/ethanol to yield 1.00 g (0.43 mmol) of white solid 2,3,6,7,10,11-hexakis(4-decyloxy-2,3,5,6-tetrafluorobenzoyl oxy)triphenylene (E).Phase transition temperature (° C.): Cry 109 Colh 302 Iso1H-NMR (CDCl3: delta ppm) 8.07 (S, 6H), 4.34 (t, 12H), 1.84 (m, 12H), 1.51 (m, 12H), 1.40-1.31 (m, 72H), 0.91 (t, 18H).

References: [1]Chemistry Letters,2007,vol. 36,p. 584 - 585.
[2]Patent: US2008/58544,2008,A1 .Location in patent: Page/Page column 15.
[3]Molecular Crystals and Liquid Crystals,2009,vol. 509,p. 186 - 194.

21
[ 2695-48-9 ]
[ 4877-80-9 ]
C₆₆H₉₆O₆ [ No CAS ]
C₇₄H₁₁₀O₆ [ No CAS ]

References: [1]Tetrahedron Letters,2007,vol. 48,p. 6700 - 6703.

22
[ 4117-09-3 ]
[ 4877-80-9 ]
C₆₀H₈₄O₆ [ No CAS ]
C₆₇H₉₆O₆ [ No CAS ]

References: [1]Tetrahedron Letters,2007,vol. 48,p. 6700 - 6703.

23
[ 4877-80-9 ]
[ 1119-51-3 ]
C₄₈H₆₀O₆ [ No CAS ]
C₅₃H₆₈O₆ [ No CAS ]

References: [1]Tetrahedron Letters,2007,vol. 48,p. 6700 - 6703.

24
[ 4877-80-9 ]
[ 2695-47-8 ]
C₅₄H₇₂O₆ [ No CAS ]
C₆₀H₈₂O₆ [ No CAS ]

References: [1]Tetrahedron Letters,2007,vol. 48,p. 6700 - 6703.

25
[ 4877-80-9 ]
[ 106-95-6 ]
[ 134025-07-3 ]

References: [1]Angewandte Chemie - International Edition,2007,vol. 46,p. 3471 - 3474.

26
[ 209325-64-4 ]
[ 4877-80-9 ]
2,3,6,7,10,11-hexakis(1H,1H,2H,2H,3H,3H-perfluoropentyloxy)triphenylene [ No CAS ]