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Sequence-controllable linear/hyperbranched polymer prepared through metal-free catalyzed multi-component polymerization, and preparation method and application thereof

A technology of hyperbranched polymers and metal-free catalysis, which is applied in the fields of fluorescence/phosphorescence, material excitation analysis, etc., can solve the problems of high cost and demanding requirements, and achieve the effects of good film formation, mild conditions and high polymer yield

Active Publication Date: 2016-12-21
SOUTH CHINA UNIV OF TECH
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

However, the traditional preparation methods of hyperbranched polymers are demanding and costly. Therefore, it is of great significance to find a method for preparing linear / hyperbranched polymers with simple operation, atom economy and mild conditions.

Method used

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  • Sequence-controllable linear/hyperbranched polymer prepared through metal-free catalyzed multi-component polymerization, and preparation method and application thereof
  • Sequence-controllable linear/hyperbranched polymer prepared through metal-free catalyzed multi-component polymerization, and preparation method and application thereof
  • Sequence-controllable linear/hyperbranched polymer prepared through metal-free catalyzed multi-component polymerization, and preparation method and application thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0056] This example is a method for preparing polytetrahydropyrimidine by metal-free multi-component polymerization of alkynes, aldehydes and amines. The specific preparation steps are as follows:

[0057] The monomer raw material 4,4'-diaminodiphenylmethane (M1) is directly ordered from Alfa Aesar, and the monomer butynedioic acid dimethyl carbitate (M2) is obtained according to the literature [Macromolecules 2012,45,3687- 3694] prepared by the disclosed method; monomer raw material mass percent is 38% formaldehyde solution (M3) directly ordered from TCI company.

[0058] Add dimethyl carbityl butyndioate (0.1910g, 0.6mmol), 4,4'-diaminodiphenylmethane (0.1190g, 0.6mmol), and 2ml methanol into the polymerization tube, at room temperature (25°C) React for 30min; then add formaldehyde solution (136ul, 1.8mmol) and acetic acid (206ul, 1.2mmol) with a mass percentage of 38%, respectively, and continue to react at room temperature (25°C) for 16h; under stirring conditions, the rea...

Embodiment 2

[0067] This example is a method for preparing polydihydropyrrole by metal-free catalyzed multi-component polymerization of alkynes, aldehydes and amines. The specific preparation steps are as follows:

[0068] The monomer raw material 4,4'-diaminodiphenylmethane (M1) is directly ordered from Alfa Aesar, and the monomer butynedioic acid dimethyl carbitate (M2) is obtained according to the literature [Macromolecules 2012,45,3687- 3694] prepared by the disclosed method; monomer raw material mass percent is 38% formaldehyde solution (M3) directly ordered from TCI company.

[0069] Add dimethyl carbityl butyndioate (0.1910g, 0.6mmol), 4,4'-diaminodiphenylmethane (0.0595g, 0.3mmol), and 2ml of ethanol into the polymerization tube, at room temperature (25°C) React for 30min; then add 4,4'-diaminodiphenylmethane (0.0595g, 0.3mmol), 38% by mass aqueous formaldehyde solution (45ul, 0.6mmol), acetic acid (206ul, 1.2mmol), at 70 The reaction was continued at ℃ for 16 h; under the conditi...

Embodiment 3

[0073] This example is a method for preparing polydihydropyrrole by metal-free catalyzed multi-component polymerization of alkynes, aldehydes and amines. The specific preparation steps are as follows:

[0074] Monomer raw material p-phenylenediamine (M4), phenylamine (M5), terephthalaldehyde (M6) are directly ordered from Alfa Aesar company, and monomer butynedioic acid dimethyl carbitate (M2) is according to document [ Prepared by the disclosed method of Macromolecules 2012,45,3687-3694].

[0075] Add dimethyl carbityl butynedioate (0.1910g, 0.6mmol), p-phenylenediamine (0.0324g, 0.3mmol), and 2ml of ethanol into the polymerization tube, and react at room temperature for 30min; then add phenylamine (0.0559g , 0.6mmol), terephthalaldehyde (0.0402g, 0.3mmol), acetic acid (206ul, 1.2mmol), continue to react at room temperature for 16h; under the condition of stirring, the solution after the reaction is added dropwise in n-hexane, After standing still for 12 h, the precipitate w...

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Abstract

The invention belongs to the technical field of organic chemistry, and discloses a sequence-controllable linear / hyperbranched polymer prepared through metal-free catalyzed multi-component polymerization, and a preparation method and an application thereof. The method comprises the following steps: 1, adding alkyne and amine into a reaction container, and carrying out a hydroamination reaction with a polar solvent as a reaction medium to obtain an alkenyl ester intermediate, wherein the alkyne is a butyldiacetyl ester compound; 2, adding amine, aldehyde and a catalyst into the reaction container provided with the alkenyl ester intermediate, and carrying out a polymerization to obtain a polymer solution, wherein the catalyst is acid; and 3, adding the polymer solution to a settling agent in a dropwise manner under a stirring condition, allowing the obtained solution to stand, filtering the solution, washing the obtained material, and drying the washed material to obtain the sequence-controllable linear / hyperbranched polymer. The method has the advantages of simplicity, mild conditions, no metal catalysis, high yield of the polymer, controllable unit sequence of the polymer structure, realization of the preparation of linear and hyperbranched polymers, and potential application values in the field of biological and chemical luminescence detection.

Description

technical field [0001] The invention belongs to the technical field of organic chemistry, and relates to a method for preparing sequence-controllable linear / hyperbranched polymers, in particular to a method for preparing sequence-controllable linear / hyperbranched polymers through metal-free catalyzed multi-component polymerization of alkynes, ammonia and aldehydes. Hyperbranched polymers and methods and applications thereof. Background technique [0002] The structure of all biological macromolecules (such as protein, DNA, RNA) has sequence, and it is the sequence of this structure that promotes the existence of unique functions of biomacromolecules. In the field of polymer chemistry, great attention is paid to the sequence controllable polymer monomer unit structure, but the development of sequence controllable polymerization systems has always been in its infancy. Therefore, it is of great significance to develop a sequence controllable polymer synthesis method. of. [0...

Claims

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Application Information

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IPC IPC(8): C08G73/06G01N21/64
CPCC08G73/06C08G73/0611C08G73/0633G01N21/64
Inventor 唐本忠危博胡蓉蓉秦安军赵祖金
Owner SOUTH CHINA UNIV OF TECH
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