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J Org Chem. 2013 Jul 5;78(13):6622-31. doi: 10.1021/jo400948s. Epub 2013 Jun 21.

meso-Tetraphenylbenzoporphyrin-2(2),2(3)-dicarboxylic anhydride: a platform to benzoporphyrin derivatives.

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Department of Chemistry, QOPNA, University of Aveiro, 3810-193 Aveiro, Portugal.


A method to synthesize meso-tetraphenylbenzoporphyrin-2(2),2(3)-dicarboxylic anhydride is reported. This compound reacts with alkylamines and arylamines to afford the corresponding "phthalimides" in moderate to excellent yields. The reaction of the title compound with benzene-1,4-diamine or with benzene-1,3-diamine yields the corresponding N,N'-(phenylene)bisphthalimides, whereas with benzene-1,2-diamine or naphthalene-1,8-diamine it affords heterocyclic-fused porphyrins. Molecular mechanics simulations elucidates the multiplicity of signals observed in the NMR spectra of the N,N'-(1,4-phenylene)bisphthalimide 11. This molecule exhibits two preferential conformations corresponding to a coplanar and an almost perpendicular arrangement of the benzoporphyrin units relative to the central benzenic ring.

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