Chemistry Letters
Online ISSN : 1348-0715
Print ISSN : 0366-7022
Letter
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
Takanori SuzukiHitomi TamaokiRyo KatoonoKenshu FujiwaraJunji IchikawaTakanori Fukushima
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Volume 42 (2013) Issue 7 Pages 703-705

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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.

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© 2013 The Chemical Society of Japan
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