New soluble amidoamine substituted phthalocyanines: synthesis, characterization, and investigation of their solution properties

Abstract

The synthesis of tetraaminopropylamid substituted phthalocyanines was targeted to prepare enhanced soluble phthalocyanines in common solvents from hydrophobic to hydrophilic that bore nonionic groups on their periphery. Metal-free (H2Pc) and metallophthalocyanines (Zn(II) (ZnPc), Cu(II) (CuPc) and Co(II) (CoPc)) were prepared and characterized by UV-Vis, FT-IR, and mass spectroscopies. The H-1 NMR spectra were recorded for the diamagnetic phthalocyanine species H2Pc and ZnPc. The phthalocyanines showed sufficient solubility in common organic solvents such as dimethyl sulfoxide, tetrahydrofuran, and ethanol. However, methanol was not a good solvent for CuPc and H2Pc. Solubility and aggregation studies of H2Pc and ZnPc were performed in different solvents and different concentrations in DMF. The solubility in water was also examined by altering pH to exhibit solubility characteristic in polar solvents for H2Pc and ZnPc.