Abstract
Preparation of some novel symmetrically tetrasubstituted metal-free phthalocyanine ( 6) and metallophthalocyanines ( 7– 10) containing four 18-membered tetrathiadiaza macrocycles moieties on peripheral positions has been achieved by cyclotetramerization reaction of phthalonitrile derivative ( 5) in a multi-step reaction sequence. Metal-free phthalocyanine ( 6) was synthesized by microwave irradiation of 13,24-bis[(4-methylphenyl)sulfonyl]-6,7,14,15,23,24-hexahydro-13 H,22 H-tribenzo[ b, h, n][1,4,10,13,7,16]tetrathiadiazacyclo-octadecine-18,19-dicarbonitrile ( 5) in 2-(dimethylamino)ethanol. The metallophthalocyanines ( 7– 10) were prepared by the reaction of the phthalonitrile compound ( 5) with NiCl 2, Zn(CH 3COO) 2, CoCl 2, CuCl 2 salts, respectively, by microwave irradiation in 2-(dimethylamino)ethanol for at 175 °C, 350 W. The new compounds were characterized by IR, 1H NMR, 13C NMR, UV–Vis, elemental analysis and MS spectra data.
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