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Öğe Advanced-designed Ru(II) complexes containing phosphinite ligands derived from chiral amino alcohols: Electrochemical behavior, DFT calculations, and biological activity(Elsevier Science Sa, 2025) Meriç, Nermin; Işık, Uğur; Dauletbakov, Anuar; Zolotareva, Darya; Zazybin, Alexey; Sever, Mehmet Serif; Okumus, Veysi; Kayan, Cezmi; Binbay, Nil Ertekin; Binbay, Veysel; Güzel, Remziye; Aydemir, MuratWe 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.Öğe 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) Meriç, Nermin; Rafikova, Khadichakhan; Zazybin, Alexey; Güzel, Remziye; Kayan, Cezmi; Karakas, Duygu Elma; Dündar, Abdurrahman; Aydemir, MuratMononuclear 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.Öğe 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; Meriç, Nermin; Kerimkulova, Aygül; Zazybin, Alexey; Binbay, Veysel; Okumuş, Veysi; Kayan, Cezmi; Işık, Uğur; Aydemir, Murat; 0000-0003-1010-9563; 0000-0002-2488-0378; 0000-0001-8028-2244; 0000-0002-6244-9327Four 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.Öğe Catalysts for the asymmetric transfer hydrogenation of various ketones from [3-[(2S)-2-[(diphenylphosphanyl)oxy]-3-phenoxypropyl]-1-methyl-1H-imidazol-3-ium chloride] and [Ru(?6-arene)(?-Cl)Cl]2, Ir(?5-C5Me5)(?-Cl)Cl]2 or [Rh(?-Cl)(cod)]2(Elsevier Science Sa, 2019) Meric, Nermin; Arslan, Nevin; Kayan, Cezmi; Rafikov, Khadichakhan; Zazybin, Alexey; Kerimkulova, Aygul; Aydemir, MuratThe combination of [3-[(2S)-2-[(diphenylphosphanyl)oxy]-3-phenoxypropyl]-1-methyl-1H-imidazol-3-ium chloride] with [Ru(eta(6)-arene)(mu-Cl)Cl](2), Ir(eta(5)-C5Me5)(mu-Cl)Cl](2) or [Rh(mu-Cl)(cod)](2), in the presence of KOH/isoPrOH, has been found to generate catalysts that are capable of enantioselectively reducing alkyl, aryl ketones to the corresponding (R)-alcohols. Under optimized conditions, when the catalysts were applied to the asymmetric transfer hydrogenation, we obtained the secondary alcohol products in high conversions and enantioselectivities using only 0.5 mol% catalyst loading. In addition, [3-[(2S)-2-{[(chloro(eta(4)-1,5-cyclooctadiene)rhodium)diphenyl phosphanyl] oxy}-3-phenoxypropyl]-1-methyl-1H-imidazol-3-ium chloride], (6) complex is much more active than the other analogous complexes in the transfer hydrogenation. Catalyst 6 acts as excellent catalysts, giving the corresponding (R)-1-phenyl ethanol in 99% conversion in 30 min (TOF <= 396 h(-1)) and in high enantioselectivity (92% ee).Öğe Increasing Sugar Content in Source for Biofuel Production Using Agrochemical and Genetic Approaches at the Stages of BioMass Preharvesting and Harvesting(Mdpi, 2022) Zolotareva, Darya; Zazybin, Alexey; Belyankova, Yelizaveta; Dauletbakov, Anuar; Tursynbek, Saniya; Rafikova, Khadichahan; Ten, AsselIn order to optimize biofuel (including bioethanol) production processes, various problems need to be solved, such as increasing the sugar content of raw materials/biomass to gain a higher yield of the product. This task can be solved in several ways, with their own advantages and disadvantages, and an integrated approach, such as using a combination of ripening agents and phytohormones or application of a superabsorbent polymer with at least one sugar-enhancing agent, can be applied as well. Here, we reviewed several methods, including pre- and postharvest factors (light, temperature, partial replacement of potassium with magnesium, etc.), genetic modifications (traditional breeding, phytohormones, etc.), chemical ripening methods (Ethephon, Moddus, etc.), and some alternative methods (DMSO treatment, ionic liquids, etc.). The aim of this review was to provide a comprehensive, up-to-date summary of methods of increasing the carbohydrate level in plants/biomass for bioethanol production.Öğe Ionic liquid based Ru(II)-phosphinite compounds and their catalytic use in transfer hydrogenation: X-ray structure of an ionic compound 1-chloro-3-(3-methylimidazolidin-1-yl)propan-2-ol(Pergamon-Elsevier Science Ltd, 2014) Aydemir, Murat; Rafikova, Khadichakhan; Kystaubayeva, Nurzhamal; Pasa, Salih; Meric, Nermin; Ocak, Yusuf Selim; Zazybin, AlexeyThe compound 1-chloro-3-(3-methylimidazolidin-1-yl)propan-2-ol chloride (1) was prepared from the reaction of 1-methylimidazole with epichlorohydrine. The corresponding phosphinite ligands were synthesized by the reaction 1-chloro-3-(3-methylimidazolidin-1-yl)propan-2-ol chloride, [C7H15N2OCl]Cl with one equivalent of chlorodiphenylphosphine or chlorodicyclohexylphosphine, in anhydrous CH2Cl2 and under an inert argon atmosphere. [Ru(eta(6)-arene)(mu-Cl)Cl](2) dimers readily react with the phosphinite ligands [(Ph2PO)-C7H14N2Cl]Cl (2) or [(Cy2PO)-C7H14N2Cl]Cl (3) at room temperature to afford the cationic derivatives [Ru((Ph2PO)-C7H14N2Cl)(eta(6)-arene)Cl-2]Cl and [Ru((Cy2PO)-C7H14N2Cl)(eta(6)-arene)Cl-2]Cl {arene: benzene (4), (5); p-cymene (6), (7)}. The structures of these ligands and their corresponding complexes have been elucidated by a combination of multinuclear NMR and IR spectroscopy, TGA/DTA and elemental analysis. The molecular structure of the ionic compound 1 was also determined by an X-ray single crystal diffraction study. Furthermore, the catalytic activity of complexes 4-7 for the transfer hydrogenation of various ketones was investigated and these complexes were found to be efficient catalysts in the transfer hydrogenation of various ketones, with excellent conversions up to 99%. Specifically, [Ru((Cy2PO)-C7H14N2Cl)(eta(6)-benzene)Cl-2]Cl (5) and [Ru((Cy2PO)-C7H14N2Cl)(eta(6)-p-cymene)Cl-2]Cl (7) act as excellent catalysts, giving the corresponding alcohols in 98-99% conversions in 5 min (TOF <= 1188 h(-1)). (C) 2014 Elsevier Ltd. All rights reserved.Öğe Ketone transfer hydrogenation reactions catalyzed by catalysts based on a phosphinite ligand(Taylor & Francis, 2022) Rafikova, Khadichakhan; Baysal, Akın; Meriç, Nermin; Zazybin, Alexey; Kayan, Cezmi; Işık, Uğur; Durap, Feyyaz; Aydemir, MuratReaction 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.Öğe A new class of well-defined ruthenium catalysts for enantioselective transfer hydrogenation of various ketones(Elsevier Science Sa, 2018) Kayan, Cezmi; Meric, Nermin; Rafikova, Khadichakhan; Zazybin, Alexey; Gurbuz, Nevin; Karakaplan, Mehmet; Aydemir, MuratA pair of novel optically pure phosphinite ligands were synthesized by ring opening reaction of chiral amines with (R)-styrene oxide or (S)-glycidyl phenyl ether oxide using a straightforward method in high yields and their ruthenium complexes were described in detail. The ruthenium complexes proved to be highly efficient catalysts for the enantioselective hydrogenation of ketones, affording products up to 99% ee. The results showed that the corresponding chiral alcohols could be obtained with high activity and excellent enantioselectivities at the desired temperature. (2S)-1-{benzyl[(1S)-1-(naphthalen-1-yl)ethyl]amino}-3-phenoxypropan-2-yl diphenylphosphinito[dichloro(eta(6)-benzene)ruthenium (II)] acts an excellent catalyst in the reduction of ketones, giving the corresponding alcohol up to 99% ee. (C) 2018 Elsevier B.V. All rights reserved.Öğe NMR study of the inclusion complexes of beta-cyclodextrin with diphenhydramine, clonidine and tolperisone(Springer International Publishing AG, 2022) Zhumakova, Symbat; Ten, Assel; Zharkynbek, Tolganay; Yu, Valentina; Seilkhanov, Tulegen; Basharimova, Anna; Bayazit, Sarah; Aydemir, Murat; Zazybin, AlexeyForming complexes with beta-cyclodextrin can enhance stability, dissolution rate, solubility, and bioavailability of an active pharmaceutical ingredient. In this study, the inclusion behavior between beta-cyclodextrin (beta-CD) and diphenhydramine, clonidine, and tolperisone in DMSO-d(6) was investigated using NMR spectroscopy. H-1, C-13, COSY, HMQC, and ROESY data were applied to determine the structure of inclusion complexes, and molecular docking analysis was engaged to identify the most favorable host-guest interactions in the inclusion complexes. Complexation of beta-CD with diphenhydramine, clonidine, and tolperisone is accompanied by the insertion of a molecular fragment of the guest molecule, one molecule of diphenhydramine and tolperisone, and two molecules of clonidine, into the inner sphere of one host molecule. The reported study provides useful information for the potential application of the complexation of beta-CD with diphenhy-dramine, clonidine, and tolperisone. This may be a good strategy for the development of solid pharmaceutical dosage forms based on beta-CDs as a drug delivery system.Öğe Rhodium-catalyzed transfer hydrogenation with aminophosphines and analysis of electrical characteristics of rhodium(I) complex/n-Si heterojunctions(Wiley, 2014) Aydemir, Murat; Ocak, Yusuf Selim; Rafikova, Khadichakhan; Kystaubayeva, Nurzhamal; Kayan, Cezmi; Zazybin, Alexey; Ok, Fatih; Baysal, Akın; Temel, HamdiA series of novel neutral mononuclear rhodium(I) complexes of the P?NH ligands have been prepared starting from [Rh(cod)Cl](2) complex. Structural elucidation of the complexes was carried out by elemental analysis, IR and multinuclear NMR spectroscopic data. The complexes were applied to the transfer hydrogenation of acetophenone derivatives to 1-phenylethanol derivatives in the presence of 2-propanol as the hydrogen source. Catalytic studies showed that all complexes are also excellent catalyst precursors for transfer hydrogenation of aryl alkyl ketones in 0.1m iso-PrOH solution. In particular, [Rh(cod)(PPh2NH?C6H4?4-CH(CH3)(2))Cl] acts as an excellent catalyst, giving the corresponding alcohols in excellent conversion up to 99% (turnover frequency588h(-1)). Furthermore, rhodium(I) complexes have been used in the formation of organic-inorganic heterojunction by forming their thin films on n-Si and evaporating Au on the films. It has been seen that the structures have rectifying properties. Their electrical properties have been analyzed with the help of current-voltage measurements. Finally, it has been shown that the complexes can be used in the fabrication of temperature and light sensors. Copyright (c) 2014 John Wiley & Sons, Ltd.Öğe 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, FeyyazTwo 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.Öğe Transfer hydrogenation of ketones catalyzed by new rhodium and iridium complexes of aminophosphine containing cyclohexyl moiety and photosensing behaviors of rhodium and iridium based devices(Elsevier Science Sa, 2014) Rafikova, Khadichakhan; Kystaubayeva, Nurzhamal; Aydemir, Murat; Kayan, Cezmi; Ocak, Yusuf Selim; Temel, Hamdi; Zazybin, AlexeyThe reaction of [Rh(mu-Cl)(cod)](2) and Ir(eta(5)-C5Me5)(mu-Cl)Cl](2) with aminophosphine ligands Cy2PNHCH2-C4H3X (X: O; S) gave a range of new monodendate [Rh(Cy(2)PNHCH(2)eC(4)H(3)O)(cod) Cl], (1), [Rh(Cy(2)PNHCH(2)eC(4)H3S)(cod) Cl], (2), [Ir(Cy2PNHCH2-C4H3O)(h(5)-C5Me5)Cl-2], (3) and [Ir(Cy2PNHCH2 -C4H3S)(eta(5)-C5Me5)Cl-2], (4) complexes, which were characterized by analytical and spectroscopic methods. The new rhodium(I) and iridium(III) catalysts were applied to transfer hydrogenation of acetophenone derivatives using 2-propanol as a hydrogen source. The results showed that the corresponding alcohols could be obtained with high activity (up to 99%) under mild conditions. Notably, [Rh(Cy2PNHCH2-C4H3O)(cod)Cl] complex (1) is much more active than the other analogous complexes in the transfer hydrogenation. Moreover, organiceinorganic rectifying contacts were fabricated forming rhodium(I) and iridium(III) complex thin films on n-Si semiconductors and evaporating Au metal on the structures. Electrical properties of the contacts including ideality factor, barrier height and series resistance were determined using their currentevoltage (IeV) data. The photoelectrical characteristics of the devices were examined under the light with 40-100 mW/cm(2) illumination conditions. It was seen that light had strong effects on IeV characteristics of the devices and the ones fabricated using 3 and 4 complexes had unusually forward and reverse bias photoconducting behavior. (C) 2014 Elsevier B.V. All rights reserved.Öğe Transfer hydrogenation reaction using novel ionic liquid based Rh(I) and Ir(III)-phosphinite complexes as catalyst(Elsevier Science Sa, 2016) Karakas, Duygu Elma; Durap, Feyyaz; Baysal, Akin; Ocak, Yusuf Selim; Rafikova, Khadichakhan; Kaya, Eda Cavus; Zazybin, AlexeyHydrogen transfer reduction methods are attracting increasing interest from synthetic chemists in view of their operational simplicity. Thus, interaction of [Rh(mu-Cl)(cod)](2) and Ir(eta(5)-C5Me5)(mu-Cl)Cl](2) with phosphinite ligand [(Ph2PO)-C7H11N2Cl]Cl, 1 gave new monodendate (1-chloro-3-(3-methylimidazolidin1-yl)propan-2-yl diphenylphosphinite chloride) (chloro eta(4)-1,5-cyclooctadiene rhodium(I))], 2 and (1chloro-3-(3-methylimidazolidin-1-yl)propan-2-yl diphenylphosphinite chloride) (dichloro n.5-pentamethylcyclopentadienyl iridium(III))1, 3 complexes, which were characterized by a combination of multinuclear NMR spectroscopy, IR spectroscopy, and elemental analysis. H-1-{P-31}NMR, H-1-C-13 HETCOR or H-1-H-1 COSY correlation experiments were used to confirm the spectral assignments. The novel catalysts were applied to transfer hydrogenation of acetophenone derivatives using 2-propanol as a hydrogen source. The results showed that the corresponding alcohols could be obtained with high activity (up to 99%) under mild conditions. Notably, (1-chloro-3-(3-methylimidazolidin-1-yl)propan-2-y1 diphenylphosphinite chloride) (chloro eta(4)-1,5-cyclooctadiene rhodium(I))], 2 complex is much more active than the other analogous complex, 3 in the transfer hydrogenation. Furthermore, compound, 2 acts as excellent catalysts, giving the corresponding alcohols in 97-99% conversions in 5 min (TOF <= 1176 h(-1)). (C) 2016 Elsevier B.V. All rights reserved.Öğe Ultrasound- and microwave-promoted synthesis, growth-regulating activity and antimicrobial behavior of trimecaine-based Ionic compounds(Wiley-V C H Verlag Gmbh, 2022) Dauletbakov, Anuar; Zazybin, Alexey; Yu, Valentina; Belyankova, Yelizaveta; Ten, Assel; Rafikova, Khadichakhan; Zolotareva, Darya; Aydemir, MuratThe present work describes the synthesis, growth-regulating activity, and antimicrobial behavior of ionic compounds based on 2-diethylamino-N-(2,4,6-trimethylphenyl)acetamide (trimecaine). Synthesis of ionic compounds was performed via N-alkylation of trimecaine with alkyl halides using microwave and ultrasound activation and the results were compared with those of classical conditions (thermal activation). The synthesized ionic compounds have been tested for germination energy and capacity with the collection of different varieties and hybrids of sweet sorghum seeds. The valuable results were obtained for the seeds stored for several years for which the significant drop in germination activity is usually observed. Furthermore, the ionic compounds were used to study their biological activity - growth -regulating activity on sweet sorghum seeds and the antimicrobial behavior against E. coli, S. typhimurium, B. subtilis, S. aureus, P. aeruginosa, and C. albicans microorganisms.
