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Ionic liquid containing triphenylamine structure as well as preparation method and application thereof

A technology of ionic liquid and triphenylamine, applied in chemical instruments and methods, color-changing fluorescent materials, organic chemistry, etc., can solve the problem of lack of systematic design of material structure and achieve the effect of reducing structural composition

Inactive Publication Date: 2020-05-08
ZHEJIANG UNIV OF TECH
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0003] At present, there are few substances that can be used as electrochromic monomers and electrolyte materials at the same time, and there is a lack of systematic design of material structures. It is urgent to further expand the types of related materials.

Method used

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  • Ionic liquid containing triphenylamine structure as well as preparation method and application thereof
  • Ionic liquid containing triphenylamine structure as well as preparation method and application thereof
  • Ionic liquid containing triphenylamine structure as well as preparation method and application thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0040] The synthesis of embodiment 1 4-(diphenylamino) benzonitrile

[0041]

[0042] 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. Using 300-400 mesh silica gel as the stationary phase, eluting with dichloromethane / petroleum ether mixed solution with a volume ratio of 1:1 as the mobile phase, collecting the eluate containing the target compound, distilling of...

Embodiment 2

[0043] Example 2 Synthesis of 4-(bis(4-bromophenyl)amino)benzonitrile

[0044]

[0045] 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. Using 300-400 mesh silica gel as the stationary phase, eluting with dichloromethane / petroleum ether mixed solution with a volume ratio of 1:1 as the mobile phase, collecting the eluate containing the target compound, distilling off the solvent under reduced pressure and drying to obtain the following: 6.01 g of the white po...

Embodiment 3

[0046] Example 3 Synthesis of 4-(bis(4-(thiophene-2)phenyl)amino)benzonitrile

[0047]

[0048] 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. Using 300-400 mesh silica gel as the stationary phase, eluting with dichloromethane / petroleum ether mixed solution with a volume ratio of 1:1 as the mobile phase, collecting the eluate containing the target c...

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Abstract

The invention discloses an ionic liquid containing a triphenylamine structure as well as a preparation method and application thereof, the ionic liquid containing the triphenylamine structure is shownas a formula (I), and the ionic liquid can be used as a polymerization monomer for electrochemical polymerization to form a film and applied to preparation of an electrochromic material. According tothe invention, a series of new ionic liquids which contain the triphenylamine structure and different kinds of anions and have electrochromic properties are synthesized, the kinds (electrochromic properties and electrolyte properties) of the multifunctional ionic liquids are expanded, and meanwhile, after the materials are subjected to electrochemical polymerization to form films, the response speed of the films is at a leading level in electrochromic materials. The ionic liquid materials with the electrochromic performance and the electrolyte function can be applied to design and assembly ofelectrochromic devices, and the structural composition of the devices is reduced. In the formula (I), X is BF4 <->, PF6 <->, TFSI <-> or TOF <->.

Description

technical field [0001] The invention relates to a method for preparing an ionic liquid containing a triphenylamine structure and having electrochromic properties, and polymerizing an ionic liquid monomer material into a film as a novel photoelectric functional material, which is applied to the fields of electrochromism, energy storage, and the like. Background technique [0002] Ionic liquids have high ionic conductivity, wide electrochemical window, high thermal stability, excellent electrochemical stability and good material compatibility. Therefore, such materials have broad application prospects in the fields of fuel cells, dye-sensitized solar cells, supercapacitors, and electrochromic devices. At the same time, electrochromic materials have attracted widespread attention as a new type of photoelectric functional material in recent years because of their rich color types and ranges and easy processing properties. It is a very forward-looking attempt to apply ionic liqu...

Claims

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Application Information

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IPC IPC(8): C07D409/14C09K9/02C25D3/66
CPCC07D409/14C09K9/02C09K2211/1007C09K2211/1014C09K2211/1029C09K2211/1092C25D3/665
Inventor 吕晓静钱亮张诚
Owner ZHEJIANG UNIV OF TECH
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