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