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    Anti-Cancer and Anti-Inflammatory Activities of Bromo- and Cyano-Substituted Azulene Derivatives
    (Springer/Plenum Publishers, 2020) Ayaz, Furkan; Yuzer, Abdulcelil; Ince, Tuncay; Ince, Mine
    Natural products and their synthetic derivatives gathered attention due to their pharmaceutical capacities. They have been in use against different types of diseases ranging from cancer to inflammatory disorders. In order to increase their efficacy and prevent the possible side effects, these natural compounds are manipulated at the laboratory conditions and modified according to our needs. Azulene is one of these compounds whose anti-inflammatory potential have been shown by the previous studies, but a detailed analysis of its effect at the cellular level in terms of pro-inflammatory cytokine production has not been studied yet. Moreover, its derivative potential has not been characterized extensively. In our study, we examined the cytotoxic, immunomodulatory and immunostimulatory potential of bromo- and cyano-substituted azulenes on the mammalian macrophages. These unique compounds had differential effects on the production of pro-inflammatory cytokines and they were anti-inflammatory immunomodulators. Furthermore, they exerted anti-proliferative effect on breast and prostate cancer cells which supports their anti-cancer potential as well.
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    Solar-light-driven photocatalytic hydrogen evolution by push-pull thiophenoxy-substituted zinc phthalocyanines
    (World Scientific Publ Co Pte Ltd, 2023) Acar, Eminegul Genc; Ince, Tuncay; Yuzer, A. Celil; Yanalak, Gizem; Gecgel, Cihan; Aslan, Emre; Ince, Mine
    Two zinc phthalocyanine derivatives (ZnPc 1 and 2) carrying bulky 2,6-diisopropylthiophenoxy peripheral substituents have been synthesized and their performances as photosensitizers in photochemical hydrogen production evaluated. To examine the influence of the spacer on the performance of ZnPc 1 and 2, the carboxyl group has been linked to the macrocycle ring either directly or via the phenyl ring, respectively. The photocatalytic activities of ZnPcs (ZnPc 1 and ZnPc 2) as sensitizers of TiO(2 )for hydrogen production were investigated in the presence of Pt. ZnPc 1 and ZnPc 2 sensitized TiO(2 )produced 0.687 mmolg(-1)h(-1) and 0.436 mmol g(-1)h(-1) hydrogens, which also reached 3.986 and 2.091 mmolg(-1) after 8h illumination, respectively, under visible light (>= 420 nm) irradiation. In addition, STH efficiencies of ZnPc 1/TiO2 and ZnPc 2/TiO2 were determined as 1.77% and 1.12%, respectively. ZnPc 1/TiO2 exhibited 1.9-fold more photocatalytic hydrogen amount than ZnPc 2/TiO2, and the hydrogen evolution performance of the photocatalyst in the presence of Pt enhanced to 3.021 mmol g(-1)h(-1) and 0.911mmol g(-1)h(-1) for ZnPc 1 and ZnPc 2, respectively.
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    Öğe
    Solution-processed small-molecule organic solar cells based on non-aggregated zinc phthalocyanine derivatives: A comparative experimental and theoretical study
    (Elsevier Sci Ltd, 2021) Yuzer, A. Celil; Kurtay, Gulbin; Ince, Tuncay; Yurtdas, Semih; Harputlu, Ersan; Ocakoglu, Kasim; Gullu, Mustafa
    A series of non-aggregated zinc phthalocyanine derivatives containing either bulky thiophenol or phenol substituents were synthesized as a novel donor component for bulk heterojunction (BHJ) solar cell applications. The molecular structure and photophysical properties of ZnPc derivatives were investigated by combined experimental and theoretical studies using density functional theory (DFT) and time-dependent DFT (TD-DFT) methods. In order to evaluate the physical properties of ZnPcs in the solvent environment, we applied the conductor-like polarizable continuum model (CPCM). Within this scope, light-harvesting efficiency (LHE), excited-state lifetime (?), maximum absorption wavelengths (?max), oscillator strength (f) and hyperpolarizability (? tensors) were calculated both in vacuum and chloroform (? = 4.9) medium. Furthermore, divergent types of global descriptors such as EHOMO, ELUMO, and bandgap (Egap) energies, ionization potential (I), electron affinity (A), hardness (?), and electrophilicity index (?) were also calculated. Our computational findings revealed that the linker heteroatoms [sulfur for the ZnPc (1?2); oxygen for the ZnPc (3?4) including the substituent type (isopropyl for the ZnPc (2?4), and phenyl for the ZnPc (1?3] severely affected the photophysical properties of the dyes. In relation, theoretical results are in good accordance with our experimental observations. Finally, ZnPc derivatives were used as a donor component and PC61BM as an acceptor material in BHJ solar cells, displaying a maximum power conversion efficiency of 0.8%. Compared with ZnPcs 1?2, ZnPc 3?4 based cells showed an inferior photovoltaic performance. These results are promising and should encourage further studies on BHJ solar cells using near-infrared absorbing and non-aggregated ZnPcs.
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    The effect of bulky electron-donating thioether substituents on the performances of phthalocyanine based dye sensitized solar cells
    (Royal Soc Chemistry, 2021) Ince, Mine; Kuboi, Ren; Ince, Tuncay; Yoshimura, Kuon; Motoyoshi, Daiki; Sonobe, Masahiro; Kudo, Ryota
    A series of novel phthalocyanine derivatives with bulky electron-donating thioether substituents were synthesized in order to investigate the effect of sulfur atoms on the solar-cell performances of zinc-phthalocyanine based dye-sensitized solar cells. Incorporation of sulfur atoms onto the phthalocyanine periphery resulted in a red shift of the absorption spectrum. In terms of solar cell performance, using sulfur atoms decreased quantum efficiency probably due to lower injection efficiency caused by the symmetrical electronic structure and lower excited state level.