Phthalocyanine photosensitizers with bathochromic shift, of suitable brightness, capable of producing singlet oxygen with effective efficiency


PİŞKİN M.

JOURNAL OF PHOTOCHEMISTRY AND PHOTOBIOLOGY A-CHEMISTRY, 2023 (SCI-Expanded) identifier

  • Yayın Türü: Makale / Tam Makale
  • Basım Tarihi: 2023
  • Doi Numarası: 10.1016/j.jphotochem.2022.114325
  • Dergi Adı: JOURNAL OF PHOTOCHEMISTRY AND PHOTOBIOLOGY A-CHEMISTRY
  • Derginin Tarandığı İndeksler: Science Citation Index Expanded (SCI-EXPANDED), Scopus, Academic Search Premier, BIOSIS, Chemical Abstracts Core, Chimica, INSPEC
  • Çanakkale Onsekiz Mart Üniversitesi Adresli: Evet

Özet

In this study, novel 3-(2,3-dimethoxyphenoxy)phthalonitrile 2 and its non-peripheral tetra-2,3-dimethox-yphenoxy substituted metal-free phthalocyanine 3 compounds were synthesized. Then, the magnesium(II), zinc (II), and indium(III) acetate phthalocyanine complex derivatives (4-6) of compound 3 were synthesized using the corresponding metal salts by the template effect. The structures of novel phthalonitrile derivative 2 and its metal-free phthalocyanine compounds 3 as well as different metal-containing phthalocyanine complexes (4-6) were characterized by elemental analysis, FTIR, UV-vis, 1H-NMR, and MALDI-TOF mass spectroscopic tech-niques. The phthalocyanines (3-6) can dissolve well in different polar protic, polar aprotic, and non-polar solvent types without aggregation, with maximum absorption intensity and bathochromic effect. Photophysicochemical properties of the phthalocyanines (3-6) in dimethyl sulfoxide and important spectral parameter values such as molar extinction coefficient, oscillator strength, and electrical dipole strength were determined, and they were also compared with each other and with their unsubstituted counterparts. It was determined that the phthalo-cyanines (3-6) have suitable and sufficient fluorescence quantum yields, fluorescence lifetimes, fluorescence brightness, and other photophysical properties, as well as singlet oxygen generation, phototoxic power, and photostability properties. The phthalocyanines (3-6), particularly zinc(II) and indium(III) acetate phthalocya-nines have remarkable potential for use as Type II photosensitizers for cancer therapy in photodynamic therapy. The phthalocyanines (3-6) may be promising candidates for various applications as photosensitizers for photodynamic therapy, especially in combination with fluorescent imaging.