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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 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 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 pursueÖğe Zinc phthalocyanine as a heterogeneous catalyst for efficient H₂ generation from NaBH₄ methanolysis(Elsevier Ltd, 2025) Işık, Uğur; Namlı, Mesut; Kantar, Cihan; Elma Karakaş, DuyguPhthalocyanines have been extensively studied for their role in photodynamic therapy, sensors, optoelectronic devices etc.; however, their use as catalysts for hydrogen generation (HG) has remained a relatively unexplored area in scientific literature. This study is the first investigation into the catalytic potential of zinc phthalocyanine (ZnPc) complex in hydrogen production via methanolysis reaction of sodium borohydride (NaBH₄). The kinetic performance of the ZnPc catalyst was evaluated based on catalyst amount, NaBH₄ concentration, temperature, and reusability. The ZnPc-catalyzed NaBH₄ methanolysis completed in 5.7 min, with a hydrogen generation rate of 8993 mLmin⁻¹gcat⁻¹—comparable to or better than many similar catalysts—and an activation energy of 28.47 kJ/mol. The catalyst exhibited remarkable reusability with no significant loss in catalytic activity when used for the three-cycle reaction. Additionally, the ZnPc-catalyzed NaBH₄ methanolysis mechanism was also examined, revealing that –OH, –O–, and –N=N– groups play key roles in its notable HG efficiency. Overall, this study presents ZnPc as a promising catalyst for HG and emphasizes its catalytic efficiency and application potential in sustainable energy technologies.
