Novel phthalocyanines containing azo chromophores; synthesis, characterization, photophysical, and electrochemical properties

Garip E. O. , Özçeşmeci M. , Nar I. , Özçeşmeci İ. , Hamuryudan E.

JOURNAL OF PORPHYRINS AND PHTHALOCYANINES, cilt.22, ss.198-206, 2018 (SCI İndekslerine Giren Dergi) identifier identifier

  • Yayın Türü: Makale / Tam Makale
  • Cilt numarası: 22
  • Basım Tarihi: 2018
  • Doi Numarası: 10.1142/s1088424618500050
  • Sayfa Sayıları: ss.198-206


A series of novel metal-free and zinc (II), copper (II), cobalt (II), and manganese (III) phthalocyanine complexes bearing peripheral 2,6-dimethyl-4-(4-tert-butyl-phenylazo) phenoxy units have been synthesized. Novel phthalonitrile derivative required for the preparation of these phthalocyanine complexes was prepared by a base-catalyzed nucleophilic aromatic nitro displacement of 4-nitrophthalonitrile with 2,6-dimethyl-4-(4-tert-butyl-phenylazo) phenol. The structures of these new compounds were characterized by using elemental analyses, proton and carbon nuclear magnetic resonance, Fourier transform infrared spectroscopy, ultraviolet-visible spectroscopy and mass spectrometry. The photophysical properties of metal-free and zinc(II) phthalocyanines were studied in tetrahydrofuran. The electrochemical properties of the phthalocyanine complexes were investigated by cyclic and square wave voltammetry.