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Synthesis, Characterization and Photocatalytic Properties of Non-peripherally 3- (pyridin-4-yl) propane-1-oxy Groups Substituted Cu (II) Phthalocyanine and Water Soluble Derivative

Year 2020, Volume: 24 Issue: 5, 1029 - 1039, 01.10.2020
https://doi.org/10.16984/saufenbilder.630325

Abstract

Cu (II) phthalocyanine compound and its water-soluble derivative containing 3- (pyridin-4-yl) propane-1-oxy groups in non-peripheral positions were synthesized for the first time and their structures were elucidated. The photocatalytic properties of Cu (II) phthalocyanine compounds, which were synthesized and characterized, were investigated on the photocatalytic degradation reactions of 4-nitrophenol, one of the important environmental pollutants. In the photocatalysis reactions that took place in the photoreactor for 2 hours without using any oxidant, 4-nitrophenol compound was completed with 94.4% and 98.6% conversion to toxic and non-harmful species. The hydroquinone compound was identified as the main product and the benzoquinone compound as the by-product. The conversion number for the non-peripheral Cu (II) phthalocyanine compound and its water-soluble derivative was 471 and 488 and the conversion frequency was 235.5 and 244,0 respectively. Finally, recovery studies were carried out for water soluble Cu (II) phthalocyanine used as photocatalyst and the number of cycles was determined as 5.

Project Number

7687

References

  • C.C. Lezznof and A.B.P. Lever, ‘’Phthalocyanines, Properties and Applications’’, 4, VCH Publisher, New York, (1996).
  • G. Guillaud, J. Simon and J.P. Germain, ‘’Metallophthalocyanines: gas sensors, resistors and field effect transistors’’, Coordination Chemistry Reviews, 178, pp 1433–1484, 1998.
  • M. Durmus and T. Nyokong ‘’The synthesis, fluorescence behaviour and singlet oxygen studies of new water-soluble cationic gallium(III)phthalocyanines’’, Inorganic Chemistry Communications, 10, pp 332–338, 2007.
  • H.A. Abdeldayem, D.O. Frazier, B.G. Penn, D.D. Smith and C.E. Banks, ‘’Non-linear op-tothermal properties of metal-freephthalocyanine’’, Thin Solid Films, 350, pp 245–248, 1999.
  • Q. Luo, H. Tian, B. Chen and W. Huang, ‘’Effective non-destructive read out of photo-chromic bisthienyletheneephthalocyanine hybrid’’, Dyes and Pigments, 73, pp 118–120, 2007.
  • W.S.G. Medina N.A.G. dosSantos C. Curti A.C. Tedesco and A.C. dosSantos, ‘’Effects of zincphthalocyaninetetrasulfonate-based photodynamic therapy on rat brain iso-lated mitochondria’’, Chemico Biological Interactions, 79, pp 402–406, 2009.
  • B.G.Fanchiotti, M.P. ZamprognoMachado, L.C. Paula, M. Durmus, T. Nyokong, A.S. Gonçalves and A.R. Silva, ‘’The photobleaching of the free and encapsulated metallic phthalocyanine and its effect on the photooxidation of simple molecules’’, Journal of Photochemistry and Photobiology B: Biology, 165, pp 10-23, 2016.
  • Z. Biyiklioglu, V. Cakir, A. Koca and H. Kantekin, ‘’Synthesis, electrochemical, in-situ spectro electrochemical and in-situelectrocolorimetric characterizationofnon-peripheraltetra substitutedmetal-free and metallophthalocyanines’’, Dyes and Pigments, 89, pp 49-55, 2011.
  • P.T. Anastas and J.C. Warner, ‘’Green Chemistry Theory and Practice’’, 148, Oxford University Press, New York, 1998.
  • Y. Ding, F. Yang, L. Zhu, N. Wang and H. Tang, ‘’Synergisticphotocatalytic properties andmechanism of g-C3N4 coupled with zinc phthalocyanine catalyst undervisiblelight irradiation’’, Applied CatalysisB: Environmental, 164, pp. 151–158, 2015.
  • F. Goettmann, A. Fischer, M. Antonietti and A. Thomas, ‘’Chemical synthesisofmesoporousarbon nitrides using hard templates and their use as a metal-free catalyst forFriedel-Crafts reaction of benzene’’, Angewandte Chemie International Edition, 45, pp. 4467–4471, 2006.
  • S. Yan, S. Lv, Z. Li and Z. Zou, ‘’Organic–inorganic composite photocatalyst of g-C3N4 and TaON with improved visible light photocatalytic activities’’, Dalton Transactions, 39, pp. 1488–1491, 2010.
  • H. Li, J. Liu, W. Hou, N. Du, R. Zhang and X. Tao, ‘’Synthesis and characterization of g-C3N4/Bi2MoO6 heterojunctions with enhanced visible light photocatalytic activity’’, Applied Catalysis B: Environmental, 160–161, pp. 89–97, 2014.
  • S. Wang, D. Li, C. Sun, S. Yang, Y. Guan and H. He, ‘’Synthesis and characterization of g-C3N4/Ag3VO4 composites with significantly enhanced visible-light photocatalytic activity for triphenylmethane dye degradation’’, Applied Catalysis B: Environmental, 144, pp. 885–892, 2014.
  • W. Wang, J.C. Yu, D. Xia, P.K. Wong and Y. Li, ‘’Graphene and g-C3N4 Nanosheets Cowrapped Elemental α-Sulfur As a Novel Metal-Free Heterojunction Photocatalyst for Bacterial Inactivation under Visible-Light’’, Environmental Science and Technology, 47, pp. 8724–8732, 2013.
  • J. Xu, G. Wang, J. Fan, B. Liu, S. Cao and J.J. Yu, ‘’g-C3N4 modified TiO2 nanosheets with enhanced photoelectric conversion efficiency in dye-sensitized solar cells’’, Power Sources, 274, pp. 77–84, 2015.
  • A. Hern ́andez-Gordillo, A.G. Romero, F. Tzompantzi and R. Gómez, ‘’Kinetic study of the 4-Nitrophenol photooxidation and photo reduction reaction susing CdS’’, Applied Catalysis B: Environmental, 144, pp. 507–513, 2014.
  • W. Muersa and G.S. Pozan Soylu, ‘’Effects of metal oxide semiconductors on the photocatalytic degradation of 4-nitrophenol’’, Journal of Molecular Structure, 1174, pp. 96-102, 2018.
  • L. Coche-Guerente, P. Labbe and V. Mengeaud, ‘’Theoretical and experimental study of the phenol-polyphenol oxidase system immobilized in Laponite hydrogels and layer-by-layer self-assembled structures’’, Analytical Chemistry, 73, pp. 3206-3216, 2001.
  • A.E. Navarro, N.A. Cuizano, R.F. Portales and B.P.Llanos, ‘’Adsorptive removal of 2- nitrophenol and 2-chlorophenol by cross-linked algae from aqueous solutions’’, Separation Science and Technology, 43, pp. 3183-3199, 2008.
  • S.Q. Yu, J. Hu and J.L. Wang, ‘’Gamma radiation-induced degradation of p-nitrophenol (PNP) in the presence of hydrogen peroxide (H2O2) in aqueous solution, Journal of Hazardous Materials, 177, 1061-1067, (2010).
  • E.T. Saka, ‘’Preparation, characterization of new Co(II) and Cu(II) phthalocyanines and their catalytic performances in aerobic oxidation of substituted phenols’’, Journal of Inclusion Phenomena and Macrocyclic Chemistry, 91, pp. 61-69, 2018.
  • Y. Unver, H. Bas and Z. Biyiklioglu, ‘’Non-peripherally 4-{[(1E)-1-benzothien-2-ylmethylene]amino}phenol substituted zinc(II), manganese(III), cobalt(II) phthalocyanines:Synthesis and electrochemistry’’, Journal of Molecular Structure, 1178, pp. 508-513, 2019.
  • E. Turker Acar, T. Akkızlar Tabakloglu, D. Atilla, F. Yüksel and G. Atun, ‘’Synthesis, electrochemistry and electrocatalytic activity of cobaltphthalocyanine complexes – Effects of substituents for oxygen reduction reaction’’, Polyhedron, 152, pp. 114-124, 2019.
  • I. Altın, M. Sokmen and Z. Bıyıklıoglu, ‘’Quaternized zinc(II) phthalocyanine-sensitized TiO2: surfactant-modified sol-gel synthesis, characterization and photocatalytic applications’’ Desalination and Water Treatment, 57, pp. 16196-16207, 2016.
  • R. Bayrak, C. Albay, M. Koç, I. Altın, I. Degirmenci and M. Sokmen, ‘’Preparation of phthalocyanine/TiO2 nanocomposites for photocatalytic removal of toxic Cr(VI) ions’’, Process Safety and Environmental Protection, 102, pp. 294-302, 2016.
  • S. Mapukata N. Kobayashi, M. Kimura and T. Nyokong, ‘’Asymmetrical and symmetrical zinc phthalocyanine-cobalt ferrite conjugates embedded in electrospun fibers for dual photocatalytic degradation of azo dyes: Methyl Orange and Orange G’’ Journal of Photochemistry and Photobiology A: Chemistry, 379, pp. 112-122, 2019.
  • W.L.He and C.D.Wu, ‘’Incorporation of Fe-phthalocyanines into a porous organic framework for highly efficient photocatalytic oxidation of arylalkane’’ Applied Catalysis B:Environmental, 234, pp. 290-295, 2018.
  • M. Lu, B. Li, Y. Zhang, Q. Liang, X. Li, S. Xu and Z. Li, ‘’Facile synthesis and characterization of a cobalt phthalocyanine sensitized SnIn4S8 composites toward enhanced photocatalytic activity, Journal of Materials Science: Materials in electronics’’ 29, pp. 16680–16690 2018.
  • P. Arunachalam, S. Zhang, T. Abe, M. Komura, T. Iyoda and K. Nagai, ‘’Weak visible light (∼mW/cm2) organophotocatalysis for mineralization of amine, thiol and aldehyde by biphasic cobalt phthalocyanine/fullerene nanocomposites prepared by wet process’’ Applied Catalysis B:Environmental, 193, pp. 240-247, 2016.
  • V. Iliev and D. Tomova, ‘’Photocatalytic oxidation of sulfide ion catalyzed by phthalocyanine modified titania’’ Catalysis Communications 3, pp. 287–292, 2002.
  • G.Mele, R. Del Sole, G. Vasapollo, E. García-López, L. Palmisano and M. Schiavello, ‘’Photocatalytic degradation of 4-nitrophenol in aqueous suspension by using polycrystalline TiO2 impregnated with functionalized Cu(II)–porphyrin or Cu(II)–phthalocyanine’’ Journal of Catalysis, 217, pp. 334–342, 2003.
  • Y. Mahmiani, A.M. Sevim and A. Gül, ‘’Photocatalytic degradation of 4-chlorophenol under visible light by using TiO2 catalysts impregnated with Co(II) and Zn(II) phthalocyanine derivatives’’ Journal of Photochemistry and Photobiology A: Chemistry, 321, pp. 24–32, 2016.
  • T.B. Ogunbayo, E. Antunes and T. Nyokong, ‘’Investigation of homogeneous photosensitized oxidation activities of palladium and platinum octasubstituted phthalocyanines: Oxidation of 4-nitrophenol’’ Journal of Molecular Catalysis A: Chemical, 334, pp. 123–129, 2011.
  • E. Marais, R. Klein, E. Antunes and T. Nyokong, ‘’Photocatalysis of 4-nitrophenol using zinc phthalocyanine complexes’’ Journal of Molecular Catalysis A: Chemical, 261, pp. 36–42, 2007.
  • A.A. Kamıloglu, I. Acar, Z. Bıyıklıoglu and E.T. Saka, ‘’Peripherally tetra-{2-(2,3,5,6-tetrafluorophenoxy)ethoxy} substituted cobalt(II), iron(II) metallophthalocyanines: Synthesis and their electrochemical, catalytic activity studies’’ Journal of Organometallic Chemistry, 828, pp. 59-67, 2017.
  • A.A. Kamıloglu, I. Acar, E.T. Saka, and Z. Bıyıklıoglu, ‘’Synthesis of polyfluoro substituted Co(II), Fe(II) phthalocyanines and their usage as catalysts for aerobic oxidation of benzyl alcohol’’ Journal of Organometallic Chemistry, 815-816, pp.1-7, 2016.
  • V. Cakır, E.T. Saka, Z. Bıyıklıoglu and H. Kantelin, ‘’Highlyselective oxidation of benzyl alcohol catalyzed by new peripherally tetra-substituted Fe(II) and Co(II) phthalocyanines’’ Synthetic Metals, 197, pp. 233-239, 2014.
  • A.A. Kamıloglu, E.T. Saka, Z. Bıyıklıoglu, I. Acar and H. Kantekin, ‘’Investigation of catalytic activity of new Co(II) phthalocyanine complexes in cyclohexene oxidation using different type of oxidants’’ Journal of Organometallic Chemistry, 745-746, pp. 18-24, 2013.
  • Z. Bıyıklıoglu, E.T. Saka, S. Gökçe and H. Kantekin, ‘’Synthesis, characterization and investigation of homogeneous oxidation activities of peripherally tetra-substituted Co(II) and Fe(II) phthalocyanines: Oxidation of cyclohexene’’ Journal of Molecular Catalysis A:Chemical, 378, pp. 156-163, 2013.
  • E.T. Saka, G. Sarkı, H. Kantekin and A. Koca, ‘’Electrochemical, spectroelectrochemical and catalytical properties of new Cu(II) and Co(II) phthalocyanines’’ Synthetic Metals, 214, pp. 82-91, 2016.
Year 2020, Volume: 24 Issue: 5, 1029 - 1039, 01.10.2020
https://doi.org/10.16984/saufenbilder.630325

Abstract

Supporting Institution

Karadeniz Teknik Üniversitesi

Project Number

7687

Thanks

Bu çalışma Karadeniz Teknik Üniversitesi Bilimsel Araştırma Projeleri Koordinasyon birimi tarafından desteklenmektedir.

References

  • C.C. Lezznof and A.B.P. Lever, ‘’Phthalocyanines, Properties and Applications’’, 4, VCH Publisher, New York, (1996).
  • G. Guillaud, J. Simon and J.P. Germain, ‘’Metallophthalocyanines: gas sensors, resistors and field effect transistors’’, Coordination Chemistry Reviews, 178, pp 1433–1484, 1998.
  • M. Durmus and T. Nyokong ‘’The synthesis, fluorescence behaviour and singlet oxygen studies of new water-soluble cationic gallium(III)phthalocyanines’’, Inorganic Chemistry Communications, 10, pp 332–338, 2007.
  • H.A. Abdeldayem, D.O. Frazier, B.G. Penn, D.D. Smith and C.E. Banks, ‘’Non-linear op-tothermal properties of metal-freephthalocyanine’’, Thin Solid Films, 350, pp 245–248, 1999.
  • Q. Luo, H. Tian, B. Chen and W. Huang, ‘’Effective non-destructive read out of photo-chromic bisthienyletheneephthalocyanine hybrid’’, Dyes and Pigments, 73, pp 118–120, 2007.
  • W.S.G. Medina N.A.G. dosSantos C. Curti A.C. Tedesco and A.C. dosSantos, ‘’Effects of zincphthalocyaninetetrasulfonate-based photodynamic therapy on rat brain iso-lated mitochondria’’, Chemico Biological Interactions, 79, pp 402–406, 2009.
  • B.G.Fanchiotti, M.P. ZamprognoMachado, L.C. Paula, M. Durmus, T. Nyokong, A.S. Gonçalves and A.R. Silva, ‘’The photobleaching of the free and encapsulated metallic phthalocyanine and its effect on the photooxidation of simple molecules’’, Journal of Photochemistry and Photobiology B: Biology, 165, pp 10-23, 2016.
  • Z. Biyiklioglu, V. Cakir, A. Koca and H. Kantekin, ‘’Synthesis, electrochemical, in-situ spectro electrochemical and in-situelectrocolorimetric characterizationofnon-peripheraltetra substitutedmetal-free and metallophthalocyanines’’, Dyes and Pigments, 89, pp 49-55, 2011.
  • P.T. Anastas and J.C. Warner, ‘’Green Chemistry Theory and Practice’’, 148, Oxford University Press, New York, 1998.
  • Y. Ding, F. Yang, L. Zhu, N. Wang and H. Tang, ‘’Synergisticphotocatalytic properties andmechanism of g-C3N4 coupled with zinc phthalocyanine catalyst undervisiblelight irradiation’’, Applied CatalysisB: Environmental, 164, pp. 151–158, 2015.
  • F. Goettmann, A. Fischer, M. Antonietti and A. Thomas, ‘’Chemical synthesisofmesoporousarbon nitrides using hard templates and their use as a metal-free catalyst forFriedel-Crafts reaction of benzene’’, Angewandte Chemie International Edition, 45, pp. 4467–4471, 2006.
  • S. Yan, S. Lv, Z. Li and Z. Zou, ‘’Organic–inorganic composite photocatalyst of g-C3N4 and TaON with improved visible light photocatalytic activities’’, Dalton Transactions, 39, pp. 1488–1491, 2010.
  • H. Li, J. Liu, W. Hou, N. Du, R. Zhang and X. Tao, ‘’Synthesis and characterization of g-C3N4/Bi2MoO6 heterojunctions with enhanced visible light photocatalytic activity’’, Applied Catalysis B: Environmental, 160–161, pp. 89–97, 2014.
  • S. Wang, D. Li, C. Sun, S. Yang, Y. Guan and H. He, ‘’Synthesis and characterization of g-C3N4/Ag3VO4 composites with significantly enhanced visible-light photocatalytic activity for triphenylmethane dye degradation’’, Applied Catalysis B: Environmental, 144, pp. 885–892, 2014.
  • W. Wang, J.C. Yu, D. Xia, P.K. Wong and Y. Li, ‘’Graphene and g-C3N4 Nanosheets Cowrapped Elemental α-Sulfur As a Novel Metal-Free Heterojunction Photocatalyst for Bacterial Inactivation under Visible-Light’’, Environmental Science and Technology, 47, pp. 8724–8732, 2013.
  • J. Xu, G. Wang, J. Fan, B. Liu, S. Cao and J.J. Yu, ‘’g-C3N4 modified TiO2 nanosheets with enhanced photoelectric conversion efficiency in dye-sensitized solar cells’’, Power Sources, 274, pp. 77–84, 2015.
  • A. Hern ́andez-Gordillo, A.G. Romero, F. Tzompantzi and R. Gómez, ‘’Kinetic study of the 4-Nitrophenol photooxidation and photo reduction reaction susing CdS’’, Applied Catalysis B: Environmental, 144, pp. 507–513, 2014.
  • W. Muersa and G.S. Pozan Soylu, ‘’Effects of metal oxide semiconductors on the photocatalytic degradation of 4-nitrophenol’’, Journal of Molecular Structure, 1174, pp. 96-102, 2018.
  • L. Coche-Guerente, P. Labbe and V. Mengeaud, ‘’Theoretical and experimental study of the phenol-polyphenol oxidase system immobilized in Laponite hydrogels and layer-by-layer self-assembled structures’’, Analytical Chemistry, 73, pp. 3206-3216, 2001.
  • A.E. Navarro, N.A. Cuizano, R.F. Portales and B.P.Llanos, ‘’Adsorptive removal of 2- nitrophenol and 2-chlorophenol by cross-linked algae from aqueous solutions’’, Separation Science and Technology, 43, pp. 3183-3199, 2008.
  • S.Q. Yu, J. Hu and J.L. Wang, ‘’Gamma radiation-induced degradation of p-nitrophenol (PNP) in the presence of hydrogen peroxide (H2O2) in aqueous solution, Journal of Hazardous Materials, 177, 1061-1067, (2010).
  • E.T. Saka, ‘’Preparation, characterization of new Co(II) and Cu(II) phthalocyanines and their catalytic performances in aerobic oxidation of substituted phenols’’, Journal of Inclusion Phenomena and Macrocyclic Chemistry, 91, pp. 61-69, 2018.
  • Y. Unver, H. Bas and Z. Biyiklioglu, ‘’Non-peripherally 4-{[(1E)-1-benzothien-2-ylmethylene]amino}phenol substituted zinc(II), manganese(III), cobalt(II) phthalocyanines:Synthesis and electrochemistry’’, Journal of Molecular Structure, 1178, pp. 508-513, 2019.
  • E. Turker Acar, T. Akkızlar Tabakloglu, D. Atilla, F. Yüksel and G. Atun, ‘’Synthesis, electrochemistry and electrocatalytic activity of cobaltphthalocyanine complexes – Effects of substituents for oxygen reduction reaction’’, Polyhedron, 152, pp. 114-124, 2019.
  • I. Altın, M. Sokmen and Z. Bıyıklıoglu, ‘’Quaternized zinc(II) phthalocyanine-sensitized TiO2: surfactant-modified sol-gel synthesis, characterization and photocatalytic applications’’ Desalination and Water Treatment, 57, pp. 16196-16207, 2016.
  • R. Bayrak, C. Albay, M. Koç, I. Altın, I. Degirmenci and M. Sokmen, ‘’Preparation of phthalocyanine/TiO2 nanocomposites for photocatalytic removal of toxic Cr(VI) ions’’, Process Safety and Environmental Protection, 102, pp. 294-302, 2016.
  • S. Mapukata N. Kobayashi, M. Kimura and T. Nyokong, ‘’Asymmetrical and symmetrical zinc phthalocyanine-cobalt ferrite conjugates embedded in electrospun fibers for dual photocatalytic degradation of azo dyes: Methyl Orange and Orange G’’ Journal of Photochemistry and Photobiology A: Chemistry, 379, pp. 112-122, 2019.
  • W.L.He and C.D.Wu, ‘’Incorporation of Fe-phthalocyanines into a porous organic framework for highly efficient photocatalytic oxidation of arylalkane’’ Applied Catalysis B:Environmental, 234, pp. 290-295, 2018.
  • M. Lu, B. Li, Y. Zhang, Q. Liang, X. Li, S. Xu and Z. Li, ‘’Facile synthesis and characterization of a cobalt phthalocyanine sensitized SnIn4S8 composites toward enhanced photocatalytic activity, Journal of Materials Science: Materials in electronics’’ 29, pp. 16680–16690 2018.
  • P. Arunachalam, S. Zhang, T. Abe, M. Komura, T. Iyoda and K. Nagai, ‘’Weak visible light (∼mW/cm2) organophotocatalysis for mineralization of amine, thiol and aldehyde by biphasic cobalt phthalocyanine/fullerene nanocomposites prepared by wet process’’ Applied Catalysis B:Environmental, 193, pp. 240-247, 2016.
  • V. Iliev and D. Tomova, ‘’Photocatalytic oxidation of sulfide ion catalyzed by phthalocyanine modified titania’’ Catalysis Communications 3, pp. 287–292, 2002.
  • G.Mele, R. Del Sole, G. Vasapollo, E. García-López, L. Palmisano and M. Schiavello, ‘’Photocatalytic degradation of 4-nitrophenol in aqueous suspension by using polycrystalline TiO2 impregnated with functionalized Cu(II)–porphyrin or Cu(II)–phthalocyanine’’ Journal of Catalysis, 217, pp. 334–342, 2003.
  • Y. Mahmiani, A.M. Sevim and A. Gül, ‘’Photocatalytic degradation of 4-chlorophenol under visible light by using TiO2 catalysts impregnated with Co(II) and Zn(II) phthalocyanine derivatives’’ Journal of Photochemistry and Photobiology A: Chemistry, 321, pp. 24–32, 2016.
  • T.B. Ogunbayo, E. Antunes and T. Nyokong, ‘’Investigation of homogeneous photosensitized oxidation activities of palladium and platinum octasubstituted phthalocyanines: Oxidation of 4-nitrophenol’’ Journal of Molecular Catalysis A: Chemical, 334, pp. 123–129, 2011.
  • E. Marais, R. Klein, E. Antunes and T. Nyokong, ‘’Photocatalysis of 4-nitrophenol using zinc phthalocyanine complexes’’ Journal of Molecular Catalysis A: Chemical, 261, pp. 36–42, 2007.
  • A.A. Kamıloglu, I. Acar, Z. Bıyıklıoglu and E.T. Saka, ‘’Peripherally tetra-{2-(2,3,5,6-tetrafluorophenoxy)ethoxy} substituted cobalt(II), iron(II) metallophthalocyanines: Synthesis and their electrochemical, catalytic activity studies’’ Journal of Organometallic Chemistry, 828, pp. 59-67, 2017.
  • A.A. Kamıloglu, I. Acar, E.T. Saka, and Z. Bıyıklıoglu, ‘’Synthesis of polyfluoro substituted Co(II), Fe(II) phthalocyanines and their usage as catalysts for aerobic oxidation of benzyl alcohol’’ Journal of Organometallic Chemistry, 815-816, pp.1-7, 2016.
  • V. Cakır, E.T. Saka, Z. Bıyıklıoglu and H. Kantelin, ‘’Highlyselective oxidation of benzyl alcohol catalyzed by new peripherally tetra-substituted Fe(II) and Co(II) phthalocyanines’’ Synthetic Metals, 197, pp. 233-239, 2014.
  • A.A. Kamıloglu, E.T. Saka, Z. Bıyıklıoglu, I. Acar and H. Kantekin, ‘’Investigation of catalytic activity of new Co(II) phthalocyanine complexes in cyclohexene oxidation using different type of oxidants’’ Journal of Organometallic Chemistry, 745-746, pp. 18-24, 2013.
  • Z. Bıyıklıoglu, E.T. Saka, S. Gökçe and H. Kantekin, ‘’Synthesis, characterization and investigation of homogeneous oxidation activities of peripherally tetra-substituted Co(II) and Fe(II) phthalocyanines: Oxidation of cyclohexene’’ Journal of Molecular Catalysis A:Chemical, 378, pp. 156-163, 2013.
  • E.T. Saka, G. Sarkı, H. Kantekin and A. Koca, ‘’Electrochemical, spectroelectrochemical and catalytical properties of new Cu(II) and Co(II) phthalocyanines’’ Synthetic Metals, 214, pp. 82-91, 2016.
There are 41 citations in total.

Details

Primary Language English
Journal Section Research Articles
Authors

Ece Tuğba Saka 0000-0002-1074-7752

Project Number 7687
Publication Date October 1, 2020
Submission Date October 7, 2019
Acceptance Date August 6, 2020
Published in Issue Year 2020 Volume: 24 Issue: 5

Cite

APA Saka, E. T. (2020). Synthesis, Characterization and Photocatalytic Properties of Non-peripherally 3- (pyridin-4-yl) propane-1-oxy Groups Substituted Cu (II) Phthalocyanine and Water Soluble Derivative. Sakarya University Journal of Science, 24(5), 1029-1039. https://doi.org/10.16984/saufenbilder.630325
AMA Saka ET. Synthesis, Characterization and Photocatalytic Properties of Non-peripherally 3- (pyridin-4-yl) propane-1-oxy Groups Substituted Cu (II) Phthalocyanine and Water Soluble Derivative. SAUJS. October 2020;24(5):1029-1039. doi:10.16984/saufenbilder.630325
Chicago Saka, Ece Tuğba. “Synthesis, Characterization and Photocatalytic Properties of Non-Peripherally 3- (pyridin-4-Yl) Propane-1-Oxy Groups Substituted Cu (II) Phthalocyanine and Water Soluble Derivative”. Sakarya University Journal of Science 24, no. 5 (October 2020): 1029-39. https://doi.org/10.16984/saufenbilder.630325.
EndNote Saka ET (October 1, 2020) Synthesis, Characterization and Photocatalytic Properties of Non-peripherally 3- (pyridin-4-yl) propane-1-oxy Groups Substituted Cu (II) Phthalocyanine and Water Soluble Derivative. Sakarya University Journal of Science 24 5 1029–1039.
IEEE E. T. Saka, “Synthesis, Characterization and Photocatalytic Properties of Non-peripherally 3- (pyridin-4-yl) propane-1-oxy Groups Substituted Cu (II) Phthalocyanine and Water Soluble Derivative”, SAUJS, vol. 24, no. 5, pp. 1029–1039, 2020, doi: 10.16984/saufenbilder.630325.
ISNAD Saka, Ece Tuğba. “Synthesis, Characterization and Photocatalytic Properties of Non-Peripherally 3- (pyridin-4-Yl) Propane-1-Oxy Groups Substituted Cu (II) Phthalocyanine and Water Soluble Derivative”. Sakarya University Journal of Science 24/5 (October 2020), 1029-1039. https://doi.org/10.16984/saufenbilder.630325.
JAMA Saka ET. Synthesis, Characterization and Photocatalytic Properties of Non-peripherally 3- (pyridin-4-yl) propane-1-oxy Groups Substituted Cu (II) Phthalocyanine and Water Soluble Derivative. SAUJS. 2020;24:1029–1039.
MLA Saka, Ece Tuğba. “Synthesis, Characterization and Photocatalytic Properties of Non-Peripherally 3- (pyridin-4-Yl) Propane-1-Oxy Groups Substituted Cu (II) Phthalocyanine and Water Soluble Derivative”. Sakarya University Journal of Science, vol. 24, no. 5, 2020, pp. 1029-3, doi:10.16984/saufenbilder.630325.
Vancouver Saka ET. Synthesis, Characterization and Photocatalytic Properties of Non-peripherally 3- (pyridin-4-yl) propane-1-oxy Groups Substituted Cu (II) Phthalocyanine and Water Soluble Derivative. SAUJS. 2020;24(5):1029-3.