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    Advanced-designed Ru(II) complexes containing phosphinite ligands derived from chiral amino alcohols: Electrochemical behavior, DFT calculations, and biological activity
    (Elsevier Science Sa, 2025) Meric, Nermin; Isik, Ugur; Dauletbakov, Anuar; Zolotareva, Darya; Zazybin, Alexey; Sever, Mehmet Serif; Okumus, Veysi
    We report two phosphinite ligands derived from chiral amino alcohols, and their complexes with ruthenium(II). These compounds were characterized by spectroscopic methods. Then, antimicrobial, antioxidant, and DNA binding activities of the chiral Ru(II)-phosphinite complexes were tested. Complex (1R)-2-{benzyl[(1S)-1(naphthalen-1-yl)ethyl]amino}-1-phenylethyl diphenylphos- phinito[dichloro(eta 6-p-cymene)ruthenium(II)], 7 showed both the highest radical scavenging activity (90.93 +/- 0.98 %) and the highest metal chelating activity (65.45 +/- 1.46 %) at 200.0 mg l-1 concentration. In addition, all of complexes had different rates of binding activity to calf thymus DNA (CT-DNA). Moreover, extensive theoretical and experimental investigations were conducted to gain a more profound understanding of the chemical descriptors and the diverse electronic transitions taking place within the ruthenium complexes, as well as their electrochemical characteristics.
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    Application of Half-Sandwich Metal-Phosphinite Compounds to Biological Activities: Determine the energies of the HOMO and LUMO levels
    (Wiley-V C H Verlag Gmbh, 2023) Meric, Nermin; Rafikova, Khadichakhan; Zazybin, Alexey; Guzel, Remziye; Kayan, Cezmi; Karakas, Duygu Elma; Dundar, Abdurrahman
    Mononuclear transition metal complexes 1-(furan-2-yl)ethyldiphenyl[dichloro(eta(6)-p-cymene)ruthenium(II)]phosphinite, (2), 1-(furan-2-yl)ethyldiphenyl[dichloro(eta(6)-benzene) ruthenium(II)] phosphinite (3), 1-(furan-2-yl)ethyldipheny[chloro(eta(4)-1,5-cyclooctadiene)rhodium(I)]phosphinite (4), 1-(furan-2-yl)ethyldiphenyl[dichloro (eta(5)pentamethylcyclopentadienyl)iridium (III)] phosphinite (5) were synthesized and characterized by microanalysis, infrared, MS, and NMR spectroscopy. The biological activities of the complexes were also tested. Compounds 2 and 5 were the best complexes at DPPH radical scavenging and reducing power activity at 73.27 % and 0.41 at 200 mu g/mL, respectively. The highest antimicrobial activity exhibited by complex 3 as 14 mm inhibition zone against S. aureus. All of the complexes have cleaved the DNA from the double-strand and exhibited three bands on gel electrophoresis. Moreover, cyclic voltammetry studies of the phosphinite complexes were carried out to determine the energies of the HOMO and LUMO levels as well as to estimate their electrochemical and some electronic properties.
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    Biological assays and theoretical density functional theory calculations of Rh(I), Ir(III), and Ru(II) complexes of chiral phosphinite ligand
    (Wiley, 2020) Rafikova, Khadichakhan; Binbay, Nil Ertekin; Meric, Nermin; Kerimkulova, Aygul; Zazybin, Alexey; Binbay, Veysel; Okumus, Veysi
    Four metal complexes, IL-OPPh2-Ru-p-cymene (3), IL-OPPh2-Ru-benzene (4), IL-OPPh2-Ir-Cp* (5), IL-OPPh2-Rh-COD (6), have been evaluated for in vitro antioxidant activity such as 2,2-diphenyl-1-picrylhydrazyl (DPPH) radical scavenging and reducing power activity. Maximum scavenging activity (71.43%) was obtained with IL-OPPh2-Ru-p-cymene, whereas IL-OPPh2-Rh-COD showed the highest reducing power ability. The complexes were also studied for their antimicrobial activity against three Gram-positive and three Gram-negative bacteria. In addition, DNA binding of the complexes was evaluated using calf thymus DNA. Both Ru(II) complexes exhibited good DNA-binding activity while the other complexes did not have any activity. Furthermore, ab initio quantum calculations of four complexes were also carried out using density functional theory to better understand their chemical behaviors.
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    Biological assays, electrochemical behavior, and theoretical DFT calculations of Ru(II) complexes of chiral phosphinite based based on ?-amino alcohols: Transfer hyrogenation of ketones using a HCOOH/ Et3N mixture
    (Elsevier, 2024) Rafikova, Khadichakhan; Meric, Nermin; Binbay, Nil Ertekin; Okumus, Veysi; Sever, M. Serif; Belyankova, Yelizaveta; Tursynbek, Saniya
    Synthesis of two phosphinite ligands based on beta-amino alcohols, in high yields has been demonstrated. When we treated [Ru(arene)(mu-Cl)Cl]2 {arene:p-cymene,benzene} with chelating phosphinite ligands, we obtained neutral Ru(II)-complexes possessing the general formula [Ru(arene)phosphiniteCl2]. The structure of the ligands and complexes was confirmed using analytical and spectroscopic techniques. The quantum chemical calculations were carried out for the ruthenium complexes at the DFT/CAM-B3LYP level of theory in gas phase. The phosphinite complexes were subjected to cyclic voltammetry studies in order to determine the energies of HOMO and LUMO levels and to estimate their electrochemical and some electronic properties. Organic complex -based memory substrates were immobilized using TiO2-modified ITO electrodes, and the memory functions of phosphinite-based organic complexes were verified by chronoamperometry (CA) and open -circuit potential amperometry (OCPA). In the present study, the antioxidant potentials of ruthenium-basedp-cymene and benzene complexes through DPPH radical scavenging, metal chelating, and reducing power activities were also determined. In addition, DNA binding abilities and antimicrobial activities of these complexes against pathogenic bacteria were studied. Finally, the ruthenium complex, (2S)-1-{[(2S)-2-[(diphenylphosphanyl)oxy]propyl][(1R)-1- phenylethyl]amino}propan-2-yldiphenyl phosphinitobis[dichloro(eta 6-benzene)ruthenium(II)] also catalyzed asymmetric transfer hydrogenation of acetophenone with high conversion (up to 99%) and good enantioselectivity (ee up to 89 %), in the existence of formic acid and triethylamine in dichloromethane medium under air atmosphere.
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    Chiral phosphinites as efficient ligands for enantioselective Ru(II), Rh(I) and Ir(III)-catalyzed transfer hydrogenation reactions
    (Springer, 2017) Baysal, Akin; Karakas, Duygu Elma; Meric, Nermin; Ak, Bunyamin; Aydemir, Murat; Durap, Feyyaz
    Metal-catalyzed enantioselective transfer reduction of ketones to enantiomerically enriched chiral alcohols has recently attracted attention. Therefore, a series of methyl alkyl or alkyl/aryl ketones have been reduced by using Ru(II), Rh(I) and Ir(III) catalysts based on C (2)-symmetric chiral ferrocenyl phosphinite ligands. The corresponding optically active secondary alcohols were obtained in excellent conversions and moderate-to-good enantioselectivities. The best results were obtained with an iridium catalyst, giving up to 98% conversion and 80% ee.
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    Ferrocene based chiral binuclear ?6-benzene-Ru(II)-phosphinite complexes: Synthesis, characterization and catalytic activity in asymmetric reduction of ketones
    (Wiley, 2018) Al-bayati, Yaser W. Abdlhmed; Karakas, Duygu Elma; Meric, Nermin; Aydemir, Murat; Durap, Feyyaz; Baysal, Akin
    In the present study, a series of chiral C-2-symmetric ferrocenyl based binuclear (6)-benzene-Ru(II) complexes bearing diphenylphosphinite and diisopropylphosphinite moieties have been synthesised. The new binuclear (6)-benzene-Ru(II)-phosphinite complexes were characterised based on nuclear magnetic resonance (H-1, C-13, P-31-NMR), FT-IR spectroscopy and elemental analysis. Then, these complexes have been screened as catalytic precursors in the transfer hydrogenation of acetophenone with 2-propanol as both the hydrogen source and solvent in the presence of KOH. The corresponding optically active secondary alcohols were obtained in excellent conversion rates between 96 and 99% and moderate to good enantioselectivities (up to 78% ee). The complex 5 was the most efficient catalyst among the four new complexes investigated herein.
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    Half-sandwich ruthenium(II) and iridium(III) complexes of imidazole based phosphinite ligands: antioxidant and antibacterial activities as well as electrochemical properties
    (Wiley-V C H Verlag Gmbh, 2024) Isik, Ugur; Rafikova, Khadichakhan; Meric, Nermin; Guzel, Remziye; Kerimkulova, Aygul; Akimbek, Arailym; Okumus, Veysi
    Ruthenium(II) and iridium(III) complexes of phosphinites including imidazole moiety were synthesized and characterized by microanalysis, IR, MS, and NMR spectroscopies. Antibacterial activity against Gram-positive and Gram-negative bacterial strains was assessed in all complexes. The highest radical scavenging (72.2 %) was obtained for [3-(3-chloro-2-({[dichloro(eta 6-benzene)ruthenium]diphenylphosphanyl}oxy)propyl)-1-butyl-1H-imidazol-3-ium chloride], 4 at 200 mu g/mL concentration, while [3-(3-chloro-2-({[dichloro(eta 5-pentamethylcyclopentadienyl)-iridium]diphenylphosphanyl}oxy)pro-pyl)-1-butyl-1H-imidazol-3-ium chloride], 6 demonstrated the highest antibacterial activity as 13 mm inhibition zone against E. hirea. Furthermore, optical and electrochemical featured of metal complexes containing imidazole phosphinite were investigated utilizing UV-vis absorption and cyclic voltammetry techniques. Consequently, all complexes can be proposed as metal-based charge convertible phosphinite complexes which may be employed as new generation and synergistic Dye-Sensitized Solar Cell (DSSC) materials. Ruthenium(II) and iridium(III) complexes of phosphinites including imidazole moiety are synthesized and characterized by microanalysis, IR, MS, and NMR spectroscopies. Their antibacterial activity against Gram-positive and Gram-negative bacterial strains is assessed. Furthermore, optical and electrochemical features of the metal complexes are investigated utilizing UV-vis absorption and cyclic voltammetry techniques. image
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    Ketone transfer hydrogenation reactions catalyzed by catalysts based on a phosphinite ligand
    (Taylor & Francis Ltd, 2022) Rafikova, Khadichakhan; Baysal, Akin; Meric, Nermin; Zazybin, Alexey; Kayan, Cezmi; Isik, Ugur; Saparbaykyzy, Islam Sholpan
    Reaction of (+/-)-1-(2-furyl) ethanol with an equivalent Ph2PCl in the presence of Et3N proceeds in dry toluene under an argon atmosphere to give 1-(furan-2-yl)ethyl diphenylphosphinite (1) in good yield. Mononuclear complexes [dichloro(eta(6)-p-cymene)(1-furan-2-ylethyl diphenylphosphinite)ruthenium(II)] (2), [dichloro(eta(6)-benzene)(1-furan-2-ylethyl diphenylphosphinite)ruthenium(II)] (3), [chloro(eta(4)-1,5-cyclooctadiene)(1-furan-2-ylethyl diphenylphosphinite)rhodium(I)] (4) and [dichloro(eta(5)-pentamethylcyclopentadienyl)(1-furan-2-ylethyl diphenylphosphinite)iridium(III)] (5) were synthesized and characterized by microanalysis, infrared, MS, and NMR spectroscopies. The complexes are employed as catalysts in transfer hydrogenation of aromatic ketones. The complexes catalyzed reduction of a variety of aromatic ketone substrates bearing electron-withdrawing or donating substituents with very high conversion rates (up to 99%); 5 was the most efficient catalyst for the transfer hydrogenation of ketones.
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    Synthesis of ionic liquid-based Ru(II)-phosphinite complexes and evaluation of their antioxidant, antibacterial, DNA-binding, and DNA cleavage activities
    (Springer International Publishing Ag, 2019) Meric, Nermin; Kayan, Cezmi; Rafikova, Khadichakhan; Zazybin, Alexey; Okumus, Veysi; Aydemir, Murat; Durap, Feyyaz
    Two Ru(II) complexes were synthesized by reaction of phosphinite-functionalized imidazolium salts [(Ph2PO)C7H11N2Cl]Cl (1) and [(Cy2PO)C7H11N2Cl]Cl (2) with 1/2 equivalent of [Ru(eta(6)-p-cymene)(mu-Cl)Cl](2) in anhydrous CH2Cl2 and under argon atmosphere. The complexes were then isolated as analytically pure substances and characterized using multinuclear NMR and infrared spectroscopies and elemental analysis. The Ru(II) compounds were used to study their biological assay. For this purpose, radical scavenging, reducing power, antibacterial activity, DNA binding, and DNA cleavage activity were fully studied. The maximum 1,1-diphenyl-2-picrylhydrazyl radicals (DPPH) scavenging (78.9%) and reducing power were obtained from compound 4 at the concentration of 200 mu g/ml. The compounds were also tested against three Gram-positive and three Gram-negative bacteria, and they were found to be more effective against Gram-positive bacteria. In addition, both compounds showed excellent DNA binding and DNA cleavage activity.
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    Transition metals of arene derivatives with functionalized ionic liquid: DFT investigation, biological applications and electrochemical behavior of complexes
    (Elsevier Science Sa, 2022) Rafikova, Khadichakhan; Meric, Nermin; Guzel, Remziye; Arslan, Nevin; Binbay, Nil Ertekin; Kayan, Cezmi; Okumus, Veysi
    Mononuclear transition metal complexes based on ionic liquid have been prepared and characterized in detail. The biological properties of the three complexes were evaluated using radical scavenging activity, reducing power, antibacterial effect, DNA binding and cleavage activity. Among the complexes, [3-[(2R)-2-({[dichloro(eta(6)-benzene)ruthenium]diphenylphosphanyl}oxy)-2-phenylethyl]-1-methyl-1H-imidazol-3-ium chloride] (4), demonstrated the highest radical scavenging (64.7 %) and reducing power activity (0.467) at 200 mu g/ml concentration. The highest zone of inhibition was obtained from [3-[(2R)-2-({[dichloro(eta(6)-p-cymene)ruthenium]diphenyl phosphanyl}oxy)-2-phenylethyl]-1-methyl-1H-imidazol-3-ium chloride] (3), against Bacillus cereus as 14 mm. Furthermore, all complexes were determined to have DNA binding and cleavage activities. Furthermore, theoretical DFT computations have also been carried out for the cationic complexes, to obtain minimum energy configuration of molecules. The effects of the chemical structures of three cationic complexes were also examined in relation to the variable property of electron-donating ligands for ruthenium-based complexes and iridium complex and their potential energy levels in ground and excited states HOMO and LUMO were determined.
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    Well designed iridium-phosphinite complexes: Biological assays, electrochemical behavior and density functional theory calculations
    (Pergamon-Elsevier Science Ltd, 2024) Rafikova, Khadichakhan; Meric, Nermin; Binbay, Nil Ertekin; Okumus, Veysi; Erdem, Kemal; Belyankova, Yelizaveta; Tursynbek, Saniya
    Mononuclear phosphinite Iridium complexes based on ferrocene group have been prepared and characterized by various spectroscopic techniques. The complexes were subjected to cyclic voltammetry studies in order to determine the energies of HOMO and LUMO levels and to estimate their electrochemical and some electronic properties. Organic complex-based memory substrates were immobilized using TiO 2 -modified ITO electrodes, and the memory functions of phosphinite-based organic complexes were verified by chronoamperometry (CA) and open-circuit potential amperometry (OCPA). Extensive theoretical and experimental investigations were directed to gain a more profound understanding of the chemical descriptors and the diverse electronic transitions taking place within the iridium complexes, as well as their electrochemical characteristics. The quantum chemical calculations were carried out for the iridium complexes at the DFT/CAM-B3LYP level of theory in the gas phase. Furthermore, the antioxidant, antimicrobial, DNA binding, and DNA cleavage activities of the complexes were tested. Complex 2 exhibited the highest radical scavenging activity (67.5 +/- 2.24 %) at 200.0 mg/L concentration. It was observed that the complexes formed an inhibition zone in the range of 8-15 mm against Gram + bacteria and in the range of 0-13 mm against Gram - bacteria. The agarose gel electrophoresis method was used to determine the DNA binding and DNA cleavage activities of the complexes. All of the tested complexes had DNA binding activity; however, complexes 1, 2 , and 8 showed better binding activity than the others.