Synthesis and characterization of metal-free and metallophthalocyanines containing N2S2-type macrocyclic moieties linked ferrocenyl groups

Abstract

The new metal-free (4) and metallophthalocyanines (5) carrying macrocyclic moieties linked ferrocenyl groups have been synthesized by direct cyclotetramerization of the pre-cursor, 12,13-dicyano-4,7-bis(ferrocenylmethyl)-2,3,4,5,6,7,8,9-octahydrocyclobenzo[k]-4,7-diaza-1,10-dithiacyclododecine (3) which has been prepared by the macrocyclization reaction of 1,2-bis(2-iodoethylmercapto)-4,5-dicyanobenzene (1) with N,N'-ethylenebis-(ferroceneylmethyl)amine (2), in the presence of 1,8-diazabicyclo[5.4.0]undec-7-ene (DBU) as a strong organic base. Nickel (II) phthalocyanine (5) was synthesized by the reaction of metal-free phthalocyanine with anhydrous NiCl2 in dry quinoline. The target compound and its intermediates have been characterized by a combination of elemental analysis and 1H, 13C NMR, IR, UV-Vis and MS spectral data. © 2006 Elsevier B.V. All rights reserved.