Synthesis and characterization of novel 4-nitro-2-(octyloxy)phenoxy substituted symmetrical and unsymmetrical Zn(II), Co(II) and Lu(III) phthalocyanines

Compounds 3 and 4 have been prepared by the reaction of 4-nitrocatechol 1 and 4-nitrophthalonitrile 2 by a common method, aromatic nucleophilic subtitution of the nitro group in 4-nitrophthalonitrile. Starting from 4 and 1-bromooctane, their alkylation reaction gave compound 5. Zn(II) 8, Co(II) 9 and Lu(III) 10 complexes were synthesized from the corresponding metal salts by the tetramerization of compound 5. Compound 7 was prepared by the statistical condensation of 5 and 4,5-bis(hexylthio)phthalonitrile 6 with CoCl2 · 6H2O in dry dimethylformamide. The new compounds were characterized by FT-IR, UV/Vis, NMR and mass spectra. The electrochemical properties of the complexes were also investigated by cyclic voltammetry in non-aqueous medium. The effect of temperature on the dc conductivity and the impedance spectra of spin coated film of the compounds was investigated at temperatures between 295 and 433 K and in the frequency range 40–105 Hz. Thermally activated conductivity dependence on temperature was observed for all compounds.

Graphical abstractStarting from 4-(3,4-dicyanophenoxy)-3-hydroxynitrobenzene (4) and 1-bromooctane, their alkylation reaction gave compound 5. Zn(II) 8, Co(II) 9, and Lu(III) 10 complexes were synthesized by the tetramerization of compound 5. Compound 7 was prepared by the condensation of 5 and 6. The new compounds were characterized by FT-IR, UV/Vis, NMR and mass spectra. The electrochemical and electrical properties of the complexes were also investigated.Figure optionsDownload full-size imageDownload as PowerPoint slide