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A kind of diamine monomer containing benzoxazole and carbazole structure and its preparation method and application

A technology of benzoxazole and diamine monomers, applied in the field of material science, can solve the problem of reducing the number of charge transfer complexes, and achieve the effects of reducing the charge transfer effect, obvious fluorescence characteristics, and good thermal stability

Active Publication Date: 2021-02-09
SUN YAT SEN UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

However, in this type of polyimide, there are still strong interactions between the main chains, between the side groups or between the main chain and the side groups, the number of charge transfer complexes cannot be reduced, and the charge transfer effect is still strong.

Method used

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  • A kind of diamine monomer containing benzoxazole and carbazole structure and its preparation method and application
  • A kind of diamine monomer containing benzoxazole and carbazole structure and its preparation method and application
  • A kind of diamine monomer containing benzoxazole and carbazole structure and its preparation method and application

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preparation example Construction

[0055] The preparation method of the diamine compound containing carbazole and benzoxazole structure shown in general structural formula Y-1 or Y-2 of the present invention comprises the following steps:

[0056] (1) Utilize substituted p-fluorophenylboronic acid and 2-chlorobenzoxazole to couple through Suzuki reaction, obtain 2-substituted phenylbenzoxazole structure, its general structural formula is as structural formula (2):

[0057]

[0058] (2) Utilize the active hydrogen grafting step (1) in the dihalogenated carbazole monomer carbazole to obtain a dihalogenated structure containing a carbazole benzoxazole structure, and its general structural formula is as structural formula (3);

[0059]

[0060] Where X can be fluorine, chlorine, bromine or iodine.

[0061] (3) The dihalogenated structure obtained in step (2) and 4-aminophenylboronic acid or 3-aminophenylboronic acid are prepared by Suzuki coupling reaction to prepare diamine, wherein, reacting with 4-aminophe...

Embodiment 1

[0064] (1) Preparation of diamine monomer

[0065] a. Synthesis of intermediate 2-(4-fluorophenyl)-benzoxazole

[0066] Add 7.65g (50mmol) of 2-chlorobenzoxazole, 7.0g (50mmol) of p-fluorophenylboronic acid, and 10.28g of potassium carbonate (75mmol) into a 250mL three-necked round-bottomed flask, and add 100mL of tetrahydrofuran solution and 50mL of deionized water , magnetically stirred and introduced argon gas, then added 0.05g tetrakistriphenylphosphine palladium, raised the temperature to 90°C and stirred for 12 hours, then cooled, poured the reaction solution into water for precipitation, extracted with ethyl acetate, and separated the layers to obtain an organic layer , spin-dried, and purified by column chromatography to obtain 7.67 g of white product 2-(4-fluorophenyl)-benzoxazole, with a yield of about 72%, and its structural formula is as follows:

[0067]

[0068] b. Synthesis of intermediate substituted dibromocarbazole derivatives

[0069] Add 6.39g (30mmol)...

Embodiment 2

[0081] (1) Synthesis of meta-substituted target diamine monomer 2

[0082] 5.18g (10mmol) of substituted dibromocarbazole derivatives prepared in step b of Example 1, 6.64g (24mmol) of potassium carbonate and 6.58g (24mmol) of 3-aminophenylboronic acid were added to a 250mL double-necked round-bottomed flask, Add 80mL tetrahydrofuran, 40mL deionized water, magnetically stir and pass through argon protection, then add a catalytic amount of tetrakistriphenylphosphine palladium, heat up to 90°C and react for 24h, cool to room temperature, pour the reaction solution into water for precipitation, After filtration, it was fully washed with methanol, and after drying, it was purified by column chromatography to obtain 4.07 g of the target diamine monomer with a yield of about 75%. Its structural formula is as follows:

[0083]

[0084] (2) At -10°C, add 2.1688g (4mmol) of the diamine monomer prepared in step (1), 3.2038g (16mmol) of 4,4'-diaminodiphenyl ether and 24.4mL of N-N dim...

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Abstract

The invention discloses a diamine monomer containing benzoxazole and carbazole structures, and a preparation method and an application thereof. Starting from dihalogenated carbazole, active hydrogen in monomer carbazole is grafted with a structural unit containing benzoxazole, and diamine is prepared through a Suzuki reaction or direct liquid ammonia ammoniation. According to the invention, the diamine monomer is simple in synthesis process and easy to be purified, so the diamine monomer is applicable to industrial production. The diamine compound prepared by using the method provided by the invention can be used for synthesizing high-performance and functional polymers like novel polyimide, polyamide and polyesterimide; and a polyimide material synthesized from the diamine compound provided by the invention is high in thermal stability, obvious in fluorescence characteristic and high in luminous intensity.

Description

technical field [0001] The invention relates to the technical field of material science, in particular to a diamine monomer containing benzoxazole and carbazole structures, a preparation method and application thereof. Background technique [0002] Most benzoxazole compounds have strong fluorescence, and some also have laser properties. They are often used as fluorescent probes, fluorescent whitening agents, laser dyes in the near ultraviolet band, and sensitizing dyes and supersensitizers in photosensitive emulsions. agent. In recent years, due to the discovery that some of them have biological activity and can be used as bactericides, preservatives and antitumor agents, such as CN103333131A, CN107778301A, etc., the research on them has become increasingly active. At present, there are few reports on the research on benzoxazole compounds in the field of polymer luminescence. Taking advantage of their good electron transport ability and excellent fluorescence performance, t...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07D413/10C07D413/14C08G73/10C08J5/18C08L79/08
CPCC07D413/10C07D413/14C08G73/1085C08J5/18C08J2379/08
Inventor 张艺吴慧焱龙禹波陈玥琪蒋星池振国刘四委许家瑞
Owner SUN YAT SEN UNIV
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