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

Research output: Contribution to journalArticle

5 Citations (Scopus)

Abstract

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
Pages (from-to)17857-17861
Number of pages5
JournalJournal of the American Chemical Society
Volume140
Issue number51
DOIs
Publication statusPublished - Dec 26 2018

ASJC Scopus subject areas

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

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    Okamoto, Y., Tanioka, M., Muranaka, A., Miyamoto, K., Aoyama, T., Ouyang, X., Kamino, S., Sawada, D., & Uchiyama, M. (2018). Stable Thiele's Hydrocarbon Derivatives Exhibiting Near-Infrared Absorption/Emission and Two-Step Electrochromism. Journal of the American Chemical Society, 140(51), 17857-17861. https://doi.org/10.1021/jacs.8b11092