Synthesis And Aggregation Of Optically Active Tetra-β-((S)-2-octanyloxy)-substituted Copper And Nickel Phthalocyanines

The Phthalocyanine (Pc) Compounds, especially the opticaliy active phthalocyanines have potential application in many areas due to their distinctive physical and chemical properties. 0ptically active Pcs have intensively attracted chemists in the last te years for the special chiral stacking of them . Optically active Pcs reported before could be mainly classified into three groups: (1) Pcs containing chiral carbons in the side chain; (2) Pcs with optically active aromatic molecules; (3) Pcs with planar asymmetry . The first group was paid more attentions to because some chiral substrates were commercially available, and from which those synthesized Pcs usually behaved multiple liquid crystal mesophases . However, the usable substrates to synthesize optically active Pcs were finite for racemization of them under synthetic conditions. Thus, to date the number of optically active Pcs was not enough to meet the requirement of investigation on them. So a significant task for chemists is to synthesize new optically active Pc compounds and characterize properties of them. Based on stability of some chiral sec-alcohols, here (S)-2-octanol was selected as the original substrate to synthesize optically active tetra-β-((S)-2-octanyloxy)-substituted copper and nickel phthalocyanines at 135℃by a modified synthetic method for that the substrate didn't occurred racemization at more than 140℃. The results of characterization on them confirm that they bear optically activation and have strong intermolecular forces compelling molecules .They were characterized by MS, 1H NMR, UV-vis, IR, CD spectra measurements as well as elemental analysis. They were characterized by MS, 1H NMR, UV-vis, IR, CD spectra measurements as well as elemental analysis. The synthesized compounds possessed excellent solubility in common organic solvents except methanol. They were inclined to exist in single molecules in chloroform and dichloromethane, but form H-aggregates in ethanol and ethyl ether. In solid films, it was concluded that they congregated to H-type congeries with left-handed helix.