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
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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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