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Carbazole-containing discotic liquid crystal compound and preparation method thereof

A discotic liquid crystal and compound technology, which is applied in the field of carbazole-containing discotic liquid crystal compounds and their preparation, and achieves the effects of enhancing p-p effect, high application value, and simple and fast synthesis route.

Inactive Publication Date: 2020-10-27
SICHUAN NORMAL UNIVERSITY
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

However, there are still few reports on the extension of p-conjugated coplanar functional materials by carbazole coupling and fusion with biphenyl and coupling with trifluoromethanesulfonate triphenylene

Method used

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  • Carbazole-containing discotic liquid crystal compound and preparation method thereof
  • Carbazole-containing discotic liquid crystal compound and preparation method thereof
  • Carbazole-containing discotic liquid crystal compound and preparation method thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0063] The compound provided in this example is an intermediate of the compound in general formula (Ⅲ), wherein R 1 for C 12 h 25， Its preparation reaction is as follows.

[0064] R 1 for C 12 h 25 Preparation of intermediate b.

[0065]

[0066]Starting from 3,3',4,4'-tetrakis(dodecyloxy)-1,1'-biphenyl (3.29 g, 3.7 mmol), it was mixed with bromine (0.59 g, 3.7 mmol) to 1:1 molar ratio is weighed in a 250ml round bottom flask, add 150ml of chloroform, put on a constant pressure dropping funnel, add chloroform (20ml) and bromine simple substance into it, put the round bottom flask in room temperature environment In the constant pressure dropping funnel, the solution in the constant pressure dropping funnel is controlled at 2 seconds per drop, and the plate is tracked every 15 minutes. After the reaction is completed, sodium bisulfite is added to terminate the reaction, filtered, spin-dried, and subjected to silica gel column chromatography (elution Agent: V dichlorome...

Embodiment 2

[0069] The compound provided in this example is a compound of general formula (Ⅲ). Wherein R 1 for C 12 h 25， Its preparation reaction is as follows.

[0070]

[0071] In a 50 ml reaction tube, b (365 mg, 0.376 mmol): c (100 mg, 0.188 mmol): K 2 CO 3 (779mg, 5.64 mmol): Pd(PPh 3 ) 4 (44mg, 0,0376 mmol)= 2 : 1 : 30 : 0.2 Weigh and add mixed solvent water (3 ml) / THF (10 ml), under the protection of argon, react at 70 ℃ for 48 h, cool to room temperature, extracted with dichloromethane, organic phase with anhydrous MgSO 4 Dry, filter and spin dry. Through silica gel column chromatography (eluent: V dichloromethane: V petroleum ether = 1:3), recrystallization with ethyl acetate and ethanol gave white solid (Ⅲ), (309 mg, yield 80%) .

[0072] H NMR 1 H NMR (CDCl 3 , TMS, 400 MHz), δ:7.85 (s, 1H, ArH), 7.83 (s, 1H,ArH), 7.05 (s, 4H, ArH), 7.02 (s, 1H, ArH),6.99 (s, 1H , ArH), 6.66-6.71 (m,4H, ArH), 6.61 (s, 4H, ArH), 4.07 (t , J = 6.4 Hz , 8H, NCH 2 , OCH 2 ), 3.87...

Embodiment 3

[0074] The compound provided in this embodiment is a compound of general formula (I), wherein R 1 for C 12 h 25， Its preparation reaction is as follows.

[0075]

[0076] In a 100ml round bottom flask with compound III (180 mg, 0.087mml): FeCl 3 (85mg, 0.052mml) = 1 : 6 molar ratio, add dichloromethane (60ml), nitromethane (5ml), react at room temperature, track the reaction every 15min, after the reaction is complete, add methanol The reaction was terminated, extracted with dichloromethane, MgSO 4 Dry, filter, spin dry, through silica gel column chromatography (eluent: V toluene: V petroleum ether = 1:1), recrystallize with ethanol and ethyl acetate to obtain yellow-green solid Ⅰ, (90 mg, yield rate 50%).

[0077] H NMR 1 H NMR (CDCl 3 , TMS, 400 MHz), δ: 9.34 (s, 2H, ArH), 8.33 (s,2H, ArH), 8.29 (s, 2H, ArH), 8.15 (s, 2 H, ArH), 7.88 (s, 4H, ArH), 4.59 (s, 2H, NCH 2 ), 4.40 (t, J = 6Hz, 4H, OCH 2 ), 4.25-4.33 (m, 12H, OCH 2 ), 2.12-2.14(m, 2H, CH 2 ), 1.96-2....

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Abstract

The invention relates to fusion of 10-octyl-2,3,6,7,13,14,17,18-octa(alkoxy)-10H-bis-phenanthro[9,10-b:9',10'-h]carbazole, substitution of a carbazole-containing discotic liquid crystal triad compound, and substitution of 9-octyl-2,7-di(3',4,4',5-tetra(alkoxy)-[1,1'-biphenyl]-9-yl)-9H carbazole, wherein the compound has structures represented by general formulas (I), (II) and (III), R1 is an alkylchain of C6-C16, R2 is an alkyl chain of C1-C16, the compound represented by the general formula (I) can be self-assembled into a hexagonal columnar liquid crystal intermediate phase in a wide temperature range, and the compound represented by the general formula (II) can be self-assembled into a columnar liquid crystal intermediate phase and a nematic phase within a certain temperature range. The invention further provides a preparation method of the structure represented by the general formulas (I), (II) and (III). The compound represented by the general formula (I) can be obtained by oxidizing and cyclizing the compound represented by the general formula (III) in FeCl3 molecules.

Description

technical field [0001] [ 9,10- b :9' ,10'- h ] Carbazole and carbazole-containing discotic liquid crystal triplet compounds. Background technique [0002] At present, discotic liquid crystals are a unique class of materials with remarkable electrical and photoconductive properties and can form nano-microstructures through self-assembly. It is a planar discoid molecule with π-bond conjugation. It was mainly used in phase compensation films in the early days. Due to its one-dimensional intermolecular columnar packing, it can self-assemble into columnar structures, especially hexagonal columnar phases. This offers unique possibilities for one-dimensional charge carrier systems. The interaction of electrons and the effect of electron migration rate make the stacking period along the column much shorter than the distance between columns. Therefore, discotic liquid crystals are considered as promising organic semiconductors for their applications in the fields of molecular el...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D209/80C07D209/86C09K19/34C09K11/06
CPCC07D209/80C07D209/86C09K19/3477C09K11/06C09K2211/1011C09K2211/1029
Inventor 杭俊方杨瑶赵可孝赵可清胡平汪必琴
Owner SICHUAN NORMAL UNIVERSITY
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