This paper describes the synthesis of three new porphyrins 1-3 of alternate A(2)B(2) structure, by condensation of arylbis(2-pyrrolyl)methanes and arylaldehydes bearing suitable reactive substituents for further synthetic manipulations. This synthetic approach allows to place the reactive groups selectively on the 5,15 meso-aryls. The new porphyrins feature an ortho-nitro group in the case of 1 and a protected para-ethynyl group in compounds 2 and 3. Porphyrin 1, after reduction of the nitro group, is a useful intermediate for the preparation of cage or regiospecifically bis-tailed porphyrins. Compounds 2 and 3, after deprotection and Glaser-Hay coupling, should give linear polymers (molecular wires) suitable for electron-transfer and light-harvesting processes.

Synthesis of regiospecifically meso-functionalized tetraarylporphyrins via arylbis(2-pyrrolyl)methanes / S. Banfi, A. Manfredi, G. Pozzi, S. Quici, A. Trebicka. - In: GAZZETTA CHIMICA ITALIANA. - ISSN 0016-5603. - 126:3(1996 Mar), pp. 179-185.

Synthesis of regiospecifically meso-functionalized tetraarylporphyrins via arylbis(2-pyrrolyl)methanes

A. Manfredi
Secondo
;
1996-03

Abstract

This paper describes the synthesis of three new porphyrins 1-3 of alternate A(2)B(2) structure, by condensation of arylbis(2-pyrrolyl)methanes and arylaldehydes bearing suitable reactive substituents for further synthetic manipulations. This synthetic approach allows to place the reactive groups selectively on the 5,15 meso-aryls. The new porphyrins feature an ortho-nitro group in the case of 1 and a protected para-ethynyl group in compounds 2 and 3. Porphyrin 1, after reduction of the nitro group, is a useful intermediate for the preparation of cage or regiospecifically bis-tailed porphyrins. Compounds 2 and 3, after deprotection and Glaser-Hay coupling, should give linear polymers (molecular wires) suitable for electron-transfer and light-harvesting processes.
ASYMMETRIC EPOXIDATIONS; PORPHYRINS; LIGAND; DERIVATIVES; RECOGNITION; SYSTEMS; OLEFINS
Settore CHIM/06 - Chimica Organica
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Utilizza questo identificativo per citare o creare un link a questo documento: http://hdl.handle.net/2434/187615
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