Discotic liquid crystals of transition metal complexes 46: mesomorphism and antagonist solubility of octaphenoxy-phthalocyaninato copper(II) complex substituted by oligoether chains

We synthesized a novel discotic liquid crystalline compound, octakis[3-(2-(2-(2-methoxyethoxy)ethoxy)ethoxy)phenoxy]phthalocyaninato copper(II) (abbreviated as [m-MeO-(EtO)(3)PhO](8)PcCu), and established the mesomorphism by using a differential scanning calorimeter, a polarizing optical microscope, and temperature-dependent wide angle X-ray diffraction diffractometer. Very interestingly, this [m-MeO(EtO)(3)PhO](8)PcCu complex showed a hexagonal ordered columnar (Col(ho)) mesophase in the virgin sample, whereas it showed a rectangular ordered columnar (Col(ro)(P2(1)/a)) mesophase in the non-virgin sample. The Col(ho) mesophase gave a dimer stacking distance at 9.26 angstrom, whereas the Col(ro) mesophase gave a short monomer stacking distance at 3.45 angstrom. Furthermore, this novel Pc derivative is readily soluble in polar solvents such as acetone, ethanol and methanol. Using antagonist solubilities of the present hydrophilic [m-MeO(EtO)(3)PhO](8)PcCu derivative in a polar solvent and the previous hydrophobic (C10O)(16)TzCu derivative in the non-polar solvent, a p-n junction layered thin films could be successfully prepared.