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Three-dimensional nanometer graphene based on triptycene and preparation method thereof

A three-dimensional nano, triptycene technology, applied in the field of chemistry, can solve the problems that have not been reported, and achieve the effects of novel structure, strong fluorescence performance and high yield

Active Publication Date: 2013-10-30
HUAZHONG UNIV OF SCI & TECH
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  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0004] However, it has not been reported yet about using triptycene as a skeleton and modifying it with hexabenzocoronene to obtain a new three-dimensional nano-graphene derivative based on triptycene and its synthesis method.

Method used

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  • Three-dimensional nanometer graphene based on triptycene and preparation method thereof
  • Three-dimensional nanometer graphene based on triptycene and preparation method thereof
  • Three-dimensional nanometer graphene based on triptycene and preparation method thereof

Examples

Experimental program
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Effect test

Embodiment 1

[0031] Example 1 Synthesis of 2,6,14-triphenylethynyl triptycene

[0032] 200mg triiodotriptycene (0.315mmol), 37mg Pd(PPh 3 ) 4 (0.036mmol) and 11.6mgCuI (0.061mmol) were added in a 100ml two-necked bottle, and argon was ventilated, and 200ul phenylacetylene (0.99mmol) and 40ml triethylamine were added, then stirred and refluxed at 70°C, and the reaction was stopped after 48 hours. Add dichloromethane to dissolve, successively wash with dilute hydrochloric acid solution, water, extract with dichloromethane, anhydrous Na 2 SO 4 After drying, column chromatography using dichloromethane-petroleum ether (1:3) as the eluent gave 2,6,14-triphenylethynyl triptycene as a white solid.

[0033] Yield: 68.0%. Melting point: 184-185°C

[0034]

[0035] 1 H NMR (400MHz, CDCl 3 ): δ5.45(s, 1H), 5.46(s, 1H), 7.25(dd, J=7.6, 1.2Hz, 3H), 7.33-7.37(m, 9H), 7.40(d, J=7.6Hz, 3H), 7.50-7.53(m, 6H), 7.60(d, J=1.2Hz, 3H). 13 CNMR (100MHz, CDCl 3 ): δ53.41, 53.50, 88.77, 89.40, 120.39, 1...

Embodiment 2

[0036] Example 2 Synthesis of 2,6,14-tri-tert-butylphenylethynyl triptycene

[0037] 200mg triiodotriptycene (0.315mmol), 37mg Pd(PPh 3 ) 4 (0.036mmol) and 11.6mgCuI (0.061mmol) were added to a 100ml two-necked flask, argon was introduced, 178ul p-tert-butylphenylacetylene (0.99mmol) and 40ml triethylamine were added, and then stirred and refluxed at 70°C for 24 hours Then stop the reaction, add dichloromethane to dissolve, wash with dilute hydrochloric acid solution, water, extract with dichloromethane, anhydrous Na 2 SO 4 After drying, column chromatography with dichloromethane-petroleum ether (1:10) was used as the eluent to obtain 2,6,14-tri-tert-butylphenylethynyltriptycene as a white solid product.

[0038] Yield: 70.4%. Melting point: 190-193°C

[0039]

[0040] 1 H NMR (400MHz, CDCl 3 ): δ1.310(s, 9H), 5.404(s, 1H), 5.413(s, 1H), 7.210(dd, J=2.8, 2.8Hz, 3H), 7.335-7.355(m, 9H), 7.421( d, J=8HZ, 6H), 7.556(s, 3H). 13 C NMR (100MHz, CDCl 3): δ29.50, 29.67, 30...

Embodiment 3

[0041] Example 3 Synthesis of 2,6,14-three (2,3,4,5,6-pentaphenyl)-phenyl triptycene

[0042] 100mg of triphenylethynyl triptycene (0.181mmol), 215mg of tetraphenylcyclopentadienone (0.560mmol) and 1.5ml of diphenyl ether were heated and stirred at 260°C under the protection of argon to react after 48 hours completely. After column chromatography, dichloromethane-petroleum ether (1:3) was used as the eluent to obtain a yellow solid 2,6,14-tris(2,3,4,5,6-pentaphenyl)-phenyltris pterene.

[0043] Yield: 52.0%. Melting point: >300°C

[0044]

[0045] 2,6,14-tris(2,3,4,5,6-pentaphenyl)-phenyl triptycene

[0046] 1 H NMR (400MHz, CDCl 3 ): δ4.05(s, 1H), 4.28(s, 1H), 6.29-6.36(m, 9H), 6.48-6.61(m, 9H), 6.72-6.82(m, 66H). 13 C NMR (100MHz, CDCl 3 ):δ52.79,53.00,121.63,125.02,125.10,125.30,125.35,126.10,126.36,126.53,126.67,126.73,127.96,128.10,129.89,129.92,131.15,131.27,131.44,131.58,131.64,131.72,135.84, 136.28,139.73,140.04,140.12,140.19,140.23,140.33,140.37,140.40,140....

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Abstract

The invention discloses three-dimensional nanometer graphene based on triptycene and a synthetic method thereof. The three-dimensional nanometer graphene based on the triptycene is a novel coronene-modified triptycene derivative. The preparation method comprises the following steps of: firstly carrying out a Sonogashira coupling reaction on triiodo triptycene to obtain a tri-acetenyl triptycene derivative; then carrying out a Diels-Alder reaction on the tri-acetenyl triptycene derivative to obtain a coronene triptycene derivative; finally carrying out an FeCl3 oxidation and cyclization reaction in an organic solvent (dichloromethane) under the conditions of gas protection (Ar) and normal temperature for 15-240 minutes to obtain the three-dimensional nanometer graphene based on the triptycene. The preparation method disclosed by the invention is novel and higher in yield. The prepared three-dimensional nanometer graphene based on the triptycene disclosed by the invention has an outstanding effect on the aspect of cell imaging.

Description

technical field [0001] The invention belongs to the field of chemistry and relates to three-dimensional nanometer graphene. Background technique [0002] Since 1942, Bartlett et al. (J.Am.Chem.Soc., 1942, 64, 2649.) started from anthracene for the first time, and obtained a new type of compound-triptycene (triptycene) through multi-step reaction synthesis. , the synthesis and research of triptycene and its derivatives have aroused widespread interest. The unique three-dimensional rigid structure and unique photoelectric properties of triptycene and its derivatives make it widely used in many fields such as molecular machines, material chemistry and supramolecular chemistry. [0003] Hexa-peri-hexabenzocoronenes (HBC for short) is a unit system with super large electron conjugation formed by 13 benzene rings. Initially by Clar et al. (Proc.Chem.Soc.1958, 150) after bromination of dibenzo-peri-naphthene, under heating conditions through its own coupling and further heating d...

Claims

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Application Information

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IPC IPC(8): C07C15/20C07C5/25C09K11/06G01N21/64
Inventor 张春刘英彭连辉王菁菁潘凯进徐辉碧杨祥良
Owner HUAZHONG UNIV OF SCI & TECH
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