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1,2-Disubstituted 1,2-Dihydro-1,2,4,5-tetrazine-3,6-dione as a Dynamic Covalent Bonding Unit at Room Temperature

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Title: 1,2-Disubstituted 1,2-Dihydro-1,2,4,5-tetrazine-3,6-dione as a Dynamic Covalent Bonding Unit at Room Temperature
Authors: Kawai, Kentaro Browse this author
Ikeda, Kazuki Browse this author
Sato, Akane Browse this author
Kabasawa, Akira Browse this author
Kojima, Masahiro Browse this author →KAKEN DB
Kokado, Kenta Browse this author →KAKEN DB
Kakugo, Akira Browse this author →KAKEN DB
Sada, Kazuki Browse this author →KAKEN DB
Yoshino, Tatsuhiko Browse this author →KAKEN DB
Matsunaga, Shigeki Browse this author →KAKEN DB
Issue Date: 18-Jan-2022
Publisher: American Chemical Society
Journal Title: Journal of the American Chemical Society
Volume: 144
Issue: 3
Start Page: 1370
End Page: 1379
Publisher DOI: 10.1021/jacs.1c11665
Abstract: Dynamic covalent bonds are useful tools in a wide range of applications. Although various reversible chemical reactions have been studied for this purpose, the requirement for harsh conditions, such as high temperature and low or high pH, to activate generally stable covalent bonds limits their potential applications involving biomolecules or household utilization. Here, we report the design, synthesis, characterization, and dynamic covalent bonding properties of 1,2-disubstituted 1,2-dihydro-1,2,4,5-tetrazine-3,6-dione (TETRAD). Hetero-Diels-Alder reactions of TETRAD with furan derivatives and their retro-reactions proceeded rapidly at room temperature under neutral conditions, enabling a chemically induced sol-gel transition system.
Rights: This document is the Accepted Manuscript version of a Published Work that appeared in final form in Journal of the American Chemical Society, copyright © American Chemical Society after peer review and technical editing by the publisher. To access the final edited and published work see
Type: article (author version)
Appears in Collections:薬学研究院 (Faculty of Pharmaceutical Sciences) > 雑誌発表論文等 (Peer-reviewed Journal Articles, etc)

Submitter: 吉野 達彦

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