One Pot Synthesis of Two Distinct Macrocycles: Aromatic p-Benzihexaphyrin and Nonaromatic Doubly Fused p-Benzihexaphyrin.

Aromatic trithia p-benzihexaphyrins and nonaromatic doubly fused trithia p-benzihexaphyrins were synthesized in a one pot reaction by condensing a p-benzithiophene based tetrapyrrane with three different bithiophene diols under acid catalyzed conditions. The aromatic and nonaromatic macrocycles showed clear differences in colour, NMR, absorption, and electrochemical properties. Theoretical studies supported the observed aromatic and nonaromatic characteristics, respectively, of the p-benzihexaphyrins and their N-fused derivatives.