2-Aminoantrakinon ile Modifiye Edilmiş Camsı Karbon Elektrot Kullanılarak Nitrobenzenin Elektrokimyasal Tayini

Year 2022, Volume: 22 Issue: 2, 291 - 300, 30.04.2022

Faysal Selimoğlu , Züleyha Kudaş

https://doi.org/10.35414/akufemubid.1076204

Abstract

PAAQ (Poli(2-amino-antrakinon)) filmler, destekleyici elektrolit tetrabütilamonyum perklorat kullanılarak susuz asetonitril içinde 2-aminoantrakinon monomerinin elektrokimyasal oksidasyonu ile hazırlandı. Polimer film oluşumu üzerinde, tarama hızının, çevrim sayısının ve monomer konsantrasyonunun etkisi incelenmiştir. PAAQ ile modifiye edilmiş camsı karbon elektrot üzerinde, nitrobenzenin (NB) elektrokimyasal tespiti dönüşümlü voltametri ve diferansiyel puls voltametri ile incelendi. Polimer modifiye elektrot, modifiye edilmemiş elektrot ile karşılaştırıldığında NB'ye karşı mükemmel indirgeme yeteneği sergiledi. Polimer modifiye elektrotta geliştirilen NB sensörü, 0.0625 - 8 mM arasında geniş bir doğrusal cevap ve 2.294 mM düşük dedeksiyon limiti gösterdi.

Keywords

2-aminoantrakinon, Camsı karbon elektrot, Nitrobenzen tayini, Poli(2-amino-antrakinon

Electrochemical Determination of Nitrobenzene Using a Glassy Carbon Electrode Modified with 2-Aminoanthraquinone

Abstract

PAAQ (Poly(2-amino-anthraquinone)) films were prepared through electrochemical oxidation of 2-amino-anthraquinone monomer in anhydrous acetonitrile using the supporting electrolyte tetrabutylammonium perchlorate. The effects of scan rate, cycle number, and monomer concentration on polymer film formation were investigated. Electrochemical detection of nitrobenzene (NB) on PAAQ modified glassy carbon electrode was examined with voltammetry and differential pulse voltammetry. The polymer-modified electrode exhibited excellent reducing ability towards NB compared to the unmodified electrode. The NB sensor developed on the polymer-modified electrode showed a wide linear response range of 0.0625 - 8 mM and a low detection limit of 2.294 mM.

Keywords

2-amino-anthraquinone, Glassy carbon electrode, Detection of nitrobenzene, Poly(2-amino-anthraquinone)

References

• Abdel-Azzem, M., Yousef, U.S., Ragab, A.Z.-E., 2010. A new modified electrode based on electrochemical oxidation of 1-amino-5,6,7,8-tetrahydronaphthalene in acetonitrile. Electrochimica Acta, 55, 1509-1518.
• Altundas, R., Demir, Ü., Ekinci, D., Horasan, N., 2000. The electrochemical oxidation of 2-amino-3-cyano-4-phenylthiophene: evidence for a new class of photoluminescent material. Journal of Electroanalytical Chemistry, 484(2), 101-106.
• Amiri, M., Bélanger, D., Donzel, N., Shul, G., 2021 Aqueous electrochemical energy storage system based on phenanthroline- and anthraquinone-modified carbon electrodes. Electrochimica Acta, 390, 138862.
• Atmaca, U., Ekinci, D., Kudas, Z., Saruhan, T., Celik, M., 2020. Electrocatalytic Reduction of Oxygen at Glassy Carbon Electrodes Coated with Diazonium‐derived Porphyrin/Metalloporphyrin Films. Electroanalysis, 32(6), 1379-1390.
• Aurelia, M., Mariana, C., Maria, C., 1989. Glucose sensor: polypyrrole-glucose oxidase electrode in the presence of p-benzoquinone. Electrochimica Acta, 37(11), 1987–1992.
• Barrière, F., and Downard, A. J., 2008. Covalent modification of graphitic carbon substrates by non-electrochemical methods. Journal of Solid-State Electrochemistry, 12(10), 1231-1244.
• Bayraktutan, T., Gür, B., Onganer, Y., 2022. A new FRET-based functional chemosensor for fluorometric detection of Fe3+ and its validation through in silico studies. Journal of Molecular Structure, 132448.
• Chen, H., Ju, H., Sun. H., 1996. Properties of poly-β-aminoanthraquinone modified carbon fiber electrode as a basis for hemoglobin biosensors. Analytica Chimica Acta, 327(2), 125-132.
• Chen, Y., Liang, K., Xun, H., Wang, S. Y., 1998. Study of nitrobenzene in wastewater by spectrophotometry. Capital Normal University Transaction Nature Science, 19, 72-76.
• Dalkıran, B. ve Kaçar, C., 2020. Amin Fonksiyonlu Karbon Nanotüp, Kalay Oksit Nanopartikül ve Diamin Oksidaz Temelli Triptamin Biyosensörü. Düzce Üniversitesi Bilim ve Teknoloji Dergisi, 8(1), 631-641.
• Demir, U., Ekinci, D., Pak, F., Tümer, F., 2007. A Mechanistic and Characteristic Investigation of Electrooxidation of 2‐Amino‐3‐cyano‐4‐methylthiophene. Macromolecular Chemistry and Physics, 208(21), 2367-2374.
• Demir, Ü., Ekinci, D., Tümer, F., 2004. Mechanistic study of the oxidation of 2-amino-3-cyano-4-naphtylthiophene by cyclic voltammetry and UV–Vis–NIR absorption spectroscopy. Journal of Electroanalytical Chemistry, 562(2), 167–172.
• Diao, F., Jansen, U. C., Qvortrup, K., Tanner, D., Ulstrup, J., Yan, X., Xiao, X., 2021. Surface-confined redox-active monolayers of a multifunctional anthraquinone derivative on nanoporous and single-crystal gold electrodes. Electrochemistry Communications, 124, 106962.
• Diaz, A. F, Logan, J. A., 1980. Electroactive polyaniline films. Journal of Electroanalytical Chemistry and Interfacial Electrochemistry, 111(1), 111-114.
• Ekinci, D., Turhan, F., Pak, F., Kudaş, Z., Yeşildağ, A., 2012. Electrochemical synthesis and characterization of poly (9-benzylfluorene). Polymer bulletin, 68(6), 1677-1687.
• Ekinci, D., Ünal, Ö.F., Yeşildağ, A., 2018. Synthesis of gold nanoparticles on diazonium generated heteroaryl films and their electrocatalytic activities. Electrochimica Acta, 290, 474-486.
• Gao, P., Gosztola, D., Weaver, M. J., 1988. Surface-enhanced Raman spectroscopy as a probe of electroorganic reaction pathways. 1. Processes involving adsorbed nitrobenzene, azobenzene, and related species. The Journal of Physical Chemistry, 92(25), 7122-7130.
• Genies, E.M., Marchesiello ,M., 1992. Glucose sensor: polypyrrole-glucose oxidase electrode in the presence of p-benzoquinone. Electrochimica Acta, 37(11), 1987–1992.
• Gryko, D., Kadish, K. M., Rybicka-Jasińska, K., Shan, W., Zawada, K., 2016. Porphyrins as photoredox catalysts: Experimental and theoretical studies. Journal of the American Chemical Society, 138(47), 15451-15458.
• Gu, X., Li, X., Wu, S., Shi, J., Jiang, G., & Tian, S., 2016. A sensitive hydrazine hydrate sensor based on a mercaptomethyl-terminated trinuclear Ni (II) complex modified gold electrode. Rsc Advances, 6(10), 8070-8078.
• Kadish, K., 2000 The Porphyrin Handbook, Smith, K. M., & Guilard, R. Eds. Vol. 3. Elsevier.
• Günaydin, H., 2012. 4-nitro-1-naftilamin diazonyum tuzunun sentezlenmesi, karakterizasyonu ve camsı karbon elektrot yüzeyinde elektokimyasal indirgenmesiyle yeni bir elektrodun hazırlanması, Yüksek Lisans Tezi, Fen Bilimleri Enstitüsü Selçuk Üniversitesi, Konya, 82.
• Gür, F., Kaya, E. D., Gür, B., Türkhan, A., Onganer, Y., 2019. Preparation of bio-electrodes via Langmuir-Blodgett technique for pharmaceutical and waste industries and their biosensor application. Colloids and Surfaces A: Physicochemical and Engineering Aspects, 583, 124005.
• Hossain, M.S., Tryk, D., Yeager, E., 1989. The electrochemistry of graphite and modified graphite surfaces: the reduction of O2. Electrochimica Acta, 34(12), 1733–1737.
• Jin, M., Liu, Y., Zhang, X., Wang, J., Zhang, S., Wang, G., Zhang, Y., Yin, H., Zhang, H., Zhao, H., 2021. Selective electrocatalytic hydrogenation of nitrobenzene over copper-platinum alloying catalysts. Experimental and theoretical studies. Applied Catalysis B: Environmental, 298, 120545.
• Karabilgin, E. E., 2012. Camsı karbon elektrot yüzeyinde 4-nitro-1-naftilaminin elektrokimyasal oksidasyonuyla yeni bir modifiye elektrot hazırlanması, Yüksek Lisans Tezi, Fen Bilimleri Enstitüsü Selçuk Üniversitesi, Konya 72.
• Kitani, A., Yano, J., Kunai, A., Saski, K., 1987. A conducting polymer derived from para-aminodiphenylamine. Journal of Electroanalytical Chemistry and Interfacial Electrochemistry, 221(1), 69–82.
• Kokkinidis, G., Jüttner, K., 1981. The electrocatalytic influence of underpotential lead adsorbates on the reduction of nitrobenzene and nitrosobenzene on silver single crystal surfaces in methanolic solutions. Electrochimica Acta, 26(8), 971-977.
• Laviron, E.J.J. 1979. General expression of the linear potential sweep voltammogram in the case of diffusionless electrochemical systems. Journal of Electroanalytical Chemistry and Interfacial Electrochemistry, 101(1), 19-28.
• Li, Y.P., Cao, HB., Liu, CM., Zhang, Y., 2007. Electrochemical reduction of nitrobenzene at carbon nanotube electrode. Journal of hazardous materials, 148 (1-2), 158-163.
• Li, X., Sun, H., Sun, X., 2021. Polysulfone grafted with anthraquinone-hydroanthraquinone redox as a flexible membrane electrode for aqueous batteries. Polymer, 234, 124245.
• Liang, S. X., Zhang, H. K., & Lu, D., 2007. Determination of nitrobenzene in wastewater using a hanging mercury drop electrode. Environmental Monitoring and assessment, 129(1), 331-337.
• Luo, L., Wang, X., Ding, Y., Li, Q., Jia, J., Deng, D., 2010. Electrochemical determination of nitrobenzene using bismuth-film modified carbon paste electrode in the presence of cetyltrimethylammonium bromide. Analytical Methods, 2(8), 1095-1100.
• Marken, F., Kumbhat, S., Sanders, G. H., & Compton, R. G., 1996. Voltammetry in the presence of ultrasound: surface and solution processes in the sonovoltammetric reduction of nitrobenzene at glassy carbon and gold electrodes. Journal of Electroanalytical Chemistry, 414(2), 95-105.
• Majumder, P. S., Gupta, S. K., 2003. Hybrid reactor for priority pollutant nitrobenzene removal. Water research, 37(18), 4331-4336.
• Nishikawa, Y., Okumura, T., 1995. Determination of nitrobenzenes in river water, sediment and fish samples by gas chromatography-mass spectrometry. Analytica chimica acta, 312(1), 45-55.
• Patil, S. F., Lonkar, S. T., 1994. Determination of benzene, aniline and nitrobenzene in workplace air: a comparison of active and passive sampling. Journal of Chromatography A, 688(1-2), 189-199.
• Pournaghi-Azar, M.H., Sabzi, R., 2003. Electrochemical characteristics of a cobalt pentacyanonitrosylferrate film on a modified glassy carbon electrode and its catalytic effect on the electrooxidation of hydrazine. Journal of Electroanalytical Chemistry, 543(2), 115-125.
• Qi, B. Lin, F., Bai, J., Liu, L., Guo, L., 2008. An ordered mesoporous carbon/didodecyldimethylammonium bromide composite and its application in the electro-catalytic reduction of nitrobenzene. Materials Letters, 62(21-22), 3670-3672.
• Qian, H., Ye, J., Jin, L., 1997. Study of the electrochemical properties of C60 modified carbon paste electrode and its application for nitrobenzene quantitation based on electrocatalytic reduction. Analytical letters, 30(2), 367-381.
• Sandeep, S., Santhosh, A. S., Swamy, N. K., Suresh, G. S., Melo, J. S., Chamaraja, N. A., 2018. A biosensor based on a graphene nanoribbon/silver nanoparticle/polyphenol oxidase composite matrix on a graphite electrode: application in the analysis of catechol in green tea samples. New Journal of Chemistry, 42(20), 16620-16629.
• Sereno, L., Silber, J.J., Vettorazzi, N., 1981. Anodic oxidation of 1-naphthylamine in acetonitrile. Journal of Electroanalytical Chemistry and Interfacial Electrochemistry 125(2), 459-475.
• Wang, S. P., Chen, H. J., 2002. Separation and determination of nitrobenzenes by micellar electrokinetic chromatography and high-performance liquid chromatography. Journal of Chromatography A, 979(1-2), 439-446.