Synthesis and Redox Properties of Pyrrole- and Azulene-Fused Azacoronene.

Synthesis of an azacoronene, in which both pyrrole and azulene moieties are circularly fused, was achieved just in three steps. This new azacoronene exhibited multistep reversible oxidations under electrochemical and chemical conditions. Formation of an aromatic 22π-electron conjugation and a tropylium cation (6π-electron conjugation) in the dicationic state was revealed by the single-crystal X-ray crystallographic analysis as well as the nucleus-independent chemical shift (NICS) and anisotropy of the induced current density (ACID) calculations.