Expanded Carbaporphyrinoids

Abstract

This Review outlines the progress in the field of synthetic expanded carbaporphyrinoids. The evolution of this topic is demonstrated with expanded porphyrin-inspired systems with a variety of incorporated entities that introduce one or more carbon atoms into the cavity. The discussion starts with platyrins-the macrocycles that were identified as parent molecules of not only the expanded carbaporphyrinoids, but the carbaporphyrinoid class in general. After historic considerations, the plethora of expanded porphyrin-like macrocycles containing N-confused or neo-confused pyrrole motifs and different carbocyclic subunits are presented. Special emphasis is given to applications of expanded carbaporphyrinoids in different areas, including organometallic chemistry, switching systems, or aromaticity, concluding with the demonstration of a covalent cage based on an expanded carbaporphyrinoid.

Keywords: antiaromaticity; aromaticity; macrocycles; porphyrins; supramolecular systems.