The synthesis and characterization of metal-free and metallophthalocyanine polymers by microwave irradiation containing diazadithia macrocyclic moieties

A tetranitrile monomer was synthesized by nucleophilic aromatic substitution of N,N'-(2,2'-(propane-1,3-diylbis(sulfanediyl))bis(ethane-2,1-diyl))bis(4-methylbenzenesulfonamide) onto 4-nitrophthalonitrile. A metal-free phthalocyanine polymer was prepared by the reaction of the tetranitrile monomer under N-2 in the presence of 2-(dimethylamino)ethanol at 145 degrees C for 24 h. Zinc(II), copper(II), cobalt(II), nickel(II), lead (II), phthalocyanine polymers were prepared by reaction of the tetranitrile with the chlorides of zinc (II), copper (II), cobalt (II), nickel (II), lead (II), employing microwave irradiation in the presence 2-(dimethylamino)ethanol at 175 degrees C, 350 W for 10 min. The thermal stabilities of the phthalocyanine compounds were determined by thermogravimetric analysis. The new compounds were characterized by a combination of IR, H-1 NMR, C-13 NMR, UV-vis, elemental analysis and MS spectral data. (C) 2009 Elsevier Ltd. All rights reserved.