Carbaporphyrins are a derivation of a traditional porphyrin in that one or more internal nitrogen atom in the porphyrin are replaced with carbon atoms. Carbaporphyrins and related systems have been well studied, and many retain aromatic character while modifying the electronic absorption spectra. In this project, a series of quinoline subunits have been incorporated into carbaporphyrinoid systems and have been further investigated. Utilization of the quinoline subunit allows the reintroduction of a nitrogen, but at the periphery of the structure. A series of quinoline diesters 2 have been prepared and reduction with diisobutylaluminum hydride afforded the related dialdehydes 3. In addition, a tripyrrolic intermediate 4 (tripyrrane) has been synthesized so that the new porphyrin analogues can be generated using a “3+1” methodology. Investigations into the properties of these quiniporphyrins 1 are currently in progress.

Utilization of the “3+1” methodology to synthesize 2,4-quiniporphyrins

ACS Spring 2022

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