Redox Switching of Conjugation Length Using 9,9,10,10-Tetraaryl-9,10-dihydrophenanthrene as an ON/OFF Unit: Preparation, X-ray Structure, and Redox Properties of Perfluorobiphenyl Derivative and Its S<sub>N</sub>Ar Reactions to π-Extended Analogues

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  • Suzuki Takanori
    Department of Chemistry, Faculty of Science, Hokkaido University
  • Tamaoki Hitomi
    Department of Chemistry, Faculty of Science, Hokkaido University
  • Katoono Ryo
    Department of Chemistry, Faculty of Science, Hokkaido University
  • Fujiwara Kenshu
    Department of Chemistry, Faculty of Science, Hokkaido University
  • Ichikawa Junji
    Division of Chemistry, Faculty of Pure and Applied Sciences, University of Tsukuba
  • Fukushima Takanori
    Chemical Resources Laboratory, Tokyo Institute of Technology

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Other Title
  • Redox Switching of Conjugation Length Using 9,9,10,10-Tetraaryl-9,10-dihydrophenanthrene as an ON/OFF Unit: Preparation, X-ray Structure, and Redox Properties of Perfluorobiphenyl Derivative and Its SNAr Reactions to π-Extended Analogues

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Abstract

Octafluorobiphenyl-2,2′-diylbis(diarylmethylium) dye 2a2+ prepared from 1,2-dibromotetrafluorobenzene is interconvertible with colorless dihydrophenanthrene donor 1a. By the SNAr reactions of 1a with acetylides, π-extended analogues 1b and 1c were obtained. Their electrochromic behavior is accompanied by a drastic absorption change not only in the visible but also UV region, because the torsion angle of the biaryl unit is modified upon redox reactions.

Journal

  • Chemistry Letters

    Chemistry Letters 42 (7), 703-705, 2013

    The Chemical Society of Japan

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