Rare vanadyl corrphycene and vanadyl 10-oxocorrole complexes were obtained via an oxidative macrocyclization process by the treatment of 6,6 '-di-p-tolyl-2,2 '-bidipyrrin with VO(acac)(2) in a hot dioxygen atmosphere. The geometric and electronic structures of the new porpyhrinoids were determined and showed the dependency of the spectral pattern from the aromaticity of the macrocyclic ligand.