Microwave-assisted synthesis and characterization of a new soluble metal-free and metallophthalocyanines peripherally fused to four 18-membered tetrathiadiaza macrocycles

Kantekin H., Dılber G., Nas A.

JOURNAL OF ORGANOMETALLIC CHEMISTRY, vol.695, no.8, pp.1210-1214, 2010 (SCI-Expanded) identifier identifier


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-13H,22H-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(3)COO)(2), CoCl(2), CuCl(2) salts, respectively, by microwave irradiation in 2-(dimethylamino) ethanol for at 175 degrees C, 350 W. The new compounds were characterized by IR, (1)H NMR, (13)C NMR, UV-Vis, elemental analysis and MS spectra data. (C) 2010 Elsevier B.V. All rights reserved.