Para-aryl substituted pyridinium salt derivative electrochromic material and preparation method thereof

A technology of electrochromic materials and derivatives, applied in the direction of color-changing fluorescent materials, chemical instruments and methods, organic chemistry, etc., can solve the problems of high mortality and human toxicity, and achieve simple synthesis, low toxicity and high yield Effect

Pending Publication Date: 2022-03-15
黎伟麒
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0003] At present, the small molecule electrochromic materials that can be industrialized are viologen compounds, also known as "paraquat", which are extremely toxic to humans, and the mortality rate of oral poisoning is very high.

Method used

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  • Para-aryl substituted pyridinium salt derivative electrochromic material and preparation method thereof
  • Para-aryl substituted pyridinium salt derivative electrochromic material and preparation method thereof
  • Para-aryl substituted pyridinium salt derivative electrochromic material and preparation method thereof

Examples

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Embodiment 1

[0048] A preparation method of a para-aryl-substituted pyridinium salt derivative electrochromic material 1-benzyl-4-phenylpyridinium bromide, comprising the following steps:

[0049] 1) Mix pyridine 4-boronate, chlorobenzene, sodium hydroxide, palladium chloride, tri-tert-butylphosphine (molar ratio 1:1:8:0.5:2) and water evenly, and place in N 2 Stir at room temperature under atmosphere for 20-30min, and reflux at 100°C for 14h; after the reaction is completed, cool the solution to room temperature, filter, and concentrate the filtrate; recrystallize with ethyl acetate to obtain 4-phenylpyridine;

[0050] 2) Mix 4-phenylpyridine, benzyl bromide (molar ratio 1:2) and DMF obtained in 1) evenly, reflux at 80-85°C for 0.1h, and remove the solvent by rotary evaporation; recrystallize with dichloromethane to obtain the molecular structure formula 1-benzyl-4-phenylpyridinium bromide salt electrochromic material, its 1 H NMR spectrum as figure 1 shown. The overall yield for the t...

Embodiment 2

[0054] A preparation method of an electrochromic material 1-benzyl-4-(3-(trifluoromethyl)phenyl)pyridinium bromide salt substituted by a para-aryl group, comprising the steps of:

[0055] 1) Mix 4-pyridine boronic acid, 3-(trifluoromethyl)bromobenzene, cesium fluoride, tridibenzylideneacetone palladium (molar ratio 1:2:4:0.01) and DMF evenly, and place in N 2 Stir at room temperature under atmosphere for 20-30min, reflux at 120°C for 70h; after the reaction is complete, cool the solution to room temperature, filter, and concentrate the filtrate; recrystallize with ethyl acetate to obtain 4-(3-(trifluoromethyl)phenyl) pyridine;

[0056] 2) Mix 4-(3-(trifluoromethyl)phenyl)pyridine, benzyl bromide (molar ratio 1:2.5) and DMF obtained in 1) evenly, reflux at 80-85°C for 2 hours, and remove the solvent by rotary evaporation; Obtain molecular structure formula 1-benzyl-4-phenylpyridinium bromide electrochromic material with dichloromethane recrystallization, its 1 H NMR spectrum ...

Embodiment 3

[0060] A preparation method of an electrochromic material 1-benzyl-4-(3-thiophene) pyridinium bromide salt substituted by a para-aryl group, comprising the steps of:

[0061] 1) Mix 4-chloropyridine, 3-(boronic acid) thiophene, potassium tert-butyl, bis(tri-tert-butyl)palladium, triphenylphosphine (molar ratio 1:1.5:5:0.025:0.5) and dioxygen Hexacyclic mixed well, in N 2 Under atmosphere, stir at room temperature for 20-30 minutes, and reflux at 100°C for 46 hours; after the reaction is completed, cool the solution to room temperature, filter, and concentrate the filtrate; recrystallize with ethyl acetate to obtain 4-(3-thiophene)pyridine;

[0062] 2) Mix 4-(3-thiophene)pyridine, benzyl bromide (molar ratio 1:2) and diethyl ether obtained in 1) evenly, reflux at 80-85°C for 2 hours, and remove the solvent by rotary evaporation; recrystallize with dichloromethane to obtain Molecular structural formula 1-benzyl-4-(3-thiophene) pyridinium bromide electrochromic material, its 1 ...

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Abstract

The invention discloses a para-aryl substituted pyridinium salt derivative as an electrochromic material and a preparation method of the para-aryl substituted pyridinium salt derivative. 4-boric acid pyridine (or 4-boric acid ester pyridine) and a halogenated aromatic compound or 4-halogenated pyridine and aromatic boric acid (or aromatic boric acid ester) are used as raw materials respectively, and a target product is obtained through Suzuki coupling, pyridine alkylation and anion exchange. The invention creatively utilizes a simple para-aryl substituted pyridinium salt derivative as an electrochromic material, aims to overcome the problems in the prior art, and provides a non-toxic electrochromic material and a preparation method thereof.

Description

technical field [0001] The invention relates to electrochromic materials, in particular to a para-aryl substituted pyridinium salt derivative as an electrochromic material and a preparation method thereof, and an electrochromic electrochromic material based on a para-aryl substituted pyridinium salt derivative The device and its preparation method belong to the technical field of photoelectric materials. Background technique [0002] Electrochromism refers to a stable and reversible phenomenon in which a material changes color by gaining and losing electrons under the action of an external electric field. Since the 21st century, electrochromic technology, as an emerging industrialization technology, can be applied to smart anti-glare mirrors for cars, smart dimming portholes for aircraft, smart windows for buildings with adjustable light and heat, etc. Different from photochromism and thermochromism, which are passive color changes, electrochromism can change colors anytime...

Claims

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Application Information

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IPC IPC(8): C07D213/16C07D213/127C09K9/02
CPCC07D213/16C07D213/127C09K9/02C09K2211/1029
Inventor 不公告发明人
Owner 黎伟麒
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