title: meso-Tetraphenylbenzoporphyrin-2(2),2(3)-dicarboxylic anhydride: a platform to benzoporphyrin derivatives.
abstract: 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.
authors.affiliation: Department of Chemistry, QOPNA, University of Aveiro, 3810-193 Aveiro, Portugal.
authors.forename: Carla M B
authors.initials: CM
authors.lastname: Carvalho
authors.forename: Sérgio M
authors.initials: SM
authors.lastname: Santos
authors.forename: Maria G P M S
authors.initials: MG
authors.lastname: Neves
authors.forename: Augusto C
authors.initials: AC
authors.lastname: Tomé
authors.forename: Artur M S
authors.initials: AM
authors.lastname: Silva
authors.forename: João
authors.initials: J
authors.lastname: Rocha
authors.forename: José A S
authors.initials: JA
authors.lastname: Cavaleiro
mesh_terms: D008958:Models, Molecular; D056004:Molecular Dynamics Simulation; D015394:Molecular Structure; D011166:Porphyrins / Q000138:chemical synthesis* / Q000737:chemistry
chemical_list: D011166:Porphyrins