5,10,15,20-tetrakis(pentafluorophenyl)porphyrin: a versatile platform to novel porphyrinic materials

Abstract

5,10,15,20-tetrakis(pentafluorophenyl)porphyrin reacts with a range of nucleophiles (amines, alcohols, thiols, nitrogen heterocycles, and others) resulting in the nucleophilic aromatic substitution of the para-F atoms of the pentafluorophenyl groups. This reaction, which was fortuitously discovered by Kadish and collaborators in 1990, is now being extensively used to synthesize porphyrins bearing electron-donating substituents in the para-position of their meso-aryl groups. This mini-review highlights the methods of synthesis of 5,10,15,20-tetrakis(pentafluorophenyl)porphyrin, the use of its metal complexes in catalysis and its reaction with nucleophiles to yield new monomeric porphyrins, porphyrins supported in polymers or new polymeric porphyrin matrices useful for heterogeneous catalysis.