Abstract
Self-assembled monolayers of thiolated β-cyclodextrins on a gold electrode have been developed for the determination of thiodianiline. Pentanethiol was employed to fill the empty space between the β-cyclodextrins on the surface. The formation of a 1:2 inclusion complex between thiodianiline and β-cyclodextrin was studied by electrochemistry. The parameters affecting the modification of the electrode and the determination of thiodianiline by square wave voltammetry were optimized. The limits of detection and determination are 190 and 205 μg L−1, respectively. The accuracy, in terms of relative error values, is <7%. The precision, in terms of RSD (for n = 5), is <5%. The method was applied to the determination of thiodianiline in real wastewater samples with RSD values of <11% and an average recovery of 98% for all the spiking levels assayed.
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References
Wang J, Zeng BZ, Zhou X (2000) Applications of self-assembled monolayers in electroanalytical chemistry. Fenxi Kexue Xuebao 16:253–258
Wanichacheva N, Soto ER, Lambert CR, McGimpsey WG (2006) Surface-based lithium ion sensor: an electrode derivatized with a self-assembled monolayer. Anal Chem 78:7132–7137
Poirier GE, Tarlov MJ, Rushmeir HE (1994) 2-Dimensional liquid-phase and the px-root-3-phase of alkanethiol self-assembled monolayers on Au (111). Langmuir 10:3383–3386
Blanco E, Domínguez CSH, Hernández P, Vicente J, Quintana C, Hernández L (2009) Alkanethiols modified gold electrodes for selective detection of molecules with different polarity and molecular size. Application to vitamin B2 analysis. Electroanalysis 21:495–500
Carrillo I, Quintana MC, Esteva AM, Hernández L, Hernández P (2008) Influence of the chain length of alkanethiols in self-assembled submonolayers on the electrochemical response of aromatic amine mixtures. Electroanalysis 20:2614–2620
Connors KA (1997) The stability of cyclodextrin complexes in solution. Chem Rev 97:1325–1357
Nelles G, Weisser M, Back R, Wohlfart P, Wenz G, Mittler-Neher S (1996) Controlled orientation of cyclodextrin derivatives immobilized on gold surfaces. J Am Chem Soc 118:5039–5046
Lee JY, Park SM (1998) Electrochemistry of guest molecules in thiolated cyclodextrin self-assembled monolayers: an implication for size-selective sensors. J Phys Chem B 102:9940–9945
Breslow R, Zhang B (1996) Cholesterol recognition and binding by cyclodextrin dimmers. J Am Chem Soc 118:8495–8496
Fang B, Zhang W, Kan X, Tao H, Deng X, Li M (2006) Fabrication and application of a novel modified electrode based on β-cyclodextrin/ferrocenecarboxylic acid inclusion complex. Sens Actuators, B 117:230–235
Kitano H, Taira Y, Yamamoto H (2000) Inclusion of phthalate esters by a self-assembled monolayer of thiolated cyclodextrin on a gold electrode. Anal Chem 72:2976–2980
Velic D, Knapp M, Köhler G (2001) Supramolecular inclusion complexes between a coumarin dye and beta-cyclodextrin, and attachment kinetics of thiolated beta-cyclodextrin to gold surface. J Mol Struct 598:49–56
Velic D, Köhler G (2003) Supramolecular surface layer: coumarin/thiolated cyclodextrin/gold. Chem Phys Lett 371:483–489
Rojas MT, Koniger R, Stoddart JF, Kaiffer AE (1995) Sopported monolayers containing preformed binding-sites—synthesis and interfacial binding-properties of a thiolated beta-cyclodextrin derivative. J Am Chem Soc 117:336–343
Rastogi SC, Barwick VJ, Carter SV (1997) Identification of organic colourants in cosmetics by HPLC diode array detection. Chromatographia 45:215–228
BgVV (2002) Amtliche Sammlung von Untersuchungsverfahren nach §35 LMBG jetzt auch online. Beuth Verlag GmbH. http://www.bfr.bund.de/cd/1600. Accessed 22 March 2010
Garrigós MC, Reche F, Marín ML, Jimenez A (2002) Determination of aromatic amines formed from azo colorants in toy products. J Chromatogr A 976:309–317
Chang W, Sung YH, Huang SD (2003) Analysis of carcinogenic aromatic amines in water samples by solid-phase microextraction coupled with high-performance liquid chromatography. Anal Chim Acta 495:109–122
Sutthivaiyakit P, Achatz ES, Lintelmann EJ, Aungpradit T, Chanwirat ER, Chumanee ES, Kettrup EA (2005) LC-MS/MS method for the confirmatory determination of aromatic amines and its application in textile analysis. Anal Bioanal Chem 381:268–276
Sabbioni CG, Schütze D (1998) Hemoglobin binding of bicyclic aromatic amines. Chem Res Toxicol 11:471–483
Martin-Calero A, Pino V, Ayala JH, González V, Alfonso AM (2009) Ionic liquids as mobile phase additives in high-performance liquid chromatography with electrochemical detection: application to the determination of heterocyclic aromatic amines in meat-based infant foods. Talanta 79:590–597
Domínguez SH, Quintana C, Vicente J, Hernández P, Hernández L (2008) Sub-monolayer assemblies of octanethiol and octadecylthiol at gold electrodes for the direct analysis of 4, 4′-oxydianiline in wastewaters and shoe-dyeing samples. Talanta 74:1014–1019
Chen Z, Xi F, Yang S, Wu Q, Lin X (2008) Development of a bienzyme system based on sugar-lectin biospecific interactions for amperometric determination of phenols and aromatic amines. Sens Actuators, B 130:900–907
Bain CD, Eval J, Whitesides GM (1989) Formation of monolayers by the coadsorption of thiols on gold—variation in the head group, tail group, and solvent. J Am Chem Soc 111:7155–7164
Yañez C, Nuñez Vergara LJ, Squella JA (2002) Determination of nitrendipine with beta-cyclodextrin modified carbon paste electrode. Electroanalysis 14:559–562
Wang Z, Xiao S, Chen BY (2006) Beta-cyclodextrin incorporated carbon nanotubes-modified electrodes for simultaneous determination of adenine and guanine. J Electroanal Chem 589:237–242
Guo YJ, Pan JH, Li XM, Lu F (2006) Electroanalytical method of acid red 1 and its supramolecular system with cyclodextrins. Dyes Pigm 70:27–30
Ferancová A, Korová E, Miko R, Labuda J (2000) Determination of tricyclic antidepressants using a carbon paste electrode modified with beta-cyclodextrin. J Electroanal Chem 492:74–77
Yañez C, Salazar R, Nuñez-Vergara LJ, Squella JA (2004) Spectrophotometric and electrochemical study of the inclusion complex between beta-cyclodextrin and furnidipine. J Pharm Biomed Anal 35:51–56
Harvey D (2002) Química Analítica Moderna. McGraw Hill/Interamericana de España, Madrid
Beulen MWJ, Bügler J, de Jong MR, Lammerink B, Huskens J et al (2000) Host-guest interactions at self-assembled monolayers of cyclodextrins on gold. J Chem Eur 6:1176–1183
Majewska UE, Chmurski K, Biesiada K, Olszyna AR, Bilewicz R (2006) Dopamine oxidation at per(6-deoxy-6-thio)-alpha-cyclodextrin monolayer modified gold electrodes. Electroanalysis 18:1463–1470
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Authors thank to Universidad Autónoma de Madrid and to the Comunidad Autónoma de Madrid for the financial support (CCG07-UAM/PPQ-1645).
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Quintana, C., Domínguez, C.S.H., Blanco, E. et al. Self-assembled host-guest nanostructures on gold electrodes for thiodianiline determination. Microchim Acta 171, 41–47 (2010). https://doi.org/10.1007/s00604-010-0400-7
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DOI: https://doi.org/10.1007/s00604-010-0400-7