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Triazole-functionalized 4,4'-difluorodiphenylsulfone compounds and synthesis method thereof

A technology of difluorodiphenylsulfone and compounds, which is applied in the field of triazole-functionalized 4,4'-difluorodiphenylsulfone compounds and their synthesis, which can solve the problem of proton conductivity being affected by water content and conductivity decline, etc. question

Inactive Publication Date: 2016-03-30
SHANGHAI UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0004] Compared with the traditional proton exchange membrane and the high temperature proton exchange membrane, the traditional one must contain solvent water, and the proton conductivity is greatly affected by the water content, and the decrease of the water content will cause the conductivity to drop sharply

Method used

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  • Triazole-functionalized 4,4'-difluorodiphenylsulfone compounds and synthesis method thereof
  • Triazole-functionalized 4,4'-difluorodiphenylsulfone compounds and synthesis method thereof
  • Triazole-functionalized 4,4'-difluorodiphenylsulfone compounds and synthesis method thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0032] In this example, 4,4'-difluorodiphenylsulfone is used as raw material to synthesize the target product through bromination, coupling, click and other reactions. The first step is 3,3'-dibromo-4,4'- Synthesis of difluorodiphenyl sulfone, step (2) is 3,3'-bistrimethylsilylethynyl-4,4'-difluorodiphenyl sulfone synthesis, step (3) is 3,3' -Synthesis of diethynyl-4,4'-difluorodiphenylsulfone, step (4) is the synthesis of triazole-functionalized 4,4'-difluorodiphenylsulfone.

[0033] Experimental steps:

[0034] (1) Add 18.32g of 4,4'-difluorodiphenyl sulfone and 45ml of concentrated H to a 50ml round bottom flask 2 SO 4 , stirred at room temperature to completely dissolve 4,4'-difluorodiphenyl sulfone, and then add 28.26g NBS to the above solution. Spot the plate to track the reaction process, after about 6 hours, the reaction is over, the solution after the reaction is poured into a beaker filled with 350 g of ice water, and a yellow-white turbid mixture is obtained afte...

Embodiment 2

[0039] (1) Synthesis of 3,3'-dibromo-4,4'-difluorodiphenylsulfone: Same as Example 1

[0040] (2) Synthesis of 3,3'-bistrimethylsilylethynyl-4,4'-difluorodiphenyl sulfone: same as Example 1

[0041] (3) Dissolve 1.2g of 3,3'-bistrimethylsilylethynyl-4,4'-difluorodiphenyl sulfone in 15ml of THF, then add 1.508g of KOH to the solution, stir the reaction at room temperature, and the reaction is complete Then add 50ml ether and 15ml water, and carry out liquid separation operation. An appropriate amount of anhydrous Na was added to the organic phase 2 SO 4 Dry it. After drying, filter, add a certain amount of silica gel to the filtrate, rotate at 40°C, and separate by column chromatography to obtain 3,3'-ditrimethylsilylethynyl-4,4'-difluorodiphenyl sulfone, which is poured through the column The washing solution is petroleum ether:dichloromethane=8:5, and the yield is 40.8%.

[0042] (4) Synthesis of triazole-functionalized 4,4'-difluorodiphenylsulfone: same as Example 1

Embodiment 3

[0044] (1) Synthesis of 3,3'-dibromo-4,4'-difluorodiphenylsulfone: Same as Example 1

[0045] (2) Synthesis of 3,3'-bistrimethylsilylethynyl-4,4'-difluorodiphenyl sulfone: same as Example 1

[0046] (3) Synthesis of 3,3'-diethynyl-4,4'-difluorodiphenylsulfone: Same as Example 1

[0047] (4) Add 0.5g of 3,3'-diethynyl-4,4'-difluorodiphenyl sulfone into a round bottom flask, fill with nitrogen, and add 0.0264g of CuSO in turn under the protection of nitrogen 4 , 1.64gNaAsc, 5mlTHF and 0.476g azidotrimethylsilane, point the plate to observe the reaction process until the reaction is complete, add ethyl acetate and water layer, the organic layer is washed with 5% ammonia water, anhydrous MgSO 4 Dried, filtered and spin-dried, and separated by column chromatography to obtain triazole-functionalized 4,4'-difluorodiphenylsulfone.

[0048] The compound synthesized in the present invention can be polycondensed with bisphenol compounds to obtain polymer polysulfone material. The polys...

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Abstract

The invention relates to a triazole-functionalized 4,4'-difluorodiphenyl sulfone compound and a preparation method thereof. The structural formula of the compound is: . This kind of compound is synthesized from 4,4'-difluorodiphenyl sulfone through bromination, coupling, click and other reactions. It is divided into four steps, including 3,3'-dibromo-4,4'-difluoro Synthesis of Diphenylsulfone, Synthesis of 3,3'-Ditrimethylsilylethynyl-4,4'-Difluorodiphenylsulfone, 3,3'-Diethynyl-4,4'-Difluorodiphenyl Synthesis of sulfones, synthesis of triazole-functionalized 4,4'-difluorodiphenylsulfone. The compound synthesized in the present invention can be polycondensed with bisphenol compounds to obtain polymer polysulfone material. The skeleton structure of polysulfone makes it have excellent alcohol resistance effect, anti-oxidation, anti-acid catalytic hydrolysis performance, and excellent mechanical properties and thermal stability, and the triazole basic functional group provides proton defects, which can be used to prepare acid-base amphoteric high-temperature proton conductive materials.

Description

technical field [0001] The invention relates to a 4,4'-difluorodiphenyl sulfone compound and a synthesis method thereof, in particular to a triazole-functionalized 4,4'-difluorodiphenyl sulfone compound and a synthesis method thereof. Background technique [0002] A fuel cell (FC) is a highly efficient energy conversion device that converts chemical energy stored in fuels and oxidants into electrical energy, and is a promising high-efficiency green energy source. Proton exchange membrane fuel cell (protonexchangemembranefuelcell, PEMFC) uses polymer membrane as the electrolyte, which has the advantages of low-temperature start-up, high energy conversion rate, no electrolyte leakage, and long life. The preferred power source for regional power stations. Electrocatalyst and proton exchange membrane are the key materials of proton exchange membrane fuel cell. Among them, the function of the anode electrocatalyst is to catalyze the oxidation reaction of fuel; the function of t...

Claims

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Application Information

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IPC IPC(8): C07D249/04C07F7/10C08G75/20
CPCC07D249/06C07F7/10
Inventor 严六明岳宝华苗思雨陈焕庆张晓明韩帅元张叶沛刘太昂
Owner SHANGHAI UNIV
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