Synthesis and characterization of tetra-substituted titanium(IV) phthalocyanines with axial ligand

In this paper, the synthesis and characterization of peripheral tetra-2-(2-ethyloxyethyloxy)ethyloxy substituted oxo-titanium phthalocyanines (TiOPcs) are reported. The reaction of 2,2,3,3-tetrafluoropropoxy substituted and [2-(2-ethoxyethoxy)ethoxy] substituted TiOPcs (1 and 3) with 4-[(6-hydroxyhexyl)oxy]benzene-1,2-diol as a strongly chelating oxygen donor ligand is described. Compounds 1a and 3a bearing the hydroxyl group as an axial ligand of the bulky group are converted into a thiol group (1c and 3c). The new compounds are characterized by elemental analysis, FT-IR, 1H NMR, and mass spectrometry. While the fluoropropoxy substituted TiOPc has good solubility in polar solvents such as acetone and THF, the other TiOPc is soluble in chloroform.