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Iridium metalation of [26]hexaphyrin 1 and [36]octaphyrin 2 gave Ir(III) complex of [26]hexaphyrin 3 and Ir(I) complex of [36]octaphyrin 4, respectively. The complex 3 is an aromatic molecule displaying considerably electron-rich nature while the complex 4 shows weak antiaromatic nature with a small HOMO–LUMO gap of 0.82 eV.