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Preparation method and application of biphenyl bridged bisbenzimidazolium

A technology of dimethyl benzimidazolium 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, achieves short reaction time, low cost, and realizes the The effect of industrial mass production

Active Publication Date: 2022-03-22
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, phthalocyanines, metal complexes, and Prussian blue are relatively complex, and the preparation is more troublesome

Method used

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  • Preparation method and application of biphenyl bridged bisbenzimidazolium
  • Preparation method and application of biphenyl bridged bisbenzimidazolium
  • Preparation method and application of biphenyl bridged bisbenzimidazolium

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Embodiment

[0017] (1) Weigh 0.2 mmol (54.8 mg) of 1,3-dimethylbenzimidazolium iodide, 0.1 mmol (40.6 mg) of 4,4'-diiodo-1,1'-biphenyl (two The feeding ratio is 2:1) as the substrate, 2 mg copper salt Cu(OAc) of Group IB 2 ·H 2 O (with respect to 4,4'-diiodo-1,1'-biphenyl dosage is 10mol% equivalent) as catalyst, 0.2 mmol (16.4 mg) sodium acetate as additive, substrate, catalyst, additive are added and mixed In the reaction kettle, an aprotic solvent N,N-dimethylformamide (1 ml) was added as a reaction solvent, and the reaction was carried out at 100° C. for 10 hours. After the reaction was completed, dichloromethane (5 ml) was added, filtered with suction, washed with secondary water (5 ml) and ethanol (5 ml) successively, and the obtained yellow filter residue was dried to obtain the pure product biphenyl bridged bisbenzimidazole Onium, yield 90%. H NMR spectrum such as figure 2 Shown: (deuterated dimethyl sulfoxide is solvent, Bruker AMX-400 nuclear magnetic resonance instrument) ...

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Abstract

The invention discloses a preparation method and application of biphenyl bridged bisbenzimidazolium. Using 1,3-dimethylbenzimidazolium iodide and 1,4-diiodobiphenyl as substrates, metal salts as catalysts, and bases as additives, react at 0-200°C for 0.1-96 hours, One-step biphenyl bridged bis-benzimidazolium. Dissolve the compound in acetonitrile, inject a small amount of the resulting solution between two pieces of ITO glass, apply a voltage, the solution changes from colorless to brown, remove the voltage, and the solution becomes colorless again, this discoloration process is reversible and can be repeated repeatedly. The invention has the advantages of simple process, convenient operation, low cost, environmental friendliness, good repeatability, etc., and is expected to realize industrialized large-scale production; the invention synthesizes an imidazolium derivative with electrochromic properties, which is expected to be applied to electronic Display, color-changing glass, automotive anti-glare rearview mirror and other fields.

Description

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

Claims

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Application Information

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Patent Type & Authority Patents(China)
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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