meso-Tetraphenylbenzoporphyrin-2(2),2(3)-dicarboxylic Anhydride: A Platform to Benzoporphyrin Derivatives
authors Carvalho, CMB; Santos, SM; Neves, MGPMS; Tome, AC; Silva, AMS; Rocha, J; Cavaleiro, JAS
nationality International
journal JOURNAL OF ORGANIC CHEMISTRY
keywords SYNTHETIC APPROACH; TETRABENZOPORPHYRINS; METHODOLOGY; PORPHYRINS; CHARGES; LIGHT
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.
publisher AMER CHEMICAL SOC
issn 0022-3263
year published 2013
volume 78
issue 13
beginning page 6622
ending page 6631
digital object identifier (doi) 10.1021/jo400948s
web of science category Chemistry, Organic
subject category Chemistry
unique article identifier WOS:000321605900025
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