Preparation and application of pyrazolone methyl thiosemicarbazone photochromic compound
A photochromic and compound technology, applied in the fields of color-changing fluorescent materials, organic chemistry, chemical instruments and methods, etc., can solve the problems of poor stability and fatigue resistance, unsatisfactory sensitivity and oxidation resistance, application limitations, etc. The effect of broad application prospects
Inactive Publication Date: 2012-05-16
XINJIANG UNIVERSITY
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And most of them change color in solution, but there are few reports about the photochromic properties of the compounds in the solid state. Most photochromic compounds have poor stability and fatigue resistance, and have poor sensitivity to light and oxidation resistance. is not ideal, which brings great limitations to its application
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[0012] The photochromic compound 1,3-diphenyl-4-(3'-chlorobenzylidene)-5-pyrazolone thiosemicarbazide concrete synthetic steps synthesized by the present invention:
[0013] Weigh 1.874g (5mmol) 1,3-diphenyl-4-(3'-chlorobenzoyl)-5-pyrazolone and 0.5258g (5mmol) N(4)-methylthiosemicarbazide in In a round-bottomed flask, 50 mL of methanol was used as a solvent and 1 mL of glacial acetic acid as a catalyst, and heated under reflux for 6 h to obtain a white product with a yield of 76%. Melting point: 200-201°C. Its synthetic route and photochromic mechanism are as follows:
[0014]
[0015] Single crystal test: Rigaku R-axis Spider single crystal diffractometer at room temperature, Mo Kα is the incident light, graphite monochromator, λ=0.71073 Data were collected in a scan of ω, whose crystal structure is as figure 2 shown. The results show that the photochromic compound exists as a ketone structure in the solid state.
[0016] UV test: After 365nm ultraviolet light, the...
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Abstract
The invention relates to preparation and application of a 1, 3-diphenyl-4-(3'-chlorobenzylidene)-5-pyrazolone methyl thiosemicarbazone photochromic compound, belonging to the field of organic photochromic materials. A structural formula of the 1, 3-diphenyl-4-(3'-chlorobenzylidene)-5-pyrazolone methyl thiosemicarbazone photochromic compound is shown as figure 1. 1, 3-diphenyl-4-(3'-chlorobenzylidene)-5-pyrazolone methyl thiosemicarbazone is prepared by the condensation reaction of 1, 3-diphenyl-4-(3'-chlorobenzoyl)-5-pyrazolone and methyl thiosemicarbazide in a methanol solution. The 1, 3-diphenyl-4-(3'-chlorobenzylidene)-5-pyrazolone methyl thiosemicarbazone photochromic compound has reversible photochromic property and good heat stability and fatigue resistance and can be used in the fields of optical information storage, counterfeit prevention, molecular switches, optical lenses, and the like.
Description
technical field [0001] The invention belongs to the field of organic photochromic materials, in particular to the preparation and application of a pyrazolone methyl thiosemicarbazide photochromic compound. technical background [0002] Photochromism is the reversible change of one or several species between two states with significantly altered absorption spectra. This change is caused by the exposure of light in at least one direction, while in the other direction it is usually a spontaneous thermal process. Photochromic media include inorganic and organic, and their color-changing principles are different. The photochromism of inorganic compounds such as metal oxides or halides is usually caused by impurities or crystal defects; while the photochromism of organic compounds is often caused by changes in the compound structure, such as valence bond isomerization, bond breaking (both cleavage or heterocleavage), dimerization or redox, etc. [0003] Photochromism is an impo...
Claims
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IPC IPC(8): C07D231/12C09K9/02
Inventor 刘浪贾殿赠张涛郭继玺
Owner XINJIANG UNIVERSITY