Benziporphyrins, e.g. 1, are porphyrin analogues that incorporate a benzene moiety in place of one of the pyrrolic subunits. Although benziporphyrin is nonaromatic, many derivatives have global diatropic properties. The benziporphyrin cavity can also facilitate the formation of organometallic derivatives. In this work, the formation of dimeric benziporphyrin structures is under investigation. Novel benziporphyrin ethers 1a,b have been synthesized from a tripyrrane 2 and alkoxybenzene dialdehydes 3 using a ‘3 + 1’ MacDonald-type condensation. As expected, these new porphyrinoids show no overall diatropicity, but protonation afforded weakly aromatic dications. In addition, a related ether-linked ester 1c has been prepared and its conversion into amide-linked dimers is being investigated. Furthermore, pyrene-derived tetraketones 4 have been converted into bis-benzitripyrrane-type structures 5, and these have been reacted with a thiophene dicarbinol to generate porphyrinoid products. Poor solubility has limited the characterization of these products and alternative substitution patterns are being considered to overcome these difficulties.

Investigations into the synthesis of benziporphyrin and pyreniporphyrin dimers

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.