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

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

Chem Commun (Camb). 2023 Jan 31;59(10):1301-1304. doi: 10.1039/d2cc06144a.

Authors

Kaho Harada¹, Chika Hasegawa², Taisuke Matsumoto³, Hiroki Sugishita¹, Chitoshi Kitamura¹, Shuhei Higashibayashi⁴, Masashi Hasegawa², Shuichi Suzuki⁵, Shin-Ichiro Kato¹

Affiliations

¹ Department of Materials Science, School of Engineering, The University of Shiga Prefecture, 2500 Hassaka-cho, Hikone, Shiga 522-8533, Japan. kato.s@mat.usp.ac.jp.
² Department of Chemistry, School of Science, Kitasato University, 1-15-1 Kitasato, Minami-ku, Sagamihara, Kanagawa 252-0373, Japan.
³ Institute for Materials Chemistry and Engineering (IMCE), Kyushu University, 6-1 Kasuga-koh-en, Kasuga 816-8580, Japan.
⁴ Faculty of Pharmacy, Keio University, 1-5-30, Shibakoen, Minato-ku, Tokyo 105-8512, Japan.
⁵ Department of Chemistry, Graduate School of Engineering Science, Osaka University, 1-3 Machikaneyama-cho, Toyonaka, Osaka 560-8531, Japan.

PMID: 36633220
DOI: 10.1039/d2cc06144a

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.