Journal of the American Chemical Society p. 19877 - 19883 (2012)
Update date:2022-08-11
Topics:
Nakashima, Takuya
Kajiki, Yoshiyuki
Fukumoto, Sayo
Taguchi, Maki
Nagao, Satoshi
Hirota, Shun
Kawai, Tsuyoshi
Electrochemical response of photochromic tearylenes was surveyed by means of cyclic voltammetry, DFT calculations, and spectroelectrochemistry. 4,5-Bis(2-phenyl-5-methylthiazolyl)-2-phenylthiazole was found to show electrochemical oxidative ring-cycloreversion reaction. The net current efficiency of the cycloreversion reaction under constant potential electrolysis was as high as 900%, which is ascribed to an electrochemical local-cell mechanism and a chain reaction mechanism. Electron transfer stopped-flow study using a chemical oxidant successfully identified radical cation intermediates of both closed- and open-ring isomers, involved in the oxidative cycloreversion process. The significantly long-lived radical cation of open-ring isomer with the lifetime of 33 s takes part in the indirect electron transfer process from the neutral closed-ring isomer to the radical cation of open-ring isomer in the chain reaction manner.
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