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

Chemical Communications Pub Date: 2022-12-31 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.

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