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Polyquinoline polymer material and preparation method thereof

A technology of polymer materials and polyquinoline, which is applied in the direction of luminescent materials, chemical instruments and methods, etc., can solve the problems of low yield of polymers, and achieve the effects of good solubility, easy synthesis, and mild reaction conditions

Inactive Publication Date: 2018-04-06
BEIJING INSTITUTE OF TECHNOLOGYGY
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

However, this method needs to be completed in two steps, and the polymer yield is low

Method used

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  • Polyquinoline polymer material and preparation method thereof
  • Polyquinoline polymer material and preparation method thereof
  • Polyquinoline polymer material and preparation method thereof

Examples

Experimental program
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Effect test

Embodiment 1

[0040] Add 7.4g (40mmol) p-bromobenzaldehyde, 701mg (1mmol) bistriphenylphosphine palladium dichloride, 190mg (1mmol) cuprous iodide, 524g (2mmol) triphenylphosphine in the reaction bottle of 500mL, extract Nitrogen was filled after vacuum to remove oxygen in the system, 150mL triethylamine was added, the temperature was raised to 65°C, and after stirring for 30min, 8.48mL (60mmol) trimethylsilylacetylene was added, reacted for 24 hours, and triethylamine was removed by rotary evaporation. The intermediate product 1 was obtained; the intermediate product 1 was dissolved in dichloromethane, washed with water, and the organic phase was separated by column chromatography using petroleum ether / dichloromethane as the eluent to obtain the intermediate product 2.

[0041] Add 2.02g (10mmol) of intermediate product 2, 1g (10mmol) of sodium carbonate, and 100mL of methanol into a 500mL reaction flask. After stirring at room temperature for 24 hours, the methanol was removed by rotary e...

Embodiment 2

[0044] In a 500mL reaction flask, add 7.64g (40mmol) 5-bromothiophene-2-carbaldehyde, 701mg (1mmol) bistriphenylphosphine palladium dichloride, 190mg (1mmol) cuprous iodide, 524g (2mmol) triphenyl In order to remove the oxygen in the system, add 150mL of triethylamine, raise the temperature to 45°C, stir for 30min, add 8.48mL (60mmol) trimethylsilylacetylene, react for 24 hours, and remove the three ethylamine to obtain intermediate product 1; intermediate product 1 was dissolved in dichloromethane, washed with water, and the organic phase was separated by column chromatography using petroleum ether / dichloromethane as eluent to obtain intermediate product 2.

[0045] Add 2.16g (10mmol) of intermediate product 2, 1g (10mmol) of sodium carbonate, and 100mL of methanol into a 500mL reaction flask. Stir at room temperature for 24 hours, remove methanol by rotary evaporation, and obtain intermediate product 3; add dichloromethane to dissolve intermediate product 3, wash with water, a...

Embodiment 3

[0048] In a 500mL reaction flask, add 11.4g (40mmol) 9-bromoanthracene-10-formaldehyde, 701mg (1mmol) bistriphenylphosphine palladium dichloride, 190mg (1mmol) cuprous iodide, 524g (2mmol) triphenyl In order to remove the oxygen in the system, add 150mL of triethylamine, raise the temperature to 65°C, stir for 30min, add 8.48mL (60mmol) of trimethylsilylacetylene, react for 24 hours, and remove the trimethylsilylacetylene by rotary evaporation. ethylamine to obtain intermediate product 1; intermediate product 1 was dissolved in dichloromethane, washed with water, and the organic phase was separated by column chromatography using petroleum ether / dichloromethane as eluent to obtain intermediate product 2.

[0049] Add 3.02g (10mmol) of intermediate product 2, 1g (10mmol) of sodium carbonate, and 100mL of methanol into a 500mL reaction flask. Stir at room temperature for 24 hours, remove methanol by rotary evaporation, and obtain intermediate product 3; add dichloromethane to dis...

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Abstract

The invention relates to a polyquinoline polymer material and a preparation method thereof, and belongs to the field of polymer material preparation. The structural formula of the polymer is shown indescription, wherein R1 refers to an aromatic ring functional group without strong electron absorption, R2 refers to an aliphatic functional group and n refers to an integer selected from 3 to 80. Thepreparation method of the polyquinoline polymer material includes the following steps that, an alkyne-aldehyde derivative monomer, an aniline derivative monomer, a catalyst and a solvent are added ina reaction container, reaction is conducted at 80-120 DEG C for 12-48 minutes, the mixture is cooled to the room temperature, and an intermediate product is obtained; the intermediate product is added in a precipitation agent to obtain a precipitate, filtration and drying are conducted, and the polyquinoline polymer material is obtained. The polymer is directly obtained by one step, no metal catalysts are needed in the reaction process, the reaction condition is mild, the strict water-free and oxygen-free condition is not needed, operation is simple, and the material is easy to synthesize.

Description

technical field [0001] The invention relates to a polyquinoline polymer material and a preparation method thereof, belonging to the field of polymer material preparation. Background technique [0002] Polyquinolines (PQs) are a class of high temperature resistant aromatic heterocyclic polymer materials with excellent mechanical and optical properties. In 1975, Stille et al. prepared a series of polymers containing anthraline and quinoline structures through the reaction of diamino and diketone groups. These polymers have high temperature resistance, and their glass transition temperature reaches 251 ° C and melting point reaches 483 ° C . However, due to the high rigidity of the polymer composed of quinoline rings, the resulting polymers have poor solubility. In 2002, Wang Lixiang's research group synthesized two polyquinoline derivatives with better solubility by introducing alkyl chains into the side chains, and used them in chemical sensor research to realize the detect...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C08G73/06C09K11/06
CPCC08G73/0688C09K11/06C09K2211/1466
Inventor 石建兵付伟强董宇平佟斌蔡政旭
Owner BEIJING INSTITUTE OF TECHNOLOGYGY
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