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

A series of non-aromatic anthripentaphyrinscontaining an anthraceneunit, two thiophenes, and two pyrrole rings as a part of a macrocyclicframework connected via three meso-carbons were synthesized.The crystal structure of one of the anthripentaphyrins revealed thatthe two thiophene rings were in an inverted orientation, and the macrocycleadopts a nonplanar Z-like ruffled structure. These anthriporphyrinoidsact as dienes and undergo Diels-Alder reaction with dienophilesto form stable non-aromatic Diels-Alder adducts.