Electrochiroptical response of a hexaarylethane derivative with a helical π-skeleton: Drastic UV-Vis and CD spectral changes upon electrolysis of 4′,5′-dibromodispiro[xanthene-9,9′(9′H,10′H)- phenanthrene-10′,9″-xanthene]

Takanori Suzuki, Rie Yamamoto, Hiroki Higuchi, Erika Hirota, Masakazu Ohkita, Takashi Tsuji

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Abstract

Upon two-electron oxidation of the title electron donor 1a, the elongated central C9-C10 bond [1.656(5) Å (X-ray)] is cleaved to give the biphenyl-2,2′-diyl bis(xanthenylium) dye 2a+2, which regenerates the colorless dispiro compound 1a by two-electron reduction. The presence of isosbestic points in the UV-Vis spectra during the electrochemical oxidation of 1a to 2a+2 indicates the negligible steady-state concentration of the intermediate cation radical. Interconversion between optically resolved 1a and 2a+2 is accompanied by drastic changes in the CD spectra again with several isosbestic points, and racemization of (P)- and (M)-1a and (S)- and (R)-2a+2 does not occur at ambient conditions. This redox pair represents a new motif for the multi-output response system, where the electrochemical input is transduced into two independent spectral outputs.

Original languageEnglish
Pages (from-to)1937-1942
Number of pages6
JournalJournal of the Chemical Society, Perkin Transactions 2
Issue number11
Publication statusPublished - 2002
Externally publishedYes

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All Science Journal Classification (ASJC) codes

  • Chemistry(all)

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