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Organic photochromic material and preparation method and application thereof

A photochromic material and chromogenic technology, applied in the field of materials science, can solve problems such as high cost and complex synthesis route, and achieve excellent fatigue resistance, simple synthesis method and high yield

Active Publication Date: 2019-11-08
SHANGHAI UNIVERSITY OF ELECTRIC POWER
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0004] The technical problem to be solved by the present invention is to provide a kind of organic photochromic material and its preparation method and application, to solve the organic photochromic material synthesis in the prior art The technical problems of complex routes and high costs, while realizing the spectral performance and molecular recognition properties of ion-regulated molecular switches

Method used

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  • Organic photochromic material and preparation method and application thereof
  • Organic photochromic material and preparation method and application thereof
  • Organic photochromic material and preparation method and application thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0040] Embodiment 1: the synthesis of organic photochromic material N1

[0041] This embodiment provides a preparation method of organic chromic material N1, the specific steps are as follows:

[0042] Its reaction equation is as follows:

[0043]

[0044]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), 3-hydroxyl-2-naphthoic acid hydrazine (compound 2) is a commercial product.

[0045] 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 (0.20g, 0.62mmol), 3-hydroxy-2-hydrazine naphthoate (0.19g, 0.94mmol), 15mL of ethanol, slowly warming up to 80°C, stirring under reflux for 12h, then cooling to room temperature naturally , filtered, and the filter cake was washed with ethanol and dried to obtain 0.19 g of light yellow powd...

Embodiment 2

[0047] Embodiment 2: the photochromic property of organic photochromic material N1

[0048] Dissolve the organic photochromic material N1 in Example 1 in dimethyl sulfoxide to a concentration of 10 μmol L -1 dimethyl sulfoxide 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 according to different time lengths (10s, 30s, 60s, 90s, 120s, 180s, 240s, 300s, 360s , 420s, 480s) irradiated the solution to be tested, and measured the absorption spectrum with a UV-Vis spectrophotometer, the results are as follows figure 1 shown. Under the irradiation of 365nm ultraviolet light, a new absorption peak appeared in the absorption spectrum at 515nm, 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 (≥500nm), the absorption spectrum returned to the original ...

Embodiment 3

[0049] Example 3: Spectral performance regulation of organic photochromic material N1 by nickel ions

[0050] Dissolve the organic photochromic material N1 obtained in Example 1 in dimethyl sulfoxide, and configure it to a concentration of 10 μmol L -1 dimethyl sulfoxide solution. Add 2.5mL of the solution to be tested into a 1cm×1cm×4cm quartz cuvette with stirring, and then add 0, 5, 10, 15, 20, 25, 30, 35, 40, 45, 50 , 55, 60, 65, 70, 75, 80 μmol L -1 Ni 2+ (Nickel chloride) after uniform mixing for 2 minutes, test its absorption spectrum, the result is as follows image 3 shown. with Ni 2+ With the continuous addition of , the ultraviolet absorption spectrum showed a two-stage change. The absorption peak at 347nm first increased and then decreased, and a new absorption peak appeared at 385nm, indicating that an obvious complexation effect occurred. Study the fluorescence change of the above solution with a fluorescence spectrophotometer, with 365nm as the excitation ...

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Abstract

The invention provides an organic photochromic material based on diarylethene, and a preparation method and an application thereof in ion regulation and molecular recognition. A structural formula ofthe material is shown as a general formula I, wherein X is selected from a halogen atom (Cl, Br, I), H, a C1-C12 alkyl group, or a phenyl group. The preparation method of the material includes the following steps: reacting a diarylethene-based monoaldehyde compound having the photochromic performance with 3-hydroxy-2-naphthoic acid hydrazide at the temperature of 20-120 DEG C for about 1-24 hours,forming precipitation in a solution and after the reaction is stopped, and subjecting the precipitate to filtration, washing, and purification to obtain a novel Schiff base photochromic compound based on the diarylethene. The ion regulation switching spectral properties and ion recognition properties of the organic photochromic material of the invention have very important functions in the fieldof photoelectric information, such as preparation of multi-addressing photoelectric molecular switches, molecular conducting wire components, photochromic light-emitting devices, and the like.

Description

technical field [0001] The invention belongs to the field of materials science, and relates to an organic photochromic material, in particular to a preparation method and application of a diarylethene compound having both photochromic gating properties and ion recognition properties. Background technique [0002] Human beings have entered the information society, and the safe and efficient transmission and storage of massive information is very important. The way of storing and transmitting information with optical signals has gradually been trusted by more and more people. With the development of science and technology, various fields have also put forward more requirements for optical information storage methods, and look forward to the birth of new materials with more prospects and advantages. As the foundation and pillar of optoelectronic information technology, the research, design, preparation and application of materials and devices for optoelectronic information tran...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C09K11/02C09K11/06C07D333/28G01N21/64
CPCC09K11/02C09K11/06C07D333/28G01N21/643C09K2211/1007C09K2211/1011C09K2211/1092G01N2021/6432
Inventor 邹祺翁韬玉朱亮亮
Owner SHANGHAI UNIVERSITY OF ELECTRIC POWER
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