Synthesis, characterization and electrochemistry of 1-phenoxypropan-2-yloxy substituted phthalocyanines

AKCAY, Hakki Turker/0000-0002-8502-9608WOS: 0005751677000124-(1-phenoxypropan-2-yloxy)phthalonitrile (3) and peripherally tetra 1-phenoxypropan-2-yloxy substituted zinc(II) (4), cobalt(II) (5) and copper(II) (6) phthalocyanine were prepared. Structural characterization of novel complexes was performed by spectrophotometric measurements. the determination of the redox active or redox inactive metal center effect on the electrochemistry, in-situ spectroelectrochemisty and electrocolorimetry of compounds were performed in dimethylformamide. the redox properties and mechanisms were examined by electrochemical measurements. the peripherally tetra substituted cobalt(II) phthalocyanine (5) showed both metal and ligand-based redox processes, while zinc(II) (4) and cobalt(II) phthalocyanines only displayed ligand-based redox processes. These results were confirmed by electrochemical and in-situ spectroelectrochemical measurements. Moreover, the semiconducting nature of the compounds were illuminated via electrochemical measurements. (C) 2020 Elsevier B.V. All rights reserved

Synthesis, Characterization and Investigation of Electrochemical and Spectroelectrochemical Properties of Peripherally Tetra Diethoxypropan Substituted Phthalocyanines

WOS: 000565405600001In this study novel peripherally tetra 1,3-diethoxy-2-propanol substituted Co(II), Cu(II), Mg(II), Ni(II) Zn(II) phthalocyanine derivatives were prepared. the characterization of the novel compounds was made by FT-IR,H-1-NMR, UV-vis and MALDI-TOF mass. Electrochemical,in-situspectroelectrochemical and electrocolorimetric measurements have been carried out with the aim to determine the redox properties, to illuminate reaction mechanism and the effect of substituent and metal center. Moreover, the color properties and aggregation tendency of compounds were also investigated

Substituted phthalocyanines and their electropolymerization properties

Biyiklioglu, Zekeriya/0000-0001-5138-214X; AKCAY, Hakki Turker/0000-0002-8502-9608WOS: 000383811300083In this study, new metal-free and metallo-phthalocyanine complexes (Co, TiO) were synthesized using a piperazine-substituted phthalonitrile derivative. All proposed structures were supported by instrumental methods. Electrochemical studies of H-2-Pc, (TiOPc)-O-IV, and (COPc)-Pc-II were examined using cyclic voltammetry (CV) and square-wave voltammetry (SWV) techniques. Voltammetric analyses of phthalocyanines supported the proposed structure of the synthesized complexes. All studied phthalocyanines were oxidatively electropolymerized on the working electrode during the repetitive anodic potential scans. (C) 2016 Elsevier B.V. All rights reserved.Karadeniz Technical UniversityKaradeniz Technical University; Sinop UniversitySinop UniversityThe authors wish to thank Karadeniz Technical University and Sinop University

Novel phthalocyanines bearing 1,2,4 triazole substituents: Synthesis, characterization, photophysical and photochemical properties

OZCIFCI, ZEHRA/0000-0001-8218-7136; AKCAY, Hakki Turker/0000-0002-8502-9608WOS: 0005237658000074-(4,5-Diphenyl-4H-1,2,4-triazol-3-ylthio)phthalonitrile ( 3) and its non-peripherally tetra substituted zinc(II) phthalocyanine (4) and magnesium(II) phthalocyanine (5) derivatives were prepared. the novel compounds 3-5 were characterized spectroscopically. To determine the photodynamic therapy potential of 4 and 5, their photophysical and photochemical properties were investigated. the magnesium(II) phthalocyanine (5) showed the highest fluorescence quantum yield. in addition, non-peripheral substitution of the 4-(4,5-diphenyl-4H-1,2,4-triazol-3-ylthio) groups on the phthalocyanine ring did not affect the fluorescence properties of the phthalocyanines. the zinc(II) phthalocyanine (4) exhibited the highest singlet oxygen quantum yield value. the 4 and 5 exhibited lower photostability than Std-ZnPc. These results show that the zinc(II) phthalocyanine (4) can be used in photodynamic therapy applications with its singlet oxygen production and photostability. (C) 2020 Elsevier Ltd. All rights reserved

Synthesis, characterization and investigation of electrochemical and spectroelectrochemical properties of peripherally tetra 4-phenylthiazole-2-thiol substituted metal-free, zinc(II), copper(II) and cobalt(II) phthalocyanines

AKCAY, Hakki Turker/0000-0002-8502-9608; KOCA, ATIF/0000-0003-0141-5817;WOS: 000401593400074In this study novel peripherally tetra 4-phenylthiazole-2-thiol substituted metal-free phthalocyanine (4) and its zinc(II) (5), copper(II) (6) and cobalt(II) (7) derivatives were synthesized and characterized by a combination of various spectroscopic techniques such as FT-IR, H-1-NMR, UV-vis and MALDI-TOF mass. Electrochemical characterizations of metallo-phthalocyanine complexes were conducted by voltammetric and in situ spectroelectrochemical measurements. (CoPc)-Pc-II went [(CoPc-2)-Pc-II]/[(CoPc-2)-Pc-I](1-), [(CoPc-2)-Pc-I](1-)/ [(CoPc-3)-Pc-I](2-), [(CoPc-3)-Pc-I](2-)/[(CoPc-4)-Pc-I](3-) and [(CoPc-2)-Pc-I]/[(CoPc-2)-Pc-II](1+) reduction and oxidation processes respectively. Differently (ZnPc)-Pc-II only showed four ligand-based reductions and two ligand based oxidation processes. (C) 2017 Elsevier B.V. All rights reserved

Synthesis, characterization, photophysical and photochemical properties of peripherally tetra benzodioxane substituted metal-free phthalocyanine and its zinc(II) and magnesium(II) derivatives

15th International Conference on Molecular Spectroscopy (ICMS) - From Molecules to Molecular Materials, Biological Molecular Systems and Nanostructures -- SEP 15-19, 2019 -- Wojanow, POLANDWOS: 000587468000045The phthalonitrile (3) including 2-(methoxymethyl)-2,3-dihydro-1,4-benzodioxane substituent and peripherally tetra substituted metal-free (4), zinc(II) (5) and magnesium(II) (6) phthalocyanines were synthesized. the photophysical (fluorescence quantum yields and lifetimes) and photochemical (singlet oxygen generation and photodegradation) properties of phthalocyanines (4-6) were examined in DMSO solutions. the zinc(II) phthalocyanine (5) showed higher singlet oxygen quantum yield (Phi(Delta)=0.82) compared to metal-free (4) (Phi(Delta)=0.13) and magnesium(II) (5) (Phi(Delta)=0.29) phthalocyanine. Also, the fluorescence quenching behaviors of phthalocyanines (4-6) by 1,4-benzoquinone (BQ) were investigated. (C) 2020 Elsevier B.V. All rights reserved.Polish Acad Sci, Inst Low Temp & Struct Re

Novel triazole substituted phthalocyanines showing high singlet oxygen quantum yields

AKCAY, Hakki Turker/0000-0002-8502-9608WOS: 000451782900032In this study, novel triazole peripherally substituted phthalocyanine zinc(II) complexes 3(a-d) were synthesized from four different phthalonitrile derivative and characterized by FT-IR NMR, MALDI-TOF, UV-Vis methods. Aggregation-concentration relations of the compounds 3(a-d) were investigated by UV-Vis spectroscopy. Fluorescence quenching properties of the phthalocyanines 3(a-d) were studied and fluorescence quantum yields were calculated by comparative method. Photodegradation quantum yields of the compound 3(a-d) were calculated. in addition, singlet oxygen quantum yields of the compounds 3(a-d) were measured by comparative method by using 1,3-diphenylisobenzofuran (DPBF) as singlet oxygen quencher. in this work, it has been observed that the synthesized novel phthalocyanines have higher quantum yield values (the range of 0.8-0.85) compared to the Zn (II) complex of unsubstituted phthalocyanine (0.67). Especially the compound 3d substituted tolyl group has the highest singlet oxygen quantum yield (0.85) seen rarely in literature.Recep Tayyip Erdogan UniversityRecep Tayyip Erdogan University [2014.101.16.01]This study was supported by Recep Tayyip Erdogan University - Research Funding - (Project no 2014.101.16.01)

4-(4-(( 5-Amino-1,3,4-thiadiazol-2-yl)methoxy) phenyl)-1-(( 5-amino-1,3,4-thiadiazol-2-yl)methyl)-3-benzyl-1H-1,2,4-triazol-5( H)-one: Synthesis, Characterization and Computational Studies

AKCAY, Hakki Turker/0000-0002-8502-9608WOS: 000390361500010Background: 1,2,4-triazole and its derivatives are known to have various biological activities such as antifungal, antiviral, antidepressant, antitumor, anti-inflammatory, antitubercular, antimigrain and anti-cancer. Computational chemistry plays an important role in determining structural and chemical properties of chemical compounds. There are many studies on computational studies of triazole derivatives. the aim of this study is to prepare new triazole derivative having potent of bio-active material and to investigate the computational properties. Methods: the molecular geometry of compound 2 was optimized by using X-ray structural parameters at the DFT calculations with a hybrid functional B3LYP (Becke's three parameter hybrid functional using the LYP correlation functional) with the 6-31G (d, p), were performed with the Gaussian 03W software package. Results: in this work, title compound was synthesized and characterized by IR and NMR techniques. the compound was crystallized in ethanol and single crystal which suitable for X-ray analysis was obtained. the geometric optimization was studied and obtained through computational data compared with crystallographic data. Vibrational data, H-1-NMR and (CNMR)-C-13 chemical shifts were calculated and compared with experimental ones. Spectral results are in agreement with each other. TD-DFT was computed and important transitions were assigned. Conclusion: Spectral results are in agreement with each other. TD-DFT was computed and important transitions were assigned. in addition, electrostatic potential map were obtained computationally. While triazole nitrogens have electrophilic character, amine groups have nucleophilic character. Moreover, natural bond orbital analysis were calculated computationally. the interactions of LP(N1) -> sigma* (C2-N2), LP(N3) -> sigma* (C1-O2), LP(O2) -> sigma* (C1-N1), LP(N6) -> pi*(C12-N5), LP(O1) -> pi* (C15-C16), LP(N9) -> sigma* (C21-N8) provide the extra stabilization energy to the molecule. the most important s -> sigma* interaction was obtained as s (C3-H) -> sigma* (C2-N1), sigma (N2-N3) -> sigma* (C2-C3), sigma (N6-H) -> sigma* (C12-S1), sigma (C19-H) -> sigma* (C20-S2), sigma (N9-H) -> sigma* (C21-S2)