Preparation of Thiaphlorins and Related Dyads

Significance

A series of functionalized thiaphlorins and alkyne-linked phlorin-porphyrin dyads has been made. The route involves initial functionalization of the 2- and 5-positions of thiophene, followed by one-pot condensations to give the macrocyclic targets. Thiaphlorins with Br or I on a phenyl ring were further linked via copper-free Sonogashira reactions to a zinc-porphyrin moiety bearing a terminal alkyne, affording three novel thia­phlorin-porphyrin dyads. The thiaphlorins and related dyads were found to be capable of binding anions.