Unmetallated and metallated phthalocyanines bearing oxadiazole groups: Synthesis, photophysical and photochemical studies

Nas A., Kantekin H., Durmus M., Gümrükçüoğlu N.

JOURNAL OF LUMINESCENCE, vol.154, pp.15-21, 2014 (SCI-Expanded) identifier identifier

  • Publication Type: Article / Article
  • Volume: 154
  • Publication Date: 2014
  • Doi Number: 10.1016/j.jlumin.2014.03.058
  • Journal Name: JOURNAL OF LUMINESCENCE
  • Journal Indexes: Science Citation Index Expanded (SCI-EXPANDED), Scopus
  • Page Numbers: pp.15-21
  • Keywords: Unmetallated phthalocyanine, Metallated phthalocyanine, Oxadiazole, Photophysical, Photochemical, Singlet oxygen, 1,3,4-OXADIAZOLE DERIVATIVES, PERFORMANCE, FABRICATION, CATALYSTS, DESIGN
  • Karadeniz Technical University Affiliated: Yes

Abstract

Unmetallated (4) and metallated (zinc(II), cobalt(II), lead(II)) phthalocyanines (5-7) carrying four 4-(4-(5-phenyl-1,3,4-oxadiazol-2-yl)phenoxy) groups on the peripheral positions were synthesized by cyclotetramerization of 4-(4-(5-phenyl-1,3,4-oxadiazol-2-yl)phenoxy)phthalonitrile (3) in the presence of corresponding metal salts (zinc(II) acetate, cobalt(II) chloride, lead(II) oxide) for metallated and without any metal for unmetallated phthalocyanines. The obtained organo-soluble phthalocyanines were characterized by infrared, electronic absorption, nuclear magnetic resonance and mass spectral techniques and elemental analysis as well. The photophysical and photochemical properties of newly synthesized tetra-substituted unmetallated (4), zinc(II) (5) and lead(II) (7) phthalocyanines were reported in N,N-dimetilformamid (DMF). The synthesized phthalocyanine compound 6 was not evaluated for photophysical and photochemical studies due to open shell and paramagnetic behavior of cobalt(II) metal ions in the phthalocyanine cavity. (C) 2014 Elsevier B.V. All rights reserved.