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Organic photochromic material based on diaryl ethylene and preparation method and application thereof

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

Active Publication Date: 2017-03-15
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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  • Organic photochromic material based on diaryl ethylene and preparation method and application thereof
  • Organic photochromic material based on diaryl ethylene and preparation method and application thereof
  • Organic photochromic material based on diaryl ethylene and preparation method and application thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0028] Example 1 (Synthesis of organic photochromic material C3-DAE):

[0029] Synthesis of compound C3-DAE

[0030]

[0031] 1-(5-Chloro-2-methyl-3-thienyl)-2-(5-formyl-2-methyl-3-thienyl)cyclopentene (compound 1) for the preparation method see document (H Tian, ​​et al., Tetrahedron, 2011, 67, 915-921), the preparation method of chlorinated triaminoguanidine salt (compound 2) is described in the literature (H. Krommer, et al., Chem. Abstr., 1986, 104 , 206730).

[0032] In the dark state, at room temperature, add 1-(5-chloro-2-methyl-3-thienyl)-2-(5-formyl-2-methyl-3-thienyl) to a 50mL single-neck bottle in turn ) Cyclopentene (0.882g, 2.73mmol), triaminoguanidine chloride (0.128g, 0.912mmol), 15mL ethanol and 4mL water, slowly increase the temperature, stir under reflux for 4h, cool to room temperature naturally, filter, 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, CDCl 3 )δ(ppm): 1...

Embodiment 2

[0033] Example 2 (Photochromic properties of organic photochromic material C3-DAE):

[0034] The compound C3-DAE obtained above was dissolved in acetonitrile and the concentration was 10μmol·L -1 Acetonitrile solution. Add 2.5mL of the solution to be tested into a stirred 1cm×1cm×4cm quartz cuvette, and use 365nm monochromatic light source according to different time lengths (10s, 30s, 60s, 90s, 120s, 180s, 240s, 300s) Irradiate the test solution, and use an ultraviolet-visible spectrophotometer to measure the absorption spectrum, the results are as follows figure 1 Shown. Under 365nm ultraviolet light irradiation, a new absorption peak appeared in the absorption spectrum at 530nm, and gradually increased with time to reach a light steady state, and the color of the solution also changed from colorless to pink. Under visible light (≥550nm) irradiation, the absorption spectrum returns to the original state and the color of the solution fades. Study the fluorescence change of the...

Embodiment 3

[0035] Example 3 (Controlling the spectral performance of the organic photochromic material C3-DAE by copper ions):

[0036] The compound C3-DAE obtained above was dissolved in acetonitrile and the concentration was 10μmol·L -1 Acetonitrile solution. Add 2.5mL of the solution to be tested into a stirred 1cm×1cm×4cm quartz cuvette, and then use a micro syringe to add different concentrations of Cu 2+ (Copper chloride) and mix it evenly for 2 minutes, test its absorption spectrum, the result is as follows image 3 Shown. With Cu 2 + The colorless solution gradually turns yellow when added continuously. Long-term irradiation of the complex solution with a 365nm monochromatic light source will not cause a change in the absorption spectrum, and the color of the solution has also not changed. It shows that the spectral properties of compound C3-DAE can be 2+ By regulation.

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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 materials science, and relates to an organic photochromic material, specifically an organic photochromic material based on diarylethylene. Background technique [0002] With the continuous development of science and technology, the development of mass information storage materials and high-speed information transmission materials has become the main goal of the development of modern information technology; the realization of information storage at the molecular level and 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 adopt the all-photon mode. Therefore, the design and preparation of high-performance organic photochromic materials has always been the goal pursued by researchers. Photochromism means that when a compound is irradiated with a certain wavelength of light, it can undergo a ...

Claims

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Application Information

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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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