Syntheses and Functionalizations of Porphyrin Macrocycles
Maria da G.H. Vicente and Kevin M. Smith
Affiliation: Department of Chemistry, Louisiana State University, Baton Rouge, Louisiana 70803, USA.
Keywords: Aromaticity, porphyrin, pyrrole, reactivity, substitutions, synthesis.
Porphyrin macrocycles have been the subject of intense study in the last century because they are widely distributed in nature,
usually as metal complexes of either iron or magnesium. As such, they serve as the prosthetic groups in a wide variety of primary metabolites,
such as hemoglobins, myoglobins, cytochromes, catalases, peroxidases, chlorophylls, and bacteriochlorophylls; these compounds
have multiple applications in materials science, biology and medicine. This article describes current methodology for preparation
of simple, symmetrical model porphyrins, as well as more complex protocols for preparation of unsymmetrically substituted porphyrin
macrocycles similar to those found in nature. The basic chemical reactivity of porphyrins and metalloporphyrin is also described, including
electrophilic and nucleophilic reactions, oxidations, reductions, and metal-mediated cross-coupling reactions. Using the synthetic approaches
and reactivity profiles presented, eventually almost any substituted porphyrin system can be prepared for applications in a variety
of areas, including in catalysis, electron transport, model biological systems and therapeutics.
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