Water-soluble manganese phthalocyanines

Abstract

Three new substituted manganese phthalocyanines (PcMns), wich are water-soluble, have been synthesized with good yields (70–80%) and high purity. Pyridiniummethyl- and cholinylsubstituted phthalocyanines have been obtained from the chloromethylsubstituted PcMns , while octacarboxysubstituted complex has been synthesized from metal-free octacarboxyphthalocyanine tetraanhydride. Compounds were characterized by elemental analysis and mass, IR and UV-vis spectroscopy. In general, coordination chemistry of the compounds studied is similar to this one of liposoluble PcMns but some new findings have been obtained. Three coordination forms — PcMn ( II ), PcMn ( III ) X ( X = Cl -, OAc -, …) and [ LPcMn ( III )]2 O ( L = Py , Et 3 N , …) have been obtained for all the new compounds. The equilibrium between three electronic isomers — Pc+• Mn ( I ) × L , PcMn ( II ) × nL , (n = 1, 2) and Pc-• Mn ( III ) × 2 L has been observed in PcMn aqueous solutions upon the addition of organic bases L ( Py , Et 3 N , …).