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Visual detection of F and CN using a novel phenylthiosemicarbazide-based chemosensor and its application in real samples

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Abstract

High toxicity and different applications of cyanide and fluoride ions in the chemical, biological, and medical fields encouraged attention for design and fabrication of new probes for their detection. Herein, a novel phenylthiosemicarbazide-based chemosensor (PTSCS) was synthesized by condensation reaction and applied for colorimetric detection of F and CN ions. Techniques including naked-eye test, paper test strips, UV–visible and 1H NMR spectroscopic techniques were used to confirm the interaction of PTSCS with F and CN ions. Addition of cyanide or fluoride ions to the solution of PTSCS results in color change from yellow to dark red with a large bathochromic shift (~ 174 nm) in absorption spectra. Probe PTSCS showed linear responses toward F and CN ions with detection limits (LOD) of 0.044 μM and 0.075 μM, respectively. It is interesting that no other tested ions caused any color change when these ions are added to the PTSCS solution. The interaction binding mode of PTSCS with F and CN was found to be 1:1 based on the Job’s plot analysis. Furthermore, the developed chemosensor was applied for the qualitative and quantitative analysis of F and CN in toothpaste, apple seeds oil and water samples. Test strips based on PTSCS were fabricated using the filter papers for possible commercialization.

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References

  • Benet M, Villabona M, Llavina C, Mena S, Hernando J, Al-Kaysi RO, Guirado G (2017) Fluorescent “Turn-Off” detection of fluoride and cyanide ions using zwitterionic spirocyclic meisenheimer compounds. Molecules 22:1842

    Article  Google Scholar 

  • Carton RJ (2006) Review of the 2006 United States National Research Council report: fluoride in drinking water. Fluoride 39:163–172

    CAS  Google Scholar 

  • Chandra S, Ruzicka A, Svec P, Lang H (2006) Organotin compounds: an ionophore system for fluoride ion recognition. Anal Chim Acta 577:91–97

    Article  CAS  Google Scholar 

  • Chavali R, Gunda NSK, Naicker S, Mitra SK (2015) Rapid detection of fluoride in portable water using a novel fluorogenic compound 7-O-tert-butyldiphenylsilyl-4-methylcoumarin. Anal Chem 6:26–31

    CAS  Google Scholar 

  • Gillis EP, Eastman KJ, Hill MD, Donnelly DJ, Meanwell NA (2015) Applications of fluorine in medicinal chemistry. J Med Chem 58:8315–8359

    Article  CAS  Google Scholar 

  • Gimeno N, Li X, Durrant JR, Vilar R (2008) Cyanide sensing with organic dyes: studies in solution and on nanostructured Al2O3 surfaces. Chem Eur J 14:3006–3012

    Article  CAS  Google Scholar 

  • González-Valoys AC, Arrocha J, Monteza-Destro T, Vargas-Lombardo M, Esbrí JM, Garcia-Ordiales E, Jiménez-Ballesta R, García-Navarro FJ, Higueras P (2022) Environmental challenges related to cyanidation in Central American gold mining; the Remance mine (Panama). J Environ Manag 302:113979

    Article  Google Scholar 

  • Han J, Zhang J, Gao M, Hao H, Xu X (2019) Recent advances in chromo-fluorogenic probes for fluoride detection. Dyes Pigm 162:412–439

    Article  CAS  Google Scholar 

  • Jali BR, Baruah JB (2021) Recent progress in Schiff bases in detections of fluoride ions. Dyes Pigm 194:109575

    Article  CAS  Google Scholar 

  • Keefe M, Benkstein K, Hupp J (2000) Luminescent sensor molecules based on coordinated metals: a review of recent developments. Coord Chem Rev 205:201–228

    Article  CAS  Google Scholar 

  • Khoshsoroor S, Mohammadi A, Khalili B, Mohammadi S (2020) A novel uracil-based chemosensor for sequential detection of copper (II) and cyanide ions and its application in real samples. J Photochem Photobiol A Chem 388:112208

    Article  Google Scholar 

  • Lacson CFZ, Lu MC, Huang YH (2021) Fluoride-containing water: a global perspective and a pursuit to sustainable water defluoridation management-an overview. J Clean Prod 280:124236

    Article  CAS  Google Scholar 

  • Lee HJ, Park SJ, Sin HJ, Na YJ, Kim C (2015) A selective colorimetric chemosensor with an electron-withdrawing group for multi-analytes CNˉ and Fˉ. N J Chem 39:3900–3907

    Article  CAS  Google Scholar 

  • Li X, Zhang M, Wang Y, Wang X, Ma H, Li P, Song W, Han XX, Zhao B (2018) Direct detection of fluoride ions in aquatic samples by surface-enhanced Raman scattering. Talanta 178:9–14

    Article  CAS  Google Scholar 

  • Ma J, Dasgupta PK (2010) Recent developments in cyanide detection: a review. Anal Chim Acta 673:117–125

    Article  CAS  Google Scholar 

  • Mohammadi A, Ghasemi Z (2020) A simple pyrimidine based colorimetric and fluorescent chemosensor for sequential detection of copper (II) and cyanide ions and its application in real samples. Spectrochim Acta A Mol Biomol Spectrosc 228:117730

    Article  CAS  Google Scholar 

  • Mohammadi A, Kianfar M (2018) A simple colorimetric chemosensor with highly performance for detection of cyanide and copper ions and its practical application in real samples. J Photochem Photobiol A Chem 367:22–31

    Article  CAS  Google Scholar 

  • Mohammadi A, Yaghoubi S (2017) A new dual colorimetric chemosensor based on quinazolinone for CNˉ, AcOˉ and Cu2+ ions. Sens Actuators B Chem 241:1069–1075

    Article  CAS  Google Scholar 

  • Mohammadi A, Dehghan Z, Rassa M, Chaibakhsh N (2016) Colorimetric probes based on bioactive organic dyes for selective sensing of cyanide and fluoride ions. Sens Actuators B Chem 230:388–397

    Article  CAS  Google Scholar 

  • Mondal S, Gupta P, Rahaman F, Gautam P, Lekshmi IC (2022) Colorimetric and fluorimetric detection of fluoride ion using thiazole derived receptor. Spectrochim Acta A Mol Biomol Spectrosc 264:120301

    Article  CAS  Google Scholar 

  • Murugesan K, Jeyasingh V, Lakshminarayanan S, Selvapalam N, Dass G, Piramuthu L (2021) Anion-binding-induced and reduced fluorescence emission (ABIFE & ABRFE): a fluorescent chemo sensor for selective turn-on/off detection of cyanide and fluoride. Spectrochim Acta A Mol Biomol Spectrosc 245:118943

    Article  CAS  Google Scholar 

  • Park IS, Heo EJ, Kim JM (2011) A photochromic phenoxyquinone based cyanide ion sensor. Tetrahedron Lett 52:2454–2457

    Article  CAS  Google Scholar 

  • Ramesh S, Kumaresan S (2021) A highly selective coumarin-based chemosensor for naked-eye detection of cyanide anions via nucleophilic addition in pure aqueous environment. Microchem J 169:106584

    Article  CAS  Google Scholar 

  • Sahu S, Sikdar Y, Bag R, Maiti DK, Cerón-Carrasco JP, Goswami S (2019) Visual detection of fluoride ion based on ICT mechanism. Spectrochim Acta A Mol Biomol Spectrosc 213:354–360

    Article  CAS  Google Scholar 

  • Sarveswari S, Beneto AJ, Siva A (2017) Colorimetric sensing of cyanide and fluoride ions by diaminomalenonitrile based Schiff bases. Sens Actuators B Chem 245:428–434

    Article  CAS  Google Scholar 

  • Sharma S, Hundal MS, Hundal G (2013) Selective recognition of fluoride ions through fluorimetric and colorimetric response of a first mesitylene based dipodal sensor employing thiosemicarbazones. Tetrahedron Lett 54:2423–2427

    Article  CAS  Google Scholar 

  • Sharma D, Moirangthem A, Kumar R, Kumar SA, Kuwar A, Callan JF, Basu A, Sahoo SK (2015) Pyridoxal-thiosemicarbazide: its anion sensing ability and application in living cells imaging. RSC Adv 5:50741–50746

    Article  CAS  Google Scholar 

  • Srivastava S, Flora SJS (2020) Fluoride in drinking water and skeletal fluorosis: a review of the global impact. Curr Environ Health Rep 7:140–146

    Article  CAS  Google Scholar 

  • Sun Y, Wang G, Guo W (2009) Colorimetric detection of cyanide with N-nitrophenyl benzamide derivatives. Tetrahedron 65:3480–3485

    Article  CAS  Google Scholar 

  • Wang F, Wang L, Chen X, Yoon J (2014) Recent progress in the development of fluorometric and colorimetric chemosensors for detection of cyanide ions. Chem Soc Rev 43:4312–4324

    Article  CAS  Google Scholar 

  • Xu Z, Chen X, Kim HN, Yoon J (2010) Sensors for the optical detection of cyanide ion. Chem Soc Rev 39:127–137

    Article  CAS  Google Scholar 

  • Yang L, Li M, Ruan S, Xu X, Wang Z, Wang S (2021) Highly efficient coumarin-derived colorimetric chemosensors for sensitive sensing of fluoride ions and their applications in logic circuits. Spectrochim Acta A Mol Biomol Spectrosc 255:119718

    Article  CAS  Google Scholar 

  • Yilmaz B, Keskinates M, Aydin Z, Bayrakci M (2022) A highly selective optical sensor for the detection of cyanide ions in aqueous solution and living cells. J Photochem Photobiol A Chem 424:113651

    Article  CAS  Google Scholar 

  • Yu B, Li CY, Sun YX, Jia HR, Guo JQ, Li J (2017) A new azine derivative colorimetric and fluorescent dual-channel probe for cyanide detection. Spectrochim Acta A Mol Biomol Spectrosc 184:249–254

    Article  CAS  Google Scholar 

  • Zhang JF, Zhou Y, Yoon J, Kim JS (2011) Recent progress in fluorescent and colorimetric chemosensors for detection of precious metal ions (silver, gold and platinum ions). Chem Soc Rev 40:3416–3429

    Article  CAS  Google Scholar 

Download references

Acknowledgements

The authors are grateful to the Research Council of University of Guilan for financial support of this research work.

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Correspondence to Asadollah Mohammadi.

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Mohammadi, A., Hadinezhad, F. Visual detection of F and CN using a novel phenylthiosemicarbazide-based chemosensor and its application in real samples. Chem. Pap. 76, 7007–7021 (2022). https://doi.org/10.1007/s11696-022-02399-3

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