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    Lu, Sm, and Y-based double-decker phthalocyanines with enhanced photodynamic therapy performance
    (Pergamon-Elsevier Science Ltd, 2024) Zeki, Ketrin; Yabas, Ebru; Erden, Fuat; Salih, Bekir; Canlica, Mevlude
    This paper focuses on the preparation of 3,5-di-tert-butylphenoxy substituted Lu, Sm, and Y-based double-decker phthalocyanines (Pcs), and investigation of their PDT properties. Briefly, 1,8,15,22-tetra-(3,5-di-tert-butylphenoxy) bisphthalocyanine derivatives (denoted LuPc2-3, SmPc2-4, YPc2-5) were synthesized by a two-step process. First, metal-free 1,8,15,22-tetra-(3,5-di-tert-butylphenoxy)phthalocyanine was prepared by tetramerization of 3,5-di-tert-butylphenoxy phthalonitrile, which is followed by reaction of different lanthanide salts with 1,8,15,22-tetra-(3,5-di-tert-butylphenoxy)bisphthalocyanine. The resultant double-decker Pcs were characterized in detail by UV-Vis, FT-IR, 1H NMR, fluorescence spectroscopy, MALDI-TOF MS, and elemental analysis. Strikingly, we report that double-decker phthalocyanines are not only photostable, but also exhibit relatively high singlet oxygen quantum yields of 0.96 (LuPc2-3), 0.91 (SmPc2-4) 0.87 (YPc2-5) and in THF.
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    The new metal-free, zinc, magnesium, indium ball-type phthalocyanines and their hybrids with graphene oxide: Synthesis, investigation of photophysical, photochemical properties and theoretical studies
    (Elsevier Science Sa, 2025) Zeki, Ketrin; Asrak, Sueda; Yabas, Fatma Nur; Cevik, Nergis; Yabas, Ebru; Khene, Samson; Salih, Bekir
    In this study, four ball-type phthalocyanines (BTPc-H2-4, BTPc-Zn-5, BTPc-Mg-6, BTPc-In-7) were synthesized from 3,3 ',((3,5-di-tert-butyl-1,2-phenylene)bis(oxy)diphthalonitrile in a single reaction step. Non-covalent balltype phthalocyanine (BTPc)-graphene oxide (GO) hybrids (BTPc-GO) were prepared by simple sonication method. The structures were confirmed by elemental analysis, ultraviolet-visible (UV-Vis), fourier-transform infrared (FT-IR), proton nuclear magnetic resonance (1H NMR), MALDI-TOF MS spectroscopies, elemental analysis and scanning electron microscope (SEM). The photophysical and photochemical properties of ball-type phthalocyanines were investigated in dimethyl sulfoxide (DMSO) and tetrahydrofuran (THF). In this way, the contribution of solution polarity to these properties was compared. The contribution of GO was examined by examining the singlet oxygen quantum yields of BTPc-GO hybrids in DMSO. In addition, the structural properties of ball-type phthalocyanines were examined through theoretical studies and the effect of structural properties on experimentally determined band gaps was examined. Interestingly, we also report that ball-type thalocyanines are both photostable and exhibit extremely high singlet oxygen quantum yields. In addition, we can state that hybrids of these compounds with GO also show the ability to increase the singlet oxygen quantum yield, depending on the degree of interaction.