Synthesis and properties of BCOD-fused trithiasapphyrin and trithiabenzosapphyrins

Bicyclo[2.2.2]octadiene(BCOD)-fused trithiasapphyrin was prepared by 3+2 condensation of BCOD-fused thiatripyrrane with BCOD-fused bithiophene. The BCOD-fused trithiasapphyrin was successfully converted to pentabenzo[b,g,l,q,v]sapphyrin by the thermal retro-Diels–Alder reaction. In this case, trithiapentabenzo[b,g,l,q,v]- and trithiadibenzo[g,q]sapphyrins were selectively prepared by control of the temperature in the thermal retro-Diels–Alder reaction.