A kind of polyquinoline dione compound and its preparation method and application

A technology of polyquinoline diones and compounds, which is applied in the fields of polymer chemistry and materials science, can solve the problems of seldom research on the construction of heterocyclic polymers, achieve high thermal stability and refractive index, wide source, and good functional group tolerance sexual effect

Active Publication Date: 2022-05-24
SOUTH CHINA UNIV OF TECH
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0004] Based on chemically active triple bond monomers and CO 2 There are few studies on the construction of heterocyclic polymers by the polymerization reaction

Method used

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  • A kind of polyquinoline dione compound and its preparation method and application
  • A kind of polyquinoline dione compound and its preparation method and application
  • A kind of polyquinoline dione compound and its preparation method and application

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0048] A kind of polyquinoline dione compound, its structural formula is shown as P1:

[0049]

[0050] Said polyquinoline dione compounds pass through CO 2, the polymerization reaction of bifunctional o-alkynyl aniline monomer and bifunctional aryl iodide monomer is prepared, and the reaction equation is as formula (1):

[0051]

[0052] Wherein, the o-iodoaniline intermediate can be synthesized with reference to the preparation method of the literature (Macromolecules, 2021,54(9): 4112-4119), and then it and phenylacetylene are synthesized by Sonogashira reaction to synthesize monomer M1; monomer N1 can refer to literature ( Chem. Commun., 2019, 55(47): 6755-6758). Synthesized.

[0053] The preparation steps of the described polyquinoline dione compounds are as follows:

[0054] To a 10 mL dry polymerization tube equipped with a magnetic stirrer was added M1 (0.1 mmol, 39.9 mg), N1 (0.1 mmol, 52.2 mg), bistriphenylphosphonium palladium dichloride (Pd (PPh) 3 ) 2 Cl...

Embodiment 2

[0057] A kind of polyquinoline dione compound, its structural formula is shown as P2:

[0058]

[0059] Said polyquinoline dione compounds pass through CO 2 , the polymerization reaction of bifunctional o-alkynyl aniline monomer and bifunctional aryl iodide monomer is prepared, and the reaction equation is such as formula (two):

[0060]

[0061]

[0062] Wherein, the synthesis method of the monomer M1 is the same as that in Example 1; the monomer N2 is purchased from Matrix Scientific Company.

[0063] The preparation steps of the described polyquinoline dione compounds are as follows:

[0064] M1 (0.1 mmol, 39.9 mg), N2 (0.08 mmol, 33.8 mg), Pd (PPh) were added to a 10 mL dry polymerization tube equipped with a magnetic stir bar 3 ) 2 Cl 2 (0.02mmol, 14mg) and Cs 2 CO 3 (0.2mmol, 65.3mg), with CO 2 three times, in CO 2 Under atmosphere, inject 0.33 mL of ultra-dry DMSO through a syringe. The reaction system was reacted at 80°C for 1 hour. After the reactio...

Embodiment 3

[0067] A kind of polyquinoline dione compound, its structural formula is shown as P3:

[0068]

[0069] Said polyquinoline dione compounds pass through CO 2 , the polymerization reaction of bifunctional o-alkynyl aniline monomer and bifunctional aryl iodide monomer is prepared, and the reaction equation is such as formula (three):

[0070]

[0071] Wherein, the synthesis method of the monomer M1 is the same as that in Example 1; the monomer N3 is purchased from Shanghai Bide Pharmaceutical Technology Co., Ltd.

[0072] The preparation steps of the described polyquinoline dione compounds are as follows:

[0073] M1 (0.1 mmol, 39.9 mg), N3 (0.12 mmol, 52.1 mg), Pd (PPh) were added to a 10 mL dry polymerization tube equipped with a magnetic stir bar 3 ) 2 Cl 2 (0.02mmol, 14mg) and Cs 2 CO 3 (0.2mmol, 65.3mg), with CO 2 three times, in CO 2 Under atmosphere, inject 2 mL of ultra-dry DMSO through a syringe. The reaction system was reacted at 140°C for 8 hours. After...

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Abstract

The invention discloses a polyquinoline dione compound and its preparation method and application. The preparation method comprises the following steps: 2 Atmosphere, CO 2 , bifunctional o-alkyne aniline monomer and bifunctional aryl iodide monomer are polymerized in an organic solvent through the joint action of a catalyst and a base; after the reaction, the product is purified and dried to obtain polyquinolinedione compound. The method of the invention has mild conditions, and the polymerization monomer is simple and easy to obtain. The polyquinolinedione compound obtained by the invention has good solubility and film-forming property, high thermal stability and refractive index, and has potential applications in the fields of optical lenses and self-assembly.

Description

technical field [0001] The invention relates to the fields of polymer chemistry and materials science, in particular to a polyquinoline dione compound and a preparation method and application thereof. Background technique [0002] carbon dioxide (CO 2 ), as an abundant, cheap, non-toxic and renewable natural resource, is a potential reaction raw material, and its chemical utilization has always been a research hotspot in academia and industry. Except for CO 2 In addition to converting into chemicals and fuels, CO 2 Participating in the construction of functional polymers as monomers has received extensive attention from polymer scientists. However, currently reported CO 2 Most of the polymers involved in the preparation are chain polymers. Utilize CO 2 The direct preparation of heterocyclic polymers as monomers presents great challenges. [0003] Since Shirakawa, MacDiarmid, and Heeger discovered that doped polyacetylenes have metallic conductivity, the use of triple-...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C08G73/06
CPCC08G73/0688Y02E10/549
Inventor 唐本忠刘东明秦安军胡蓉蓉赵祖金王志明
Owner SOUTH CHINA UNIV OF TECH
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