Protonation, deprotonation, and protonation: conjugated photochemical reactions of ferrocenylazophenol |
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Authors: | Men Yi Korupoju Srinivas R Kurihara Masato Mizutani Jun Nishihara Hiroshi |
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Institution: | Department of Chemistry, School of Science, University of Tokyo, Hongo, Bunkyo-ku, Tokyo 113-0033, Japan. |
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Abstract: | 4-Ferrocenylazophenol (FAP) and 8-(4-ferrocenylazophenoxy)octanyl-1-bromide (FAOB) have been synthesized and their protonation and photochemical behavior have been investigated. FAP showed reversible protonation and deprotonation behavior in the presence of trifluoroacetic acid and potassium tert-butylate, respectively. FAP and FAOB exhibit high photoreactivity, which was induced through excitation of not only the pi-pi* band by UV light but also the d-pi* band by green light. The photoreaction of FAP and FAOB in ethanol or acetonitrile with a trace amount of water afforded phenylhydrazonocyclopentadiene (PHP) derivatives, indicating that hydrolysis of the photoexcited species occurs. |
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Keywords: | azo compounds ferrocenes isomerization photochemistry protonation |
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