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Diamine monomer containing tetraphenylethylene-bis-arylamine structure, preparation method and application of diamine monomer in super-stable electrochromic material

A technology of tetraphenylethylene and diamine monomers, which is applied in the direction of color-changing fluorescent materials, preparation of organic compounds, preparation of nitro compounds, etc., can solve the influence of material stability, high electrochromic oxidation potential, and limit black electrochromic The application of color-changing materials and other problems can reduce the oxidation potential and improve the stability.

Pending Publication Date: 2022-05-27
JILIN UNIV
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  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

However, this method tends to produce higher electrochromic oxidation potentials
The high electrochromic oxidation potential greatly affects the stability of the material, which severely limits the application of black electrochromic materials

Method used

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  • Diamine monomer containing tetraphenylethylene-bis-arylamine structure, preparation method and application of diamine monomer in super-stable electrochromic material
  • Diamine monomer containing tetraphenylethylene-bis-arylamine structure, preparation method and application of diamine monomer in super-stable electrochromic material
  • Diamine monomer containing tetraphenylethylene-bis-arylamine structure, preparation method and application of diamine monomer in super-stable electrochromic material

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0035] Example 1: N-{4-[1,2-bis(4-aminophenyl)-2-{4-[bis(4-methoxyphenyl)amino]phenyl}vinyl]phenyl} Preparation of -4-methoxy-N-(4-methoxyphenyl)aniline

[0036] The first step reaction: add 24g of 4-bromobenzophenone, 15.7g of zinc powder to a 1000mL three-necked flask equipped with mechanical stirring, cool to -78°C after 500mL of tetrahydrofuran, stir and slowly drip under nitrogen protection Add 23g of titanium tetrachloride, return to room temperature and then heat to 85°C for 24h reaction. After the mixture was cooled to room temperature again, the reaction was quenched with 500 mL, 10 wt% aqueous potassium carbonate solution, the organic layer was collected after filtration, the aqueous layer of the filtrate was extracted three times with ethyl acetate, the organic phases were combined and dried with magnesium sulfate overnight, and the ethyl acetate was evaporated. After mixing with tetrahydrofuran, a solid crude product was obtained. The crude product was recrystalli...

Embodiment 2

[0041] Example 2: N-{4-[1,2-Bis(4-aminophenyl)-2-{4-[bis(4-methoxyphenyl)amino]phenyl}vinyl]phenyl} -4-Methoxy-N-(4-methoxyphenyl)aniline to prepare pyromellitic dianhydride type polyimide.

[0042] To a three-necked flask equipped with a magnetron, a nitrogen inlet and outlet, and a thermometer, add 0.290 g of N-{4-[1,2-bis(4-aminophenyl)-2-{4- [bis(4-methoxyphenyl)amino]phenyl}vinyl]phenyl}-4-methoxy-N-(4-methoxyphenyl)aniline and 0.078 g of pyromellitic acid bis anhydride, added 4 mL of N,N-dimethylacetamide (solid content 27%), reacted at room temperature for 24 h to obtain a viscous polyamic acid, then added 1.4 mL of acetic anhydride and 0.7 mL of pyridine, heated to 110 °C and reacted for 3 h , after the reaction is completed, cooled to room temperature, discharged into ethanol to obtain a white fibrous product, washed with ethanol under reflux for 30 min, washed with water under reflux, washed with ethanol under reflux for 30 min, and dried in a vacuum oven at 90° C. ...

Embodiment 3

[0044] Example 3: N-{4-[1,2-Bis(4-aminophenyl)-2-{4-[bis(4-methoxyphenyl)amino]phenyl}vinyl]phenyl} Preparation of polyimide by polymerization of -4-methoxy-N-(4-methoxyphenyl)-p-3,3',4,4'-benzophenone tetraacid dianhydride

[0045] To a three-necked flask equipped with a magnetron, nitrogen inlet and outlet, and a thermometer, add 0.29 g of N-{4-[1,2-bis(4-aminophenyl)-2-{4- [bis(4-methoxyphenyl)amino]phenyl}vinyl]phenyl}-4-methoxy-N-(4-methoxyphenyl)aniline and 0.112 g of 3,3', 4,4'-benzophenone tetraacid dianhydride, added 4mL of N,N-dimethylacetamide, reacted at room temperature for 24h to obtain a viscous polyamic acid, then put in 1.4mL of acetic anhydride and 0.7mL of pyridine, heated up The reaction was carried out at 110 °C for 3 h. After the reaction was completed, it was cooled to room temperature and discharged into ethanol to obtain a yellow-white fibrous product. The ethanol was refluxed for 30 min, washed once with water, washed with ethanol under reflux for 30...

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PUM

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Abstract

The invention discloses a diamine monomer containing a tetraphenylethylene-bis-arylamine structure, a preparation method and application of the diamine monomer in an ultra-stable electrochromic material, and belongs to the technical field of preparation of organic compounds. The invention relates to a diamine monomer containing a tetraphenyl ethylene-bis arylamine structure, and the monomer is named as N-{4-[1, 2-bis (4-aminophenyl)-2-{4-[bis (4-methoxyphenyl) amino] phenyl} vinyl] phenyl}-4-methoxy-N-(4-methoxyphenyl) aniline. A twisted tetraphenylethylene structure and propeller type bis-arylamine are combined together and are introduced into polyimide in a diamine monomer form, the high lower light absorption coefficient of tetraphenylethylene effectively provides an all-black electrochromic color, and meanwhile, the oxidation potential of polyimide can be reduced by utilizing disproportionation; according to the method, the stability of the black electrochromic polymer material can be remarkably improved.

Description

technical field [0001] The invention belongs to the technical field of organic compound preparation, and in particular relates to a diamine monomer containing a tetraphenylethylene-bisarylamine structure, a preparation method and a polyimide with ultra-high stability and electrochromic function in the preparation thereof applications in . Background technique [0002] Electrochromism refers to the phenomenon that the color of a material can change under the condition of an external electric field, and at the same time, it can return to its original color under the condition of applying a reverse electric field. Under the action of an external electric field, the bisarylamine group is easy to form a stable cationic free radical, resulting in a color change. Among many electrochromic materials, electrochromic materials that change from transparent state to black have been widely studied for a long time due to their huge application prospects. [0003] Compared with inorganic...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07C217/92C07C213/08C07C17/263C07C25/24C07C201/08C07C205/12C09K9/02C08G73/12
CPCC07C217/92C07C213/08C07C17/263C07C201/08C09K9/02C08G73/126C08G73/124C08G73/127C08G73/123C09K2211/1466C09K2211/1425C09K2211/1433C07C25/24C07C205/12
Inventor 关绍巍于铁琛姚洪岩祝世洋舒萌张跃李嘉昊
Owner JILIN UNIV
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