Skip to main content
SpringerLink
Log in

Coumarin Linked Cyanine Dye for the Selective Detection of Cyanide Ion in Environmental Water Sample

  • Research
  • Published:
Journal of Fluorescence Aims and scope Submit manuscript

Abstract

A benzoxazole-coumarin-based probe BOC, was synthesized and validated for its anion sensing ability and found to be effective in recognizing cyanide ions. Upon addition of cyanide, a spontaneous color change was observed that was visible to the naked eye. The sensitization process takes place with nucleophilic addition, and the cyanide ion added to the probe disrupts the intra molecular charge transfer transition (ICT) between the donor and acceptor units, causing the pink colored probe to become yellow. Ultraviolet and fluorescence methods were applied to measure the detection limits of probes with added cyanide ions, which were found to be 3.47 µM and 2.48 nM. The stoichiometry of the probe with the cyanide ion was determined by the Job’s method, NMR titration, and mass spectrometry and was found to be in a 1:1 ratio. The results obtained from the visual and UV-visible spectral studies are justified by theoretical calculations. The cyanide-loaded probe induced visual changes, which enabled the development of a test strip for field application, and the prepared strip can be used to detect the ppm level of cyanide in water samples. The developed probe, BOC, can be used to detect cyanide ions in various water samples.

This is a preview of subscription content, log in via an institution to check access.

Access this article

Log in via an institution

Price excludes VAT (USA)
Tax calculation will be finalised during checkout.

Instant access to the full article PDF.

Institutional subscriptions

Scheme 1
Fig. 1
Fig. 2
Fig. 3
Fig. 4
Fig. 5
Fig. 6
Fig. 7
Fig. 8
Fig. 9
Fig. 10

Similar content being viewed by others

Data Availability

No datasets were generated or analysed during the current study.

References

  1. Ashton TD, Jolliffe KA, Pfeffer FM (2015) Luminescent probes for the bioimaging of small anionic species in vitro and in vivo. Chem Soc Rev 44:4547–4595

    Article  CAS  PubMed  Google Scholar 

  2. Busschaert N, Caltagirone C, Rossom WV, Gale PA (2015) Applications of supramolecular anion recognition. Chem Rev 115:8038–8155

    Article  CAS  PubMed  Google Scholar 

  3. Zhang L, Zou LY, Guo JF, Ren AM (2016) Theoretical investigation on the one- and two-photon responsive behavior of fluoride ion probes based on diketopyrrolopyrrole and its π-expanded derivatives. New J Chem 40:4899–4910

    Article  CAS  Google Scholar 

  4. De silva AP, Gunaratne HQN, Gunnlaugsson T, Huxley AJM, McCoy CP, Rademacher JD, Rice TE (1997) Signaling recognition events with fluorescent sensors and switches. Chem Rev 97:1515–1566

    Article  PubMed  Google Scholar 

  5. Sessler JL, Camiolo S, Gale PA (2003) Pyrrolic and polypyrrolic anion binding agents. Coord Chem Rev 240:17–55

    Article  CAS  Google Scholar 

  6. Beer PD, Gale PA (2001) Anion recognition and sensing: the state of the art and future perspectives. Angew Chem Int Ed 40:486–516

    Article  CAS  Google Scholar 

  7. Kulig KW (1991) Case study 12, Cyanide toxicity. U.S. department of health and human services Atlanta, GA, USA 312-331

  8. Shahid M, Misra A (2013) A simple and sensitive intramolecular charge transfer fluorescent probe to detect CN- in aqueous media and living cells. Anal Methods 5:434–437

    Article  CAS  Google Scholar 

  9. Kim HJ, Lee H, Lee JH, Choi DH, Jung JH, Kim JS (2011) Bisindole anchored mesoporous silica nanoparticles for cyanide sensing in aqueous media. Chem Commun 47:10918–10920

    Article  CAS  Google Scholar 

  10. Vennesland B, Comm EE, Knownles CJ, Westly J, Wissing F (1981) Cyanide in biology. Academic, London

    Google Scholar 

  11. Kulig KW, Ballantyne B (1991) Cyanide toxicity. Agency for toxic substances and disease registry, US department of health & human services, public health service, Atlanta, GA, 15

  12. Xu ZC, Chen XQ, Kim HN, Yoon JY (2010) Sensors for the optical detection of cyanide ion. Chem Soc Rev 39:127–137

    Article  CAS  PubMed  Google Scholar 

  13. Ishii A, Seno H, Watanabe-Suzuki K, Suzuki O (1998) Determination of cyanide in whole blood by capillary gas chromatography with cryogenic oven trapping. Anal Chem 70:4873–4876

    Article  CAS  PubMed  Google Scholar 

  14. Shan D, Mousty C, Cosnier S (2004) Subnanomolar cyanide detection at polyphenol oxidase/clay biosensors. Anal Chem 76:178–183

    Article  CAS  PubMed  Google Scholar 

  15. Safavi A, Maleki N, Shahbaazi HR (2004) Indirect determination of cyanide ion and hydrogen cyanide by adsorptive stripping voltammetry at a mercury electrode. Anal Chim Acta 503:213–231

    Article  CAS  Google Scholar 

  16. Rao VK, Suresh SR, Rao NBSN, Rajaram P (1997) An electrochemical sensor for detection of hydrogen cyanide gas. Bull Electrochem 13:327–329

    CAS  Google Scholar 

  17. Christison TT, Rohrer JS (2007) Direct determination of free cyanide in drinking water by ion chromatography with pulsed amperometric detection. J Chromatogr A 1155:31–39

    Article  CAS  PubMed  Google Scholar 

  18. Suzuki T, Hiolki A, Kurahashi M (2003) Development of a method for estimating an accurate equivalence point in nickel titration of cyanide ions. Anal Chim Acta 476:159–165

    Article  CAS  Google Scholar 

  19. Surleva AR, Nikolova VD, Neshkova MT (2007) A new generation of cyanide ion-selective membranes for flow injection application: part II. Comparative study of cyanide flow-injection detectors based on thin electroplated silver chalcogenide membranes. Anal Chim Acta 583:174–181

    Article  CAS  PubMed  Google Scholar 

  20. Tian Y, Dasgupta PK, Mahon SB, Ma J, Brenner M, Wang J, Boss GR (2013) A disposable blood cyanide sensor. Anal Chim Acta 768:129–135

    Article  CAS  PubMed  PubMed Central  Google Scholar 

  21. Sessler JL, Cho DG (2008) The benzil rearrangement reaction: trapping of a hitherto minor product and its application to the development of a selective cyanide anion indicator. Org Lett 10:73–75

    Article  CAS  PubMed  Google Scholar 

  22. Lin Q, Lu TT, Zhu X, Sun B, Yang QP, Wei TB, Zhang YM (2015) A novel supramolecular metallogel-based high-resolution anion sensor array. Chem Commun 51:1635–1638

    Article  CAS  Google Scholar 

  23. Lin Q, Sun B, Yang QP, Fu YP, Zhu X, Wei TB, Zhang YM (2014) Double metal ions competitively control the guest-sensing process: a facile approach to stimuli-responsive supramolecular gels. Chem Eur J 20:11457–11462

    Article  CAS  PubMed  Google Scholar 

  24. Jin WJ, Fernandez-Arguelles MT, Costa-Fernandez JM, Pereiro R, Sanz-Medel A (2005) Photoactivated luminescent CdSe quantum dots as sensitive cyanide probes in aqueous solutions. Chem Commun 7:883–885

    Article  Google Scholar 

  25. Garcia F, Garcia JM, Garcia-Acosta B, Martinez-Manez R, Sancenon F, Soto J (2005) Pyrylium-containing polymers as sensory materials for the colorimetric sensing of cyanide in water. Chem Commun 22:2790–2792

    Article  Google Scholar 

  26. Tomasulo M, Raymo FM (2005) Colorimetric detection of cyanide with a chromogenic oxazine. Org Lett 7:4633–4636

    Article  CAS  PubMed  Google Scholar 

  27. Lee H, Chung YM, Ahn KH (2008) Selective fluorescence sensing of cyanide with an o-(carboxamido)trifluoroacetophenone fused with a cyano-1,2-diphenylethylene fluorophore. Tetrahedron Lett 49:5544–5547

    Article  CAS  Google Scholar 

  28. Chung Y, Ahn KH (2006) N-acyl triazenes as tunable and selective chemodosimeters toward cyanide ion. J Org Chem 71:9470–9474

    Article  ADS  CAS  PubMed  Google Scholar 

  29. Chen CL, Chen YH, Chen CY, Sun SS (2006) Dipyrrole carboxamide derived selective ratiometric probes for cyanide ion. Org Lett 8:5053–5056

    Article  CAS  PubMed  Google Scholar 

  30. Yang YK, Tae J (2006) Acridinium salt based fluorescent and colorimetric chemosensor for the detection of cyanide in water. Org Lett 8:5721–5723

    Article  CAS  PubMed  Google Scholar 

  31. Jo J, Lee D (2009) Turn-on fluorescence detection of cyanide in water: activation of latent fluorophores through remote hydrogen bonds that mimic peptide β-turn motif. J Am Chem Soc 131:16283–16291

    Article  CAS  PubMed  Google Scholar 

  32. Miyaji H, Sessler JL (2001) Off-the‐shelf colorimetric anion sensors. Angew Chem Int Ed 40:154–157

    Article  CAS  Google Scholar 

  33. Udhayakumari D (2018) Chromogenic and fluorogenic chemosensors for lethal cyanide ion a comprehensive review of the year 2016. Sens Actuators Chem 259:1022–1057

    Article  CAS  Google Scholar 

  34. Wu D, Sedgwick AC, Gunnlaugsson T, Akkaya EU, Yoon J, James TD (2017) Fluorescent chemosensors: the past, present and future. Chem Soc Rev 46:7105–7123

    Article  CAS  PubMed  Google Scholar 

  35. Thai DA, Lee NY (2021) A paper-based colorimetric chemosensor for rapid and highly sensitive detection of sulfide for environmental monitoring. Anal Methods 13:1332–1339

    Article  CAS  PubMed  Google Scholar 

  36. El-Shishtawy RM, Al-Zahrani FAM, Al-amshany ZM, Asiri AM (2017) Synthesis of a new fluorescent cyanide chemosensor based on phenothiazine derivative. Sens Actuators B Chem 240:288–296

    Article  CAS  Google Scholar 

  37. Cheng X, Zhou Y, Qin J, Li Z (2012) Reaction-based colorimetric cyanide chemosensors: rapid naked-eye detection and high selectivity. ACS Appl Mater Interfaces 4:2133–2138

    Article  CAS  PubMed  Google Scholar 

  38. Saravanan E, Sathishkumar M, Sathiyanathan P, Dhanapal J, Selin MK, Kulathu IS (2023) AIE active luminous dye with a triphenylamine attached benzothiazole core as a portable polymer film for sensitively detecting CN- ions in food samples. Talanta 264:124726

    Article  Google Scholar 

  39. Selin MK, Sathishkumar M, Dhanapal J, Saravanan E, Jebiti H, Sathiyanarayanan KI (2023) Imidazole-based dual functional chemosensor for the recognition of Cu2+ and CN–: applications in real water samples and colorimetric test strips. Opt Mater 144:114382

    Article  Google Scholar 

  40. Selin MK, Dhanapal J, Sathishkumar M, Saravanan E, Jebiti H, Sathiyanarayanan KI (2022) Imidazole-derived new colorimetric/fluorometric chemosensor for the sensitive recognition of CN– ions: real-time application in food samples and fluorescence bio-imaging. J Photochem Photobiol A 434:114269

    Google Scholar 

  41. Dhanapal J, Sathishkumar M, Saravanan E, Selin MK, Sathiyanarayanan KI (2022) Dibenzothiazole appended 4-hydroxyphenyl acrylonitrile as a highly selective visual and fluorimetric detection of cyanide ion. Opt Mater 133:112888

    Article  Google Scholar 

  42. Dhanapal J, Sathishkumar M, Saravanan M, Saravanan E, Selin MK, Sathiyanarayanan KI (2022) Benzothiazole appended 2,2′-(1,4-phenylene)diacetonitrile for the colorimetric and fluorescence detection of cyanide ions. RSC Adv 12:30045–30050

    Article  Google Scholar 

  43. WHO, Guidelines for drinking-water quality, (1996) Health criteria and other supporting information, vol 2, 2nd edn. Switzerland, Geneva

    Google Scholar 

Download references

Acknowledgements

The authors extend their appreciation to the Researchers supporting project number (RSP2024R465) King Saud University, Riyadh, Saudi Arabia.

Funding

The authors extend their appreciation to the Researchers supporting project number (RSP2024R465) King Saud University, Riyadh, Saudi Arabia.

Author information

Authors and Affiliations

  1. Department of Chemistry, Subramanya College of Arts and Science, Palani, Tamilnadu, 624618, India

    Jayasudha Palanisamy

  2. Department of Botany & Microbiology, College of Science, King Saud University, Riyadh, 11451, Saudi Arabia

    Rajakrishnan Rajagopal & Ahmed Alfarhan

Authors
  1. Jayasudha Palanisamy
    View author publications

    You can also search for this author in PubMed Google Scholar

  2. Rajakrishnan Rajagopal
    View author publications

    You can also search for this author in PubMed Google Scholar

  3. Ahmed Alfarhan
    View author publications

    You can also search for this author in PubMed Google Scholar

Contributions

Jayasudha Palanisamy: Methodology, Investigation, Formal analysis, Visualization, Writing - original draft.Rajakrishnan Rajagopal: Investigation, Writing - review & editing.Ahmed Alfarhan: Investigation, Writing - review & editing.

Corresponding author

Correspondence to Jayasudha Palanisamy.

Ethics declarations

Ethics Approval

Not applicable.

Consent to Participate

Informed consent obtained from all individual participants included in the study.

Consent for Publication

Not applicable.

Competing Interests

The authors declare no competing interests.

Additional information

Publisher’s Note

Springer Nature remains neutral with regard to jurisdictional claims in published maps and institutional affiliations.

Electronic Supplementary Material

Below is the link to the electronic supplementary material.

Supplementary Material 1

Rights and permissions

Springer Nature or its licensor (e.g. a society or other partner) holds exclusive rights to this article under a publishing agreement with the author(s) or other rightsholder(s); author self-archiving of the accepted manuscript version of this article is solely governed by the terms of such publishing agreement and applicable law.

Reprints and permissions

About this article

Check for updates. Verify currency and authenticity via CrossMark

Cite this article

Palanisamy, J., Rajagopal, R. & Alfarhan, A. Coumarin Linked Cyanine Dye for the Selective Detection of Cyanide Ion in Environmental Water Sample. J Fluoresc (2024). https://doi.org/10.1007/s10895-024-03620-0

Download citation

  • Received:

  • Accepted:

  • Published:

  • DOI: https://doi.org/10.1007/s10895-024-03620-0

Keywords

Search

Navigation