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

3 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
JournalJournal of the American Chemical Society
DOIs
Publication statusAccepted/In press - Jan 1 2018

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Electrochromism
Infrared absorption
Hydrocarbons
Skeleton
X-Rays
Infrared radiation
Derivatives
Computational methods
Energy gap
X rays

ASJC Scopus subject areas

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

Cite this

Stable Thiele's Hydrocarbon Derivatives Exhibiting Near-Infrared Absorption/Emission and Two-Step Electrochromism. / Okamoto, Yuta; Tanioka, Masaru; Muranaka, Atsuya; Miyamoto, Kazunori; Aoyama, Tetsuya; Ouyang, Xingmei; Kamino, Shinichiro; Sawada, Daisuke; Uchiyama, Masanobu.

In: Journal of the American Chemical Society, 01.01.2018.

Research output: Contribution to journalArticle

Okamoto, Yuta ; Tanioka, Masaru ; Muranaka, Atsuya ; Miyamoto, Kazunori ; Aoyama, Tetsuya ; Ouyang, Xingmei ; Kamino, Shinichiro ; Sawada, Daisuke ; Uchiyama, Masanobu. / Stable Thiele's Hydrocarbon Derivatives Exhibiting Near-Infrared Absorption/Emission and Two-Step Electrochromism. In: Journal of the American Chemical Society. 2018.
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AU - Miyamoto, Kazunori

AU - Aoyama, Tetsuya

AU - Ouyang, Xingmei

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