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Polyacetylene containing benzophenanthrene disk-like mesogens on side chain and preparation method thereof

A discotic liquid crystal and triphenylene technology, applied in the field of polymer compounds and their preparation, can solve the problems of poor film-forming performance, low thermal stability, low molecular weight of polyacetylene, etc., and achieve good film-forming performance and molecular rigidity Increased, good solubility effects

Inactive Publication Date: 2012-04-18
SICHUAN NORMAL UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

Due to the low molecular weight of the polyacetylene obtained by the above method, poor film-forming performance, and low thermal stability, the decomposition temperature is only about 300 ° C, which makes the application of this type of polyacetylene subject to certain limitations.

Method used

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  • Polyacetylene containing benzophenanthrene disk-like mesogens on side chain and preparation method thereof
  • Polyacetylene containing benzophenanthrene disk-like mesogens on side chain and preparation method thereof
  • Polyacetylene containing benzophenanthrene disk-like mesogens on side chain and preparation method thereof

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Experimental program
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Embodiment 1

[0040] What this embodiment prepares is the polyacetylene of general formula I, wherein R is the linear alkyl group that carbon number is 4, and m is 8. Its reaction equation is as follows:

[0041]

[0042] First add 0.66 mmol of 2-hydroxyl-3,6,7,10,11-penta-butoxytriphenylene (1) (400 mg), 2 mmol of potassium carbonate (276 mg) to 15 ml of dry N, N-dimethylformamide until dissolved, then add 1 mmole of 8-chloro-n-octanol (165 mg) and stir to mix and under the protection of argon, heat up to 80 ° C for 24 hours; naturally cool after the reaction to room temperature, then the reaction solution was poured into 20 ml of water, and the solid crude product was separated out, filtered, extracted with dichloromethane successively, washed three times with water, dried, concentrated, separated and purified by column chromatography (mobile phase: dichloromethane: ethyl acetate volume ratio=50:1), and finally recrystallized with petroleum ether to obtain 326 mg of white solid 2-(8-h...

Embodiment 2

[0054]What this embodiment prepares is the polyacetylene of general formula I, wherein R is the straight-chain alkyl group with 6 carbon atoms, and m is 8. Its reaction equation is as follows:

[0055]

[0056] First, 0.54 mmol of 2-hydroxy-3,6,7,10,11-penta-n-hexyloxytriphenylene (1) (400 mg), 2 mmol of cesium carbonate (651.6 mg) were added to 15 ml of dry N , to dissolve in N-dimethylacetamide, then add 0.8 mmoles of 8-chlorooctanol (150 mg) and stir to mix and under argon protection, heat up to 88°C for 20 hours of reaction; naturally cool to At room temperature, the reaction solution was poured into 20 ml of water, and the solid crude product was separated out, filtered, extracted with chloroform successively, washed with water three times, dried, concentrated, separated and purified by column chromatography (mobile phase: dichloromethane: ethyl acetate) volume ratio=50:1), and finally recrystallized with petroleum ether to obtain white solid 2-(8-hydroxyoctyloxy)-3,6...

Embodiment 3

[0068] What this embodiment prepares is the polyacetylene of general formula I, wherein R is the straight-chain alkyl group with 8 carbon atoms, and m is 8. Its reaction equation is as follows:

[0069]

[0070] First add 0.51 mmol of 2-hydroxy-3,6,7,10,11-penta-n-octyloxytriphenylene (1) (450 mg), 2 mmol of potassium carbonate (276 mg) to 15 ml of dry Dissolve in ethanol, then add 1 mmol of 8-bromooctanol (208 mg) and stir to mix and under argon protection, heat up to 100°C for 30 hours of reaction; naturally cool to room temperature after the reaction, then pour the reaction solution into 20 milliliters of water, the solid crude product was precipitated, filtered, extracted with ethyl acetate successively, washed three times with water, dried, concentrated, separated and purified by column chromatography (mobile phase: dichloromethane: volume ratio of ethyl acetate=50:1) , and finally recrystallized with petroleum ether to obtain 230 mg of white solid 2-(8-hydroxyoctylox...

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Abstract

The invention discloses polyacetylene containing benzophenanthrene disk-like mesogens on a side chain. A repetitive structure unit of the polyacetylene is as follows, in the formula, R represents linear alkyl benzene with 4 to 9 carbon atoms; m is an integer between 2 and 10; and the weight-average molecular weight is between 100,000 and 550,000. The invention also discloses a preparation method for the polyacetylene. A pi-pi conjugated structure formed by double bond on a benzene ring and conjugated alkenes double bond on the polyacetylene can greatly improve the degree of polymerization, sothe polyacetylene has better film forming performance; through Heat weightlessness analysis tests, the polyacetylene also has high decomposition temperature and good solubility; moreover, the reaction conditions are mild and the operation is easy.

Description

technical field [0001] The invention belongs to the technical field of polymer compounds containing discotic mesogens and the preparation thereof, and in particular relates to a polyacetylene whose side chain contains triphenylene discotic mesogens and a preparation method thereof. The polyacetylene is a liquid crystal macromolecule compound which is directly connected to an aryl group through a main chain of a conjugated olefin, and then directly connected to a triphenylene through a flexible chain spacer. Background technique [0002] The 2000 Nobel Prize in Chemistry was awarded to physicist Alan J. Heeger of the University of California, Alan G. MacDiamid of the University of Pennsylvania, and Japanese chemist Hideki Shirakawa for their research in the field of "synthesis of conductive organic polymers such as polyacetylene" . Due to the large conjugated π electron system, polyacetylene polymers use I 2 The conductivity after vapor doping is equivalent to that of metal...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C08F138/00C08F4/80C09K19/38
Inventor 赵可清孙作鹏余文浩汪必琴胡平
Owner SICHUAN NORMAL UNIV