A practical one-pot synthesis of soluble hexa-peri-hexabenzocoronene and isolation of its cation-radical salt.
A simple and practical synthesis of soluble hexa-peri-hexabenzocoronene (HBC) from readily available hexaphenylbenzene (HPB) is described. In this simple procedure, the substitution of the free para positions of the propeller-shaped HPB with tert-butyl groups and the oxidative cyclodehydrogenation to planar HBC is achieved in a one-pot reaction using ferric chloride both as a Lewis acid catalyst and as an oxidant in excellent yields. The ready availability of HBC allows the isolation of its pure cation-radical salt using a variety of chemical oxidants such as antimony pentachloride and triethyloxonium and nitrosonium hexachloroantimonate salts.
Department of Chemistry, Marquette University, P.O. Box 1881, Milwaukee, Wisconsin 53201-1881, USA. rajendra.rathore@marquette.edu
Rajendra
R
Rathore
Carrie L
CL
Burns