Synthesis, electrochemical and spectroelectrochemical properties of highly soluble tetra substituted phthalocyanines with [4-(thiophen-3-yl)-phenoxy]

Zinc, oxo-titanium, cobalt, and manganese phthalocyanine derivatives substituted with nonperipheral 3-(tetra[4-(thiophen-3-yl)-phenoxy] moieties have been synthesized and characterized by elemental analysis, IR, 1H NMR spectroscopy, electronic spectroscopy, and mass spectra. The compounds have good solubility in various polar and nonpolar organic solvents and not aggregated (in the same solvents) within a wide concentration range. Electrochemical and spectroelectrochemical measurements exhibit that incorporation redox active metal centers, CoII, TiIVO and MnIIIOAc into the phthalocyanine core extend the redox richness of the Pc ring with the reversible metal-based reduction and oxidation couples of the metal centers in addition to the common Pc ring-based electron transfer processes.

► Zinc, oxo-titanium, cobalt, and manganese phthalocyanine derivatives substituted with nonperipheral 3-(tetra[4-(thiophen-3-yl)-phenoxy] moieties have been synthesized and characterized.
► The introduction of [4-(thiophen-3-yl)-phenoxy] on the ring results in precludes aggregation.
► Incorporation redox active metal centers, CoII, TiIVO and MnIIIOAc into the phthalocyanine core extend the redox richness of the Pc ring.
► Quantification of xyz color coordinates of the each electrogenerated anionic and cationic redox species indicates possible polyelectrochromic applications.