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.
keywords
SYNTHETIC APPROACH; TETRABENZOPORPHYRINS; METHODOLOGY; PORPHYRINS; CHARGES; LIGHT
subject category
Chemistry
authors
Carvalho, CMB; Santos, SM; Neves, MGPMS; Tome, AC; Silva, AMS; Rocha, J; Cavaleiro, JAS
our authors
João Rocha
Full Professor
Sérgio Miguel Fernandes dos Santos
Assistant Researcheracknowledgements
Thanks are due to Fundacao para a Ciencia e a Tecnologia (FCT), European Union, QREN, FEDER and COMPETE for funding the QOPNA research unit (project PEst-C/QUI/UI0062/2011), CICECO (PEst-C/CTM/LA0011/2011), the Project PTDC/QUI/74150/2006, and the Portuguese National NMR Network. C.M.B.C. and S.M.S. thank FCT for their grants SFRH/BD/38611/2007 and SFRH/BPD/64752/2009, respectively.