Expanded porphyrin is a term we introduced into the literature in 1988 to describe larger homologues of natural and synthetic tetrapyrrolic macrocycles. Expanded porphyrins, along with many other contracted, isomeric, and core-modified porphyrin analogues, are now known. Expanded porphyrins, in particular, have seen application in areas as diverse as anion recognition and transport, self-assembly, liquid-liquid ion extraction, photodynamic therapy, and anticancer drug development. In recent years expanded porphyrins have helped increase our understanding of aromaticity and antiaromaticity. In this lecture, an update on recent systems that have been synthesized to study the relationship between structure and electronic configuration will presented. Particular emphasis will be focused on systems that support unexpected electronic configurations, including unusual [4n +1] π-electron semi-aromatic peripheries or which support expanded porphyrin-based self-assembly and supramolecular chemical recognition. New work involving 3D-aromaticity will also be presented.

Expanded porphyrins: Adventures in aromaticity, antiaromaticity, and semi-aromaticity

255th National Meeting (2018)

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