The microwave-assisted synthesis and characterization of novel metal-free and metallophthalocyanines peripherally fused to four 13-membered diazadithia macrocycles

The novel tetrasubstituted metal-free phthalocyanine and metallophthalocyanines 7, bearing four 13-membered diazadithia macrocycle moieties at peripheral positions were synthesized by cyclotetramerization of the corresponding phthalonitrile derivative in a multi-step reaction sequence. The metal-free phthalocyanine was synthesized by microwave irradiation of the corresponding dicyano compound in 2-(dimethylamino)ethanol for 10 min. Metallophthalocyanines were obtained from the respective dicyano derivative and corresponding anhydrous metal salts NiCl2 and ZnCl2, CoCl2, CuCl2, respectively, by microwave irradiation in 2-(dimethylamino)ethanol at 175 degrees C, 350W for 10 min. 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) 2008 Elsevier Ltd. All rights reserved.