Anthriporphyrinoids: Design, Synthesis, and Reactivity towards Diels-Alder Reaction.

A series of non-aromatic anthripentaphyrins containing an anthracene unit, two thiophenes, and two pyrrole rings as a part of a macrocyclic framework connected via three meso -carbons were synthesized. The crystal structure of one of the anthripentaphyrins revealed that the two thiophene rings were in an inverted orientation, and the macrocycle adopts a nonplanar Z-like ruffled structure. These anthriporphyrinoids act as dienes and undergo Diels-Alder reaction with dienophiles to form stable non-aromatic Diels-Alder adducts.