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

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 °C for 24 h under N2 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 1H NMR, 13C 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.

Compound (3) was synthesized by the reaction of 4-(4,5-diphenyl-1H-imidazol-2-yl)phenol with 4-nitrophthalonitrile. Vibrational assignments and electronic transitions of the compound (3) were calculated. Compounds (4–8) were obtained from compound (3) with addition of the corresponding metal salts and spectroscopic behaviors were investigated.Figure optionsDownload as PowerPoint slideHighlights
► The preperation of the imidazole substituted phthalonitrile 3.
► X-ray and computational study of the compound 3.
► Synthesis and characterization of metal free 4 and metallophthalocyanines 5–8.
► Investigation of aggregation behaviors of the compounds 5.
► Investigation of spectroscopic behaviors in acidic media of the compound 5.