Electrochemical Behaviors of Azopurine on Gold Electrodes

Authors

Ming-xue LI, Department of Chemistry,College of Chemistry and Chemical Engineering, Xiamen University, Xiamen 361005, Fujian, China;
Hang SHI, Department of Chemistry,College of Chemistry and Chemical Engineering, Xiamen University, Xiamen 361005, Fujian, China;
Jia LIU, Department of Chemistry,College of Chemistry and Chemical Engineering, Xiamen University, Xiamen 361005, Fujian, China;
Meng ZHANG, Department of Chemistry,College of Chemistry and Chemical Engineering, Xiamen University, Xiamen 361005, Fujian, China;
Jian-zhang ZHOU, Department of Chemistry,College of Chemistry and Chemical Engineering, Xiamen University, Xiamen 361005, Fujian, China;
De-yin WU, Department of Chemistry,College of Chemistry and Chemical Engineering, Xiamen University, Xiamen 361005, Fujian, China;Follow
Zhong-qun TIAN, Department of Chemistry,College of Chemistry and Chemical Engineering, Xiamen University, Xiamen 361005, Fujian, China;

Corresponding Author

De-yin WU(dywu@xmu.edu.cn)

Abstract

In this paper, we studied the electrochemical behaviors of azopurine on polished gold electrodes with cyclic voltammetry (CV). On the basis of analyzing scan rate and peak current, it was supposed that the redox process belonged to a reversible process controlled by adsorption in 0.2 mol·L^-1 PBS (pH = 4.0 ~ 10.0) solutions. The potentials of redox peaks moved more negatively with increasing pH value. This proved that the H⁺ proton has participcted in the electrochemical reaction. The further data analysis and the calculation of surface adsorption excess demonstrated that the reaction was a two-proton and two-electron process. Finally, the apparent transfer coefficient α and the apparent rate constant ks were determined by the fast-scan cyclic voltammetry method.

Graphical Abstract

Keywords

azopuine, surface adsorption excess, cyclic voltammetry, gold electrode, electrode kinetics

DOI Link

https://doi.org/10.13208/j.electrochem.180401

Publication Date

2019-12-28

Online Available Date

2018-05-09

Revised Date

2018-04-08

Received Date

2018-04-01

Recommended Citation

Ming-xue LI, Hang SHI, Jia LIU, Meng ZHANG, Jian-zhang ZHOU, De-yin WU, Zhong-qun TIAN. Electrochemical Behaviors of Azopurine on Gold Electrodes[J]. Journal of Electrochemistry, 2019 , 25(6): 651-659.
DOI: 10.13208/j.electrochem.180401
Available at: https://jelectrochem.xmu.edu.cn/journal/vol25/iss6/2

References

[1] Tony B D, Goyal D, Khanna S. Decolorization of textile azo dyes by aerobic bacterial consortium[J]. International Bio-deterioration & Biodegradation,2009, 63(4): 462-469.
[2] Yamaguchi T, Sasaki K, Kurosaki Y, et al. Biopharmaceutical evaluation of salicylazosulfanilic acid as a novel colon-targeted prodrug of 5-aminosalicylic acid[J]. Journal of Drug Targeting, 1994, 2(2): 123-131.
[3] Wachi T. Researches on chemotherapeutic drugs against viruses. XVIII.: Synthesis and antiviral effects of 3-heterocyclic azo-4-amino-(or hydroxy)-naphthalenesulfonic acids and their derivatives[J]. Pharmaceutical Bulletin,1954, 2(4): 412-415.
[4] Zbaida S. The mechanism of microsomal azoreduction: Predictions based on electronic aspects of structure-activity relationships[J]. Drug Metabolism Reviews,1995, 27(3): 497-516.
[5] Jadhav A L, Bhansali K G, Davis J R. 6,6'-Azopurine, a potent in vitro inhibitor of rabbit liver aldehyde oxidase[J]. Journal of Pharmaceutical Sciences,1979, 68(9): 1202-1203.
[6] Pryde D C, Dalvie D, Hu Q Y, et al. Aldehyde oxidase: An enzyme of emerging importance in drug discovery[J]. Journal of Medicinal Chemistry, 2010, 53(24): 8441-8460.
[7] Mandic Z, Nigovic B, Simunic B. The mechanism and kinetics of the electrochemical cleavage of azo bond of 2-hydroxy-5-sulfophenyl-azo-benzoic acids[J]. Electrochimica Acta, 2004, 49(4): 607-615.
[8] Sadler J L, Bard A J. Electrochemical reduction of aromatic azo compounds[J]. Journal of the American Chemical Society,1968, 90(8): 1979-1989.
[9] Zanoni M V B, Carneiro P A, Furlan M, et al. Determination of the vinylsulphone azo dye, remazol brilliant orange 3R, by cathodic stripping voltammetry[J]. Analytica Chimica Acta, 1999, 385(1): 385-392.
[10] Song S, Fan J Q, He Z Q, et al. Electrochemical degradation of azo dye C.I. Reactive Red 195 by anodic oxidation on Ti/SnO₂-Sb/PbO₂ electrodes[J]. Electrochimica Acta, 2010, 55(11): 3606-3613.
[11] Kariyajjanavar P, Jogttappa N, Nayaka Y A. Studies on degradation of reactive textile dyes solution by electrochemical method[J]. Journal of Hazardous Materials, 2011, 190(1): 952-961.
[12] Yang X(杨星), Chen P(陈平). An electrochemical investigation of p-sulfophenylazo calix[4]arene in a buffer solution[J]. Journal of Electrochemistry(电化学), 2016, 22(1): 37-42.
[13] Liu Z F, Loo B H, Hashimoto K, et al. A novel photoelectrochemical hybrid €œone-way€ process observed in the azobenzene system[J]. Journal of Electroanalytical Chemistry and Interfacial Electrochemistry, 1991, 297(1): 133-144.
[14] Jain R, Sharma N, Radhapyari K. Electrochemical treatment of pharmaceutical azo dye amaranth from waste water[J]. Journal of Applied Electrochemistry, 2008, 39(5): 577-582.
[15] Laviron E. General expression of the linear potential sweep voltammogram in the case of diffusionless electrochemical systems[J]. Journal of Electroanalytical Chemistry and Interfacial Electrochemistry, 1979, 101(1): 19-28.
[16] Laviron E. Adsorption, autoinhibition and autocatalysis in polarography and in linear potential sweep voltammetry[J]. Journal of Electroanalytical Chemistry and Interfacial Electrochemistry, 1974, 52(3): 355-393.
[17] Michael D J, Joseph J D, Kilpatrick M R, et al. Improving data acquisition for fast-scan cyclic voltammetry[J]. Analytical Chemistry, 1999, 71(18): 3941-3947.
[18] Mahon P J, Oldham K B. Convolutive modelling of electrochemical processes based on the relationship between the current and the surface concentration[J]. Journal of Electroanalytical Chemistry, 1999, 464(1): 1-13.
[19] Jackson B P, Dietz S M, Wightman R M. Fast-scan cyclic voltammetry of 5-hydroxytryptamine[J]. Analytical Chemistry, 1995, 67(6): 1115-1120.
[20] Narula P M, Noftle R E. Investigation of the lifetimes of some pyrrole species by rapid scan cyclic voltammetry and double potential step techniques[J]. Journal of Electroanalytical Chemistry, 1999, 464(1): 123-127.
[21] Hirst J, Armstrong F A. Fast-scan cyclic voltammetry of protein films on pyrolytic graphite edge electrodes: Characteristics of electron exchange[J]. Analytical Chemistry, 1998, 70(23): 5062-5071.
[22] Giner-Sorolla A. Reactions of 6-hydrazino-, 6-hydroxylaminopurines and related derivatives[J]. Journal of Heterocyclic Chemistry, 2009, 7(1): 75-79.
[23] Montgomery J A, Holum L B. Synthesis of potential anticancer agents. III. Hydrazino analogs of biologically active purines2[J]. Journal of the American Chemical Society, 1957, 79(9): 2185-2188.
[24] Ogunbiyi O, Kajbaf M, Lamb J H, et al. Characterization of 2-amino-1-benzylbenzimidazole and its metabolites using tandem mass spectrometry[J]. Toxicology Letters,1995, 78(1): 25-33.
[25] Bard A J, Faulkner L R. Electrochemical methods, principle and application[M]. Bejing: Chemical Industry Press Co., Ltd., 2005.
[26] Nicholson R S, Shain I. Theory of stationary electrode polarography single scan and cyclic methods applied to reversible, irreversible, and kinetic systems[J]. Analytical Chemistry, 1964, 36: 706-723.
[27] Wang J X, Li M X, Shi Z J, et al. Direct electrochemistry of cytochrome c at a glassy carbon electrode modified with single-wall carbon nanotubes[J]. Analytical Chemistry, 2002, 74(9): 1993-1997.
[28] Zhou Y L, Zhi J F, Zou Y S, et al. Direct electrochemistry and electrocatalytic activity of cytochrome c covalently immobilized on a boron-doped nanocrystalline diamond electrode[J]. Analytical Chemistry, 2008, 80(11): 4141-4146.
[29] Nagaraju D H, Pandey R K, Lakshminarayanan V. Electrocatalytic studies of Cytochrome c functionalized single walled carbon nanotubes on self-assembled monolayer of 4-ATP on gold[J]. Journal of Electroanalytical Chemistry, 2009, 627(1): 63-68.
[30] Laviron E, Roullier L. Electrochemical reactions with adsorption of the reactants and electrosorption. Simple analytical solutions for a Henry isotherm[J]. Journal of Electroanalytical Chemistry, 1998, 443(2): 195-207.
[31] Lv G Q(吕桂琴), Ma S X(马淑贤). Determination of 4,5-diazafluorene-9-one diffusion coefficients and rate constants by chronocoulometry[J]. Transactions of Beijing Institute of Technology(北京理工大学学报), 2014, 34(6): 650-654.
[32] Duan C Q(段成茜), Liu L H(刘立红), Chen D G(陈德刚), et al. Electrochemical behavior of tiamulin fumarate at carbon paste electrode and its electrochemical determination[J]. Journal of Analytical Science (分析科学学报), 2011, 27(1): 40-44.
[33] Sun S G(孙世刚), Wang Y（王野）,Chen L T(陈良坦), et al. Physical chemistry (Part II)[M]. Xiamen: Xiamen University Press, 2008.
[34] Zhu N, Ulstrup J, Chi Q. Long-range interfacial electron transfer and electrocatalysis of molecular scale Prussian Blue nanoparticles linked to Au(111)-electrode surfaces by different chemical contacting groups[J]. Russian Journal of Electrochemistry, 2017, 53(10): 1204-1221.