Environ Monit Assess (2015) 187:257 DOI 10.1007/s10661-015-4506-6

Construction of a nanostructure-based electrochemical sensor for voltammetric determination of bisphenol A Hadi Beitollahi & Somayeh Tajik

Received: 28 January 2015 / Accepted: 6 April 2015 # Springer International Publishing Switzerland 2015

Abstract A novel carbon paste electrode modified with graphene oxide nanosheets and an ionic liquid (n-hexyl3-methylimidazolium hexafluoro phosphate) was fabricated. The electrochemical study of the modified electrode, as well as its efficiency for voltammetric oxidation of bisphenol A, is described. The electrode was also employed to study the electrochemical oxidation of bisphenol A, using cyclic voltammetry, chronoamperometry, square wave voltammetry and electrochemical impedance spectroscopy as diagnostic techniques. Square wave voltammetry exhibits a linear dynamic range from 9.0×10−8 to 2.5×10−4 M and a detection limit of 55.0 nM for bisphenol A. Finally, this new sensor was used for determination of bisphenol A in water samples using the standard addition method. Keywords Bisphenol A . Graphene oxide nanosheets . Carbon paste electrode . Ionic liquids

Introduction Bisphenol A is a chemical intermediate widely used in the synthesis of polycarbonate and epoxy resins, H. Beitollahi (*) Environment Department, Institute of Science and High Technology and Environmental Sciences, Graduate University of Advanced Technology, Kerman, Iran e-mail: [email protected] S. Tajik Department of Chemistry, Shahid Bahonar University of Kerman, P.O. Box 76175-133, Kerman, Iran

unsaturated polyester-styrene resins and flame retardants (Lee et al. 2015). Bisphenol A is mainly released into the environment in wastewater from plasticsproducing industrial plants and landfill sites. Bisphenol A can also migrate into food and drinking water from a wide variety of food contact materials mainly derived from polycarbonates and epoxy resins, such as infant feeding bottles, tableware, storage containers and food can linings. Recently, bisphenol A has received a great deal of attention from regulatory agencies and scientists because it has estrogenic activity and serves as an environmental endocrine disruptor (Wu et al. 2015). Bisphenol A was reported to show potential detrimental reproductive effects on wildlife and humans through altering endocrine function and may disrupt growth and development by interfering with the production, release, transport, metabolism, binding, and regulation of development processes (Goldstone et al. 2015). Since its ubiquitous nature and its endocrine-disrupting potential, bisphenol A has been included in the environmental water monitoring or determining study. At present, several techniques have been developed to determine bisphenol A, such as fluorescence (FL) (Wang et al. 2014a, b); molecularly imprinted solidphase extraction coupled with capillary electrophoresis (MISPE–CE) (Mei et al. 2011); cloud point extraction coupled with capillary zone electrophoresis (CPE–CZE) (Zhong et al. 2011); chemiluminescence (CL) (Amjadi et al. 2015); electrochemiluminescence (ECL) (Battal et al. 2014); high-performance liquid chromatography (HPLC) (Deng et al. 2006); liquid chromatography coupled with electrochemical, ultraviolet and fluorescence detection (Inoue et al. 2000); liquid

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chromatography coupled with mass spectrometry (LC– MS) (Pedersen and Lindholst 1999); gas chromatography (GC) (Shin et al. 2001); gas chromatography coupled with mass spectrometry (GC–MS) (Deceuninck et al. 2014) and enzyme-linked immunosorbent assays (ELISAs) (Kuruto-Niwa et al. 2007). Fluorescence, chemiluminescence and capillary electrophoresis techniques either suffer from low sensitivity, narrow linear range and high detection limit or are time consuming and expensive to implement. Furthermore, fluorescent-based procedures may suffer from interference from other fluorescent compounds in urine since separation efficiency of the reported methods is less as compared to that of GC and the needed excitation of bisphenol A in the low UV range may reduce selectivity. Although the chromatographic methods can offer good selectivity and detection limit, they often require a timeconsuming detection process and complex pretreatment steps. Thus, these methods do not allow rapid processing of multiple samples and real-time detection. Moreover, these instrumentations are rather complicated and expensive, and are hardly employed for on-site measurement. In recent years, various ELISAs for the determination of bisphenol A have also been reported. However, the use of immunosensors is less advantageous as compared to chromatography techniques because the stability of the biological material is lower, complicated multistage steps are often required, large and expensive equipment is needed and specific antibodies from killed animals or particular proteins obtained by recombinant techniques are required. Therefore, there is a demand for new analytical technique with cheap instruments, low consumption, simplified operation, quick response, high sensitivity and real-time detection. In this regard, a pure electrochemical method is an alternative to determine lower concentrations of bisphenol A in aqueous solutions. However, a major obstacle encountered in the detection of bisphenol A by bare electrodes is the relatively high overpotential together with poor reproducibility resulting from a fouling effect, which causes rather poor selectivity and sensitivity. An effective way to overcome these barriers is electrode modification. Some chemically modified electrodes have been reported (Zhao et al. 2014; Yu et al. 2013; Najafi et al. 2014; Niu et al. 2013; Peng et al. 2014; Wang et al. 2014a, b; Gao et al. 2012; Deng et al. 2013). Each approach has its particular sensitivity and is subject to various limitations. So there is still a need for the development of reliable electrochemically

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based sensors for the determination of bisphenol A which are superior in accuracy, precision and speed at the levels commonly encountered in different natural samples. Graphene, a new class of promising carbon material, is of great interest. Graphene is a two-dimensional (2D) material that is composed of a planar monolayer of sp2 carbon atoms bonding in a hexagonal configuration (Vashist and Luong 2015). The unit cell of graphene contains two carbon atoms with an inter-atomic length of 0.142 nm. In addition, it exhibits good electrical conductivity and optical properties, is lightweight and has a large specific surface area and chemical stability. Because of these properties, a widespread range of novel materials and applications (Vashist and Luong 2015) have already been generated in various fields, including biomedical sensors, nanoelectronic devices, transparent electrodes, photodetectors, hydrogen storage, solar cells, fuel cells, electrical batteries and supercapacitors (Vashist and Luong 2015). Furthermore, compared to carbon nanotubes (CNTs), graphene provides the advantages of low cost and low metallic contamination levels. Therefore, graphene has begun to be exploited as an alternative choice for electrical sensors, especially during the fabrication of electrochemical-sensing devices (Beitollahi et al. 2014; Jouikov et al. 2015; Tajik et al. 2014a, b; Norouzi et al. 2011; Shi et al. 2015; Chang, et al. 2015; Sun, et al. 2015). Ionic liquids (ILs) are suitable materials for electrode modification because of their high ionic conductivity, wide electrochemical windows, good thermal stability and biocompatibility. Some researchers have reported different kinds of ILs in electrode modification for fabricating new biosensors (Tajik et al. 2014a, b). The results suggested that the use of ILs could facilitate efficient electron transfer and increase the sensitivity of response. Furthermore, ILs present a shielding effect to the Π–Π stacking interaction among graphene sheets; thus, they can promote the dispersion of graphene sheets. For example, Yang’s group has synthesized ILfunctionalized graphene sheets (IL-GR) with good dispersibility and long-term stability in various solvents (Du et al. 2011). In addition, other related reports found in the literature substantiated that the use of IL-GR could increase the sensitivity of response and facilitate efficient direct electron transfer of various redox biomolecules. Thus, IL-GR nanocomposites are expected to be useful and powerful materials for enhancing the

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electrochemical performance for the detection of different target molecules in electroanalytical applications (Li et al. 2013; Zhao et al. 2013; Yang et al. 2013; Wu et al. 2013; Liu, et al. 2013; Sun et al. 2013). Electrochemical methods offer practical advantages including operation simplicity, satisfactory sensitivity, wide linear concentration range, low expense of instruments, possibility of miniaturization, suitability for realtime detection and less sensitivity to matrix effects in comparison with separation and spectral methods (Gupta et al. 2006a, b, c, d; Goyal et al. 2008a, b, c; Beitollahi and Sheikhshoaie 2011a, b, c; Srivastava et al. 1996; Goyal et al. 2007; Mashhadizadeh and Shamsipur 1997; Norouzi et al. 2010; Jain et al. 2010; Guo and Khoo 1997; Alizadeh et al. 2010; Gupta et al. 2006a, b, c, d; Gupta et al. 2003a, b; Beitollahi and Sheikhshoaie 2011a, b, c; Gupta et al. 2003a, b; Moyo et al. 2014; Ganjali et al. 2005; Gupta et al. 2006a, b, c, d; Rafati et al. 2014; Gupta et al. 2006a, b, c, d; Goyal et al. 2008a, b, c; Gupta et al. 2007; Molaakbari et al. 2014; Prasad et al. 2004; Devnani and Satsangee 2013; Gupta et al. 2011a, b; Beitollahi et al. 2012; Jain et al. 1997; Deng et al. 2008; Gupta et al. 2013; Beitollahi and Sheikhshoaie 2011a, b, c; Gupta et al. 2012; Fonseca et al. 2011; Jain et al. 2006; Goyal et al. 2008a, b, c; Gupta et al. 2005; Hashemnia et al. 2012; Gupta et al. 2002; Beitollahi and Mostafavi 2014; Gupta et al. 2000; Yari and Sepahvand 2011; Gupta et al. 2011a, b; Mahmoudi Moghaddam, et al. 2014; Gupta et al. 1999). In the present work, we describe the preparation of a new ionic liquids/graphene oxide nanosheets paste electrode (ILGNPE) and investigate its performance for the determination of bisphenol A in aqueous solutions.

Experimental Apparatus and chemicals The electrochemical measurements were performed with an Autolab potentiostat/galvanostat (PGSTAT 302N, Eco Chemie, the Netherlands). The experimental conditions were controlled with General Purpose Electrochemical System (GPES) software. A conventional three-electrode cell was used at 25±1 °C. An Ag/AgCl/ KCl (3.0 M) electrode (Azae Electrode, Urmia, Iran), a platinum wire (Azae Electrode, Urmia, Iran) and ILGN PE were used as the reference, auxiliary and working

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electrodes, respectively. A Metrohm 710 pH meter was used for pH measurements. Bisphenol A and all of the other reagents were of analytical grade and were obtained from Merck (Darmstadt, Germany). The buffer solutions were prepared from orthophosphoric acid and its salts in the pH range of 2.0–9.0. Synthesis of graphene oxide nanosheets Graphene oxide nanosheets were synthesized from natural graphite flakes based on the modified Hummers and Offeman’s method. In a typical synthesis process, 1.0 g of pristine graphite flakes was immersed in 50 mL of formic acid and then sonicated for 2 h at room temperature. These resulting graphite plates were washed with acetone and then dried in an oven at 95 °C for 12 h. Then, 100 mL H2SO4 (95 %) was added into a 500-mL flask and cooled by immersion in an ice bath followed by stirring. About 1.0 g treated graphite powder and 0.5 g NaNO3 were added under vigorous stirring to avoid agglomeration. After the graphite powder was well dispersed, 3 g KMnO4 was added gradually under stirring and cooling so that the temperature of the mixture was maintained at below 10 °C. The mixture was stirred for 2 h and diluted with deionized doubledistilled water (in an ice bath). After that, 25 mL 15 % H2O2 was slowly added to the mixture until the colour of the mixture changed to brilliant yellow, indicating fully oxidized graphite. The as-obtained graphite oxide slurry was re-dispersed in deionized double-distilled water and then exfoliated to generate graphene oxide nanosheets by sonication for 2 h. Then, the solution was filtered and washed with diluted HCl solution to remove metal ions. Finally, the product was washed with deionized double-distilled water until the solution became acid free, and dried under vacuum at 50 °C. A typical transmission electron microscopy (TEM) for synthesized graphene oxide nanosheets is shown in Fig. 1. Preparation of the electrode ILGNPEs were prepared by mixing 0.1 g of graphene oxide nanosheets with 0.9 g graphite powder and approximately ∼0.8 mL of ionic liquids with a mortar and pestle. The paste was then packed into the end of a glass tube (ca. 3.4 mm i.d. and 15 cm long). A copper wire inserted into the carbon paste provided the electrical contact.

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Fig. 1 TEM image of synthesized graphene oxide nanosheets

For comparison, an ionic liquid/carbon paste electrode (ILCPE) in the absence of graphene oxide nanosheets, graphene oxide nanosheets carbon paste electrode (GNCPE) consisting of graphene oxide nanosheets and paraffin oil and bare carbon paste electrode (CPE) consisting of graphite powder and paraffin oil were also prepared in the same way.

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GNCPE (curve b) and bare CPE (curve a). The results showed that the oxidation of bisphenol A is very weak at the surface of the bare CPE but in the presence of ILs in CPE could enhance the peak current and decrease the oxidation potential (decreasing the overpotential). A substantial negative shift of the currents starting from oxidation potential for bisphenol A and a dramatic increase of the current indicate the catalytic ability of ILGNPE (curve d) and ILCPE (curve c) to bisphenol A oxidation. The results showed that the combination of graphene oxide nanosheets and the ionic liquid (curve d) definitely improved the characteristics of bisphenol A oxidation. However, ILGNPE shows a much higher anodic peak current for the oxidation of bisphenol A compared to ILCPE, indicating that the combination of graphene oxide nanosheets and IL has significantly improved the performance of the electrode toward bisphenol A oxidation. Effect of scan rate

Result and discussion Electrochemical behaviour of bisphenol A at the surface of various electrodes Figure 2 displays cyclic voltammetric responses from the electrochemical oxidation of 175.0 μM bisphenol A at the surface of ILGNPE (curve d), ILCPE (curve c),

The effect of potential scan rates on the oxidation current of bisphenol A has been studied (Fig. 3). The results showed that increasing the potential scan rate induced an increase in the peak current. In addition, the oxidation process is diffusion controlled as deduced from the linear dependence of the anodic peak current (Ip) on the square root of the potential scan rate (ν1/2) over a wide range from 10 to 300 mV s−1. Figure 4 shows the linear sweep voltammogram of an ILGNPE obtained in 0.1 M phosphate-buffered saline (PBS) (pH 7.0) containing 100.0 μM bisphenol A, with a sweep rate of 10 mV s−1. The points show the rising part of the voltammogram (known as the Tafel region), which is affected by the electron transfer kinetics between morphine and ILGNPE. The inset of Fig. 4 shows a Tafel plot that was drawn from points of the Tafel region of the linear sweep voltammogram. The Tafel slope of 0.085 V obtained in this case agrees well with the involvement of one electron in the rate-determining step of the electrode process, assuming a charge transfer coefficient of α=0.3. Chronoamperometric measurements

Fig. 2 CVs of a CPE, b GNCPE, c ILCPE and d ILGNPE in the presence of 175.0 μM bisphenol A at pH 7.0. In all cases, the scan rate was 50 mV s−1

Chronoamperometric measurements of bisphenol A at ILGNPE were carried out by setting the working electrode potential at 0.6 V vs. Ag/AgCl/KCl (3.0 M) for the various concentrations of bisphenol A in PBS (pH 7.0)

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Fig. 3 CVs of ILGNPE in 0.1 M PBS (pH 7.0) containing 100.0 μM bisphenol A at various scan rates; numbers 1–9 correspond to 10, 25, 50, 75, 100, 150, 200, 250 and 300 mV s−1, respectively. Inset: variation of anodic peak current vs. square root of scan rate

(Fig. 5). For an electroactive material (bisphenol A in this case) with a diffusion coefficient of D, the current observed for the electrochemical reaction at the mass transport-limited condition is described by the Cottrell equation (Bard and Faulkner 2001). Experimental plots of I vs. t−1/2 were employed, with the best fits for different concentrations of bisphenol A (Fig. 5(A)). The slopes of the resulting straight lines were then plotted vs. bisphenol A concentration (Fig. 5(B)). From Fig. 4 Linear sweep voltammetry (LSV) (at 10 mV s−1) of an ILGNPE in 0.1 M PBS (pH 7.0) containing 100.0 μM bisphenol A. The points are the data used in the Tafel plot. The inset shows the Tafel plot derived from the LSV

the resulting slope and Cottrell equation, the mean value of the D was found to be 2.5×10−6 cm2 s−1. Electrochemical impedance spectroscopy Electrochemical impedance spectroscopy (EIS) was also employed to study the oxidation of bisphenol A at the surface of various electrodes. Figure 6 shows Nyquist diagrams of ILGNPE (curve a), ILCPE (curve b),

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Fig. 5 Chronoamperograms obtained at ILGNPE in 0.1 M PBS (pH 7.0) for different concentrations of bisphenol A. Numbers 1–6 correspond to 0.25, 0.75, 1.0, 1.25, 1.5 and 1.75 mM of bisphenol A. Insets: A plots of I vs. t−1/2 obtained from chronoamperograms 1–6; B plot of the slope of the straight lines against bisphenol A concentration

GNCPE (curve c) and bare CPE (curve d) in the presence of bisphenol A at pH 7.0. A Nyquist diagram consists of a semicircle and a straight line with a slope of nearly 45° that is due to the occurrence of a mass transport process via diffusion. The semicircle diameters of a Nyquist plot reflect the electron transfer resistance (Rct), which is from the electron transfer of the bisphenol A solution. The results showed that for ILGNPE (curve a), the diameter of the semicircle is smaller than that of the other electrodes, which is due to the presence of highly conductive IL and graphene oxide nanosheets in the carbon paste. All Fig. 6 Nyquist plots of a ILGNPE, b ILCPE, c GNCPE and d CPE in the presence of 150.0 μM bisphenol A at a pH 7.0 PBS

these results indicated that morphine can successfully oxidize on the surface of ILGNPE. Calibration plot and limit of detection The peak current of bisphenol A oxidation at the surface of the modified electrode can be used for determination of bisphenol A in solution. Therefore, square wave voltammetry (SWV) experiments were done for different concentrations of bisphenol A (Fig. 7) (initial potential = 0.05 V, end potential= 0.7 V, step potential=

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Fig. 7 SWVs of ILGNPE in 0.1 M PBS (pH 7.0) containing different concentrations of bisphenol A. Numbers 1–12 correspond to 0.09, 0.3, 1.0, 5.0, 10.0, 25.0, 50.0, 75.0, 100.0, 150.0, 200.0 and 250.0 μM of bisphenol A. The inset shows the plots of the peak current as a function of bisphenol A concentration in the range of 0.09–250.0 μM

0.005 V, amplitude=0.02 V, frequency=10 Hz). The oxidation peak currents of bisphenol A at the surface of a modified electrode were proportional to the concentration of the bisphenol A within the ranges 9.0×10−8 to 2.5×10−4 M with a detection limit (3σ) of 55.0 nM.

Real sample analysis In order to evaluate the analytical applicability of the proposed method, also it was applied to the Table 1 Determination of bisphenol A in water samples. All the concentrations are in micromolars (n=5)

The repeatability and stability of IL-G-CPE The long-term stability of the ILGNPE was tested over a 3-week period. When cyclic voltammetries (CVs) were recorded after the modified electrode was stored in atmosphere at room temperature, the peak potential for bisphenol A oxidation was unchanged and the current signals showed a less than 2.6 % decrease relative to the initial response. The antifouling properties of the modified electrode toward bisphenol A oxidation and its oxidation products were investigated by recording the CVs of the modified electrode before and after use in the presence of morphine. CVs were recorded in the presence of bisphenol A after having cycled the potential 15 times at a scan rate of 50 mV s−1. The peak potentials were unchanged and the currents decreased by less than 2.43 %. Therefore, at the surface of ILGNPE, not only does the sensitivity increase but also the fouling effect of the analyte and its oxidation product decreases.

Sample Drinking water

River water

Wastewater

ND Not detected

Spiked

Found

Recovery (%)

R.S.D. (%)

0

ND





5.0

5.1

102.0

3.2

7.5

7.3

97.3

2.6

10.0

10.1

101.0

2.1

12.5

12.6

100.8

2.9

0

ND





2.5

2.4

96.0

2.8

7.5

7.7

102.7

3.4

12.5

12.4

99.2

3.1

17.5

17.6

100.6

1.7

0

ND





5.0

4.9

98.0

2.1

10.0

9.9

99.0

2.7

20.0

20.3

101.5

3.3

30.0

30.8

102.7

2.3

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determination of bisphenol A in some water samples. The results are given in table 1.

Conclusion In the present study, a modified paste electrode is constructed. The modified electrode was applied for bisphenol A determination. Excellent features, like a wide linear range, low detection limit, high reproducibility and repeatability and long-time stability proved the successful application of this sensor for the determinations of bisphenol A in real samples. Acknowledgments The authors acknowledge the financial support provided for this project (No. 7.5616) by the Institute of Science and High Technology and Environmental Sciences, Graduate University of Advanced Technology, Kerman, Iran.

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Construction of a nanostructure-based electrochemical sensor for voltammetric determination of bisphenol A.

A novel carbon paste electrode modified with graphene oxide nanosheets and an ionic liquid (n-hexyl-3-methylimidazolium hexafluoro phosphate) was fabr...
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