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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 Ltd, 2024) Meriç, Nermin; Işık, Uğur; Dauletbakov, Anuar; Zolotareva, Darya; Zazybin, Alexey; Sever, Mehmet Şerif; Okumuş, Veysi; Ertekin Binbay, Nil; Binbay, Veysel; Kayan, Cezmi; 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 phthalocyanine complexes of Cu(II), Co(II), Ni(II), and Zn(II) as catalysts in the transfer hydrogenation of acetophenone and its derivatives(Elsevier B.V., 2024) Namlı, Mesut; Işık, Uğur; Kantar, Cihan; Aydemir, MuratIn this study, tetra substituted metallophthalocyanines (M: Ni, Zn, Co, and Cu) containing imine and azo groups were synthesized using microwave irradiation. The structures of all complexes have been totally characterized via ¹HNMR, ¹³ CNMR, TGA/DTA, LC-MS/MS, elemental analysis, UV–Vis, FT-IR spectroscopy. The comparison of the catalytic features of phthalocyanine based on metals is also discussed briefly. These phthalocyanine-complexes were also used in the transfer hydrogenation (TH) of acetophenone derivatives in the existence of KOH, utilizing isoPrOH as a hydrogen source. Acetophenone compounds determined a TH of up to 99 % conversion. Copper phthalocyanines were first used as catalysts in transfer hydrogenation reactions. The Cu(II) complexes showed higher catalytic activity, converting up to 97 % at 1.0 mol% catalyst loading. Furthermore, we have discovered that the catalytic characteristics of this class of molecules are significantly influenced by both steric and electronic variables.Öğe Half-sandwich ruthenium(II) and iridium(III) complexes of imidazole based phosphinite ligands: antioxidant and antibacterial activities as well as electrochemical properties(John Wiley and Sons Inc, 2024) Işık, Uğur; Rafikova, Khadichakhan; Meriç, Nermin; Güzel, Remziye; Kerimkulova, Aygül; Akimbek, Arailym; Okumuş, Veysi; Durap, Feyyaz; Kayan, Cezmi; Aydemir, MuratRuthenium(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(?6-benzene)ruthenium]diphenylphosphanyl}oxy)propyl)-1-butyl-1H-imidazol-3-ium chloride], 4 at 200 ?g/mL concentration, while [3-(3-chloro-2-({[dichloro(??-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.Öğe New metallophthalocyanine (M: Ni(II) and Fe(II)) complexes as efficient catalysts for transfer hydrogenation of various ketones(Elsevier B.V., 2024) Işık, Uğur; Namlı, Mesut; Kantar, Cihan; Şaşmaz, Selami; Aydemir, MuratHydrogen transfer reduction methods are attracting increasing attention from synthetic chemists in view of their operational simplicity. Therefore, the novel Ni(II) and Fe(II) tetra substituted metallophthalocyanines containing resorcinol and guaiacol groups were synthesized using microwave irradiation and characterized via elemental analysis, UV-Vis and FT-IR spectroscopy, and TGA. The comparison of the catalytic features of phthalocyanine based on metals is discussed in detail. These phthalocyanine-complexes were tested in transfer hydrogenation (TH) of ketones in the existence of KOH, utilizing 2-propanol as a hydrogen source. Examination of different carbonyl substrates revealed that Nickel (II) phthalocyanine, (Ni2) complex was a remarkable catalyst for the catalytic reduction of acetophenones (1.0 mol % of catalyst, 99 % conversion). Furthermore, we have discovered that the catalytic characteristics of this class of molecules are significantly influenced by both steric and electronic variables.Öğe Novel azo-substituted metallophthalocyanines (M: Co, Ni, Cu, Zn) bearing hydroxy, carbonyl, and methoxy groups: Synthesis and evaluation as pre-catalysts for the transfer hydrogenation of aldehydes and ketones(ELSEVIER, 2025) Namlı, Mesut; Işık, Uğur; Kantar, Cihan; Şaşmaz, Selami; Aydemir, MuratIn this study, four novel metallophthalocyanine (MPc) compounds derived from phthalonitrile ligands incorporating o-vanillin were synthesized, characterized, and evaluated as pre-catalysts in the acetophenone and benzaldehyde transfer hydrogenation (TH) reactions. The molecular structures of the complexes were confirmed by FTIR and UV-Visible spectroscopy and elemental analysis. Among the complexes, copper phthalocyanine compound (5) exhibited the highest catalytic efficiency, promoting the acetophenone and benzaldehyde transfer hydrogenation reactions in propan-2-ol under inert conditions, and the corresponding alcohols have a 98 % conversion rate within 1 h (A1) and 99 % conversion within 6 h (K1). The results show that both the electronic effects of substituents on the phthalonitrile ligands and the central metal nature play key roles in determining the catalytic performance of the MPc complexes in TH reactions.Öğe Novel bridged binuclear ruthenium-aminophosphine complexes for the transfer hydrogenation of ketones using isopropanol: Synthesis, catalytic performance, and electrochemical behavior(ELSEVIER, 2025) Tanrıverdi Gergin, Zuhal; Toksoy, Mahmut Ozan; Işık, Uğur; Baysal, Akın; Güzel, Remziye; Aydemir, Murat; Durap, FeyyazThe starting material N,N '-bis(diphenylphosphino) ethane-1,2-diamine (1) was prepared for the first time in this study by a one-step reaction of 1,2-ethylenediamine with one equivalent of diphenylchlorophosphine. The reaction of 1 with either [Ru(p-cymene)(mu-Cl)Cl](2) or [Ru(benzene)(mu-Cl)Cl](2) afforded a series of novel bridged binuclear complexes of [C2H4-{NHPPh2-Ru(benzene)Cl-2}(2)], 1a and [C2H4-{NHPPh2-Ru(p-cymene)Cl-2}(2)], 1b, respectively. All newly synthesized complexes were comprehensively characterized using various analytical and spectroscopic techniques. H-1-, C-13-, P-31{H-1} NMR, (HH)-H-1-H-1 COSY or (HC)-H-1-C-13 HETCOR correlation experiments were employed to validate the spectral assignments. Both complexes are appropriate catalyst precursors for transfer hydrogenation of acetophenone derivatives. In particular, the complex [C2H4-{NHPPh2-Ru(benzene)Cl-2}(2)], referred to as 1a, demonstrates outstanding catalytic efficiency, by producing the relevant alcohols in 99 % conversion at 82 degrees C (TOF similar to 1200 h(-1)) in 5 min, outperforming analogous complexes in transfer hydrogenation reactions. Furthermore, the chemical characterizations, electronic transitions, and electrochemical properties of the Ru(II) complexes were systematically investigated by experimental methods.Öğe Synthesis of half-sandwich ruthenium(II) and iridium(III) complexes containing imidazole-based phosphinite ligands and their use in catalytic transfer hydrogenation of acetophenone with isopropanol(Elsevier B.V., 2023) Işık, Uğur; Meriç, Nermin; Kayan, Cezmi; Kılıç, Ahmet; Belyankova, Yelizaveta; Zazybin, Alexey; Aydemir, MuratTwo ionic liquids (3-(3‑chloro-2-hydroxypropyl)-1-vinyl-1H-imidazol-3-ium chloride and 3-(3‑chloro-2-hydroxypropyl)-1‑butyl‑1H-imidazol-3-ium chloride) were prepared from commercially available, inexpensive 1-vinyl imidazole or 1‑butyl imidazole, respectively, in ethanol at room temperature. Then, these ionic liquids were treated with PPh2Cl to obtain ionic liquid-based phosphinite ligands and the reaction of these phosphinites with [Ru(η6-benzene)(μ-Cl)Cl]2, [Ru(η6−p-cymene)(μ-Cl)Cl]2, or [Ir(η5-C5Me5)(μ-Cl)Cl]2 gave the corresponding ruthenium and iridium complexes. Structures of the synthesized compounds were clarified by multinuclear NMR and IR spectroscopy as well as microanalysis. Furthermore, the complexes were applied as catalysts in the transfer hydrogenation of acetophenone derivatives to afford the corresponding alcohols with high conversions. Notably, [Ru(Ph2PO–C8H11N2Cl2)(η6-benzene)Cl2] acts as a good catalyst, giving the corresponding alcohols in 97–98% yields in 15 min at 82 °C (TOF ≤ 400 h−1) for the transfer hydrogenation reaction in comparison to analogous complexes. The catalysts are also useful for a variety of related ketone substrates with various electronic and steric regulating groups.Öğe Synthesis of Phthalocyanine Compounds Utilizing Thymol and Carvacrol Azo Dyes as Catalysts in Transfer Hydrogenation of Aromatic Aldehydes and Ketones With 2-Propanol(John Wiley and Sons Ltd, 2025) Namlı, Mesut; Işık, Uğur; Kantar, Cihan; Şaşmaz, Selami; Aydemir, MuratHydrogen transfer reduction systems are attracting increasing interest from synthetic chemists because of their simplicity in functioning. In this work, eight new metallophthalocyanine (MPc) compounds ligated on phthalonitrile ligands, including thymol or carvacrol, have been structurally elucidated and used as precatalysts in the transfer hydrogenation (TH) of acetophenone. FT-IR and UV–vis spectroscopies, elemental analyses, and LC-MS spectrometry were used to establish the molecular structures of the new phthalocyanine complexes. The nickel compounds (1b and 2b) act as efficient catalysts, which bring about catalytic TH reactions of a broad array of ketones in propan-2-ol and inert conditions (99% conversion in 3.5 h for 1b and 97% conversion in 4 h for 2b, respectively). The electronic properties arising from the position of the groups on the ligand and the nature of the metals appear to regulate the catalytic performances of the complexes in transfer hydrogenation. Furthermore, the modular construction of these catalysts and their flexibility toward transfer hydrogenation (TH) make these systems to pursue
