The synthesis, using microwave irradiation and characterization of novel, organosoluble metal-free and metallophthalocyanines substituted with flexible crown ether moieties

Cyclotetramerization of a phthalonitrile derivative to the metal-free phthalocyanine was accomplished in n-pentanol in the presence of 1,8-diazabicyclo[5.4.0]undec-7-ene at reflux under an argon atmosphere. Ni(II), Zn(II), Co(II), Cu(II) phthalocyanines with four, peripheral 4-[methyleneoxy(12-crown-4)] groups were synthesized from 4-[{(12-crown-4)-yl}methyleneoxy]phthalonitrile in the presence of the anhydrous, divalent metal salts (NiCl2, Zn(CH3COO)(2), COCl2 and CUCl2). The green phthalocyanines were soluble in common organic solvents such as CHCl3, CH2Cl2, CH3COCH3, THF, DMF and DMSO. The structures of the target compounds were confirmed using elemental analysis, IR, H-1 NMR, C-13 NMR, UV-vis and MS spectral data. (C) 2008 Elsevier Ltd. All rights reserved.