Benzo[cd]Perylenyl: A π-Expanded Phenalenyl Radical With Enhanced Aggregation Enthalpy and Stability

Ono, Yuga; Goto, Yuko; Tani, Yosuke et al.

Asian Journal of Organic Chemistry, 2025, e202500300

アクセス数:351件（2025-09-01 21:49 集計）

固定URL: https://hdl.handle.net/11094/101399

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タイトル
Benzo[cd]Perylenyl: A π-Expanded Phenalenyl Radical With Enhanced Aggregation Enthalpy and Stability
著者
著者名
Ono, Yuga
著者名
Goto, Yuko
NRID
1000000769383 1000000769383
著者名
Tani, Yosuke
著者名
Nakasuji, Kazuhiro
NRID
1000090264796 1000090264796
著者名
Sato, Kazunobu
NRID
1000010117955 1000010117955
著者名
Takui, Takeji
NRID
1000010845019 1000010845019
著者名
Shimizu, Daiki
NRID
1000080262145 1000080262145
著者名
Matsuda, Kenji
NRID
1000060324745 1000060324745
ORCID
0000-0001-6809-7396 0000-0001-6809-7396
researchmap permalink
read0076571 read0076571
Scopus Author ID
55576439300 55576439300
著者名
Kubo, Takashi
キーワード等
Neutral radical
Phenalenyl radical
Polycyclic aromatic hydrocarbon
Two electron multicenter bonding
Π-dimer
内容
Ono Y., Goto Y., Tani Y., et al. Benzo[cd]Perylenyl: A π-Expanded Phenalenyl Radical With Enhanced Aggregation Enthalpy and Stability. Asian Journal of Organic Chemistry (2025); https://doi.org/10.1002/ajoc.202500300.
抄録
We report the synthesis and characterization of a π-expanded neutral PAH radical, benzo[cd]perylenyl (1) derived from the phenalenyl radical (2). Hückel molecular orbital (HMO) analysis reveals a uniformly distributed SOMO that enables effective two-electron 20-center bonding in a π-dimer. ESR measurements of 1 show a long half-life of 63 days in air-saturated toluene at room temperature. Temperature-dependent ESR and absorption spectra as well as DFT calculations confirm the preferential formation of a π-dimer over a σ-dimer with an association energy of approximately −65 kJ mol⁻¹, driven by enhanced dispersion interactions. These findings demonstrate that π-expansion stabilizes organic radicals without bulky substituents while preserving intermolecular interactions offering new prospects for advanced materials in electronics and spintronics.
出版者
John Wiley and Sons Inc
収録物名
Asian Journal of Organic Chemistry
ページ
e202500300
刊行年月
2025-03-27
言語
英語
ハンドルURL
https://hdl.handle.net/11094/101399
eISSN
21935815
関連情報 (isIdenticalTo)
DOI (出版社版)
https://doi.org/10.1002/ajoc.202500300
アクセス権
open access
権利情報
This article is licensed under a Creative Commons Attribution 4.0 International License.
出版タイプ
Version of Record
カテゴリ
学術雑誌論文 Journal Article