Three-way output molecular response system based on tetrakis(3,4-dialkoxyphenyl)-3,4-dihydro[5]helicenes: Perturbation of properties by long alkyl chains

Yusuke Ishigaki, Satoshige Yoshida, Hidetoshi Kawai, Ryo Katoono, Kenshu Fujiwara, Takanori Fukushima, Takanori Suzuki

Research output: Contribution to journalArticle

3 Citations (Scopus)

Abstract

Starting from (S)-dimethyl 1,1'-binaphthyl-2,2'-dicarboxylate, optically pure (P)-3,3,4,4-tetrakis(3,4-dialkoxyphenyl)-3,4-dihydro[5]helicenes (P)-1 were prepared via bis(diarylhydroxymethyl)binaphthyl and/or tetraaryldinaphthodihydroxepin as key intermediates. Upon electrochemical oxidation to the corresponding (S)-1,1'-binaphthyl-2,2'-diylbis(diarylcarbenium)s (S)-22+, three kinds of spectral changes (UV-Vis, circular dichroism, fluorescence) were successfully observed. Compared to the methoxy compound, the octyloxy and hexadecyloxy derivatives exhibit a redshifted emission maxima in the dihydro[5]helicenes. The long alkyl chains induce step-by-step two-electron reduction of the binaphthyldiyl(dicarbenium)s whereas the dication with methoxy groups exhibits one-wave two-electron process.

Original languageEnglish
Pages (from-to)126-135
Number of pages10
JournalHeterocycles
Volume90
Issue number1
DOIs
Publication statusPublished - 1 Jan 2015

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