A Hybrid of Corannulene and Azacorannulene: Synthesis of a Highly Curved Nitrogen-Containing Buckybowl.

A highly curved nitrogen-containing buckybowl, which can be considered as a corannulene/azacorannulene hybrid, was synthesized and characterized. This molecule has a polycyclic aromatic C40 N core, corresponding to a partial azafullerene structure C80-x Nx (x=1,2,3…), and exhibits interesting properties that arise from its large and highly curved π surface and the embedded nitrogen atom, which include association with C60 , a lower LUMO level relative to azapentabenzocorannulene, and the formation of a radical cationic species upon oxidation.