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Near-Infrared Electrochromic Behavior of Dibenzothiepin Derivatives Attached with Two Michler's Hydrol Blue Units

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Title: Near-Infrared Electrochromic Behavior of Dibenzothiepin Derivatives Attached with Two Michler's Hydrol Blue Units
Authors: Ishigaki, Yusuke Browse this author →KAKEN DB
Takata, Masaki Browse this author
Shimajiri, Takuya Browse this author
Wu, Luyan Browse this author
Zeng, Wenhui Browse this author
Ye, Deju Browse this author
Suzuki, Takanori Browse this author
Keywords: absorption
cyclic voltammetry
redox chemistry
Issue Date: 15-Sep-2022
Publisher: Wiley-Blackwell
Journal Title: Chemistry-A European journal
Volume: 28
Issue: 70
Start Page: e202202457
Publisher DOI: 10.1002/chem.202202457
Abstract: 10,11-Bis[bis(4-dimethylaminophenyl)methylene]dibenzo[bf]thiepin (1) and -oxepin (2) were prepared as stable yellow crystalline compounds, which are the cyclic analogues of electron-donating hexaarylbutadienes. Upon two-electron oxidation, they are reversibly transformed into the title dications (1(2+) and 2(2+)) exhibiting near-infrared (NIR) absorptions, which were also isolated as stable salts. These redox pairs can serve as new entries into less well-explored organic NIR-electrochromic systems, and the separation of redox peaks (electrochemical bistability) was attained for 1/1(2+) and 2/2(2+), thanks to drastic geometrical changes between neutral and dicationic states, as revealed by a series of X-ray analyses. Thiepin-S,S-dioxide analogue (3/3(2+)) exhibits quite similar dynamic redox behavior due to nonaromatic nature of the dibenzothiepin and -oxepin unit in 1(2+) and 2(2+), whereas the thiepin-S-oxide derivative (4/4(2+)) does not exhibit bistability due to the smaller change in geometry upon electron transfer, showing that a subtle change of a bridging atom in the central seven-membered ring can modify the redox properties.
Rights: This is the peer reviewed version of the following article: Chemistry-A European journal Vol.28(70),Near-Infrared Electrochromic Behavior of Dibenzothiepin Derivatives Attached with Two Michler's Hydrol Blue Units 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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