Synthesis, characterization and spectroscopic studies of novel peripherally tetra-imidazole substituted phthalocyanine and its metal complexes, the computational and experimental studies of the novel phthalonitrile derivative

Akcay H. T., Bayrak R., KARSLIOĞLU S., ŞAHİN E.

JOURNAL OF ORGANOMETALLIC CHEMISTRY, vol.713, pp.1-10, 2012 (SCI-Expanded) identifier identifier


Compound (3) was synthesized by the reaction of 4-(4,5-diphenyl-1H-imidazol-2-yl) phenol and 4-nitrophthalonitrile in dry DMF in presence of K2CO3 and obtained as single crystal form suitable for x-ray analysis. Vibrational assignments and electronic transitions of the compound (3) were calculated and compared with the experimental results. Compound (4) was obtained from compound (33), by heating at 160 degrees C for 24 h under N-2 atmosphere in dry N,N dimethyl aminoethanol. Compounds (5-8) were synthesized by the same method applied for the synthesis of compound (4) with addition of the corresponding metal salts (ZnCH3COO2, NiCl2, CoCl2, CuCl2). Prepared phthalocyanines were purified by column chromotography using appropriate solvent system and characterized by elemental analysis H-1 NMR, C-13 NMR, UV-vis, IR and mass spectra. Aggregation behavior of compound (5) was studied in different solvents and different concentrations in DMSO. In addition, protonation behavior of the compound (5) was investigated in different mixtures of sulfuric acid and DMSO. (C) 2012 Elsevier B.V. All rights reserved.