In collaboration with Payame Noor University and Iranian Chemical Science and Technologies Association

Document Type : Full research article

Authors

Department of Chemistry, Payame Noor University, P.O. Box 19395-4697, Tehran, Iran

Abstract

Bromopyrogallol Red (BPR) dye (Dibromopyrogallolsulfonphthalein), was evaluated as a highly selective colorimetric chemosensor for tin and citrate ion. BPR displayed rapid response, high specificity, visual determination and good selectivity toward tin and citrate ion over other competing cations and anions in DMSO/H2O (1:1 v/v) media. The sensing mechanism was discussed by UV–Vis, titration, and a comparison study. Over a wide range from 0.4 µmol L-1 to 153.8 µmol L-1 and 0.02 µmol L-1 to 1.08 µmol L-1, a good linear relationship between the absorbance and the concentration of tin and citrate ion was found respectively and the detection limit was estimated to be as low as 0.06 and 0.003 µmol L-1 (S/N = 3) for tin and citrate ion. This proposed chemosensor has also been successfully applied for the determination of citrate in real samples which demonstrates its value of practical applications in food and biological systems. 

Keywords

[1]     P.A. Gale, S.E. Garcia-Garrido and J. Garric, Anion receptors based on organic frameworks: highlights from 2005 and 2006, Chem. Soc. Rev. 37 (2008) 151–190, https://doi.org/10.1039/B715825D.
[2]     R. Martínez-Manez and F. Sancenon, Fluorogenic and chromogenic chemosensors and reagents for anions, Chem. Rev. 103 (2003) 4419–4476, https://doi.org/ 10.1021/cr010421e.
[3]     Y. Zhou, J.F. Zhang, J. Yoon, Fluorescence and colorimetric chemosensors for fluoride-ion detection, Chem. Rev. 114 (2014) 5511–5571, https://doi.org/ 10.1021/cr400352m.
[4]     H. Sohn, S. Letan, M.J. Sailor and W.C. Trogler, Detection of fluorophosphonate chemical warfare agents by catalytic hydrolysis with a porous silicon interferometer, J. Am. Chem. Soc. 122 (2000) 5399–5400, https://doi.org/ 10.1021/ja0006200.
[5]     A.P. de Silva, H.Q.N. Gunaratne, T. Gunnlaugsson, A.J.M. Huxley, C.P. McCoy, J. T. Rademacher and T.E. Rice, Signaling recognition events with fluorescent sensors and switches, Chem. Rev. 97 (1997) 1515–1566, https://doi.org/10.1021/ cr960386p.
[6]     A.W. Czarnik, Chemical communication in water using fluorescent chemosensors, Acc. Chem. Res. 27 (1994) 302–308, https://doi.org/10.1021/ar00046a003.
[7]     L. Yuan, W. Lin, K. Zheng, L. He and W. Huang, Far-red to near infrared analyteresponsive fluorescent probes based on organic fluorophore platforms for fluorescence imaging, Chem. Soc. Rev. 42 (2013) 622–661, https://doi.org/ 10.1039/C2CS35313J.
[8]     N. Boens, V. Leen and W. Dehaen, Fluorescent indicators based on BODIPY, Chem. Soc. Rev. 41 (2012) 1130–1172, https://doi.org/10.1039/C1CS15132K.
[9]     M. Beija, C.A.M. Afonso and J.M.G. Martinho, Synthesis and applications of Rhodamine derivatives as fluorescent probes, Chem. Soc. Rev. 38 (2009) 2410–2433, https://doi.org/10.1039/B901612K.
[10] X. Chen, T. Pradhan, F. Wang, J.S. Kim and J. Yoon, Fluorescent chemosensors based on spiroring-opening of Xanthenes and related derivatives, Chem. Rev. 112 (2012) 1910–1956, https://doi.org/10.1021/cr200201z.
[11] S. Blunden and T. Wallace, Tin in canned food: A review and understanding of occurrence and effect, Food Chem. Toxicol. 41 (2003) 1651–1662, https://doi.org/10.1016/S0278-6915(03)00217-5.
[12] A. Kassoufab, H. Chebiba, N. Lebbosc and R. Ouainia, Migration of iron, lead, cadmium and tin from tinplate-coated cans into chickpeas, Food Addit Contam Part A Chem Anal Control Expo Risk Assess, 30, (2013). 1987–1992, https://doi.org/10.1080/19440049.2013.832399.
[13] U. Itodo and I.U. Happiness, Estimation of toxic metals in canned milk products from unlaquered tin plate cans, J. Am. Sci. 6 (2010) 173–178.
[14] I. Arvanitoyannis, The effect of storage of canned meat on concentration of the metals Fe, Cu, Zn, Pb, Sn, Al, Cd and Ni, Food/Nahrung 34 (1990) 147–151, https://doi.org/10.1002/food.19900340211
[15] E. Sunday, N. Ukoha and P. Onyeoziri, Tin and aluminium concentration in canned foods, drinks and beverages sold in nigerian markets, Chem. Mater. Res. 3 (2013) 32–40.
[16] G. Xiang, Y. Huang and Y. Luo, Solid phase extraction of trace cadmium and lead in food samples using modified peanut shell prior to determination by flame atomic absorption spectrometry, Microchim. Acta 165 (2009) 237–242, https://doi.org/10.1007/s00604-008-0126-y.
[17] E. Czopa, A. Economou and A. Bobrowski, A study of in situ plated tin-film electrodes for the determination of trace metals by means of square-wave anodic stripping voltammetry., Electrochim. Acta, 56 (2011) 2206–2212, https://doi.org/10.1016/j.electacta.2010.12.017.
[18] E.A. Hutton, S.B. Hocˇevar, L. Mauko and B. Ogorevc, Bismuth film electrode for anodic stripping voltammetric determination of tin, Anal. Chim. Acta, 24 (2006) 244–250, https://doi.org/10.1016/j.aca.2006.07.075.
[19] S.M. Sabry and A.M. Wahbi, Application of orthogonal functions to differential pulse voltammetric analysis: Simultaneous determination of tin and lead in soft drinks, Anal. Chim. Acta 40 (1999)173–183, https://doi.org/10.1016/S0003-2670(99)00473-0.
[20] D. Bakircioglu, Y.B. Kurtulus and G. Ucar, Determination of some traces metal levels in cheese samples packaged in plastic and tin containers by ICPOES after dry, wet and microwave digestion, Food Chem. Toxicol. 49 (2011) 202–207, https://doi.org/10.1016/j.fct.2010.10.017.
[21] E. Morte, S. Barbosa, E.C. Santos, J.A. Nobregac and M.G. Korn, Axial view inductively coupled plasma optical emission spectrometry for monitoring tin concentration in canned tomato sauce samples, Food Chem. 131 (2012) 348–352, https://doi.org/10.1016/j.foodchem.2011.08.015
[22] Y. Sahan, F. Basoglu and S. Gucer, ICP-MS analysis of a series of metals (namely: Mg, Cr Co, Ni, Fe, Cu, Zn, Sn, Cd and Pb) in black and green olive samples from Bursa, Turkey, Food Chem. 105 (2007) 395–399, https://doi.org/10.1016/j.foodchem.2006.12.026.
[23] L. Perring and M. Basic-Dvorzak, Determination of total tin in canned food using inductively coupled plasma atomic emission spectroscopy, Anal. Bioanal. Chem. 374 (2002) 235–243, https://doi.org/10.1007/s00216-002-1420-x.
[24]  X. Huang, W. Zhang, S. Han and X. Wang, Determination of tin in canned foods by UV/visible spectrophotometric technique using mixed surfactants, Talanta 44 (1997) 817–822, https://doi.org/10.1016/S0039-9140(96)02119-4.
[25] I.N. Pasias, V. Papageorgiou, N.S. Thomaidis, and C. Proestos, Development and validation of an ET-AAS method for the determination of tin in canned tomato paste samples. Food Anal. Methods 5 (2012) 835–840, https://doi.org/10.1007/s12161-011-9320-3.
[26] J.L. Manzoori, M. Amjadi and D. Abolhasani, Spectrofluorimetric determination of tin in canned foods, J. Hazard. Materials 137 (2006) 1631–1635, https://doi.org/10.1016/j.jhazmat.2006.04.058.
[27] H. Abedi and H. Ebrahimzadeh, Imprinted polymer-based extraction for speciation analysis of inorganic tin in food and water samples. React. Func. Polym. 73, (2013).  634–640, https://doi.org/10.1016/j.reactfunctpolym.2013.01.011.
[28] M.B. Gholivanda, A. Babakhanian and E. Rafiee, Determination of Sn(II) and Sn(IV) after mixed micelle-mediated cloud point extraction using apolyoxometalate as a complexing agent by flame atomic absorption spectrometry, Talanta 76 (2008) 503–508, https://doi.org/10.1016/j.talanta.2008.03.057.
[29] J.L. Sessler, P.A. Gale, W.S. Cho and J.F. Stoddart, (Ed.), In Anion Receptor Chemistry (Mono graphs in Supra molecular Chemistry), RSC, Cambridge, UK, 2006.
[30] Z. Xu, S.K. Kim and J. Yoon, Revisit to imidazolium receptors for the recognition of anions: highlighted research during 2006-2009, Chem.Soc.Rev. 39 (2010) 1457–1466, https://doi.org/10.1039/B918937H.
[31] D.Y. Lee, N. Singh and D.O. Jang, A benzimidazole-based single molecular multi- analyte fluorescent probe for the simultaneous analysis of Cu2+ and Fe3+, Tetrahedron Lett. 51 (2010) 1103–1106, https://doi.org/10.1016/j.tetlet.2009.12.085.
[32] M.I. Burguete, F. Galindo, S.V. Luis and L. Vigara, A turn-on fluorescent indicator for citrate with micromolar sensitivity,Dalton Trans. (2007) 4027–4033. https://doi.org/10.1039/B711139H
[33] A.S. Tripathi and I. Sheikh, “Development and validation of RP-HPLC method for sildenafil citrate in rat plasma”, J. Saudi. Pharma, 21 (2013) 317-321, https://doi.org/10.1016/j.jsps.2012.09.003.
[34] S. Azzouzi and H.K. Patra, “Citrate-selective electrochemical µ-sensor for early stage detection of prostate cancer”, Sensor Actuat. B-Chem. 228 (2016) 335-346, https://doi.org/10.1016/j.snb.2016.01.056.
[35]  H. Tavallali, M.R. Baezzat, G. Deilamy-Rad, A. Parhami and N. Hasanli, An ultra- sensitive and highly selective fluorescent and colorimetric chemosensor for citrate ions basedon rhodamineB and its application as the first molecular security keypad lock basedon phosphomolybdic acid and citrate inputs, J. Lumin. 160 (2015) 328–336. https://doi.org/10.1016/j.jlumin.2014.12.034.
[36] H. Tavallali, G. Deilamy-Rad, A. Parhami and S.Z. Mosavi, Dithizone as novel and efficient chromogenic probe for cyanide detection, Spectrochim. Acta A, 121 (2014) 139-146. https://doi.org/10.1016/j.saa.2013.10.083.
[37] H. Tavallali, M.R. Baezzat, G. Deilamy-Rad, A. Parhami and N. Hasanli, A novel cyanide-selective colorimetric and fluorescent chemosensor: First molecular security keypad lock based on phosphotungstic acid and CN inputs, J. Hazard. Mater. 266 (2014) 189-197. https://doi.org/10.1016/j.jhazmat.2013.12.026.
[38]  H. Tavallali, G. Deilamy-Rad, A. Parhami and E. Abbasiyan, A new application of bromopyrogallol red as a selective and sensitive competition assay for recognition and determination of acetate anion in DMSO/water media, Dyes. Pigment. 94(2012)541–547. https://doi.org/10.1016/j.dyepig.2012.03.006.
[39] H. Tavallali, G. Deilamy-Rad, A. Parhami and S. Kiyani, Dithizone as novel and efficient chromogenic probe for cyanide detection in aqueous media through nucleophilic addition in to diazenylthione moiety, Spectrochim. Acta A 121(2014)139–146. https://doi.org/10.1016/j.saa.2013.10.083.
[40] . Tavallali, G. Deilamy-Rad, A. Parhami and N. Hasanli, An efficient and ultra- sensitive rhodamineB-based reversible colorimetric chemosensor for naked- eye recognition of molybdenum and citrate ions in aqueous solution: sensing behavior and logic operation, Spectrochim. Acta A 139 (2015) 253–261. https://doi.org/10.1016/j.saa.2014.11.110.
[41] H.A. Benesi and J.H. Hildebrand, A spectrophotometric investigation of the interaction of iodine with aromatic hydrocarbons, J. Am. Chem. Soc. 71 (1949) 2703–2707. https://doi.org/10.1021/ja01176a030.
[42] A. Afkhami and N. Sarlak, Design and characteristics of a sulfide and sulfite optode based on immobilization of methyl violet on a triacetylcellulose membrane, Sens. Actuators B.Chemical 124 (2007) 285-289. https://doi.org/10.1016/j.snb.2006.12.041.
[43] . Cacace, H. Ashbaugh, N. Kouri, S. Bledsoe, S Lancaster and S. Chalk,Spectrophotometric determination of aqueous cyanide using a revised phenolphthalin method,Anal. Chim. Acta 589 (2007) 137-141. https://doi.org/10.1016/j.aca.2007.02.004.
[44] D.G. Themelis, S.C. Karastogianni and P.D. Tzanavaras, Selective determination of cyanides by gas diffusion-stopped flow-sequential injection analysis and an on-line standard addition approach,Anal. Chim. Acta 632 (2009) 93-100. https://doi.org/10.1016/j.aca.2008.10.074 .
[45] J.N. Miller and J.C. Miller, Statistics and Chemometrics for Analytical Chemistry, 5th ed., Pearson Education Limited, Prentice Hall, NY, 2005.