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

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.

Graphical abstractMetal-free phthalocyanine and metallophthalocyanines containing macrocyclic moietis linked ferrocenyl units has been synthesized by direct cyclotetramerization of the precursor substituted dicyano compound. These compounds were characterized using elemantal analysis, UV–Visible, IR, 1H NMR, 13C NMR and MS spectroscopy techniques.Figure optionsDownload full-size imageDownload as PowerPoint slide