Synthetic protocols for the nitration of corroles

The modification of peripheral positions of corroles by introduction of nitro groups is an important functionalization of this macrocycle. The nitro substituent strongly influences the corrole behavior leading to the preparation of macrocycles with different properties, which can be of interest for their exploitation as catalysts, sensing layers in chemical sensors or in the field of supramolecular chemistry. In the last few years we have developed different routes for the β-nitration of the corrole ring, and we report here novel synthetic protocols which can allow the formation of tri- and tetra-nitro derivatives, as demonstrated by X-ray analysis. In all of the methodologies used, the presence of isocorrole species as reaction intermediates was established, which regenerated the corresponding corrole by metal insertion. © 2011 World Scientific Publishing Company.