Please use this identifier to cite or link to this item: http://hdl.handle.net/10773/20085
Title: meso-Tetraphenylbenzoporphyrin-2(2),2(3)-dicarboxylic Anhydride: A Platform to Benzoporphyrin Derivatives
Author: Carvalho, Carla M. B.
Santos, Sergio M.
Neves, Maria G. P. M. S.
Tome, Augusto C.
Silva, Artur M. S.
Rocha, Joao
Cavaleiro, Jose A. S.
Keywords: SYNTHETIC APPROACH
TETRABENZOPORPHYRINS
METHODOLOGY
PORPHYRINS
CHARGES
LIGHT
Issue Date: 2013
Publisher: AMER CHEMICAL SOC
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.
Peer review: yes
URI: http://hdl.handle.net/10773/20085
DOI: 10.1021/jo400948s
ISSN: 0022-3263
Publisher Version: 10.1021/jo400948s
Appears in Collections:CICECO - Artigos



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