Synthesis and Redox Property of Diazoniacoronene

Abstract

A new approach towards the synthesis of the elusive dicationic heterocoronene, diazoniacoronene, is presented. The fundamental synthetic strategy is based on the intramolecular photo-Diels-Alder type cycloaddition of an azaazoniathia[6]helicene. The improved procedure completely suppress subsequent reaction to form pyridone type byproduct.
Electrochemical study shows the diazoniacoronene has four reversible reduction processes, converted to the monocation radical, the neural, the monoanion radical, and the dianion.