Stable Thiele's Hydrocarbon Derivatives Exhibiting Near-Infrared Absorption/Emission and Two-Step Electrochromism

Yuta Okamoto, Masaru Tanioka, Atsuya Muranaka, Kazunori Miyamoto, Tetsuya Aoyama, Xingmei Ouyang, Shinichiro Kamino, Daisuke Sawada, Masanobu Uchiyama

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3 Citations (Scopus)


We report synthesis and characterization of near-infrared (NIR)-absorbing/emitting Thiele's hydrocarbon derivatives, in which four aryl groups are bridged to a quinodimethane skeleton. The quinoid structure of the bridged-tetra-aryl-p-quinodimethanes (BTAQs) was confirmed by spectroscopic, X-ray crystallographic, and computational methods. Although quinodimethane derivatives with a small HOMO-LUMO energy gap often exhibit biradical character, BTAQs showed no biradical character. Instead, they exhibited two-step near-infrared electrochromism. The donor/acceptor properties of the aryl groups were found to play a key role in the unique properties of BTAQs.

Original languageEnglish
JournalJournal of the American Chemical Society
Publication statusAccepted/In press - Jan 1 2018


ASJC Scopus subject areas

  • Catalysis
  • Chemistry(all)
  • Biochemistry
  • Colloid and Surface Chemistry

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