Material of imidazole type ionic liquid modified triphenylamine derivative and preparation method and application thereof

A technology of derivatives and triphenylamines, which is applied to materials based on imidazole-type ionic liquid-modified triphenylamine derivatives and the fields of preparation and application thereof, can solve the problems of high cost and expensive ionic liquids, and achieve fast response time, The effect of high optical contrast

Active Publication Date: 2018-12-28
ZHEJIANG UNIV OF TECH
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

However, ionic liquids are relatively expensive and costly when used as electrolytes

Method used

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  • Material of imidazole type ionic liquid modified triphenylamine derivative and preparation method and application thereof
  • Material of imidazole type ionic liquid modified triphenylamine derivative and preparation method and application thereof
  • Material of imidazole type ionic liquid modified triphenylamine derivative and preparation method and application thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0037] The synthesis of embodiment 1 4-(diphenylamino) benzonitrile

[0038] Under nitrogen protection, sodium hydride (1.496 g, 62.3 mmol) was dissolved in DMF (40 mL), and stirred well until no bubbles were generated. Diphenylamine (5.11g, 30.2mmol) was added to the solution, and after the temperature rose to 110°C and stabilized, p-fluorobenzonitrile (4.49g, 37.1mmol) was slowly added, and the system was refluxed for 12h. After the reaction was completed, the reaction liquid was cooled to room temperature, and saturated brine and dichloromethane were added for extraction, and the organic phase was collected, dried over anhydrous magnesium sulfate, concentrated under reduced pressure, and separated and purified by column chromatography. Use 300-400 mesh silica gel as the stationary phase, elute with dichloromethane / petroleum ether mixed solution with a volume ratio of 1:1 as the mobile phase, collect the eluate containing the target compound, distill off the solvent under re...

Embodiment 2

[0039] Example 2 Synthesis of 4-(bis(4-bromophenyl)amino)benzonitrile

[0040] Under dark conditions, the intermediate product 4 (dianilino) benzonitrile compound (4 g, 14.8 mmol) was dissolved in DMF (30 mL), and NBS (6.59 g, 37.1 g) dissolved in DMF (15 mL) was added dropwise. mmol) solution, reacted at room temperature for 24h. After the reaction was completed, the reaction liquid was cooled to room temperature, and saturated brine and dichloromethane were added for extraction, and the organic phase was collected, dried over anhydrous magnesium sulfate, concentrated under reduced pressure, and separated and purified by column chromatography. Use 300-400 mesh silica gel as the stationary phase, elute with dichloromethane / petroleum ether mixed solution with a volume ratio of 1:1 as the mobile phase, collect the eluate containing the target compound, distill off the solvent under reduced pressure and dry to obtain a white The powdery intermediate product 4(bis(4-bromophenyl)a...

Embodiment 3

[0041] Example 3 Synthesis of 4-(bis(4-(thiophene-2)phenyl)amino)benzonitrile

[0042] Under nitrogen protection, the intermediate product 4-(bis(4-bromophenyl)amino)benzonitrile (3.75g, 8.76mmol), potassium carbonate (5.4g, 39.12mmol), bis(triphenylphosphine) di Palladium chloride (780mg, 1.11mmol) and 2-thiopheneboronic acid (3.9g, 30.47mmol) were dissolved in a mixed solution of methanol (50mL) and toluene (50mL), and reacted at 100°C for 24h. After the reaction was completed, the reaction liquid was cooled to room temperature, and saturated brine and dichloromethane were added for extraction, and the organic phase was collected, dried over anhydrous magnesium sulfate, concentrated under reduced pressure, and separated and purified by column chromatography. Use 300-400 mesh silica gel as the stationary phase, elute with dichloromethane / petroleum ether mixed solution with a volume ratio of 1:1 as the mobile phase, collect the eluate containing the target compound, distill of...

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Abstract

The invention discloses an imidazole type ionic liquid modified triphenylamine derivative represented by a formula (I) and a preparation method thereof, and application of the triphenylamine derivative in the preparation of an electrochromic film as a polymerization monomer. The film obtained by the polymerization of the material synthesized by the method can be applied to the field of electrochromism. The film has a faster response time than an ionic liquid material, and is an electrochromic material with excellent performance. The formula (I) is in the description below.

Description

(1) Technical field [0001] The invention relates to a preparation method of a triphenylamine derivative modified by an imidazole-type ionic liquid, and the application of the material into a film as a new photoelectric functional material in the fields of electrochromism and the like. (2) Background technology [0002] Since the concept of electrochromism was proposed in the last century, electrochromic materials have attracted widespread attention as a new type of photoelectric functional material. Early research work in related fields mainly focused on inorganic electrochromic materials, such as tungsten trioxide, etc. Although these materials have good electrochemical stability, their color types are too monotonous, which limits their large-scale popularization and application. On the other hand, polymer electrochromic (PEC) materials have the advantages of various structures, wide color range, high optical contrast, and good processing performance, and are considered to ...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C08J5/18C08G73/02C08L79/02C09K9/02
CPCC07D409/14C08G73/0266C08J5/18C08J2379/02C09K9/02C09K2211/1044C09K2211/1092
Inventor 张诚钱亮吕晓静黄从惠毕茜胡旭明邵熊超
Owner ZHEJIANG UNIV OF TECH
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