Functional fluoro substituted tetrakis-metallophthalocyanines: Synthesis, spectroscopy, electrochemistry and spectroelectrochemistry

In this study, electron-withdrawing fluoro-functional ligand and its tetrakis 2,9,16,23-4-(2,3,5,6-tetrafluoro)-phenoxy-phthalocyaninatometal (II) complexes, (ZnPcOBzF16, CuPcOBzF16 and CoPcOBzF16) (Bz: benzene) which are organo-soluble have been prepared. Their structures were confirmed by elemental analysis, FT-IR, 1H NMR, UV/vis and MS (Maldi-TOF) spectral data. Electron-withdrawing fluorine atoms on 2,3,5,6-position of benzene at the peripheral sites increases the solubility of the tetrakis-metallophthalocyanines. The cyclic voltammetry and differential pulsed voltammetry of the complexes show that while CuPcOBzF16 and ZnPcOBzF16 give ligand-based reduction and oxidation processes, CoPcOBzF16 gives both ligand and metal-based redox processes, in harmony with the common MPc complexes. Spectroelectrochemical measurements confirm the assignments of the complexes.

Graphical abstractElectron-withdrawing fluoro-functional ligand and its tetrakis 2,9,16,23-tetrakis-4-(2,3,5,6-tetrafluoro)-phenoxy-phthalocyaninatometal (II) complexes, have been prepared and characterized by elemental analysis, FT-IR, 1H NMR, UV/vis MS (Maldi-TOF), electrochemistry, and spectroelectrochemistry.Figure optionsDownload full-size imageDownload as PowerPoint slide