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

doi:10.1021/jacs.8b11092

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 journal › Article › peer-review

19 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 language	English
Pages (from-to)	17857-17861
Number of pages	5
Journal	Journal of the American Chemical Society
Volume	140
Issue number	51
DOIs	https://doi.org/10.1021/jacs.8b11092
Publication status	Published - Dec 26 2018

ASJC Scopus subject areas

Catalysis
Chemistry(all)
Biochemistry
Colloid and Surface Chemistry

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

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.",

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

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T1 - Stable Thiele's Hydrocarbon Derivatives Exhibiting Near-Infrared Absorption/Emission and Two-Step Electrochromism

AU - Okamoto, Yuta

AU - Tanioka, Masaru

AU - Muranaka, Atsuya

AU - Miyamoto, Kazunori

AU - Aoyama, Tetsuya

AU - Ouyang, Xingmei

AU - Kamino, Shinichiro

AU - Sawada, Daisuke

AU - Uchiyama, Masanobu

PY - 2018/12/26

Y1 - 2018/12/26

N2 - 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.

AB - 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.

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

Abstract

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