Electron Donating Group Effect on C─C Bond Scission Ability of Indanedione Dimers in Their Solution and Solid State

Yamamoto, Yukina; Yakiyama, Yumi; Nishiuchi, Tomohiko et al.

Asian Journal of Organic Chemistry, 2025, e00546

Number of Access:44（2025-11-04 10:01 Counts）

Identifier to cite or link to this item: https://hdl.handle.net/11094/102749

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Title
Electron Donating Group Effect on C─C Bond Scission Ability of Indanedione Dimers in Their Solution and Solid State
Creator
CreatorName
Yamamoto, Yukina
NRID
1000060636819 1000060636819
ORCID
0000-0003-4278-2015 0000-0003-4278-2015
researchmap permalink
yumiyakiyama yumiyakiyama
Scopus Author ID
57195377416 57195377416
CreatorName
Yakiyama, Yumi
NRID
1000010706774 1000010706774
ORCID
0000-0002-2113-0731 0000-0002-2113-0731
researchmap permalink
t-nishiuchi t-nishiuchi
Scopus Author ID
24529011200 24529011200
CreatorName
Nishiuchi, Tomohiko
NRID
1000060324745 1000060324745
ORCID
0000-0001-6809-7396 0000-0001-6809-7396
researchmap permalink
read0076571 read0076571
Scopus Author ID
55576439300 55576439300
CreatorName
Kubo, Takashi
NRID
1000000262147 1000000262147
ORCID
0000-0001-5783-4151 0000-0001-5783-4151
researchmap permalink
read0184917 read0184917
Scopus Author ID
7402869823 7402869823
CreatorName
Sakurai, Hidehiro
Subject
Captodative effect
Dynamic covalent bond
Indanedione dimers
Phase transitions
Radicals
Description
Yamamoto Y., Yakiyama Y., Nishiuchi T., et al. Electron Donating Group Effect on C─C Bond Scission Ability of Indanedione Dimers in Their Solution and Solid State. Asian Journal of Organic Chemistry, e00546 (2025); https://doi.org/10.1002/ajoc.202500546.
Abstract
Light, heat and mechanical stress-responsive molecules are of great interest in the field of modern materials chemistry. In this work, indanedione dimers 1–3 introduced with an electron-donating thiophene group were designed with the expectation of easy cleavage of the central C─C single bond by the captodative effect. Our synthetic approach led to the successful preparation of dimethylthiophenyl and methylbenzothiophenyl derivatives 1 and 2, while benzothiophenyl compound 3 was not formed; instead, the bridged product 3' was obtained. The sequential UV–vis absorption and ESR measurements of 1 and 2 in the solution state confirmed the effectiveness of the presence of an electron-donating group, which stabilized the radical form to realize a relatively low bond cleavage temperature. Meanwhile, it was also clarified that the bond scission event was strongly affected by the packing structure; much harder in the tightly packed crystalline 1 than its solution state, while almost the same as the solution state in the glassy solid of 2, in which the intermolecular interaction should be much weaker and each molecule could move as easily as in the solution state. Further investigation of 3' revealed the loss of bond scission ability by bridging.
Publisher
John Wiley and Sons Inc
Source Title
Asian Journal of Organic Chemistry
Page
e00546
Date of Issued
2025-01-25
Language
English
Handle URL
https://hdl.handle.net/11094/102749
eISSN
21935815
Relation.isIdenticalTo
DOI (Publisher Version)
https://doi.org/10.1002/ajoc.202500546
Access Rights
open access
CopyRight
This article is licensed under a Creative Commons Attribution-NonCommercial-NoDerivatives 4.0 International License.
© 2025 The Author(s). Asian Journal of Organic Chemistry published by Wiley-VCH GmbH.
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Category
学術雑誌論文 Journal Article