Organic photochromic material and preparation method and application thereof
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A photochromic material and organic technology, applied in the field of color-changing materials, to achieve the effects of excellent fatigue resistance, easy process and fast light response ability
Active Publication Date: 2019-02-01
SHANGHAI UNIVERSITY OF ELECTRIC POWER
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[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.
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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 powdersolid 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 a preparation method and application thereof. The specific preparation method comprises the following steps: successively adding a substituted diarylethene-based monoaldehyde compound, 4-aminoantipyrine and an organic solvent, conducting a heating reflux reaction, cooling and filtering, washing filter cake, and drying to obtain an organic photochromic material. The material itself has no photochromic performance. Under the action of certain ions, color and / or fluorescence of the material can change specifically in the light environment. That is to say, the material is endowed with the photochromic performance under the action of certain ions. In comparison with the prior art, the preparation method is simple and efficient, has high yield and good economy, has large-scale production value, and is environment-friendly; and the prepared organic photochromic material has ion regulatory molecular switchspectral properties, and can be used in the preparation of multihoming photoelectric molecular switches, molecular wire elements, 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...
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