Synthesis, characterization and aggregation properties of peripheral and non-peripheral hydrobenzoin substituted optically active phthalocyanines

The synthesis and characterization of a novel hydrobenzoin substituted optically active phthalonitrile 2and 3 together with optically active tetra-substituted zinc(II) phthalocyanine 4 and 6, and cobalt(II) phthalocyanine 5 and 7bearing hydrobenzoinat peripheral and non-peripheral positions, respectively, were described. Structures of the newly synthesized compounds are determined by 1H NMR, UV-Vis, Circular Dichroism (CD), IR and mass spectral data. The solvent and concentration effects on the aggregation properties of the phthalocyanines were determined. To investigate the aggregation behaviors of phthalocyanine complexes 4-7, Beer-Lambert's experiment was carried out at the concentrations between 10x10-6 and 2x10-6 mol dm-3 in tetrahydrofuran and N,N-dimethylformamide. The phthalocyanine complexes 4-7 demonstrated no aggregation behavior in N,N-dimethylformamide and tetrahydrofuran from concentrations in the range of 2-10x10-6 mol dm-3.