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  1. Ana Sayfa
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Yazar "Boyacioglu, Bahadir" seçeneğine göre listele

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  • [ X ]
    Öğe
    A Schiff base colorimetric probe for real-time naked-eye detection of biologically important fluoride and cyanide ions: Single crystal, experimental, theoretical, biological and antioxidant studies
    (Elsevier, 2020) Unver, Huseyin; Boyacioglu, Bahadir; Demir, Neslihan; Zeyrek, Celal Tugrul; Yıldız, Mustafa
    The synthesis and characterization of a Schiff base (E)-2-((3,5-bis(trifluoromethyl)phenylimino)methyl)4-methylphenol from the reaction of 2-hydroxy-5-methylbenzaldehyde with 3,5-bis(trifluoromethyl) aniline has been studied using X-ray single-crystal techniques and compared to the results from theoretical calculations using density functional theory (DFT). We have investigated the antimicrobial activities of the title compound for their minimum inhibitory concentration (MIC). We have also examined the interactions with DNA by using the UV-Visible and agarose gel electrophoresis methods. It is shown that the title compound interacts with CT-DNA via electrostatic binding. The antioxidant activity of the title compound was measured by using the DPPH method. It is furthermore shown that it indicates lower antioxidant activity than butylated hydroxytoluene (BHT). It is also found that activity remained constant with increasing compound concentration. We have also investigated the colorimetric response of the title compound in dimethyl sulfoxide (DMSO) to the addition of an equivalent amount of anions (F-, Br-, I-, CN-, SCN-, ClO4-, HSO4-, AcO-, H2PO4 and OH-). In this context, while the addition of Fand CN anions into the solution containing the title compound resulted in a significant colour change, the addition of Br-, I-, SCN-, ClO4-, HSO4-, AcO-, H2PO4 and OH anions resulted in no colour change. In the presence of these anion solutions, only Fand CN solutions underwent impressive colour change detectable with the naked eye from colourless to orange-red and purple, and orange and blue-violet in both daylight and UV light, respectively. The most discernible colour change in the Schiff base was caused by Fand CN-, which demonstrated that the Schiff base could be used to selectively detect Fand CN-. Also, various sensor applications of Schiff base were investigated. For this, the alumina oxide sheet and filter paper impregnated with the title compound were used. (C) 2020 Elsevier B.V. All rights reserved.
  • [ X ]
    Öğe
    Colorimetric chemical sensing properties of 3-amino-4-hydroxybenzene- sulfonic acid-based Schiff bases containing electron donor-acceptor groups
    (Elsevier, 2023) Yildiz, Elif Akhuseyin; Pepe, Yasemin; Erdener, Digdem; Karatay, Ahmet; Boyacioglu, Bahadir; Unver, Huseyin; Yapar, Gonul
    A new series of aminobenzene sulfonic acid-based Schiff bases (1-3) were synthesized from the reaction of 3-amino-4-hydroxybenzenesulfonic acid with 5-methyl, 5-nitro and 5-bromo-salicylaldehyde. The colorimetric and UV-Vis spectroscopic responses of compounds in DMSO to addition of equivalent number of anions (F-, Br-, I-, CN-, SCN-, ClO4-, HSO4-, AcO-, H2PO4-, N3- and OH-) were investigated. Additionally, biological activities of the compounds; antimicrobial and DNA binding properties, were investigated. A DPPH (2,2-diphenyl-1-picryl-hydrazyl-hydrate) free radical method was used to measure antioxidant activity, and 4-hydroxy-3-(2-hydroxy-5-methylbenzylideneamino)benzene sulfonic acid (1) displayed greater antioxidant activity than butylated hydroxytoluene (BHT). Studied compounds demonstrated emission properties over a wide range of visible spectrum, and compound 4-hydroxy-3-(2-hydroxy-5-nitrobenzylideneamino)benzenesulfonic acid (2) has hyp-sochromic shift by incorporating NO2 in comparison with other compounds. Femtosecond transient absorption spectroscopy measurements showed that compounds 4-hydroxy-3-(2-hydroxy-5-nitrobenzylideneamino)benze-nesulfonic acid (2) and 3-(5-bromo-2-hydroxybenzylideneamino)-4-hydroxybenzenesulfonic acid (3), incorpo-rated nitro and bromine groups and possessing electron accepting features have fast triplet transition. This study provides a novel design strategy for biological activity and colorimetric probing features of aminobenzene sul-fonic acid-based Schiff bases.
  • [ X ]
    Öğe
    Colorimetric probe and optical behaviours of new azomethine derivatives of sulfonamide
    (Elsevier, 2022) Tekin, Sezen; Karatay, Ahmet; Erdener, Digdem; Yildiz, Elif Akhuseyin; Boyacioglu, Bahadir; Unver, Huseyin; Yıldız, Mustafa
    Syntheses, colorimetric anion probe properties, density functional theory (DFT) studies, and optical properties of the Schiffbases; 4-fluoro-N-(2-hydroxy-5-methylbenzylidene) benzenesulfonamide (1), 4fluoro-N-(2-hydroxy-5-nitrobenzylidene)benzenesulfonamide (2) and 4-fluoro-N-[(2-hydroxynaphthalen1-yl)methylene]benzenesulfonamide (3) were reported. The structure of the compounds was elucidated using MS, FTIR, and UV-visible spectroscopic techniques. Their structures were examined by theoretical calculations using density functional theory (DFT). The colorimetric response of the Schiffbase receptors in DMSO was investigated before and after the addition of an equivalent amount of each anion to evaluate the anion recognition properties. The ultrafast transient absorption spectroscopy measurements were performed to investigate the energy transfer dynamics and decay kinetics of the compounds 1-3. The fluorescence and wavelength-dependent pump-probe measurements of the compounds showed that the excited state lifetime of compound 2 is shorter than compounds 1 and 3. The fluorescence properties of compounds 1-3 were compatible with the pump-probe spectroscopy measurements. The compounds with longer ESA lifetimes showed higher fluorescence. (c) 2021 Published by Elsevier B.V.
  • [ X ]
    Öğe
    Colorimetric probing and fluorescent chemosensor features of functionalized sulphonamide-azomethine derivatives
    (Elsevier Science Sa, 2022) Yildiz, Elif Akhuseyin; Erdener, Digdem; Tekin, Sezen; Karatay, Ahmet; Boyacioglu, Bahadir; Unver, Huseyin; Yıldız, Mustafa
    In this work, we have experimentally synthesized bromosulfonamide-based azomethine compounds through the reaction of 4-bromobenzenesulfonamide with 2-hydroxy-5-iodobenzaldehyde, 2-hydroxy-5-nitrobenzaldehyde, and 2-hydroxy-l-naphthaldehyde. We have also characterized the molecular structure of the investigated compounds with MS, H-1 NMR, FTIR and UV-vis spectra. Theoretically, using DFT and TD-DFT methods, we computed frontier molecular orbitals (FMOs) energies and UV-vis spectra as well. We have also obtained the electron localization function (ELF) maps to identify electrophilic substitution sites in the molecules and density of states (DOS) diagrams to show the composition of the fragment orbitals that contribute to the molecular orbitals. We have investigated steady-state absorption, emission features, and excited state dynamics to better understand the photophysical process of bromosulfonamide-based azomethines. It has been demonstrated that by adding a naphthalene unit, the absorption properties of azomethine into two branches. Besides, azomethine, including heavy iodo atoms, presents a slight decrement in the fluorescence intensity. According to thorough calculations of charge transfer dynamics using femtosecond transient absorption spectra, the bromosulfonamidebased azomethines with iodo atoms and incorporating naphthalene units exhibit an intersystem crossing mechanism following photoexcitation. The colorimetric response of the compounds in DMSO to the addition of the equivalent amount of anions (F- , Br- , I-, CN-, SCN-, ClO4-, HSO4-, AcO-, H2PO4- , N-3(-) and OH-) was investigated. In this regard, while the addition of F- ,CN- ,AcO- , H2PO4- and OH(- )anions into the solution containing the compounds resulted in a significant color change, the addition of Br-, I-, SCN-, ClO4- HSO4- and N-3 anions resulted in no color change.
  • [ X ]
    Öğe
    DFT calculation, biological activity, anion sensing studies and crystal structure of (E)-4-chloro-2-[(pyridin-2-ylimino)-methyl]phenol
    (Serbian Chemical Soc, 2018) Yildirim, Nuray; Demir, Neslihan; Alpaslan, Gokhan; Boyacioglu, Bahadir; Yıldız, Mustafa; Unver, Huseyin
    (E)-4-Chloro-2-[(pyridin-2-ylimino)methyl]phenol was synthesized in the reaction of 2-aminopyridine with 5-chlorosalicylaldehyde. The structure of compound was investigated by FTIR, UV-Vis, 1H-NMR, C-13-NMR and X-ray data. In addition, characterization of the compound was realized using theoretical quantum mechanical calculations and experimental spectroscopic methods. The molecular structure of the compound was confirmed using X-ray single-crystal data, NMR, FTIR and UV-Vis, which were in good agreement with the structure predicted by the theoretical calculations using the density functional theory (DFT). Moreover, the antimicrobial activity of the compound was investigated against some bacteria and yeast cultures by the broth microdilution test. UV-Vis spectroscopy studies of the interactions between the Schiff base and calf thymus DNA (CT-DNA) showed that the compound interacts with CT-DNA via electrostatic binding. The colorimetric response of the compound receptors was investigated before and after the addition of an equivalent amount of each anion to evaluate anion recognition properties.
  • [ X ]
    Öğe
    Experimental, DFT Calculation, Biological Activity, Anion Sensing Application Studies and Crystal Structure of (E)-4-[(pyridin-3-ylimino)methyl]benzene-1,3-diol
    (Springer/Plenum Publishers, 2018) Unver, Huseyin; Boyacioglu, Bahadir; Zeyrek, Celal Tugrul; Yolal, Devrim; Yıldız, Mustafa; Yildirim, Nuray; Demir, Neslihan
    Crystallographic and spectroscopic studies of (E)-4-[(pyridin-3-ylimino)methyl]benzene-1,3-diol have been performed. Optimized molecular structure, conformational analysis, theoretical vibrational band assignments, nonlinear optical effects, UV-Vis, properties have also been investigated by using density functional theory with the functional B3LYP using the 6-311++G(d,p) basis set. The antimicrobial activities of the compound were investigated for its minimum inhibitory concentration. The colorimetric response of the Schiff base receptors was investigated before and after the addition of an equivalent amount of each anion to evaluate anion recognition properties. A new Schiff base was prepared and characterized. Experimental and theoretical studies on a new Schiff base have been reported. The tautomeric stability of the compound was investigated by experimental and theoretical (DFT). The nonlinear optical (NLO) effects of the compound was predicted using DFT. The antimicrobial activity and anion-sensor properties of the compound were examined. [GRAPHICS] .
  • [ X ]
    Öğe
    Exploring Charge Transfer Mechanisms in Schiff Base-Modified N-Doped GQDs: Insights from DFT and Pump-Probe Spectroscopy for Bioimaging Applications
    (Wiley-V C H Verlag Gmbh, 2024) Hance, Saadet; Erdener, Digdem; Ozturk, Berfin Ilayda; Yildiz, Elif Akhuseyin; Karatay, Ahmet; Boyacioglu, Bahadir; Unver, Huseyin
    In recent developments, graphene quantum dots (GQDs) have emerged as valuable tools for imaging and biosensing. Various modifications on the GQDs with any desired functionality and attachment of organic molecules and/or nanostructures allow tuning their photophysical properties as well as charge transfer dynamics for bioimaging applications. This study focuses on synthesizing and characterizing of polyethyleneimine-functionalized nitrogen-doped GQDs (NC1), Schiff base- functionalized nitrogen-doped GQDs (NC2), and silver nanocomposites of these Schiff base-functionalized nitrogen-doped GQDs (NC3). We explore their absorption and emission properties to understand their interactions in the ground state. Furthermore, ultrafast transient absorption spectroscopy measurements reveal that the presence of NC3 shortens the excited state lifetime of NC1 due to charge transfer, resulting in reduced fluorescence intensity. Both experimental and DFT results suggest the potential of NC3 for bioimaging and sensing applications, making them promising candidates for phototheranostic purposes.
  • [ X ]
    Öğe
    Naked-eye colorimetric anion probing and fluorescent switching features of conjugated Schiff Bases derived from 4-(Trifluoromethyl) benzenesulfonamide
    (Elsevier, 2022) Yildiz, Elif Akhuseyin; Tekin, Sezen; Erdener, Digdem; Karatay, Ahmet; Boyacioglu, Bahadir; Unver, Huseyin; Yıldız, Mustafa
    In this work, synthesis, spectroscopic, density functional theory (DFT) and photophysical studies of the three conjugated benzenesulfonamide Schiff bases were reported. We also calculated the energies of the frontier molecular orbitals (FMOs) and UV-Vis spectra of Schiff bases theoretically using the DFT and TD-DFT methods. Additionally, photophysical properties were investigated by UV-Vis and fluorescence spectroscopy techniques. The ground state interactions show that the absorption band has been separated into two branches and bathochromatically tuned to the visible region, and fluorescence intensity decreased in the case of the Schiff base incorporated naphthalene unit. Furthermore, the charge transfer dynamics of the compounds were analyzed using femtosecond transient absorption spectroscopy measurements proving the triplet-triplet transitions via intersystem crossing mechanism. Based on the ultrafast pump-probe experimental results, as well as decay kinetics of the compounds, the Schiff base with naphthalene unit, showed a fast transition to the triplet state (1.2 ps) as compared to Schiff bases including methyl (4 ps) and chloro (2.7 ps) units. However, upon the addition of various anions, the molecule structure gains anion sensing and fluorescence switching capabilities under daylight and UV light. The obtained experimental results pointed out that the modification of Schiff base molecules with methyl, chlorine and naphthalene units affected its photophysical properties as well as excited-state dynamics significantly.
  • [ X ]
    Öğe
    Palladium Metal Nanocomposites Based on PEI-Functionalized Nitrogen-Doped Graphene Quantum Dots: Synthesis, Characterization, Density Functional Theory Modeling, and Cell Cycle Arrest Effects on Human Ovarian Cancer Cells
    (Amer Chemical Soc, 2024) Gunes, Buket Altinok; Kirlangic, Omer Faruk; Kilic, Murat; Sunguroglu, Asuman; Ozgurtas, Taner; Sezginer, Ecem Kaya; Boyacioglu, Bahadir
    In this study, the synthesis, characterization, density functional theory calculations (DFT), and effect of polyethylenimine (PEI)-functionalized nitrogen-doped graphene quantum dots (PEI N-GQDs) and their palladium metal nanoparticles nanocomposites (PdNPs/PEI N-GQDs) on cancer cells were extensively investigated. The focus also includes investigating their cytotoxic and apoptotic effects on ovarian cancer cells, which pose a serious risk to women's health and have high death rates from delayed diagnosis, inadequate response to treatment, and decreased survival. Graphene quantum dots and their palladium nanocomposites were differentially effective against ovarian cancer cell lines. In particular, the smaller particle size and morphology of PdNPs/PEI N-GQDs nanocomposites compared with PEI N-GQDs probably enhance their activity through highly improved uptake by cells. These findings emphasize the importance of particle size in composite drugs for efficient cancer treatment. DFT results revealed that the Pd-containing nanocomposite, with a smaller highest occupied molecular orbital-lowest unoccupied molecular orbital gap, exhibited higher reactivity and anticancer effects in human ovarian cancer cell line, OVCAR-3. Significantly, the application of nanocomposites to ovarian cancer cells initiated apoptosis, offering valuable insights into the intricate interplay between nanomaterials and cancer biology.
  • [ X ]
    Öğe
    Synthesis, biological activity, DNA binding and anion sensors, molecular structure and quantum chemical studies of a novel bidentate Schiff base derived from 3,5-bis(triflouromethyl)aniline and salicylaldehyde
    (Elsevier, 2015) Yıldız, Mustafa; Karpuz, Ozge; Zeyrek, Celal Tugrul; Boyacioglu, Bahadir; Dal, Hakan; Demir, Neslihan; Yildirim, Nuray
    Synthesis, biological activity, spectroscopic and crystallographic characterization and density functional theory (DFT) studies of the Schiff base 3,5-bis(triflouromethyl)aniline and salicylaldehyde are reported. It crystallizes as a monoclinic space group P2(1)/c with a = 7.7814(3)angstrom, b = 26.8674(9)angstrom, c = 7A520(2) angstrom, V = 1379.98(8), Z = 4, D-c = 1.6038 g cm(-3), and mu = 0.156 mm(-1). The molecular structure obtained from X-ray single-crystal analysis of the investigated compound in the ground state was compared using Hartree-Fock (HF) and density functional theory (DFT) with the functionals B3LYP and B1B95 using the 6-311++G(d,p) basis set. The antimicrobial activities of the compound were investigated for its minimum inhibitory concentration (MIC). The interaction of the Schiff base with calf thymus DNA was investigated using UV-visible spectra. The colorimetric response of the Schiff base receptors in DMSO was investigated before and after the addition of an equivalent amount of each anion to evaluate the anion recognition properties. (C) 2015 Elsevier B.V. All rights reserved.
  • [ X ]
    Öğe
    Synthesis, characterization, and evaluation of (E)-methyl 2-((2-oxonaphthalen-1(2H)-ylidene)methylamino)acetate as a biological agent and an anion sensor
    (Pergamon-Elsevier Science Ltd, 2016) Zeyrek, Celal Tugrul; Boyacioglu, Bahadir; Yıldız, Mustafa; Unver, Hilseyin; Yolal, Devrim; Demir, Neslihan; Elmali, Ayhan
    An amino acid based and bidentate Schiff base, (E)-methyl 2-((2-oxonaphthalen-1(2H)-ylidene)methylamino)acetate (ligand), was synthesized from the reaction of glycine-methyl ester hydrochloride with 2-hydroxy-l-naphthaldehyde. Characterization of the ligand was carried out using theoretical quantum -mechanical calculations and experimental spectroscopic methods. The molecular structure of the compound was confirmed using X-ray single-crystal data, NMR, FTIR and UV-Visible spectroscopy, which were in good agreement with the structure predicted by the theoretical calculations using density functional theory (DFT). Antimicrobial activity of the ligand was investigated for its minimum inhibitory concentration (MIC) to several bacteria and yeast cultures. UV-Visible spectroscopy studies also shown that the ligand can bind calf thymus DNA (CT-DNA) electrostatic binding. In addition, DNA cleavage study showed that the ligand cleaved DNA without the need for external agents. Energetically most favorable docked structures were obtained from the rigid molecular docking of the compound with DNA. The compound binds at the active site of the DNA proteins by weak non-covalent interactions. The colorimetric response of the ligand in DMSO to the addition of equivalent amount of anions (F-, Br-, I-, CN-, SCN-, ClO4-, HSO4-, AcO-, H2PO4-, N-3(-) and OH-) was investigated and the ligand was shown to be sensitive to CN- anion. (C) 2016 Elsevier Ltd. All rights reserved.
  • [ X ]
    Öğe
    Synthesis, characterization, biological activity and theoretical studies of a 2-amino-6-methoxybenzothiazole-based fluorescent Schiff base
    (Elsevier, 2019) Alpaslan, Gokhan; Boyacioglu, Bahadir; Demir, Neslihan; Tumer, Yasemin; Yapar, Gonul; Yildirim, Nuray; Yıldız, Mustafa
    A new Schiff base, (E)-3,5-dimethoxy-2-((6-methoxybenzo[d]thiazol-2-ylimino)methyl)- phenol, was prepared from the reaction of 2-amino-6-methoxybenzothiazole and 2-hydroxy-4,6-dimethoxybenzaldehyde and characterized with elemental analysis, FTIR, UV-VIS, NMR and single crystal X-ray diffraction techniques. Frontier molecular orbitals, molecular electrostatic potential, and chemical reactivity descriptors of the synthesized compound were studied using molecular modeling methods. The antibacterial and antifungal activities of the Schiff base were studied for its minimum inhibitory concentration. The compound showed a higher effect on yeast than against bacteria. The interactions of the compound with DNA were studied with the ultraviolet-visible (UV-VIS) spectra and gel electrophoresis method. The experimental results indicated that the 2-amino-6-methoxybenzothiazole-based Schiff base could bind to DNA via an intercalative mode and showed that it cleaved DNA without the need for external agents. Additionally, the Schiff base showed colorimetric sensor properties for fluoride and cyanide anions in dimethyl sulfoxide.
  • [ X ]
    Öğe
    Synthesis, Crystal Structure, Anion Sensing Applications and DFT Studies of (E)-2-[(3,5-Bis(trifluoromethyl)phenylimino)methyl]-4-chlorophenol
    (Springer/Plenum Publishers, 2019) Unver, Huseyin; Zeyrek, Celal Tugrul; Boyacioglu, Bahadir; Yıldız, Mustafa; Demir, Neslihan; Elmali, Ayhan
    We report the synthesis and characterization, colorimetric anion sensors properties, density functional theory (DFT) calculation studies of a Schiff base (E)-2-[(3,5-bis(trifluoromethyl)phenylimino)methyl]-4-chlorophenol. The molecular structure of the title compound was experimentally determined using X-ray single-crystal data and was compared to the structure predicted by theoretical calculations using DFT. The experimental and calculated data (using DFT) of the title compound have been compared. To investigate the tautomeric stability, some properties such as total energy, HOMO and LUMO energies, the chemical hardness (eta), the ionization potential, the electron affinity, the absolute electronegativity (chi), the absolute softness (sigma) of the compound were obtained at B3LYP/6-311++G(d,p) level in the gas phase and solvent phase. The calculated results showed that the enol-imine form of the compound was more favorite than keto-amine form. The colorimetric response of the Schiff base receptors in DMSO was investigated. [GRAPHICS] .
  • [ X ]
    Öğe
    Synthesis, Quantum Chemical Calculations and Molecular Docking Studies, Biological and Anion Sensor Properties of (E)-4-[(4-ethoxy-phenylimino)methyl]-2-methoxyphenol
    (Croatian Chemical Soc, 2018) Zeyrek, Celal Tugrul; Unver, Huseyin; Boyacioglu, Bahadir; Demir, Neslihan; Yapar, Gonul; Dal, Hakan; Yıldız, Mustafa
    We report the synthesis and characterization, biological activity, DNA binding, colorimetric anion sensor properties, computational (HF) and molecular docking studies of a novel Schiff base (E)-4-[(4-ethoxyphenylimino)methyl]-2-methoxyphenol. The molecular structure of the title compound was experimentally determined using spectroscopic data and was compared to the structure predicted by theoretical calculations using density functional theory (DFT). In addition, atomic charges, molecular electrostatic potential (MEP), nonlinear optical (NLO) effects, the potential energy surface (PES) scans about two important torsion angles and thermodynamic properties of the title compound were predicted using DFT. The antimicrobial activity of the compound was investigated for minimum inhibitory concentration. UV-Vis spectroscopy studies of the interactions between the compound and calf thymus DNA (CT-DNA) showed that the compound interacts with CT-DNA via intercalative binding. The colorimetric response of the Schiff base receptors in DMSO was investigated. The most discernable color change in the Schiff base was caused by CN-, which demonstrated that the ligand can be used to selectively detect CN-.
  • [ X ]
    Öğe
    Synthesis, spectral and quantum chemical studies and use of (E)-3-[(3,5-bis(trifluoromethyl)phenylimino)methyl]benzene-1,2-diol and its Ni(II) and Cu(II) complexes as an anion sensor, DNA binding, DNA cleavage, anti-microbial, anti-mutagenic and anti-cancer agent
    (Elsevier, 2016) Unver, Huseyin; Boyacioglu, Bahadir; Zeyrek, Celal Tugrul; Yıldız, Mustafa; Demir, Neslihan; Yildrim, Nuray; Karaosmanoglu, Oguzhan
    We report the synthesis of a novel Schiff base (E)-3-[(3,5-bis(trifluoromethyl) phenylimino)methyll benzene-1,2-diol from the reaction of 2,3-dihydroxybenzaldehyde with 3,5-bis(trifluoromethyl)aniline, and its Ni(II) and Cu(II) complexes. The molecular structure of the Schiff base was experimentally determined using X-ray single-crystal data and was compared to the structure predicted by theoretical calculations using density functional theory (DFT), Hartree-Fock (HF) and Moller-Plesset second-order perturbation (MP2). In addition, nonlinear optical (NLO) effects of the compound was predicted using DFT. The antimicrobial activities of the compounds were investigated for their minimum inhibitory concentration. UV-Vis spectroscopy studies of the interactions between the compounds and calf thymus DNA (CT-DNA) showed that the compounds interacts with CT-DNA via intercalative binding. A DNA cleavage study showed that the Cu(II) complex cleaved DNA without any external agents. The compounds inhibited the base pair mutation in the absence of S9 with high inhibition rate. In addition, in vitro cytotoxicity of the Ni(II) complex towards HepG2 cell line was assayed by the MIT method. Also, the colorimetric response of the Schiff base in DMSO to the addition of equivalent amount of anions (F-, Br-, I-, CN-, SCN-, ClO4-, HSO4-,AcO-, H2PO4-, N-3(-) and OH-) was investigated. In this regard, while the addition of F-, CN-, AcO- and OH- anions into the solution containing Schiff base resulted in a significant color change, the addition of Br-, I-, SCN-, ClO4-, HSO4-, H2PO4- and N-3(-) anions resulted in no color change. The most discernable color change in the Schiff base was caused by CN-, which demonstrated that the ligand can be used to selectively detect CN-. (C) 2016 Elsevier B.V. All rights reserved.
  • [ X ]
    Öğe
    UV-Vis spectroscopic and colorimetric anion detection and fluorescence properties of new 3-amino-4-hydroxybenzenesulfonic acid-based Schiff bases depending on the strength and position of the electron donor substitution
    (Iop Publishing Ltd, 2023) Yildiz, Elif Akhuseyin; Pepe, Yasemin; Erdener, Digdem; Karatay, Ahmet; Boyacioglu, Bahadir; Unver, Hueseyin; Yapar, Gonul
    In this study, 3-amino-4-hydroxybenzenesulfonic acid-based imine compounds; 3-(2,5-dihydroxybenzylideneamino)-4-hydroxybenzenesulfonic acid (1), 3-(2,4-dihydroxybenzylideneamino)-4-hydroxybenzenesulfonic acid (2) and 4-hydroxy-3-(2-hydroxy-3-methoxybenzylideneamino)-4-hydroxybenzenesulfonic acid (3) was synthesized. The compounds were analyzed using various spectroscopy methods, and the experimental UV-vis data matched the theoretical predictions. The compound 1 displayed lower stability, higher reactivity, and easier photoexcitation due to a smaller HOMO-LUMO energy gap. The investigated compounds 1-3 showed promise as chemosensors for anions, providing visible detection in daylight conditions. The compound 3 exhibited selective fluorescence at specific wavelengths. The compounds 1-3 interacted with DNA through electrostatic interactions. Also, compounds 1-3 showed higher antioxidant activity than BHT. However, fluorescence measurements indicated that the emission signals were strongly influenced by the position and strength of the electron-donating group. Adding a hydroxy or methoxy moiety near the -OH group on the phenyl ring decreased the fluorescence signal due to intersystem crossing and intramolecular charge transfer mechanisms, respectively. These findings were supported by femtosecond transient absorption spectroscopy measurements. The results emphasize the significance of substituents in imines derived from 3-amino-4-hydroxybenzenesulfonic acid in determining their biological activities, as well as their optical and sensor properties.

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