Synthesis and electrochemical properties of a series of novel tetra(4-benzoyl)phenoxyphthalocyanine derivatives

Abstract

A novel phthalocyanine, 2,9(10),16(17),23(24)-tetra(4-benzoyl)phenoxyphthalocyanine, and its complexes with Zn(II), Cu(II), Co(II), and Ni(II) have been synthesized and characterized by a combination of elemental analysis, IR, 1H NMR, UV-vis spectroscopy and mass spectrometry. All of the materials are very soluble in common organic solvents such as dichloromethane, chloroform, tetrahydrofuran, N,N-dimethylformamide and dimethyl sulfoxide. The Q band wavelengths of the complexes decrease in the order: Zn > Cu > Ni > Co. Redox processes were observed at −1.06, −0.74, 0.51 and 0.98 V for the free phthalocyanine, at −0.72 and 1.04 V for the Co(II) complex, at −1.24, −0.77, −0.24, 0.61 and 0.91 V for the Cu(II) complex, and at −0.74 and 1.20 V for the Ni(II) complex. The cyclic voltammograms of the phthalocyanine ring of the four species are similar, with reduction and oxidation couples each involving a one-electron transfer process.

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Correspondence to Qiang Fu.

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Wang, K., Fu, Q., Ma, J. et al. Synthesis and electrochemical properties of a series of novel tetra(4-benzoyl)phenoxyphthalocyanine derivatives. Sci. China Chem. 55, 1872–1880 (2012). https://doi.org/10.1007/s11426-012-4675-x

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Keywords

  • synthesis
  • electrochemical
  • (4-benzoyl)phenoxy
  • phthalocyanine