Synthesis and aggregation study of optically active tetra-β-[(S)-2-octanyloxy]-substituted copper and nickel phthalocyanines

The optically active tetra-β-[(S)-2-octanyloxy]-substituted copper and nickel phthalocyanines were synthesized via a two-step route with 4-nitro-phthalonitrile and (S)-2-octanol as the starting materials. Both compounds are fully characterized by MS, 1H NMR, UV-Vis, IR, CD and elemental analysis, and soluble in common organic solvents except methanol. The results showed that they were dispersed into single molecules in chloroform and dichloromethane, but prone to congregate into H-type aggregates in ethanol and diethyl ether. They assembled to H-type aggregates with left-handed helix when deposited as thin films.