Metal-free, zinc(II) and lead(II) phthalocyanines functioning with 3-(2H-benzo[d][1,2,3]triazol-2-yl)-4-hydroxyphenethyl methacrylate groups: Synthesis and investigation of photophysical and photochemical properties

DEMIRBAS Ü., PİŞKİN M., Barut B., Bayrak R., Durmus M., KANTEKİN H.

SYNTHETIC METALS, vol.220, pp.276-285, 2016 (SCI-Expanded) identifier identifier

  • Publication Type: Article / Article
  • Volume: 220
  • Publication Date: 2016
  • Doi Number: 10.1016/j.synthmet.2016.06.026
  • Journal Name: SYNTHETIC METALS
  • Journal Indexes: Science Citation Index Expanded (SCI-EXPANDED), Scopus
  • Page Numbers: pp.276-285
  • Keywords: Phthalocyanine, Benzotriazole, Photosensitizer, Photophysical, Photochemical, QUANTUM YIELDS, PHOTOSENSITIZERS, BEHAVIOR, FILMS
  • Karadeniz Technical University Affiliated: Yes


In this study, the synthesis and characterization of 3-(2H-benzo[d][1,2,3]triazol-2-yl)-4-hydroxyphenethyl methacrylate substituted novel phthalonitrile compound and its peripherally substituted zinc(II) lead(II) and metal-free phthalocyanine derivatives were performed for the first time. This novel compounds were characterized by obtained data from general spectroscopic methods such as FT-IR, H-1 NMR, C-13 NMR and mass. The photophysical and photochemical properties of these phthalocyanines were investigated in N,N-dimethylformamide solutions for determination of their photosensitizing abilities in photocatalytic applications such as photodynamic therapy. The lead(II) phthalocyanine complex did not produce any fluorescent in N,N-dimethylformamide because of the heavy atom effect of bigger lead atom. The fluorescence quantum yields of studied zinc(II) and metal-free phthalocyanines were found to quite higher than unsubstituted zinc(II) phthalocyanine due to substitution of the phthalocyanine skeleton. The influence of substituent and variety of the central metal ions on spectroscopic, photophysical and photochemical properties were also determined and compared. (C) 2016 Elsevier B.V. All rights reserved.