Photoswitching of an alcohol-sensitive photochromic diarylethene |
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Authors: | Seiya Kobatake Shotaro ImaoYosuke Yamashiro Yuko Terakawa |
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Affiliation: | Department of Applied Chemistry, Graduate School of Engineering, Osaka City University, 3-3-138 Sugimoto, Sumiyoshi-ku, Osaka 558-8585, Japan |
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Abstract: | The closed-ring isomer of diarylethene 1a, 1-(2-methyl-5-(4-N,N-diethylaminophenyl)thien-3-yl)-2-(2-methyl-5-phenylthien-3-yl)perfluorocyclopentene was found to cause the substitution reaction with primary alcohols at room temperature. The open-ring isomer 1a was stable in the alcohols. The product obtained in methanol was isolated by HPLC, and the structure was identified by 1H NMR, mass spectrometry, and X-ray crystallographic analysis. It was revealed that two fluorine atoms were replaced with methoxy groups. The substitution reaction was also caused with ethylene glycol to form the five-membered ring. Both the products also showed photochromism, and had absorption maxima and photocycloreversion quantum yields different from those of 1a. |
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Keywords: | Photochromism Diarylethene Substitution reaction Quantum yield Optical property |
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