Research Article
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Year 2021, , 33 - 38, 29.06.2021
https://doi.org/10.51435/turkjac.935057

Abstract

Project Number

FHD-2018-7631

References

  • [1] A. Arul, M. Christy, M. Y. Oh, Y. S. Lee, K. S. Nahm, Nanofiber Carbon-Supported Phthalocyanine Metal Complexes as Solid Electrocatalysts for Lithium-Air Batteries, Electrochim Acta, 218, 2016, 335-344.
  • [2] Y. Xuan, L. Xie, X. Huang, B. Su, Molecular electrocatalysis of oxygen reduction by iron(II) phthalocyanine at the liquid/liquid interface, J Electroanal Chem, 766, 2016 37-43.
  • [3] H. Karaca, Redox chemistry, spectroelectrochemistry and catalytic activity of novel synthesized phthalocyanines bearing four schiff bases on the periphery, J Organomet Chem, 822, 2016, 39-45.
  • [4] I.A. Tarasyuk, I. A. Kuzmin, Y. S. Marfin, A. S. Vashurin, A. A. Voronina, E. V. Rumyantsev, Synthesis and catalytic properties of hybrid materials based on organically modified silica matrix with cobalt phthalocyanine, Synth Met, 217, 2016, 189-196.
  • [5] N. Li, Z. Sun, R. Liu, L. Xu, K. Xu, X.-M. Song, Enhanced power conversion efficiency in phthalocyanine-sensitized solar cells by modifying TiO2 photoanode with polyoxometalate, Sol Energy Mater Sol Cells, 157, 2016, 853-860.
  • [6] H. S. Majumdar, A. Bandyopadhyay, A. J. Pal, Data-storage devices based on layer-by-layer self-assembled films of a phthalocyanine derivative, Org Electron, 4, 2003, 39-44.
  • [7] S.M.A. Pinto, V.A. Tomé, M. J.F. Calvete, M.M. Pereira, H.D. Burrows, A.M.S. Cardoso, A.Pallier, M. M. C.A. Castro, É. Tóth, C. F.G.C. Geraldes, The quest for biocompatible phthalocyanines for molecular imaging: Photophysics, relaxometry and cytotoxicity studies, J Inorg Biochem, 154, 2016, 50-59.
  • [8] V.Chauke, ve T. Nyokong, Photocatalytic oxidation of 1-hexene using GaPc and InPc octasubstituted derivatives, J Mol Catal A-Chem, 289, 2008, 9-13.
  • [9] Y. Zorlu, F. Dumoulin, D. Bouchu, V.Ahsen, D. Lafont, Monoglycoconjugated water-soluble phthalocyanines. Design and synthesis of potential selectively targeting PDT photosensitisers, Tetrahedron Lett, 51, 2010, 6615-6618.
  • [10] T. Nyokong, Electronic spectral and electrochemical behaviour of near infrared absorbing metallophthalocyanines". In: Structure and Bonding: Functional Phthalocyanine Molecular Materials. Editors: J. Jianzhuang, 2010, Berlin, Springer.
  • [11] Z. Biyiklioglu, O. Bekircan, Synthesis and electrochemical properties of axially disubstituted silicon phthalocyanine and peripherally tetra substituted manganese(III) phthalocyanine bearing 1,2,4-triazole substituents, Synth Met, 200, 2015, 148-155.
  • [12] A. Nas, H.Kantekin, A. Koca, Novel 4-(2-(benzo[d]thiazol-2-yl)phenoxy) substituted phthalocyanine derivatives: Synthesis, electrochemical and in situ spectroelectrochemical characterization, J Organomet Chem, 757, 2014, 62-71.
  • [13] Z. Bıyıklıoğlu, V. Çakır, D. Çakır, H. Kantekin, Crown ether-substituted water soluble phthalocyanines and their aggregation, electrochemical studies, J Organomet Chem, 749, 2014, 18-25.
  • [14] E. T. Saka, G. Sarkı, H.Kantekin, A. Koca, Electrochemical, spectroelectrochemical and catalytical properties of new Cu(II) and Co(II) phthalocyanines, Synth Met, 214 ,2016, 82-91.
  • [15] E.T. Saka, R. Z. U. Kobak, H. Alp, G. Sarkı, A. Koca, H. Kantekin, Electrochemical and spectroelectrochemical properties of new metal free, nickel(II), lead(II) and zinc(II) phthalocyanines, Synth Met, 217, 2016, 295-303.
  • [16] Ö. İpsiz, H. Y. Yenilmez, K. Kaya, A. Koca, Z. A. Bayır, Carbazole-substituted metallo-phthalocyanines: Synthesis, electrochemical, and spectroelectrochemical properties, Synthetic Metals, 217, 2016, 94-101.
  • [17] Ü. Demirbaş, R. Z. U. Kobak, H. T. Akçay, D. Ünlüer, A. Koca, F. Çelik, H. Kantekin, Synthesis, characterization, electrochemical and spectroelectrochemical properties of novel peripherally tetra-1,2,4-triazole substituted phthalocyanines, Synth Met, 215, 2016, 68-76.
  • [18] A. Koca, H. A. Dinçer, H. Çerlek, A.Gül, M. B. Koçak, Spectroelectrochemical characterization and controlled potential chronocoulometric demetallation of tetra- and octa-substituted lead phthalocyanines, Electrochim Acta, 52, 2006, 1199-1205.
  • [19] A. L. Uğur, A. Erdoğmuş, A. Koca, U. Avcıata, Synthesis, spectroscopic, electrochemical and spectroelectrochemical properties of metal free, manganese, and cobalt phthalocyanines bearing peripherally octakis-[4-(thiophen-3-yl)-phenoxy] substituents, Polyhedron, 29, 2010, 3310-3317.
  • [20] H.R. P. Karaoğlu, A. Koca, M. B. Koçak, The synthesis and electrochemistry of novel, symmetrical, octasubstituted phthalocyanines, Synth Met, 182, 2013, 1-8.
  • [21] A. Nas. The photo-physicochemical properties of an octa-substituted zinc phthalocyanine containing 1,2,4-triazole moieties, J Coord Chem, 69, 2016, 1326-1336.
  • [22] G. Dilber, H. Altunparmak, A. Nas, H. Kantekin, M. Durmuş, The peripheral and non-peripheral 2H-benzotriazole substituted phthalocyanines: Synthesis, characterization, photophysical and photochemical studies of zinc derivatives, Spectrochim Acta A, 217, 2019, 128-140.
  • [23] M.J. Stillman, T. Nyokong, Phthalocyanines: properties and applications, Editors: C. C. Leznoff, 1989, New York, VCH Publishers.
  • [24] G. G. Köse, G. K. Karaoğlan, S. N. Işık, D. Akyüz, A. Koca, The Synthesis, Characterization, Electrochemical and Spectroelectrochemical Properties of Novel Unsymmetrical Phthalocyanines Containing Naphthoic Acid and Di-tert-butylphenoxy, Synth Met, 264, 2020, 116386.

New octa-benzothiazole substituted metal free and metallophthalocyanines: Synthesis, characterization and electrochemical studies

Year 2021, , 33 - 38, 29.06.2021
https://doi.org/10.51435/turkjac.935057

Abstract

The synthesis, spectroscopic and electrochemical properties of the following octa-benzothiazole substituted metal-free (4), cobalt(II) (5) and zinc (II) (6) phthalocyanines are reported for the first time. The novel phthalocyanines have been characterized by FT-IR, NMR spectroscopy, electronic spectroscopy and mass spectroscopy. Voltammetric analysis of benzothiazole group substituted phthalocyanines were determined by cyclic (CV) and square wave voltammetry (SWV). According to the results, phthalocyanines revealed metal and ligand-based quasi-reversible reduction and oxidation processes.

Supporting Institution

Karadeniz Technical University

Project Number

FHD-2018-7631

References

  • [1] A. Arul, M. Christy, M. Y. Oh, Y. S. Lee, K. S. Nahm, Nanofiber Carbon-Supported Phthalocyanine Metal Complexes as Solid Electrocatalysts for Lithium-Air Batteries, Electrochim Acta, 218, 2016, 335-344.
  • [2] Y. Xuan, L. Xie, X. Huang, B. Su, Molecular electrocatalysis of oxygen reduction by iron(II) phthalocyanine at the liquid/liquid interface, J Electroanal Chem, 766, 2016 37-43.
  • [3] H. Karaca, Redox chemistry, spectroelectrochemistry and catalytic activity of novel synthesized phthalocyanines bearing four schiff bases on the periphery, J Organomet Chem, 822, 2016, 39-45.
  • [4] I.A. Tarasyuk, I. A. Kuzmin, Y. S. Marfin, A. S. Vashurin, A. A. Voronina, E. V. Rumyantsev, Synthesis and catalytic properties of hybrid materials based on organically modified silica matrix with cobalt phthalocyanine, Synth Met, 217, 2016, 189-196.
  • [5] N. Li, Z. Sun, R. Liu, L. Xu, K. Xu, X.-M. Song, Enhanced power conversion efficiency in phthalocyanine-sensitized solar cells by modifying TiO2 photoanode with polyoxometalate, Sol Energy Mater Sol Cells, 157, 2016, 853-860.
  • [6] H. S. Majumdar, A. Bandyopadhyay, A. J. Pal, Data-storage devices based on layer-by-layer self-assembled films of a phthalocyanine derivative, Org Electron, 4, 2003, 39-44.
  • [7] S.M.A. Pinto, V.A. Tomé, M. J.F. Calvete, M.M. Pereira, H.D. Burrows, A.M.S. Cardoso, A.Pallier, M. M. C.A. Castro, É. Tóth, C. F.G.C. Geraldes, The quest for biocompatible phthalocyanines for molecular imaging: Photophysics, relaxometry and cytotoxicity studies, J Inorg Biochem, 154, 2016, 50-59.
  • [8] V.Chauke, ve T. Nyokong, Photocatalytic oxidation of 1-hexene using GaPc and InPc octasubstituted derivatives, J Mol Catal A-Chem, 289, 2008, 9-13.
  • [9] Y. Zorlu, F. Dumoulin, D. Bouchu, V.Ahsen, D. Lafont, Monoglycoconjugated water-soluble phthalocyanines. Design and synthesis of potential selectively targeting PDT photosensitisers, Tetrahedron Lett, 51, 2010, 6615-6618.
  • [10] T. Nyokong, Electronic spectral and electrochemical behaviour of near infrared absorbing metallophthalocyanines". In: Structure and Bonding: Functional Phthalocyanine Molecular Materials. Editors: J. Jianzhuang, 2010, Berlin, Springer.
  • [11] Z. Biyiklioglu, O. Bekircan, Synthesis and electrochemical properties of axially disubstituted silicon phthalocyanine and peripherally tetra substituted manganese(III) phthalocyanine bearing 1,2,4-triazole substituents, Synth Met, 200, 2015, 148-155.
  • [12] A. Nas, H.Kantekin, A. Koca, Novel 4-(2-(benzo[d]thiazol-2-yl)phenoxy) substituted phthalocyanine derivatives: Synthesis, electrochemical and in situ spectroelectrochemical characterization, J Organomet Chem, 757, 2014, 62-71.
  • [13] Z. Bıyıklıoğlu, V. Çakır, D. Çakır, H. Kantekin, Crown ether-substituted water soluble phthalocyanines and their aggregation, electrochemical studies, J Organomet Chem, 749, 2014, 18-25.
  • [14] E. T. Saka, G. Sarkı, H.Kantekin, A. Koca, Electrochemical, spectroelectrochemical and catalytical properties of new Cu(II) and Co(II) phthalocyanines, Synth Met, 214 ,2016, 82-91.
  • [15] E.T. Saka, R. Z. U. Kobak, H. Alp, G. Sarkı, A. Koca, H. Kantekin, Electrochemical and spectroelectrochemical properties of new metal free, nickel(II), lead(II) and zinc(II) phthalocyanines, Synth Met, 217, 2016, 295-303.
  • [16] Ö. İpsiz, H. Y. Yenilmez, K. Kaya, A. Koca, Z. A. Bayır, Carbazole-substituted metallo-phthalocyanines: Synthesis, electrochemical, and spectroelectrochemical properties, Synthetic Metals, 217, 2016, 94-101.
  • [17] Ü. Demirbaş, R. Z. U. Kobak, H. T. Akçay, D. Ünlüer, A. Koca, F. Çelik, H. Kantekin, Synthesis, characterization, electrochemical and spectroelectrochemical properties of novel peripherally tetra-1,2,4-triazole substituted phthalocyanines, Synth Met, 215, 2016, 68-76.
  • [18] A. Koca, H. A. Dinçer, H. Çerlek, A.Gül, M. B. Koçak, Spectroelectrochemical characterization and controlled potential chronocoulometric demetallation of tetra- and octa-substituted lead phthalocyanines, Electrochim Acta, 52, 2006, 1199-1205.
  • [19] A. L. Uğur, A. Erdoğmuş, A. Koca, U. Avcıata, Synthesis, spectroscopic, electrochemical and spectroelectrochemical properties of metal free, manganese, and cobalt phthalocyanines bearing peripherally octakis-[4-(thiophen-3-yl)-phenoxy] substituents, Polyhedron, 29, 2010, 3310-3317.
  • [20] H.R. P. Karaoğlu, A. Koca, M. B. Koçak, The synthesis and electrochemistry of novel, symmetrical, octasubstituted phthalocyanines, Synth Met, 182, 2013, 1-8.
  • [21] A. Nas. The photo-physicochemical properties of an octa-substituted zinc phthalocyanine containing 1,2,4-triazole moieties, J Coord Chem, 69, 2016, 1326-1336.
  • [22] G. Dilber, H. Altunparmak, A. Nas, H. Kantekin, M. Durmuş, The peripheral and non-peripheral 2H-benzotriazole substituted phthalocyanines: Synthesis, characterization, photophysical and photochemical studies of zinc derivatives, Spectrochim Acta A, 217, 2019, 128-140.
  • [23] M.J. Stillman, T. Nyokong, Phthalocyanines: properties and applications, Editors: C. C. Leznoff, 1989, New York, VCH Publishers.
  • [24] G. G. Köse, G. K. Karaoğlan, S. N. Işık, D. Akyüz, A. Koca, The Synthesis, Characterization, Electrochemical and Spectroelectrochemical Properties of Novel Unsymmetrical Phthalocyanines Containing Naphthoic Acid and Di-tert-butylphenoxy, Synth Met, 264, 2020, 116386.
There are 24 citations in total.

Details

Primary Language English
Subjects Analytical Chemistry
Journal Section Research Articles
Authors

Gülsev Dilber 0000-0001-7114-4421

Asiye Nas 0000-0003-0627-0645

Zekeriya Bıyıklıoğlu 0000-0001-5138-214X

Project Number FHD-2018-7631
Publication Date June 29, 2021
Submission Date May 10, 2021
Acceptance Date June 4, 2021
Published in Issue Year 2021

Cite

APA Dilber, G., Nas, A., & Bıyıklıoğlu, Z. (2021). New octa-benzothiazole substituted metal free and metallophthalocyanines: Synthesis, characterization and electrochemical studies. Turkish Journal of Analytical Chemistry, 3(1), 33-38. https://doi.org/10.51435/turkjac.935057
AMA Dilber G, Nas A, Bıyıklıoğlu Z. New octa-benzothiazole substituted metal free and metallophthalocyanines: Synthesis, characterization and electrochemical studies. TurkJAC. June 2021;3(1):33-38. doi:10.51435/turkjac.935057
Chicago Dilber, Gülsev, Asiye Nas, and Zekeriya Bıyıklıoğlu. “New Octa-Benzothiazole Substituted Metal Free and Metallophthalocyanines: Synthesis, Characterization and Electrochemical Studies”. Turkish Journal of Analytical Chemistry 3, no. 1 (June 2021): 33-38. https://doi.org/10.51435/turkjac.935057.
EndNote Dilber G, Nas A, Bıyıklıoğlu Z (June 1, 2021) New octa-benzothiazole substituted metal free and metallophthalocyanines: Synthesis, characterization and electrochemical studies. Turkish Journal of Analytical Chemistry 3 1 33–38.
IEEE G. Dilber, A. Nas, and Z. Bıyıklıoğlu, “New octa-benzothiazole substituted metal free and metallophthalocyanines: Synthesis, characterization and electrochemical studies”, TurkJAC, vol. 3, no. 1, pp. 33–38, 2021, doi: 10.51435/turkjac.935057.
ISNAD Dilber, Gülsev et al. “New Octa-Benzothiazole Substituted Metal Free and Metallophthalocyanines: Synthesis, Characterization and Electrochemical Studies”. Turkish Journal of Analytical Chemistry 3/1 (June 2021), 33-38. https://doi.org/10.51435/turkjac.935057.
JAMA Dilber G, Nas A, Bıyıklıoğlu Z. New octa-benzothiazole substituted metal free and metallophthalocyanines: Synthesis, characterization and electrochemical studies. TurkJAC. 2021;3:33–38.
MLA Dilber, Gülsev et al. “New Octa-Benzothiazole Substituted Metal Free and Metallophthalocyanines: Synthesis, Characterization and Electrochemical Studies”. Turkish Journal of Analytical Chemistry, vol. 3, no. 1, 2021, pp. 33-38, doi:10.51435/turkjac.935057.
Vancouver Dilber G, Nas A, Bıyıklıoğlu Z. New octa-benzothiazole substituted metal free and metallophthalocyanines: Synthesis, characterization and electrochemical studies. TurkJAC. 2021;3(1):33-8.



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