Supertrityl Radical and Cation: The Effect of a Large π-Surface for Intermolecular Interactions and Spin/Charge Delocalization

Organic Letters 2026

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Authors: Tomohiko Nishiuchi, Seiji Hamazaki, Hiroyasu Sato, Takashi Kubo
DOI: 10.1021/acs.orglett.6c00791
Cited by: 1
References: 47

Abstract

We report the synthesis and properties of supertrityl radical and cation bearing three hexa- peri -hexabenzocoronenes (HBCs). X-ray analysis of the cation revealed a propeller-shaped structure forming a two-dimensional honeycomb assembly via π–π stacking. The radical exists in monomer–dimer equilibrium with a multicenter pancake bond. Despite large π-surfaces, spin/charge remain localized at the central carbon, rationalized by Clar’s sextet rule.

Fields of Study & Subjects

Synthesis and Properties of Aromatic Compounds Organoboron and organosilicon chemistry Fullerene Chemistry and Applications

Publication details

Journal / source
Organic Letters
Publisher
American Chemical Society (ACS)
Volume
28
Issue
17
Pages
5363–5369
Publication date
18 April 2026
Language
EN