Brush-type difluoro monomer and synthetic method thereof

A synthesis method and technology of fluorine monomers, applied in the field of materials, can solve the problems of difficult synthesis, few types of side chain monomers, and high solubility

Active Publication Date: 2015-01-07
SHAANXI NORMAL UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

Compared with the main chain functional polymer, the side chain functional polymer has the advantages of low melting point and high solubility, and the functional group is ...

Method used

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  • Brush-type difluoro monomer and synthetic method thereof
  • Brush-type difluoro monomer and synthetic method thereof
  • Brush-type difluoro monomer and synthetic method thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0031] Taking the preparation of a brush-type difluoromonomer with the following structural formula as an example, the specific preparation method is as follows:

[0032]

[0033] 1. Preparation of compound a

[0034] Under the protection of nitrogen, add 0.79g (32.42mmol) of magnesium powder and 5mL of dry tetrahydrofuran to a 100mL three-necked flask, turn on the magnetic stirring, raise the temperature to 65°C, and slowly add 5.00g (27.02mmol) of 3,5-dimethyl A mixed solution of bromobenzene and 40 mL of dry tetrahydrofuran was stirred at 65°C for 3 hours to prepare a Grignard reagent, and then a mixed solution of 3.76 g (27.02 mmol) of 2,6-difluorobenzonitrile and 40 mL of dry tetrahydrofuran was slowly added dropwise, Continue to stir at 65°C for 6 hours. After the reaction is over, add 80mL of 0.1mol / L hydrochloric acid aqueous solution, stir and reflux at 80°C for 12 hours, wash the reaction solution until neutral, concentrate the organic phase, and prepare compound ...

Embodiment 2

[0042] Taking the preparation of a brush-type difluoromonomer with the following structural formula as an example, the specific preparation method is as follows:

[0043]

[0044] In step 3 of Example 1, the 3,5-dimethylphenylboronic acid used was replaced with equimolar 4-methylbenzeneboronic acid, and the other steps were the same as in Example 1 to prepare a brush-type difluoromonomer, which The yield is 60.1%, and the structural characterization data are as follows:

[0045] 1 H-NMR (DMSO-d 6 as solvent, TMS as internal standard, 300MHz, ppm): 7.66(m, 1H), 7.48(s, 3H), 7.26(t, 2H), 7.11(s, 8H), 3.89(s, 4H), 2.19( s, 6H).

Embodiment 3

[0047] Taking the preparation of a brush-type difluoromonomer with the following structural formula as an example, the specific preparation method is as follows:

[0048]

[0049] In step 3 of Example 1, the 3,5-dimethylphenylboronic acid used was replaced with equimolar 2,4-dimethylphenylboronic acid, and the other steps were the same as in Example 1 to prepare a brush-type difluoromono body, its yield is 56.9%, and the structural characterization data are as follows:

[0050] 1 H-NMR (DMSO-d 6 as solvent, TMS as internal standard, 300MHz, ppm): 7.56(m, 1H), 7.41(s, 3H), 7.22(t, 2H), 7.12(s, 2H), 6.99(s, 2H), 6.98( s, 2H), 3.96 (s, 4H), 2.34 (s, 12H).

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Abstract

The invention discloses a brush-type difluoro monomer and a synthetic method thereof. The structure formula of the monomer is as shown in the specification, wherein X represents CH3 or OCH3; and n is an integer of 1-3. The monomer is prepared through Grignard reaction, nucleophilic addition reaction, bromination reaction and coupled reaction with 3,5-dimethyl bromobenzene as a raw material. The brush-type difluoro monomer contains polymerizable difluoro group and functionalized methyl or methoxy group, quaternization or sulfonated polymer can be obtained after polycondensation reaction and functional group conversion of the brush-type difluoro monomer, and the functionalized polymer can be used as a fuel cell polymer electrolyte membrane material.

Description

technical field [0001] The invention belongs to the technical field of materials, and in particular relates to a brush-type difluoro monomer and a preparation method thereof. Background technique [0002] With the continuous development of science and technology, ordinary polymer materials can no longer meet the needs of specific functions, and then functional polymer materials emerged as the times require. At present, polymer materials can be used in many fields after functionalization, such as fuel cells, photovoltaic cells, separation membranes and other fields. For polymers containing specific functional groups, for example, polymers containing methyl functional groups are brominated and ammonized to form quaternized polymer materials, which can be used for anion exchange membranes for fuel cells. The sulfonated polymer can be obtained by demethylating the polymer containing the methoxy functional group and reacting with the sulfonated lactone. This sulfonated polymer m...

Claims

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Application Information

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IPC IPC(8): C07C49/813C07C49/84C07C45/68
CPCC07C45/004C07C45/63C07C45/68C07C49/813C07C49/84C07F3/02
Inventor 陈新兵石倩陈沛安忠维
Owner SHAANXI NORMAL UNIV
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