A kind of organic photochromic material based on diarylethene and its preparation method and application

A photochromic material and diarylethene technology, which is applied in the field of materials science, can solve the problems of lack of spectral performance of ion-gated molecular switches, complex synthesis route and high cost, and achieve fast photoresponse ability, simple and excellent synthesis method. The effect of fatigue resistance

Active Publication Date: 2019-03-05
SHANGHAI UNIVERSITY OF ELECTRIC POWER
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  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

[0004] Aiming at the above-mentioned technical problems in the prior art, the present invention provides a diarylethene-based organic photochromic material and its preparation method and application, said diarylethene-based organic photochromic material The preparation method and application thereof can solve the technical problems of complex synthetic route and high cost of organic photochromic materials in the prior art, and can solve the technical problem of lack of spectral performance of ion-gated molecular switches at the same time

Method used

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

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Embodiment 1

[0028] Embodiment 1 (the synthesis of organic photochromic material C3-DAE):

[0029] Synthesis of compound C3-DAE

[0030]

[0031] 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), the preparation method of triaminoguanidine chloride salt (compound 2) is referred to literature (H.Krommer, et al., Chem.Abstr., 1986,104 , 206730).

[0032] 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 (0.882g, 2.73mmol), triaminoguanidine chloride salt (0.128g, 0.912mmol), 15mL ethanol and 4mL water, slowly warming up, stirring under reflux for 4h, naturally cooling to room temperature, filtering, The filter cake was washed with ether and dried to obtain 0.630 g of golden yellow powdery solid C3-DAE with a yield of 65.5%. 1 HNMR (400MHz,...

Embodiment 2

[0033] Embodiment 2 (photochromic performance of organic photochromic material C3-DAE):

[0034] The compound C3-DAE obtained above was dissolved in acetonitrile, and the concentration was 10 μmol L -1 acetonitrile solution. Add 2.5mL of the solution to be tested into a 1cm×1cm×4cm quartz cuvette with stirring, and use a 365nm monochromatic light source to treat it according to different time lengths (10s, 30s, 60s, 90s, 120s, 180s, 240s, 300s) The solution was irradiated, and the absorption spectrum was measured with a UV-Vis spectrophotometer, the results were as follows figure 1 shown. Under the irradiation of 365nm ultraviolet light, a new absorption peak appeared in the absorption spectrum at 530nm, and gradually increased to reach the photostable state with the prolongation of time, and the color of the solution also changed from colorless to pink. Under the irradiation of visible light (≥550nm), the absorption spectrum returned to the original state and the color of ...

Embodiment 3

[0035] Embodiment 3 (copper ion controls the spectral performance of organic photochromic material C3-DAE):

[0036] The compound C3-DAE obtained above was dissolved in acetonitrile, and the concentration was 10 μmol L -1 acetonitrile solution. Add 2.5mL of the solution to be tested into a 1cm×1cm×4cm quartz cuvette with stirring, and then add different concentrations of Cu with a micro-syringe 2+ (Cupric chloride) After mixing evenly for 2 minutes, test its absorption spectrum, the result is as follows image 3 shown. With Cu 2 + With continuous addition, the colorless solution gradually turned yellow. Using 365nm monochromatic light source to irradiate the complex solution for a long time will not cause changes in the absorption spectrum, and the color of the solution will not change either. It shows that the spectral properties of compound C3-DAE can be controlled by Cu 2+ Regulated.

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Abstract

The invention provides an organic photochromic material based on diaryl ethylene having the structural formula represented by the general formula I, where X is Cl, Br, and I. The invention also provides a preparation method of the organic photochromic material, wherein the diarylene-based monoaldehyde compound having the photochromic property is reacted with triaminoguanidine chloride salt, and after the reaction is stopped, the mixture is filtered, washed and purified to obtain a novel optical switch molecule compound based on Schiff base of diaryl ethylene. Under the action of ions, the organic photochromic material can specifically prevent the material from producing color and / or fluorescence variations in the illumination environment, and can be used to prepare multi-address photoelectron molecular switches, molecular conductor elements and photochromic light emitting devices.

Description

technical field [0001] The invention belongs to the field of material science, and relates to an organic photochromic material, specifically a diarylethene-based organic photochromic material. 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 chemi...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C09K9/02C09K11/06G01N21/64G02F1/01
CPCC09K9/02C09K11/06C09K2211/1007C09K2211/1092G01N21/643G01N2021/6432G02F1/0126
Inventor 陈文博邹祺王上上朱亮亮
Owner SHANGHAI UNIVERSITY OF ELECTRIC POWER
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