Synthesis and properties of BCOD-fused trithiasapphyrin and trithiabenzosapphyrins

Bicyclo2.2.2]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 pentabenzob,g,l,q,v]sapphyrin by the thermal retro-Diels-Alder reaction. In this case, trithiapentabenzob,g,l,q,v]- and trithiadibenzog,q]sapphyrins were selectively prepared by control of the temperature in the thermal retro-Diels-Alder reaction.