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Peripherally tetra 1,2,4-triazol substituted novel phthalocyanines: Synthesis, characterization, electrochemical and spectroelectrochemical properties

Year 2017, Issue: 1, 22 - 30, 31.12.2017

Abstract



In
this study, the synthesis, electrochemical and spectroelectrochemical
properties of new peripherally 1,2,4-triazole substituted metal-free 4, Zn(II) 5, Ti(IV) 6, Ni(II) 7 and Co(II) 8 phthalocyanine derivatives were reported.
Voltammetric and in situ spectroelectrochemical
characterization of the complexes were performed in solution. Since nickel and
zinc phthalocyanines gave common phthalocyanine ring based electron transfer
reactions with the characteristic “energy gaps”, “peak to peak potential separations”
and “half wave peak potential values”, CoII and TiIVO
metal ions behaved as redox active cations in the core of the cobalt and
titanium phthalocyanine complexes, respectively. While cobalt phthalocyanine
gave a one-electron [CoIIPc-2]/[CoIPc-2]-1
reduction reaction, titanium phthalocyanine illustrated two metal based
reduction reactions, [TiIVOPc-2]/[TiIIIOPc-2]-1
and [TiIIIOPc-2]-1/[TiIIIOPc-2]-2,
in addition to the Pc ligand reduction processes. Electron transfer reactions
altered the spectra of the complexes considerably, which is one of the most
important expectations for the practical applications of the complexes
especially in display technologies. Redox and spectral responses of cobalt and
titan complexes were affected by the molecular oxygen present in the
electrolyte, which indicates electrocatalytic and electrosensing activity of
the complexes towards the molecular oxygen.

References

  • [1] McKeown, N.B., Phthalocyanine Materials, (Cambridge University Press, Cambridge, 1998.
  • [2] Liu, H., Shen, Q., Zhang, J., Fu, W., Evaluation of various inverse docking schemes in multiple targets identification, J. Mol. Graph. Model. 2010, 29, 326-330.
  • [3] Leznoff, C.C., Lever, A. B. P., Phthalocyanines: properties and applications, New York: VCH Publisher 1996, 4.
  • [4] Jori, G., Tumour photosensitizers: approaches to enhance the selectivity and efficiency of photodynamic therapy, J. Photochem. Photobiol B: Biol. 1996, 36, 87-93.
  • [5] Moser, F.H., Thomas, L. R., Phthalocyanine compound. New York: Reinhold, 1963, 123-1451.
  • [6] Bouvet, M., Phthalocyanine-based field-effect transistors as gas sensors, Analytical and Bioanalytical Chemistry, 2006, 384, 366-373.
  • [7] Ogunsipe, A., Maree, D., Nyokong, T., Solvent effects on the photochemical and fluorescence properties of zinc phthalocyanine derivatives, J. Mol. Struct. 2003, 650, 131-140.
  • [8] Zhou, C.H., Wang, Y., Recent Researches in Triazole Compounds as Medicinal Drugs, Curr. Med. Chem. 2012, 19, 239-280.
  • [9] Barbera, J., Marcos, M., Melendez, E., Ros, B., New Liquid Crystals: 6-n-Alkoxy-3-Pyridinecarboxaldehyde Derivatives, J.L.Serrano Mol. Cryst. Liq. Cryst. 1985, 123, 159-167.
  • [10] Velazquez, S., Alvarez, R., Perez, C., De C. Gago, F., Balzarini, J., Camaraza, M., Regiospecific Synthesis and Anti-Human Immunodeficiency Virus Activity of Novel 5-Substituted N-Alkylcarbamoyl and N,N-Dialkyl Carbamoyl 1,2,3-Triazole-TSAO Analogues, J. Antivir Chem. Chemoth. 1998, 9, 481.
  • [11] Milaeva, E.R., Speier, G., Lever, A.B.P., Leznoff, C.C., Lever, A.B.P.(Eds.): The Phthalocyanines, Properties and Applications, Wiley, 1992, 162–227.
  • [12] Bekircan, O., Kahveci, B., Küçük, M., Synthesis and Anticancer Evaluation of Some New Unsymmetrical 3,5-Diaryl-4H-1,2,4-Triazole Derivatives, Turk. J. Chem, 2006, 30, 29-40.
  • [13] Gök, Y., Kantekin, H., Kılıçaslan, M. B., Alp, H., Synthesis and Characterization of new Metal-free and Nickel(II) phthalocyanines Containing Tetraazatrioxa Macrotricyclic Moieties, Dyes and Pigments, 2007, 74, 692-698.
  • [14] Arslanoğlu, Y., Hamuryudan, E., Synthesis and derivatization of near-IR absorbing titanylphthalocyanines with dimethylaminoethylsulfanyl substituents, Dyes and Pigments, 2007, 75, 150-155.
  • [15] Peter Kissinger, W. R. H., Laboratory Techniques in Electroanalytical Chemistry, 2 ed., Marcel Decker, New York, 1996. [16] Sen, P., Dumludağ, F., Salih, B., Özkaya, A. R., Bekaroğlu, O., Synthesis and electrochemical, electrochromic and electrical properties of novel s-triazine bridged trinuclear Zn (II), Cu (II) and Lu (III) and a tris double-decker Lu (III) phthalocyanines, Synthetic Met., 2011, 161, 1245-1254.
  • [17] Agboola, B.O., Ozoemena, K.I., Nyokong, T., Electrochemical properties of benzylmercapto and dodecylmercapto tetra substituted nickel phthalocyanine complexes: electrocatalytic oxidation of nitrite, Electrochim. Acta, 2006, 51, 6470-6478.
  • [18] Aktaş, A., Acar, I., Koca, A., Bıyıklıoğlu, Z., Kantekin, H., Synthesis, Characterization, Electrochemical And Spectroelectrochemical Properties Of Peripherally Tetra-Substituted Metal-Free And Metallophthalocyanines, Dyes and Pigment, 2013, 99, 613-619.
  • [19] Alemdar, A., Özkaya, A. R., Bulut, M., Preparation, characterization, electrochemistry and in situ spectroelectrochemistry of novel α-tetra[7-oxo-3-(2-chloro-4-fluorophenyl)coumarin]-substituted metal-free, cobalt and zinc phthalocyanines, Synthetic Met. 2010, 160, 1556-1565.
  • [20] Perez, E. F., Kubota, L. T., Tanaka, A. A., Neto, G. D., Anodic-Oxidation Of Cysteıne Catalyzed by Nickel Tetrasulfonated Phthalocyanine Immobilized on Silica-gel Modified with Titanium(IV) Oxide, Electrochim. Acta, 1998, 43, 1665-1673.
  • [21] Leznoff, A. B. P. L. C. C., Phthalocyanines, Properties and Applications. 4 ed., Wiley-VCH, 1993.
  • [22] Tau, P., Nyokong, T., Electrocatalytic oxidation of nitrite by tetra-substituted oxotitanium(IV) phthalocyanines adsorbed or polymerised on glassy carbon electrode, J. Electroanal. Chem., 2007, 611, 10-18.
  • [23] Tau, P., Nyokong, T., Electrochemical characterisation of tetra- and octa-substituted oxo(phthalocyaninato)titanium(IV) complexes., Electrochim. Acta, 2007, 52, 3641-3650.
  • [24] Demir, F., Erdoğmuş, A., Koca, A., Titanyl phthalocyanines: Electrochemical and spectroelectrochemical characterizations and electrochemical metal ion sensor applications of Langmuir films, J. Electroanal. Chem. 2013, 703, 117-125.
  • [25] Arici, M., Arican, D., Uğur, A. L., Erdoğmuş, A., Koca A., Electrochemical and spectroelectrochemical characterization of newly synthesized manganese, cobalt, iron and copper phthalocyanines, Electrochim. Acta, 2013, 87, 554-566.
  • [26] Arican, D., Aktaş, A., Kantekin, H., Koca, A., Electrochromism of Electropolymerized Phthalocyanine-Tetrahydroquinoline Dyads, Journal of the Electrochemical Society, 2014, 161, 670-676.
  • [27] Ortiz, B., Park, S. M., Doddapaneni, N., Electrochemical and spectroelectrochemical studies of cobalt phthalocyanine polymers, J. Electrochem. Soc., 1996, 143,1800-1805.
  • [28] Nevin, W. A., Liu, W., Melnik, M., Lever, A. B. P., Spectro electrochemistry of Cobalt and Iron Tetrasulphonated Phthalocyanines, J. Electroanal. Chem., 1986, 213, 217-234.
  • [29] Koca, A., Arslanoğlu, Y., Hamuryudan, E., Voltammetric and spectroelectrochemical properties of titanylphthalocyanines bearing catecholato and naphthalenediolato moieties, J. Electroanal. Chem. 2008, 616, 107-116. [30] Erdoğmuş, A., Koca, A., Uğur, A. L., Erden, I., Synthesis, Electrochemical and Spectroelectrochemical Properties of Highly Soluble Tetra Substituted Phthalocyanines with [4-(Thiophen-3yl)-phenoxy], Synthetic Met. 2011, 161, 1319-1329.
  • [31] Kamiloğlu, A. A., Acar, I., Bıyıklıoğlu, Z., Novel peripherally tetra substituted metal-free, cobalt(II), copper(II) and manganese(III) phthalocyanines bearing polyethoxy chain attached by 2,6-diphenylphenol groups: synthesis, characterization and their electrochemical studies, Journal of Inclusion Phenomena and Macrocyclic Chemistry, 2017, 88(3,4), 219-228.
  • [32] Özçeşmeci, I., Koca, A., Gül, A., Synthesis and electrochemical and in situ spectroelectrochemical characterization of manganese, vanadyl, and cobalt phthalocyanines with 2-naphthoxy substituents, Electrochim. Acta, 2011, 56, 5102-5114.
  • [33] Agboola, B., Ozoemena, K.I., Nyokong, T., Synthesis and electrochemical characterisation of benzylmercapto and dodecylmercapto tetra substituted cobalt, iron, and zinc phthalocyanines complexes, Electrochim. Acta, 2006, 51, 4379-4387.
  • [34] Aktaş, A., Ünlüer, D., Uslu Kobak, R. Z., Acar, I., Düğdü, E., Koca, A., Kantekin, H., 1,2,4-triazole-5(4H)-one based novel peripherally tetra substituted metal-free and metallophthalocyanines: Synthesis, Characterization and Electrochemical and Spectroelectrochemical Properties, Synt. and React. in Inorg. Metal Org. and Nano-Metal Chem. 2017, 47(6), 830-840.
  • [35] Snow, A. W., Kadish, K. M., Smith, K. M., Guilard, R., The Porphyrin Handbook, in: Phthalocyanine Aggregation, Elsevier Science, Amsterdam, 2003, 17, 129-173.

Periferal tetra 1,2,4,-triazol sübstitüe yeni ftalosiyaninler: sentez, karakterizasyon, elektrokimyasal ve spektroelektrokimyasal özellikler

Year 2017, Issue: 1, 22 - 30, 31.12.2017

Abstract

Bu çalışmada, yeni peripheral 1,2,4-triazol substitue
metalsiz 4, Zn(II) 5, Ti(IV) 6, Ni(II) 7 ve Co(II) 8 ftalosiyanin türevlerinin sentezi, elektrokimyasal ve
spektroelektrokimyasal özellikleri rapor edilmiştir. Komplekslerin voltametrik
ve in situ spektroelektrokimyasal karakterizasyonu çözelti içinde
gerçekleştirildi. Nikel ve çinko ftalosiyaninler karakteristik   olarak ortak “enerji aralığı”,” pikten pike
potansiyel ayrımlar” ve “yarım dalga pik potansiyel değerleri” ile ftalosiyanin
halka bazlı elektron transfer reaksiyonu verirken, kobalt ve titanyum
ftalosiyanin komplekslerinin kavitesinde bulunan CoII ve TiIVO
metal iyonları redoks aktif katyon olarak davranmıştır. Kobalt ftalosiyanin
indirgenme reaksiyonunda bir elektron [CoIIPc-2]/[CoIPc-2]-1 verirken, titanyum ftalosiyanin Pc
ligand indirgenme işlemine ek olarak, iki tane metal bazlı indirgenme
reaksiyonu [TiIVOPc-2]/[TiIIIOPc-2]-1
ve [TiIIIOPc-2]-1/[TiIIIOPc-2]-2
göstermiştir. Elektron transfer reaksiyonları komplekslerin spektrumlarını oldukça
değiştirmiştir. Bu durum komplekslerin özellikle görüntüleme teknolojisinde
pratik uygulamalarda en önemli beklentidir. Kobalt ve titanyum komplekslerinin
redoks ve spektral yanıtları elektrolitte var olan moleküler oksijen tarafından
etkilenmiştir. Bu da komplekslerin moleküler oksijene karşı elektrokatalitik ve
elektosensör aktivitesini göstermektedir.

References

  • [1] McKeown, N.B., Phthalocyanine Materials, (Cambridge University Press, Cambridge, 1998.
  • [2] Liu, H., Shen, Q., Zhang, J., Fu, W., Evaluation of various inverse docking schemes in multiple targets identification, J. Mol. Graph. Model. 2010, 29, 326-330.
  • [3] Leznoff, C.C., Lever, A. B. P., Phthalocyanines: properties and applications, New York: VCH Publisher 1996, 4.
  • [4] Jori, G., Tumour photosensitizers: approaches to enhance the selectivity and efficiency of photodynamic therapy, J. Photochem. Photobiol B: Biol. 1996, 36, 87-93.
  • [5] Moser, F.H., Thomas, L. R., Phthalocyanine compound. New York: Reinhold, 1963, 123-1451.
  • [6] Bouvet, M., Phthalocyanine-based field-effect transistors as gas sensors, Analytical and Bioanalytical Chemistry, 2006, 384, 366-373.
  • [7] Ogunsipe, A., Maree, D., Nyokong, T., Solvent effects on the photochemical and fluorescence properties of zinc phthalocyanine derivatives, J. Mol. Struct. 2003, 650, 131-140.
  • [8] Zhou, C.H., Wang, Y., Recent Researches in Triazole Compounds as Medicinal Drugs, Curr. Med. Chem. 2012, 19, 239-280.
  • [9] Barbera, J., Marcos, M., Melendez, E., Ros, B., New Liquid Crystals: 6-n-Alkoxy-3-Pyridinecarboxaldehyde Derivatives, J.L.Serrano Mol. Cryst. Liq. Cryst. 1985, 123, 159-167.
  • [10] Velazquez, S., Alvarez, R., Perez, C., De C. Gago, F., Balzarini, J., Camaraza, M., Regiospecific Synthesis and Anti-Human Immunodeficiency Virus Activity of Novel 5-Substituted N-Alkylcarbamoyl and N,N-Dialkyl Carbamoyl 1,2,3-Triazole-TSAO Analogues, J. Antivir Chem. Chemoth. 1998, 9, 481.
  • [11] Milaeva, E.R., Speier, G., Lever, A.B.P., Leznoff, C.C., Lever, A.B.P.(Eds.): The Phthalocyanines, Properties and Applications, Wiley, 1992, 162–227.
  • [12] Bekircan, O., Kahveci, B., Küçük, M., Synthesis and Anticancer Evaluation of Some New Unsymmetrical 3,5-Diaryl-4H-1,2,4-Triazole Derivatives, Turk. J. Chem, 2006, 30, 29-40.
  • [13] Gök, Y., Kantekin, H., Kılıçaslan, M. B., Alp, H., Synthesis and Characterization of new Metal-free and Nickel(II) phthalocyanines Containing Tetraazatrioxa Macrotricyclic Moieties, Dyes and Pigments, 2007, 74, 692-698.
  • [14] Arslanoğlu, Y., Hamuryudan, E., Synthesis and derivatization of near-IR absorbing titanylphthalocyanines with dimethylaminoethylsulfanyl substituents, Dyes and Pigments, 2007, 75, 150-155.
  • [15] Peter Kissinger, W. R. H., Laboratory Techniques in Electroanalytical Chemistry, 2 ed., Marcel Decker, New York, 1996. [16] Sen, P., Dumludağ, F., Salih, B., Özkaya, A. R., Bekaroğlu, O., Synthesis and electrochemical, electrochromic and electrical properties of novel s-triazine bridged trinuclear Zn (II), Cu (II) and Lu (III) and a tris double-decker Lu (III) phthalocyanines, Synthetic Met., 2011, 161, 1245-1254.
  • [17] Agboola, B.O., Ozoemena, K.I., Nyokong, T., Electrochemical properties of benzylmercapto and dodecylmercapto tetra substituted nickel phthalocyanine complexes: electrocatalytic oxidation of nitrite, Electrochim. Acta, 2006, 51, 6470-6478.
  • [18] Aktaş, A., Acar, I., Koca, A., Bıyıklıoğlu, Z., Kantekin, H., Synthesis, Characterization, Electrochemical And Spectroelectrochemical Properties Of Peripherally Tetra-Substituted Metal-Free And Metallophthalocyanines, Dyes and Pigment, 2013, 99, 613-619.
  • [19] Alemdar, A., Özkaya, A. R., Bulut, M., Preparation, characterization, electrochemistry and in situ spectroelectrochemistry of novel α-tetra[7-oxo-3-(2-chloro-4-fluorophenyl)coumarin]-substituted metal-free, cobalt and zinc phthalocyanines, Synthetic Met. 2010, 160, 1556-1565.
  • [20] Perez, E. F., Kubota, L. T., Tanaka, A. A., Neto, G. D., Anodic-Oxidation Of Cysteıne Catalyzed by Nickel Tetrasulfonated Phthalocyanine Immobilized on Silica-gel Modified with Titanium(IV) Oxide, Electrochim. Acta, 1998, 43, 1665-1673.
  • [21] Leznoff, A. B. P. L. C. C., Phthalocyanines, Properties and Applications. 4 ed., Wiley-VCH, 1993.
  • [22] Tau, P., Nyokong, T., Electrocatalytic oxidation of nitrite by tetra-substituted oxotitanium(IV) phthalocyanines adsorbed or polymerised on glassy carbon electrode, J. Electroanal. Chem., 2007, 611, 10-18.
  • [23] Tau, P., Nyokong, T., Electrochemical characterisation of tetra- and octa-substituted oxo(phthalocyaninato)titanium(IV) complexes., Electrochim. Acta, 2007, 52, 3641-3650.
  • [24] Demir, F., Erdoğmuş, A., Koca, A., Titanyl phthalocyanines: Electrochemical and spectroelectrochemical characterizations and electrochemical metal ion sensor applications of Langmuir films, J. Electroanal. Chem. 2013, 703, 117-125.
  • [25] Arici, M., Arican, D., Uğur, A. L., Erdoğmuş, A., Koca A., Electrochemical and spectroelectrochemical characterization of newly synthesized manganese, cobalt, iron and copper phthalocyanines, Electrochim. Acta, 2013, 87, 554-566.
  • [26] Arican, D., Aktaş, A., Kantekin, H., Koca, A., Electrochromism of Electropolymerized Phthalocyanine-Tetrahydroquinoline Dyads, Journal of the Electrochemical Society, 2014, 161, 670-676.
  • [27] Ortiz, B., Park, S. M., Doddapaneni, N., Electrochemical and spectroelectrochemical studies of cobalt phthalocyanine polymers, J. Electrochem. Soc., 1996, 143,1800-1805.
  • [28] Nevin, W. A., Liu, W., Melnik, M., Lever, A. B. P., Spectro electrochemistry of Cobalt and Iron Tetrasulphonated Phthalocyanines, J. Electroanal. Chem., 1986, 213, 217-234.
  • [29] Koca, A., Arslanoğlu, Y., Hamuryudan, E., Voltammetric and spectroelectrochemical properties of titanylphthalocyanines bearing catecholato and naphthalenediolato moieties, J. Electroanal. Chem. 2008, 616, 107-116. [30] Erdoğmuş, A., Koca, A., Uğur, A. L., Erden, I., Synthesis, Electrochemical and Spectroelectrochemical Properties of Highly Soluble Tetra Substituted Phthalocyanines with [4-(Thiophen-3yl)-phenoxy], Synthetic Met. 2011, 161, 1319-1329.
  • [31] Kamiloğlu, A. A., Acar, I., Bıyıklıoğlu, Z., Novel peripherally tetra substituted metal-free, cobalt(II), copper(II) and manganese(III) phthalocyanines bearing polyethoxy chain attached by 2,6-diphenylphenol groups: synthesis, characterization and their electrochemical studies, Journal of Inclusion Phenomena and Macrocyclic Chemistry, 2017, 88(3,4), 219-228.
  • [32] Özçeşmeci, I., Koca, A., Gül, A., Synthesis and electrochemical and in situ spectroelectrochemical characterization of manganese, vanadyl, and cobalt phthalocyanines with 2-naphthoxy substituents, Electrochim. Acta, 2011, 56, 5102-5114.
  • [33] Agboola, B., Ozoemena, K.I., Nyokong, T., Synthesis and electrochemical characterisation of benzylmercapto and dodecylmercapto tetra substituted cobalt, iron, and zinc phthalocyanines complexes, Electrochim. Acta, 2006, 51, 4379-4387.
  • [34] Aktaş, A., Ünlüer, D., Uslu Kobak, R. Z., Acar, I., Düğdü, E., Koca, A., Kantekin, H., 1,2,4-triazole-5(4H)-one based novel peripherally tetra substituted metal-free and metallophthalocyanines: Synthesis, Characterization and Electrochemical and Spectroelectrochemical Properties, Synt. and React. in Inorg. Metal Org. and Nano-Metal Chem. 2017, 47(6), 830-840.
  • [35] Snow, A. W., Kadish, K. M., Smith, K. M., Guilard, R., The Porphyrin Handbook, in: Phthalocyanine Aggregation, Elsevier Science, Amsterdam, 2003, 17, 129-173.
There are 33 citations in total.

Details

Primary Language English
Subjects Chemical Engineering
Journal Section Research Article
Authors

Ayşe Aktaş Kamiloğlu

Mehmet Aydemir This is me

İrfan Acar This is me

Gülbınar Sarkı This is me

Atıf Koca

Nurhan Gümrükçüoğlu

Ümmühan Ocak This is me

Halit Kantekin

Publication Date December 31, 2017
Published in Issue Year 2017 Issue: 1

Cite

APA Aktaş Kamiloğlu, A., Aydemir, M., Acar, İ., Sarkı, G., et al. (2017). Peripherally tetra 1,2,4-triazol substituted novel phthalocyanines: Synthesis, characterization, electrochemical and spectroelectrochemical properties. Karadeniz Chemical Science and Technology(1), 22-30.
AMA Aktaş Kamiloğlu A, Aydemir M, Acar İ, Sarkı G, Koca A, Gümrükçüoğlu N, Ocak Ü, Kantekin H. Peripherally tetra 1,2,4-triazol substituted novel phthalocyanines: Synthesis, characterization, electrochemical and spectroelectrochemical properties. Karadeniz Chem. Sci. Tech. December 2017;(1):22-30.
Chicago Aktaş Kamiloğlu, Ayşe, Mehmet Aydemir, İrfan Acar, Gülbınar Sarkı, Atıf Koca, Nurhan Gümrükçüoğlu, Ümmühan Ocak, and Halit Kantekin. “Peripherally Tetra 1,2,4-Triazol Substituted Novel Phthalocyanines: Synthesis, Characterization, Electrochemical and Spectroelectrochemical Properties”. Karadeniz Chemical Science and Technology, no. 1 (December 2017): 22-30.
EndNote Aktaş Kamiloğlu A, Aydemir M, Acar İ, Sarkı G, Koca A, Gümrükçüoğlu N, Ocak Ü, Kantekin H (December 1, 2017) Peripherally tetra 1,2,4-triazol substituted novel phthalocyanines: Synthesis, characterization, electrochemical and spectroelectrochemical properties. Karadeniz Chemical Science and Technology 1 22–30.
IEEE A. Aktaş Kamiloğlu, M. Aydemir, İ. Acar, G. Sarkı, A. Koca, N. Gümrükçüoğlu, Ü. Ocak, and H. Kantekin, “Peripherally tetra 1,2,4-triazol substituted novel phthalocyanines: Synthesis, characterization, electrochemical and spectroelectrochemical properties”, Karadeniz Chem. Sci. Tech., no. 1, pp. 22–30, December 2017.
ISNAD Aktaş Kamiloğlu, Ayşe et al. “Peripherally Tetra 1,2,4-Triazol Substituted Novel Phthalocyanines: Synthesis, Characterization, Electrochemical and Spectroelectrochemical Properties”. Karadeniz Chemical Science and Technology 1 (December 2017), 22-30.
JAMA Aktaş Kamiloğlu A, Aydemir M, Acar İ, Sarkı G, Koca A, Gümrükçüoğlu N, Ocak Ü, Kantekin H. Peripherally tetra 1,2,4-triazol substituted novel phthalocyanines: Synthesis, characterization, electrochemical and spectroelectrochemical properties. Karadeniz Chem. Sci. Tech. 2017;:22–30.
MLA Aktaş Kamiloğlu, Ayşe et al. “Peripherally Tetra 1,2,4-Triazol Substituted Novel Phthalocyanines: Synthesis, Characterization, Electrochemical and Spectroelectrochemical Properties”. Karadeniz Chemical Science and Technology, no. 1, 2017, pp. 22-30.
Vancouver Aktaş Kamiloğlu A, Aydemir M, Acar İ, Sarkı G, Koca A, Gümrükçüoğlu N, Ocak Ü, Kantekin H. Peripherally tetra 1,2,4-triazol substituted novel phthalocyanines: Synthesis, characterization, electrochemical and spectroelectrochemical properties. Karadeniz Chem. Sci. Tech. 2017(1):22-30.