A double-helical S,C-bridged tetraphenyl-para-phenylenediamine and its persistent radical cation

Kaho Harada; Chika Hasegawa; Taisuke Matsumoto; Hiroki Sugishita; Chitoshi Kitamura; Shuhei Higashibayashi; Masashi Hasegawa; Shuichi Suzuki; Shin-ichiro Kato

doi:10.1039/D2CC06144A

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A double-helical S,C-bridged tetraphenyl-para-phenylenediamine and its persistent radical cation†

Kaho Harada,^a Chika Hasegawa,^b Taisuke Matsumoto,^c Hiroki Sugishita,^a Chitoshi Kitamura,^a Shuhei Higashibayashi,

^d Masashi Hasegawa,

^b Shuichi Suzuki

^e and Shin-ichiro Kato

*^a

Author affiliations

* Corresponding authors

^a Department of Materials Science, School of Engineering, The University of Shiga Prefecture, 2500 Hassaka-cho, Hikone, Shiga 522-8533, Japan
E-mail: kato.s@mat.usp.ac.jp

^b Department of Chemistry, School of Science, Kitasato University, 1-15-1 Kitasato, Minami-ku, Sagamihara, Kanagawa 252-0373, Japan

^c Institute for Materials Chemistry and Engineering (IMCE), Kyushu University, 6-1 Kasuga-koh-en, Kasuga 816-8580, Japan

^d Faculty of Pharmacy, Keio University, 1-5-30, Shibakoen, Minato-ku, Tokyo 105-8512, Japan

^e Department of Chemistry, Graduate School of Engineering Science, Osaka University, 1-3 Machikaneyama-cho, Toyonaka, Osaka 560-8531, Japan

Abstract

A structurally constrained, double-helical S,C-bridged tetraphenyl-para-phenylenediamine (TPPD) has been synthesized. The stable radical cation of the S,C-bridged TPPD was generated by chemical oxidation, and the electron spin was found to be delocalized over the entire π-conjugated framework. The excellent conformational stability of the neutral molecule facilitated the separation of its enantiomers.

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DOI: https://doi.org/10.1039/D2CC06144A
Article type: Communication
Submitted: 14 Nov 2022
Accepted: 30 Dec 2022
First published: 31 Dec 2022

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Chem. Commun., 2023,59, 1301-1304

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A double-helical S,C-bridged tetraphenyl-para-phenylenediamine and its persistent radical cation

K. Harada, C. Hasegawa, T. Matsumoto, H. Sugishita, C. Kitamura, S. Higashibayashi, M. Hasegawa, S. Suzuki and S. Kato, Chem. Commun., 2023, 59, 1301 DOI: 10.1039/D2CC06144A

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Chemical Communications

A double-helical S,C-bridged tetraphenyl-para-phenylenediamine and its persistent radical cation†

Abstract

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A double-helical S,C-bridged tetraphenyl-para-phenylenediamine and its persistent radical cation

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