Photocontrol of micellar catalyses

Seiji Shinkai, Katsuta Matsuo, Akiko Harada, Osamu Manabe

Research output: Contribution to journalArticle

41 Citations (Scopus)

Abstract

Three photoresponsive surfactants, C7H15CONHC 6H4N=NC6H4N+Me 3MeOSO3- (1), C8H 17OC6H4N=NC6H4 - CH2N+Me3I- (2), and C16H33OC6H4N=NC6H 4CH2N+Me3I- (3), have been synthesised. The absorption spectrum of 2,6-dichlorophenolindophenol † as a probe for micelle formation indicated that the aggregation mode of these photoresponsive surfactants is affected by photoinduced trans-cis isomerisation of the azobenzene head groups. The catalytic activities of these surfactant aggregates in base-catalysed proton abstraction from benzoin and alkaline hydrolysis of p-nitrophenyl cyclohexanecarboxylate were estimated in the dark and under photoirradiation. It was found that the rate constants in the micellar systems change sensitively in response to photoirradiation. The results imply that photoinduced isomerisation of the head groups leads to a change in the catalytic activity. This is the first example of photocontrol of micellar catalysis.

Original languageEnglish
Pages (from-to)1261-1265
Number of pages5
JournalJournal of the Chemical Society, Perkin Transactions 2
Issue number10
DOIs
Publication statusPublished - 1982

All Science Journal Classification (ASJC) codes

  • Chemistry(all)

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