Novel nonperipheral octa-3-hydroxypropylthio substituted metallo-phthalocyanines: synthesis, characterization, and investigation of their electrochemical, photochemical and computational properties

Authors: NİLGÜN KABAY, YASEMİN BAYĞU, METİN AK, İZZET KARA, ESRA NUR KAYA, MAHMUT DURMUŞ, YAŞAR GÖK

Abstract: The current study describes the synthesis, electrochemical, computational, and photochemical properties of octa (3-hydroxypropylthio) substituted cobalt (II) (4), copper (II) (5), nickel (II) (6) and zinc(II) (7) phthalocyanine derivatives. These novel compounds were characterized by elemental analysis, ¹H, ¹³C NMR, FT-IR, UV-Vis, and MS. The redox behaviors of these metallo-phthalocyanines were investigated by the cyclic voltammetric method. The optimized molecular structure and gauge-including atomic orbital (GIAO) ¹H and ¹³C NMR chemical shift values of these phthalocyanines in the ground state had been calculated by using B3LYP/6-31G(d,p) basis set. The outcomes of the optimized molecular structure were given and compared with the experimental NMR values. The photochemical properties including photodegradation and singlet oxygen generation of zinc(II) phthalocyanine were studied in DMSO solution for the determination of its photosensitizer behaviors.

Keywords: Metallo-phthalocyanines, cyclic voltammetry, computational chemistry, photodynamic therapy, photochemical properties

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