A dithia analogue of meso-alkylidenyl sapphyrin, a class of compounds that was hitherto unknown, was prepared via the condensation of a 1,3-phenylenebispyrrole wilh a bithiophene diol. The resulting system was found to be stable and highly nonplaner. It was also characterized by a partially conjugated electronic structure. As such, this system helps to underscore the emerging impression that conjugation and aromatilcity effects in expanded porphyrins may be more protean than previously appreciated. Specifically, this work serves to demonstrate that even nonplanar structures can show partial conjugation effects.