Polymerization and complex formation of phthalocyanine substituted by trioxyethylene in solution

Phthalocyanine substituted by eight trioxyethylenemonomethylethers (EOPc) was prepared, and the solvent effect on the polymerization has been studied at 25.0 °C through absorption and emission spectroscopies. EOPc is soluble in a wide range of solvents from water to nonpolar solvents because of the amphiphilic property of the compound. EOPc predominantly is present as a polymer in polar solvents, such as water. The degree of dissociation to monomer in nonpolar solvent increases by the increase in the ET value (acceptor) of the solvent, and it completely dissociates to monomer in chloroform. The complex formation with alkali metal ions in chloroform was studied by means of H-1 NMR spectroscopy. The structure of the complex, in which the metal ion is pinched by two trioxyethylene groups locating close to the benzene group, was estimated. The degree of polymerization increases by the complex formation in relatively low ET solvents, such as carbon tetrachloride, although the complex is hardly polymerized in chloroform. The structure of the ion pair of the complex with picrate ion was estimated.