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Geometrical and Electronic Structure of Cation Radical Species of Tetraarylanthraquinodimethane: An Intermediate for Unique Electrochromic Behavior

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Title: Geometrical and Electronic Structure of Cation Radical Species of Tetraarylanthraquinodimethane: An Intermediate for Unique Electrochromic Behavior
Authors: Ishigaki, Yusuke Browse this author →KAKEN DB
Fukagawa, Reina Browse this author
Sugawara, Kazuma Browse this author
Harimoto, Takashi Browse this author
Suzuki, Takanori Browse this author
Keywords: Redox System
Issue Date: 16-Nov-2022
Publisher: Wiley-Blackwell
Journal Title: Chemistry-an asian journal
Volume: 17
Issue: 22
Start Page: e202200914
Publisher DOI: 10.1002/asia.202200914
Abstract: Two tetraarylanthraquinodimethane (Ar(4)AQD) derivatives having two different aryl groups (aminophenyl and methoxyphenyl) were prepared by sequential dibromomethylation and Suzuki-coupling reactions. X-ray analyses showed that they adopt a folded structure in the neutral state whereas the corresponding dications have a planar anthracene ring, to which diarylmethylium units are perpendicularly attached. Different from Ar(4)AQD having the same substituents that undergoes facile two-electron transfer during interconversion with the dicationic state, the intermediary cation radical becomes long-lived in the newly prepared unsymmetric derivatives. The geometric and electronic structures of the open-shell intermediates were elucidated through electrochemical and theoretical investigation, with revealing that the cation radicals adopt the twisted geometry like dications. Upon electrolyses of the dications, the twisted cation radicals were involved in the electrochromism whereas their steady-state concentration is negligible in the oxidation process, thus realizing unique tricolor electrochromic behavior with a hysteretic pattern of color change (colorless -> purple -> blue -> colorless).
Rights: This is the peer reviewed version of the following article: Y. Ishigaki, R. Fukagawa, K. Sugawara, T. Harimoto, T. Suzuki, Chem. Asian J. 2022, 17, e202200914., which has been published in final form at This article may be used for non-commercial purposes in accordance with Wiley Terms and Conditions for Use of Self-Archived Versions. This article may not be enhanced, enriched or otherwise transformed into a derivative work, without express permission from Wiley or by statutory rights under applicable legislation. Copyright notices must not be removed, obscured or modified. The article must be linked to Wiley’s version of record on Wiley Online Library and any embedding, framing or otherwise making available the article or pages thereof by third parties from platforms, services and websites other than Wiley Online Library must be prohibited.
Type: article (author version)
Appears in Collections:理学院・理学研究院 (Graduate School of Science / Faculty of Science) > 雑誌発表論文等 (Peer-reviewed Journal Articles, etc)

Submitter: 石垣 侑祐

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