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Protonation, Deprotonation, and Protonation: Conjugated Photochemical Reactions of Ferrocenylazophenol
Author(s) -
Men Yi,
Korupoju Srinivas R.,
Kurihara Masato,
Mizutani Jun,
Nishihara Hiroshi
Publication year - 2005
Publication title -
chemistry – a european journal
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.687
H-Index - 242
eISSN - 1521-3765
pISSN - 0947-6539
DOI - 10.1002/chem.200500713
Subject(s) - protonation , deprotonation , chemistry , photochemistry , trifluoroacetic acid , bromide , acetonitrile , potassium bromide , conjugated system , hydrolysis , organic chemistry , ion , polymer
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 π–π* band by UV light but also the d–π* 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.