Electroanalytical characterization of chloroquinoline substituted redox-active phthalocyanines

Year 2023, Volume: 5 Issue: 1, 25 - 31, 30.06.2023

Asiye Nas Gülsev Dilber Zekeriya Bıyıklıoğlu

https://doi.org/10.51435/turkjac.1307391

Cited By: 1

Abstract

In the first part of this study, the synthesis and characterization of organosoluble 5-chloroquinolin-8-yloxy substituted iron(II) (2) and oxo-titanium (IV) phthalocyanines (3) are reported for the first time. These compounds have been characterized by elemental analysis, Fourier transform infrared, electronic spectroscopy, and mass spectra. Electrochemical behaviors of metal-free and cobalt phthalocyanines and further new types of iron and oxo-titanium phthalocyanines were investigated using electroanalytical methods, such as cyclic (CV) and square wave voltammetry (SWV). According to the electrochemical results, phthalocyanines by and large showed one-electron metal- and/or ligand-based reversible or quasi-reversible reduction and oxidation processes.
All in all, this study's results inevitably create a useful way to use them in possible future studies, which will particularly attempt to use the compound investigated in potential areas of use.

Keywords

Iron, Titanium, Electrochemistry, Redox-active

Supporting Institution

KARADENİZ TEKNİK ÜNİVERSİTESİ BİLİMSEL ARAŞTIRMA FONU

Project Number

FHD-2018-7631

Thanks

This study was supported by the Karadeniz Technical University Research Fund, Project No: FHD-2018-7631 (Trabzon-Turkey).

References

• A. Suzuki, H. Okumura, Y. Yamasaki, T. Oku, Fabrication and characterization of perovskite type solar cells using phthalocyanine complexes, Appl Surf Sci, 488, 2019, 586-596 (https://doi.org/10.1016/j.apsusc.2019.05.305)
• J. Xu, W. Yang, R. Chen, The photovoltaic performance of highly asymmetric phthalocyanine-sensitized brookite-based solar cells, Optik, 200, 2020, 163413. (https://doi.org/10.1016/j.ijleo.2019.163413)
• B. Yıldız, E. Güzel, D. Akyüz, B.S. Arslan, A. Koca, M.K. Şener, Unsymmetrically pyrazole-3-carboxylic acid substituted phthalocyanine-based photoanodes for use in water splitting photoelectrochemical and dye-sensitized solar cells, Sol Energy, 191, 2019, 654-662. (https://doi.org/10.1016/j.solener.2019.09.043)
• S. Kong, X. Wang, L. Bai, Y. Song, F. Meng, Multi-arm ionic liquid crystals formed by pyridine-mesophase and copper phthalocyanine, J Mol Liq, 288, 2019, 111012. (https://doi.org/10.1016/j.molliq.2019.111012)
• J.A. Jiménez-Tejada, A. Romero, J. González, N.B. Chaure, A.N. Cammidge, I. Chambrier, A.K. Ray, M.J. Deen, Evolutionary Computation for Parameter Extraction of Organic Thin-Film Transistors Using Newly Synthesized Liquid Crystalline Nickel Phthalocyanine, Micromachines, 10, 2019, 683. ( https://doi.org/10.3390/mi10100683)
• E.M. Bauer, T. De Caro, P. Tagliatesta, M. Carbone, Unraveling The Real pigment composition of tattoo inks: the case of bi-components phthalocyanine based greens, Dyes Pigments, 167, 2019, 225-235. ( http://dx.doi.org/10.1016/j.dyepig.2019.04.018)
• Y. Zhao, J. W. Ying, Q. Sun, M. R. Ke, B. Y. Zheng, J. D. Huang, A novel silicon(IV) phthalocyanine-oligopeptide conjugate as a highly efficient photosensitizer for photodynamic antimicrobial therapy, Dyes Pigments, 172, 2020, 107834. (https://doi.org/10.1016/j.dyepig.2019.107834)
• Q. Li, Z. Sun, Q. Liang, M. Zhou, D. Sun, Novel tetrasubstituted zinc phthalocyanine-attapulgite composites for efficient catalytic oxidation of styrene with tert-butyl hydroperoxide as oxidant, Solid State Sci, 97, 2019, 106010. (https://doi.org/10.1016/j.solidstatesciences.2019.106010)
• R. Bahluli, S. Keshipour, Microcrystalline cellulose modified with Fe(II)- and Ni(II)-phthalocyanines: Syntheses, characterizations, and catalytic applications, Polyhedron, 169, 2019, 176-182. ( https://doi.org/10.1016/j.poly.2019.05.010)
• 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. (https://doi:10.1016/S1566-1199(03)00007-7)
• M.P. Malathesh, N.Y.P. Kumara, B.S. Jilani, K.R.V. Reddy, Synthesis and Characterization of Tetra-Ganciclovir Cobalt (II) Phthalocyanine for Electroanalytical Applications of AA/DA/UA, Heliyon, 5, 2019, e01946 (https://doi:10.1016/j.heliyon.2019.e01946)
• L.F. de Holanda, F.W.P. Ribeiro, C.P. Sousa, P.N. da S. Casciano, A.N. Correia, Multi-walled carbon nanotubes–cobalt phthalocyanine modified electrode for electroanalytical determination of acetaminophen, J Electroanal Chem, 772, 2016, 9-16. (https://doi.org/10.1016/j.jelechem.2016.04.021)
• L.F. de Lima, C.C. Maciel, A.L. Ferreira, J.C. de Almeida, M. Ferreira, 2020. Nickel (II) phthalocyanine-tetrasulfonic-Au nanoparticles nanocomposite film for tartrazine electrochemical sensing, Mater Lett, 262, 127186. (https://doi.org/10.1016/j.matlet.2019.127186)
• E.O. Moiseeva, Y.B. Platonova, D.V. Konev, S.A. Trashin, L.G. Tomilova, Electrochemical and spectroelectrochemical properties of tetra-tert-butylphthalocyanine indium(III), Mendeleev Commun, 29, 2019, 212-214. (https://doi.org/10.1016/j.mencom.2019.03.033)
• F. Demir, H.Y. Yenilmez, A. Koca, Z.A. Bayır, Metallo-phthalocyanines containing thiazole moieties: Synthesis, characterization, electrochemical and spectroelectrochemical properties and sensor applications, J Electroanal Chem, 832, 2019, 254-265. (https://doi.org/10.1016/j.jelechem.2018.11.003)
• S.G. Feridun, E.B. Orman, Ü. Salan, A.R. Özkaya, M. Bulut, Synthesis, characterization, and electrochemical and in-situ spectroelectrochemical properties of novel peripherally and non-peripherally 7-oxy-3-(3,4-dimethoxyphenyl) coumarin substituted phthalocyanines, Dyes Pigments, 160, 2019, 315-327 (https://doi.org/10.1016/j.dyepig.2018.08.017)
• T. Nyokong, Electronic spectral and electrochemical behaviour of near infrared absorbing metallophthalocyanines". In: Structure and Bonding: Functional Phthalocyanine Molecular Materials, Editors: D.M.P Mingos, 2010, Germany, Springer.
• A. Nas, H. Kantekin, A. Koca, Electrochemical and Spectroelectrochemical Analysis of 4-(4-(5-Phenyl-1,3,4-oxadiazole-2-yl)phenoxy)-Substituted Cobalt(II), Lead(II) and Metal-Free Phthalocyanines, Electroanal, 27, 2015, 1602-1609. (https://doi.org/10.1002/elan.201400700)
• A. Nas, Z. Biyiklioglu, S. Fandaklı, G. Sarkı, H. Yalazan, H. Kantekin, Tetra(3-(1,5-diphenyl-4,5-dihydro-1H-pyrazol-3-yl) phenoxy) substituted cobalt, iron and manganese phthalocyanines: Synthesis and electrochemical analysis, Inorg Chim Acta, 466, 2017, 86-92. (https://doi.org/10.1016/j.ica.2017.05.050)
• Ç.C. Koçak, A. Nas, H. Kantekin, Z. Dursun, Simultaneous determination of theophylline and caffeine on novel [Tetra-(5-chloroquinolin-8-yloxy) phthalocyanato] manganese(III)-Carbon nanotubes composite electrode, Talanta. 184, 2018, 452-460. (https://doi.org/10.1016/j.talanta.2018.03.029)
• B.S. Jilani, M.P. Malathesh, C.D. Mruthyunjayachari, K.R.V. Reddy, Cobalt (II) tetra methyl-quinoline oxy bridged phthalocyanine carbon nano particles modified glassy carbon electrode for sensing nitrite: A voltammetric study, Mater Chem Phys, 239, 2020, 121920. (https://doi.org/10.1016/j.matchemphys.2019.121920)
• A. Nas, Ü. Demirbaş, M. Pişkin, M. Durmuş, H. Kantekin, The photophysical and photochemical properties of new unmetallated and metallated phthalocyanines bearing four 5-chloroquinolin-8-yloxy substituents on peripheral sites, J Lumin, 145, 2014, 635-642. (https://doi.org/10.1016/j.jlumin.2013.07.056)
• Perrin DD, Armarego WLF, Purification of laboratory chemicals, Oxford, 1989, New York, Pergamon.
• J.G. Young, W. Onyebuagu, Synthesis and characterization of di-disubstituted phthalocyanines, J Org Chem, 55, 1990, 2155-2159. (https://doi.org/10.1021/jo00294a032)
• D. Liang , W. Peng , Y. Wang, Solvent‐Stabilized Y‐Type Oxotitanium Phthalocyanine Photoconductive Nanoparticles: Preparation and Application in Single‐Layered Photoreceptors, Adv Mater, 24, 2012, 5249-5253 (https://doi.org/10.1002/adma.201201720)
• H. Zhu, H. Song, W. Zhao, Z. Peng, D. Liu, B. Di, L. Xing, H. Chen, Z. Huang, Y. Wang, K. Wu, Precursor Structures for Polymorphic Titanyl Phthalocyanine Crystal Phases on Au(111): A High-Resolution STM Study, J Phys Chem C, 123, 2019, 17390-17396. (https://doi.org/10.1021/acs.jpcc.9b04451)
• İ. Yalçın, H. Yanık, H.T. Akçay, İ. Değirmencioğlu, M. Durmuş, Photophysical and photochemical study on the tetra 4-isopropylbenzyloxy substituted phthalocyanines, J Lumin, 192, 2017, 739-744 (https://doi.org/10.1016/j.jlumin.2017.07.062)
• İ. Ömeroğlu, Z. Bıyıklıoğlu, Synthesis and electrochemistry of phthalocyanines bearing [(3,4-dimethoxybenzyl)oxy] groups, Turk J Chem, 39, 2015, 347-358. (https://doi.org/10.3906/kim-1408-71)
• D. Akyuz, T. Keleş, Z. Bıyıklıoğlu, A. Koca, Metallophthalocyanines Bearing Polymerizable {[5-({(1E)-[4-(Diethylamino)phenyl]methylene}amino)-1-naphthy1]oxy} Groups as Electrochemical Pesticide Sensor Electroanal, 29, 2017, 2913-2924. (https://doi.org/10.1002/elan.201700366)
• A. Aktaş, İ. Acar, Z. Bıyıklıoğlu, E.T. Saka, H. Kantekin, Synthesis, electrochemistry of metal-free, copper, titanium phthalocyanines and investigation of catalytic activity of cobalt, iron phthalocyanines on benzyl alcohol oxidation bearing 4-{2-[3-trifluoromethyl)phenoxy]ethoxy} groups, Synthetic Metals, 198, 2014, 212-220 (https://doi.org/10.1016/j.synthmet.2014.10.022)
• Ö. Koyun. S. Gördük, B. Keskin, A. Çetinkaya, A. Koca, U. Avcıata, Microwave-assisted synthesis, electrochemistry and spectroelectrochemistry of phthalocyanines bearing tetra terminal-alkynyl functionalities and click approach, Polyhedron, 113, 2016, 35-49. (https://doi.org/10.1016/j.poly.2016.03.019)
• Ü. Demirbaş, D. Akyüz, A. Mermer, H.T. Akçay, N. Demirbaş, A. Koca, H. Kantekin, The electrochemical and spectroelectrochemical properties of metal free and metallophthalocyanines containing triazole/piperazine units, Spectrochim Acta Part:A Mol Biomol Spect, 153, 2016, 478-487. (https://doi.org/10.1016/j.saa.2015.08.050)