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

Arslanoglu Y., Koca A. , Hamuryudan E.

POLYHEDRON, cilt.26, sa.4, ss.891-896, 2007 (SCI İndekslerine Giren Dergi) identifier identifier

  • Yayın Türü: Makale / Tam Makale
  • Cilt numarası: 26 Konu: 4
  • Basım Tarihi: 2007
  • Doi Numarası: 10.1016/j.poly.2006.09.006
  • Dergi Adı: POLYHEDRON
  • Sayfa Sayıları: ss.891-896


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, H-1 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. (c) 2006 Elsevier Ltd. All rights reserved.