Synthesis and Properties of meso-Arylated Corrphycenes.

A novel synthetic procedure for meso-aryl-substituted corrphycenes has been developed. Suzuki-Miyaura coupling of α,α'-dibromodipyrrin with vic-diborylalkene and o-diborylbenzene afforded ethenylene- and phenylene-bridged bisdipyrrins, respectively, which were transformed to the corresponding corrphycenes upon treatment with palladium acetate. The bridging units significantly affect the macrocyclic π-conjugation circuits, thus changing the aromatic characters and absorption features of corrphycenes.