Methodologies to modify the electronic properties of porphyrins include the preparation of porphyrin analogues containing non-pyrrolic building blocks, so-called pyrrole-modified porphyrins (PMP). Total synthesis approaches toward PMPs are frequently taken but for their brevity the conversion of porphyrins – particularly along the ‘porphyrin breaking and mending’ route – remain an attractive option. The replacement of one of the pyrrole rings in meso-tetraarylporphyrins with an oxazolone moiety generates a class of PMPs referred to as porpholactones. Porpholactones, and their downstream derivatives (porpholactols, porpholactams, thionolactones, imidazoloporphyrins, etc.) have found broad utility in catalysis, chemosensing, and photomedicine. The formation of porpholactones along more than a dozen routes was described (either by design or chance), but the success of most routes is dependent on the specific meso-arylporphyrin considered or the central metal present. In most cases, however, no systematic assessment of the scope and limits of the method was performed. We evaluate here which routes are the most suitable for the preparation of which meso-aryl(metallo)porpholactone. We thereby make this attractive PMP more readily accessible to a wider range of fields.

Efficient synthetic pathways of replacing a pyrrole in porphyrins by an oxazole

Macromolecular Chemistry: The Second Century

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ACS Spring 2020 National Meeting & Expo

The official archive and repository for all ACS Meetings & Expositions abstracts and select posters or presentations.