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Preparation method of benzophenanthrene-pyrene-benzophenanthrene discotic liquid crystal triad compound

A discotic liquid crystal, triphenylene technology, applied in the field of discotic liquid crystal triplet compounds

Active Publication Date: 2021-06-18
SICHUAN NORMAL UNIVERSITY
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

However, there are still a few reports on pyrene extending the p-conjugated coplanarity by coupling with triphenylene perfluorobutanesulfonate to form organic functional materials with both liquid crystallinity and luminescence.

Method used

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  • Preparation method of benzophenanthrene-pyrene-benzophenanthrene discotic liquid crystal triad compound
  • Preparation method of benzophenanthrene-pyrene-benzophenanthrene discotic liquid crystal triad compound
  • Preparation method of benzophenanthrene-pyrene-benzophenanthrene discotic liquid crystal triad compound

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0040] The compound provided in this example is an intermediate (c) of the compound in general formula (I), and its preparation reaction is as follows:

[0041]

[0042] Using pyrene (1.0 g, 4.944 mmol) as raw material, it was mixed with bis-linked pinacol borate (2.763 g, 10.88 mmol), [Ir(OMe)COD] 2 (0.1707 g, 0.2472 mmol) and dtbpy (0.1354 g, 0.4944 mmol) molar pyrene: double pinacol borate: [Ir(OMe)COD] 2 : dtbpy= 1 : 2.2 : 0.05 : 0.1 was weighed into a 100 ml reaction tube and 30 ml cyclohexane was added, under the protection of nitrogen, reacted at 80°C for 16 h, cooled to room temperature after the reaction, Chloromethane for extraction, organic phase with anhydrous MgSO 4 dried, filtered, spin-dried, and subjected to silica gel column chromatography (eluent: V 二氯甲烷 :V 石油醚 =1:1), recrystallized from ethyl acetate and ethanol to obtain white crystals (c) (1.4 g, yield 62%) .

[0043] H NMR 1 H NMR (CDCl 3 , TMS, 400 MHz), δ:8.62(s, 2H, ArH), 8.08(s, 4H,ArH), 1.46...

Embodiment 2

[0045] The compound provided in this example is R 1 and R 2 Both are -C 6 h 13 Intermediate (b) ， Its preparation reaction is as follows:

[0046]

[0047] Starting from 3,6,7,10,11-penta(hexyloxy)-2-hydroxytriphenylene (a) (3.0 g, 4.03 mmol), it was mixed with triethylamine (4.07 g, 40.3 mmol) Weigh it in a 50ml reaction tube at a molar ratio of 1:10, add 20 ml of dichloromethane dried with sintered anhydrous calcium chloride, degas and protect with nitrogen at a temperature of -50°C, and then Then, perfluorobutylsulfonyl fluoride (3.65 g, 12.1 mmol) was added slowly according to the molar ratio of compound (a) and perfluorobutylsulfonyl fluoride being 1:3, and then the reaction was returned to room temperature for 20 h. After the reaction was finished, extract with dichloromethane, and the organic phase was extracted with anhydrous MgSO 4 dried, filtered, spin-dried, and subjected to silica gel column chromatography (eluent: V 二氯甲烷 :V 石油醚 =1:3) separated and purif...

Embodiment 3

[0050] This example provides the preparation of the compound of general formula (I), wherein R 1 and R 2 Both are -C 6 h 13 , the preparation reaction is as follows:

[0051]

[0052] Weigh (c) (100 mg, 0.2202 mmol), (b) (633.3 mg, 0.6165 mmol), K 2 CO 3 (912.8 mg, 6.605 mmol) and Pd(PPh 3 ) 4 (50.89mg, 0.044 mmol) in a 50 ml reaction tube and add mixed solvent water (3 ml) / THF (10 ml), under the protection of nitrogen, react at 70 ℃ for 48 h, cool to room temperature after the reaction, use Dichloromethane was extracted, and the organic phase was extracted with anhydrous MgSO 4 dried, filtered, spin-dried, and subjected to silica gel column chromatography (eluent: V 二氯甲烷 :V 石油醚 =1:2, recrystallized with ethyl acetate and ethanol to obtain white solid (I) (249.6 mg, yield 68%).

[0053] H NMR 1 H NMR (CDCl 3 , TMS, 400 MHz), δ:8.62(s, 2H, ArH), 8.54(s, 4H,ArH), 8.18(s, 4H, ArH), 8.03(s, 2H, ArH), 7.97(s, 4H , ArH), 7.89(s, 4H, ArH),4.22-4.29(m, 20H, OCH 2 ), 1...

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Abstract

The invention relates to synthesis of a discotic liquid crystal triad compound containing a plurality of alkoxy chains and based on 2,7-bis(3,6,7,10,11-penta(alkoxy)benzophenanthren-2-yl)pyrene. The synthesis is characterized in that the discotic liquid crystal triad compound has a structure as shown in a general formula (I), wherein R1 is a C6-C10 alkyl chain, and R2 is a C1-C10 alkyl chain. The compound shown in the general formula (I) can be self-assembled into a hexagonal columnar liquid crystal intermediate phase and a nematic phase within a wide temperature range. The invention further provides the preparation method of the discotic liquid crystal triad compound containing the multiple alkoxy chains and based on the 2,7-bis(3,6,7,10,11-penta(alkoxy)benzophenanthren-2-yl)pyrene, and the preparation method is simple and rapid in synthetic route, mild in condition and high in yield of the discotic liquid crystal triad compound containing.

Description

technical field [0001] The invention relates to a discotic liquid crystal triplet compound of 2,7-bis(3,6,7,10,11-penta(alkoxy)triphenylene-2-yl)pyrene and a preparation method thereof. Background technique [0002] Discotic liquid crystals are a unique class of materials that have remarkable electrical and photoconductive properties and can form nano-microstructures through self-assembly. Discotic liquid crystal molecules usually consist of two basic components: a rigid planar or near-planar aromatic core surrounded by flexible aliphatic side chains. Such discotic molecules can spontaneously self-assemble in the liquid crystal phase, and form an ordered nematic phase or an ordered columnar phase and lamellar phase through the interaction of π-π bonds between benzene rings. This offers unique possibilities for one-dimensional charge-carrier systems, where the interaction of electrons and the influence of electron mobility rates make their stacking period along the column mu...

Claims

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Application Information

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IPC IPC(8): C07C43/20C07C303/28C07C309/65C07F5/02C07C41/30C09K11/06C09K19/32H01L51/05
CPCC07C43/20C07C303/28C07F5/025C07C41/30C09K11/06C09K19/32C09K2211/1011C07C2603/42C07C2603/50H10K10/46C07C309/65
Inventor 刘帅赵可孝赵可清胡平汪必琴
Owner SICHUAN NORMAL UNIVERSITY
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