Synthesis, characterization and aggregation properties of peripheral 1,2-di(1-naphtyl)-1,2-ethanediol substituted phthalocyanines

The synthesis and characterization of a novel 1,2-dinaphthyl ethanediol substituted phthalonitrile 2 together with tetra-substituted zinc(II) phthalocyanine 3 and cobalt(II) phthalocyanine 4 bearing 1,2-di(naphthalen-1-yl)ethane-1,2-diol at peripheral positions were described. The solvent and concentration effects on the aggregation properties of the phthalocyanines were determined. To investigate the aggregation behaviors of phthalocyanine complexes 3 and 4, Beer-Lambert's experiment was carried out at the concentrations between 10 x 10-6 and 2 x 10-6 mol dm-3 in THF and DMF. The phthalocyanine complexes 3 and 4 demonstrated no aggregation behavior in DMF and THF from concentrations between 10 x 10-6 and 2 x 10-6 mol dm-3. The structures of the newly synthesized compounds are characterized by 1H NMR, IR, UV-Vis and MALDI-TOF MS spectral data.