Polyquinoline diketone compound as well as preparation method and application thereof

A technology for polyquinoline diones and compounds, which is applied in the fields of polymer chemistry and materials science, can solve the problems of little research on the construction of heterocyclic polymers, and achieve the effects of high thermal stability and refractive index, low cost and simple operation.

Active Publication Date: 2021-11-23
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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  • Polyquinoline diketone compound as well as preparation method and application thereof
  • Polyquinoline diketone compound as well as preparation method and application thereof
  • Polyquinoline diketone compound as well as preparation method and application thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

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

[0049]

[0050] The polyquinoline diones are passed through CO 2, the polyreaction of bifunctional group o-alkyne aniline monomer and bifunctional aryl iodide monomer is prepared, and the reaction equation is as formula (1):

[0051]

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

[0053] The preparation steps of described polyquinolinedione compound are as follows:

[0054] Add M1 (0.1 mmol, 39.9 mg), N1 (0.1 mmol, 52.2 mg), bistriphenylphosphine palladium dichloride (Pd(PPh 3 ) 2 Cl 2 ) (0.02mmol, 14mg) and cesium carbonate (Cs 2 CO 3 ) (0.2mmol, 65.3mg), replace CO 2 three times in CO 2 Under at...

Embodiment 2

[0057] A polyquinolinedione compound, its structural formula is as shown in P2:

[0058]

[0059] The polyquinoline diones are passed through CO 2 , the polyreaction of bifunctional group o-alkyne aniline monomer and bifunctional aryl iodide monomer is prepared, and the reaction equation is as formula (two):

[0060]

[0061]

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

[0063] The preparation steps of described polyquinolinedione compound are as follows:

[0064] Add M1 (0.1mmol, 39.9mg), N2 (0.08mmol, 33.8mg), Pd(PPh 3 ) 2 Cl 2 (0.02mmol, 14mg) and Cs 2 CO 3 (0.2mmol, 65.3mg), replace CO 2 three times in CO 2 Under atmosphere, 0.33 mL of ultra-dry DMSO was injected via syringe. The reaction system was reacted at 80° C. for 1 hour. After the reaction, cool to room temperature, add 2.6mL DMSO, stir and dilute. Then the polymer solution obtained is passed through a...

Embodiment 3

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

[0068]

[0069] The polyquinoline diones are passed through CO 2 , the polyreaction of bifunctional group o-alkyne aniline monomer and bifunctional aryl iodide monomer is prepared, and the reaction equation is as formula (three):

[0070]

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

[0072] The preparation steps of described polyquinolinedione compound are as follows:

[0073] Add M1 (0.1mmol, 39.9mg), N3 (0.12mmol, 52.1mg), Pd(PPh 3 ) 2 Cl 2 (0.02mmol, 14mg) and Cs 2 CO 3 (0.2mmol, 65.3mg), replace CO 2 three times in CO 2 Under atmosphere, inject 2 mL of ultra-dry DMSO via syringe. The reaction system was reacted at 140° C. for 8 hours. After the reaction was completed, cool to room temperature, add 1 mL DMSO, and stir to dilute. Then the polymer ...

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PUM

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Abstract

The invention discloses a polyquinoline diketone compound as well as a preparation method and application thereof, and the preparation method comprises the following steps: in a CO2 atmosphere, carrying out polymerization reaction on CO2, a bifunctional ortho-alkyne aniline monomer and a bifunctional aryl iodide monomer in an organic solvent under the combined action of a catalyst and alkali; and after the reaction is finished, purifying and drying the product to obtain the polyquinoline diketone compound. The method is mild in condition, and the polymerization monomer is simple and easy to obtain. The polyquinoline diketone compound obtained by the invention is good in solubility and film-forming property, has relatively high thermal stability and refractive index, and has potential application in the fields of optical lenses and self-assembly.

Description

technical field [0001] The invention relates to the fields of polymer chemistry and material science, in particular to a polyquinolinedione compound and its preparation method and application. 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. In addition to the CO 2 converted to chemicals and fuels, CO 2 Participating in the construction of functional polymers as monomers has attracted extensive attention from polymer scientists. However, currently reported CO 2 Most of the polymers involved in the preparation are chain polymers. Using CO 2 The direct preparation of heterocyclic polymers as monomers is quite challenging. [0003] Since Shirakawa, MacDiarmid and Heeger found that doped polyacetylene has metal conductivity, the use of triple-bond monomers such as alkyne monome...

Claims

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Application Information

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Patent Type & Authority Applications(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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