Synthesis of novel unsymmetrical phthalocyanines substituted with crown ether and nitro groups

Yasin Arslanoǧlu, Atif Koca, Esin Hamuryudan*

*Corresponding author for this work

Research output: Contribution to journalArticlepeer-review

19 Citations (Scopus)

Abstract

This work reports on the synthesis of new unsymmetrically substituted phthalocyanines (M = Zn, Cu, Co, Ni) bearing three benzo-15-crown-5 units through oxy bridges and a nitro group. Phthalocyanines were prepared by a statistical condensation of 4-nitro phthalonitrile and 1-{[(benzo-15-crown-5)-4′-yl]oxy}phthalonitrile in the presence of anhydrous metal salts. All the target unsymmetrical phthalocyanines were separated by column chromatography and characterized elemental analyses, 1H NMR, IR, mass and UV-Vis spectral data. Electrochemical behaviors of Cu (II) phthalocyanine by cyclic voltammetry and differential pulse voltammetry techniques gave two common phthalocyanine ring reductions and one ring oxidation processes. Peak-to-peak separation of the processes II and III (388 mV) and the measure of gap (1.672 V) between the HOMO and LUMO for the complex, fits a phthalocyanine with electrochemically inactive metal center.

Original languageEnglish
Pages (from-to)891-896
Number of pages6
JournalPolyhedron
Volume26
Issue number4
DOIs
Publication statusPublished - 1 Mar 2007

Keywords

  • Cyclic voltammetry
  • Metallophthalocyanines
  • Synthesis
  • Unsymmetrical

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