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Method for preparing polycarbonyl enol ester compound by catalyzing alkyne carboxylic acid polymerization through organic base

An organic base catalyzed alkyne carboxylic acid and polycarbonyl enol ester technology, which is applied in the fields of polymer chemistry and materials science, can solve the problems of inability to achieve atom utilization, and achieve the effects of low price, mild reaction conditions and wide range

Active Publication Date: 2022-02-18
SOUTH CHINA UNIV OF TECH
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

However, almost all the polymerization reactions in which carboxylic acid monomers directly participate are to prepare the target polymer through condensation polymerization, which cannot achieve 100% atom utilization, and at the same time, by-products will be generated
In particular, the polymerization reaction with alkyne monomers capable of constructing a conjugated skeleton has not been reported yet.

Method used

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  • Method for preparing polycarbonyl enol ester compound by catalyzing alkyne carboxylic acid polymerization through organic base
  • Method for preparing polycarbonyl enol ester compound by catalyzing alkyne carboxylic acid polymerization through organic base
  • Method for preparing polycarbonyl enol ester compound by catalyzing alkyne carboxylic acid polymerization through organic base

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0053] A polycarbonyl enol ester compound is prepared by polymerizing a dibasic carbonyl alkyne compound and a dibasic carboxylic acid compound, and the reaction equation is as formula (1):

[0054]

[0055] Among them, the synthesis method of monomer M1 can be synthesized according to the synthesis method of the applicant in the published literature (Macromolecules, 2020, 53, 2516-2525); M2 is 4,4'-diphenyl ether dicarboxylic acid, which can be purchased from the market In this example, it was purchased from Anaiji Chemical; the catalyst DABCO can be purchased from the market, and in this example and the examples described below, it was purchased from TCIA (Shanghai) Chemical Industry Development Co., Ltd.

[0056] The preparation steps of described polycarbonyl enol ester compound are as follows:

[0057] Weigh 37.4mg (0.1mmol) of monomer M1, 25.8mg (0.1mmol) of monomer M2 into a 10mL polymerization tube, and then add 0.9mL tetrahydrofuran / N,N-dimethylformamide (volume ra...

Embodiment 2

[0060] A polycarbonyl enol ester compound is prepared by polymerizing a dicarbonyl alkyne compound and a dibasic carboxylic acid compound, and the reaction equation is as formula (2):

[0061]

[0062] Wherein, the synthesis method of monomer M1 is the same as that in Example 1; M3 is 2,2-bis(4-carboxyphenyl)hexafluoropropane, which can be purchased from the market, and in this example, it was purchased from Anaiji Chemical.

[0063] The preparation steps of described polycarbonyl enol ester compound are as follows:

[0064] Weigh 37.4mg (0.1mmol) of monomer M1, add 39.2mg (0.1mmol) of monomer M3 into a 10mL polymerization tube, and then add 0.9mL tetrahydrofuran / N,N-dimethylformamide (volume ratio 7 / 3) After the monomer is completely dissolved, the temperature of the reaction system is controlled at 25°C. Dissolve 0.56mg (0.005mmol) DABCO in 0.1mL tetrahydrofuran / N,N-dimethylformamide (volume ratio 7 / 3) mixed solvent, add the DABCO solution to the above monomer solution, ...

Embodiment 3

[0067] A polycarbonyl enol ester compound is prepared by polymerizing a dibasic carbonyl alkyne compound and a dibasic carboxylic acid compound, and the reaction equation is as formula (3):

[0068]

[0069]

[0070] Wherein, the synthesis method of monomer M1 is the same as that in Example 1; M4 is 1,4-cyclohexanedicarboxylic acid, which can be purchased from the market, and in this example, it was purchased from Anaiji Chemical.

[0071] The preparation steps of described polycarbonyl enol ester compound are as follows:

[0072] Weigh 37.4mg (0.1mmol) of monomer M1, add 17.2mg (0.1mmol) of monomer M4 into a 10mL polymerization tube, and then add 0.9mL tetrahydrofuran / N,N-dimethylformamide (volume ratio 7 / 3) After the monomer is completely dissolved, the temperature of the reaction system is controlled at 25°C. Dissolve 0.56mg (0.005mmol) DABCO in 0.1mL tetrahydrofuran / N,N-dimethylformamide (volume ratio 7 / 3) mixed solvent, add the DABCO solution to the above monomer s...

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Abstract

The invention belongs to the field of polymer chemistry and material science, and discloses a method for preparing a polycarbonyl enol ester compound by catalyzing alkyne carboxylic acid polymerization through organic base. The preparation method comprises the following step: carrying out polymerization reaction on a binary carbonyl alkyne compound and a dicarboxylic acid compound in an organic solvent under the catalysis of an organic base catalyst to obtain the polycarbonyl enol ester compound. The method disclosed by the invention is mild in reaction condition and has atom economy. The polycarbonyl enol ester compound prepared by using the method has good solubility, thermal stability and aggregation-induced emission characteristics.

Description

technical field [0001] The invention belongs to the field of macromolecular chemistry and material science, and in particular relates to a method for preparing polycarbonyl enol ester compounds by organic base-catalyzed alkyne carboxylic acid polymerization. Background technique [0002] The development of new polymerization reactions is of great importance to polymer materials science. Different from the increasingly mature and fast-developing polymerization reaction of olefinic monomers, there is still a very large room for development in the research and development of the polymerization reaction of easy-to-synthesize chemical raw materials such as acetylenic monomers. The use of alkyne monomers to construct functional polymer materials has important academic and technical significance, so the reaction based on alkyne monomers has become a research hotspot in the field of chemistry. In particular, the polymerization reaction based on alkyne monomers and nucleophilic reag...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C08G67/00
CPCC08G67/00
Inventor 唐本忠秦安军佀涵
Owner SOUTH CHINA UNIV OF TECH
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