Peripherally and non-peripherally tetra-benzothiazole substituted metal-free zinc (II) and lead (II) phthalocyanines: Synthesis, characterization, and investigation of photophysical and photochemical properties

DEMIRBAS Ü., Gol C., Barut B., Bayrak R., Durmus M., KANTEKİN H., ...More

JOURNAL OF MOLECULAR STRUCTURE, vol.1130, pp.677-687, 2017 (SCI-Expanded) identifier identifier

  • Publication Type: Article / Article
  • Volume: 1130
  • Publication Date: 2017
  • Doi Number: 10.1016/j.molstruc.2016.11.017
  • Journal Name: JOURNAL OF MOLECULAR STRUCTURE
  • Journal Indexes: Science Citation Index Expanded (SCI-EXPANDED), Scopus
  • Page Numbers: pp.677-687
  • Keywords: Singlet oxygen, Phthalocyanine, Benzothiazole, Fluorescence quenching, Photosensitizer, FILMS
  • Karadeniz Technical University Affiliated: Yes

Abstract

In this study, novel phthalonitrile compounds bearing 2-methylbenzofdlthiazol-5-yloxy groups (4 and 5) and their peripherally and non-peripherally tetra-substituted metal-free (6 and 7), zinc (II) (8 and 9), and lead (II) (10 and 11) phthalocyanine derivatives were synthesized and characterized for the first time. These novel compounds showed extremely good solubility in most common organic solvents. The novel phthalocyanine compounds presented excellent results from photophysical and photochemical examinations in DMF solution. Especially, the singlet oxygen quantum yield (Phi(Delta)) values of the substituted zinc (II) phthalocyanines indicate that these compounds have significant potential as photosensitizers in cancer treatment by the photodynamic therapy (PDT) technique. The fluorescence quenching behaviour of these novel phthalocyanine compounds by 1,4-benzoquinone (BQ) was also examined in DMF solution. (C) 2016 Elsevier B.V. All rights reserved.