Preparation method and application of biphenyl bridged bis-benzimidazolium

A technology of dimethylbenzimidazolium and benzimidazolium, which is applied in the field of chemical synthesis and application, can solve the problems of troublesome preparation, complex structure, and high cost of inorganic metal oxides, and achieve short reaction time, low cost, and realization of The effect of industrial mass production

Active Publication Date: 2019-05-10
GUILIN UNIVERSITY OF TECHNOLOGY
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  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

The cost of inorganic metal oxides is relatively high, and the structures of conjugated conductive polymers, pht

Method used

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  • Preparation method and application of biphenyl bridged bis-benzimidazolium
  • Preparation method and application of biphenyl bridged bis-benzimidazolium
  • Preparation method and application of biphenyl bridged bis-benzimidazolium

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Embodiment

[0017] (1) Weigh 0.2 mmol (54.8 mg) of 1,3-dimethylbenzimidazolium iodide salt, 0.1 mmol (40.6 mg) of 1,4-diiodobiphenyl (the ratio of the two is 2:1 ) As a substrate, 2 mg of group IB copper salt Cu(OAc) 2 ·H 2 O (10 mol% equivalent relative to the amount of 1,4-diiodobiphenyl) is used as the catalyst, and 0.2 mmol (16.4 mg) of sodium acetate is used as the additive. The substrate, catalyst, and additives are mixed into the reactor and added The protic solvent N,N-dimethylformamide (1 ml) was used as the reaction solvent to react at 100°C for 10 hours. After the reaction is complete, add dichloromethane (5 ml), filter with suction, and wash with water (5 ml) and ethanol (5 ml) successively. The yellow filter residue obtained is dried to obtain the pure product biphenyl bridged bisbenzimidazole. Onium, the yield is 90%. Proton NMR spectra such as figure 2 Shown: (Deuterated dimethyl sulfoxide as solvent, Bruker AMX-400 nuclear magnetic resonance instrument) 1 H NMR (400 MHz, ...

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Abstract

The invention discloses a preparation method and application of biphenyl bridged bis-benzimidazolium. 1,3-dimethyl benzimidazolium iodate and 1,4-diiodobiphenyl as substrates, a metal salt as a catalyst and an alkali as an additive are subjected to reaction at 0-200 DEG C for 0.1-96 hours to obtain biphenyl bridged bis-benzimidazolium via one step. The compound biphenyl bridged bis-benzimidazoliumis dissolved in acetonitrile; a little quality of the obtained solution is injected between two ITO (indium tin oxide) glass sheets; a voltage is applied; the solution turns from no color to coffee;the voltage is removed, and the solution turns colorless; the color variation process is irreversible many times. The preparation method has the advantages that, for instance, the process is simple, operation is convenient, the cost is low, and the preparation method is environmentally friendly and good in repeatability; it is expected to achieve industrial large-scale production. The imidazoliumderivative with electrochromic property is synthesized herein and is expectedly applicable to the fields, such as electronic displays, variable color glass, and automotive anti-dazzling rearview mirrors.

Description

Technical field [0001] The invention belongs to the technical field of chemical synthesis and application, and particularly relates to a preparation method and application of biphenyl bridged bisbenzimidazolium. Background technique [0002] The material molecules with electrochromic properties reported so far mainly include inorganic metal oxides, viologen, conjugated conductive polymers, phthalocyanines, metal complexes, and Prussian blue. Electrochromic materials are widely used in electronic displays, automotive anti-glare glasses, smart windows, and color-changing glass. The cost of inorganic metal oxides is relatively high, and the structures of conjugated conductive polymers, phthalocyanines, metal complexes, Prussian blue, etc. are relatively complex and the preparation is relatively troublesome. Ziluojing has simple structure, easy modification and stable properties, and is favored by scientists. 2,2'-(-4,4'-biphenyl)-bis(1,3-dimethylbenzimidazolium) diiodide salt is s...

Claims

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Application Information

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IPC IPC(8): C07D235/18C09K9/02
Inventor 李世清李永树梁霞静刘运烽陈紫园潘梅玲
Owner GUILIN UNIVERSITY OF TECHNOLOGY
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