Synthesis of meso-Substituted Porphyrin Metal Complexes Bearing Multiple Functional Groups

Abstract

The acid-catalyzed porphyrin syntheses of a set of rare and novel meso-substituted porphyrins possessing substitution at the meta and para positions have been completed. Such porphyrins have been prepared which possess at least one of the following peripheral functional groups namely, a free amine, a carboxylic acid, an ester, or a terminal alkyne group. Functionalized dipyrromethanes at the 3-position were condensed with the corresponding aldehydes under acidic conditions (AcOH, TFA or BF3 ethereate) to afford the meso-substituted porphyrins. Characterization of products was accomplished by NMR and MALDI-TOF analyses. ©2014 Oklahoma Academy of Science