Synthesis, characterization and aggregation behaviour of novel peripherally tetra-substituted octacationic water soluble metal-free and metallophthalocyanines

摘要

In this study, a new phthalonitrile derivative 3 bearing 1,3-bis[3(dimethylamino)phenoxy]propan-2-ol 1, metal-free phthalocyanine (Pc) 4, metallophthalocyanines (MPcs) 5-7 and their quaternized derivatives 4a-7a were synthesized. Metal-free Pc 4 was prepared by cyclotetra-merization of phthalonitrile derivate 3 and MPcs 5-7 were synthesized by heating 3 with NiCl2, CoCl2 and CuCl2 in n-pentanol in the presence of l,8-diazabicyclo[5.4.0]undec-7-ene, respectively. Quaternization of the dimethylamino functionality produced quaternized octacationic water soluble metal-free, Ni, Co and Cu Pcs which were soluble in water, DMF, DMSO. The aggregation behaviour of these compounds were investigated in different concentrations of chloroform for metal-free, Ni, Co and Cu Pcs. The effect of solvents on absorption spectra were studied in various organic solvents. The novel compounds were characterized using IR, ~1H-, ~(13)C NMR, UV-vis and MS spectral data.