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A kind of organic photochromic material and its preparation method and application

A photochromic material and organic technology, applied in the field of color-changing materials, to achieve the effects of few synthesis steps, excellent fatigue resistance and good thermal stability

Active Publication Date: 2021-10-08
SHANGHAI UNIVERSITY OF ELECTRIC POWER
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0003] Although the research on the photochromic properties of dithiophene vinyl compounds has made great progress, there are still some problems to be solved to meet the needs of practical applications.

Method used

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  • A kind of organic photochromic material and its preparation method and application
  • A kind of organic photochromic material and its preparation method and application
  • A kind of organic photochromic material and its preparation method and application

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0037] 1. Synthesis of organic photochromic material P1

[0038] Synthesis of Compound P1

[0039]

[0040] The preparation method of 1-(5-chloro-2-methyl-3-thienyl)-2-(5-formyl-2-methyl-3-thienyl)cyclopentene (compound 1) refers to literature (H .Tian, ​​et al., Tetrahedron, 2011, 67, 915-921), 4-aminoantipyrine (compound 2) can be purchased directly.

[0041] In the dark, at room temperature, sequentially add 1-(5-chloro-2-methyl-3-thienyl)-2-(5-formyl-2-methyl-3-thienyl) into a 50mL single-necked bottle ) cyclopentene (0.225g, 0.699mmol), 4-aminoantipyrine (0.142g, 0.7mmol), 15mL ethanol, slowly warming up to 78°C, stirring under reflux for 6h, cooling to room temperature naturally, filtering , the filter cake was washed with ethanol and dried to obtain 0.201 g of golden yellow powder solid P1 with a yield of 59.2%. 1H NMR (400MHz, Chloroform-d) δ1.84(s,3H),2.00-2.07(m,5H),2.42(s,3H),2.70-2.79(m,4H),3.11(s,3H), 6.59(s,1H),7.01(s,1H),7.31(t,J=8.0Hz,1H),7.39(d,J=8.0Hz,...

Embodiment 2

[0047] Synthesis of organic photochromic materials:

[0048] In the dark, at room temperature, sequentially add 1-(5-chloro-2-methyl-3-thienyl)-2-(5-formyl-2-methyl-3-thienyl) into a 50mL single-necked bottle ) cyclopentene (0.225g, 0.699mmol), 4-aminoantipyrine (0.284g, 1.4mmol), 42mL toluene, slowly warming up to 65°C, stirring under reflux for 24h, cooling to room temperature naturally, filtering , The filter cake was washed with ethanol and dried to obtain a golden yellow powdery solid.

Embodiment 3

[0050] Synthesis of organic photochromic materials:

[0051] In the dark, at room temperature, sequentially add 1-(5-chloro-2-methyl-3-thienyl)-2-(5-formyl-2-methyl-3-thienyl) into a 50mL single-necked bottle ) cyclopentene (0.45g, 1.4mmol), 4-aminoantipyrine (0.426g, 2.1mmol), 10.5mL toluene, slowly warming up to 110°C, stirring for 1h under reflux, and cooling to room temperature naturally, After filtering, the filter cake was washed with ethanol and dried to obtain a golden yellow powdery solid.

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Abstract

The invention relates to an organic photochromic material and its preparation method and application. The specific preparation method is: sequentially adding a substituted diarylethene-based monoaldehyde compound, 4-aminoantipyrine and an organic solvent, and heating to reflux After the reaction, cool and filter, wash the filter cake, and dry to obtain an organic photochromic material. The material itself does not have photochromic properties. Changes in color and / or fluorescence in the medium, that is, the material obtains photochromic properties under the action of certain (type) ions. Compared with the prior art, the preparation method of the present invention is simple and efficient, high in yield, good in economy, has the value of large-scale production, and is environmentally friendly. The prepared organic photochromic material has ion-regulated molecular switch spectrum performance, It can be used to prepare multi-address photoelectric molecular switches, molecular wire components, photochromic light-emitting devices and the like.

Description

technical field [0001] The invention relates to a color-changing material, in particular to an organic photochromic material and its preparation method and application. Background technique [0002] With the continuous development of science and technology, the development of massive information storage materials and high-speed information transmission materials has become the main goal of the development of modern information technology; realizing information storage at the molecular level or even the atomic level on the time scale is also the research direction of modern information technology. For organic photochromic materials, the reading and writing of information all adopts the all-photon mode, so designing and preparing high-performance organic photochromic materials has always been the goal pursued by researchers. Photochromic phenomenon means that when a compound is irradiated by a certain wavelength of light, it can undergo a specific chemical reaction to obtain a...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07D409/14C09K9/02G01N21/31G01N21/63G01N21/64
CPCC07D409/14C09K9/02C09K2211/1007C09K2211/1044C09K2211/1092G01N21/31G01N21/63G01N21/64G01N2021/634
Inventor 邹祺陈炫颖陈文博
Owner SHANGHAI UNIVERSITY OF ELECTRIC POWER
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