Skip to main content
SpringerLink
Log in

A Highly Selective Turn‐on Fluorescent and Naked‐eye Colourimetric Dual‐channel Probe for Cyanide Anions Detection in Water Samples

  • Original Article
  • Published:
Journal of Fluorescence Aims and scope Submit manuscript

Abstract

A highly selective turn-on fluorescent and naked-eye colourimetric dual-channel probe for cyanide anions (CNˉ) has been designed and characterized. In the mixed solution (DMSO / H2O, 9:1, v / v), only CNˉ could cause an increase in the UV absorption intensity and the corresponding fluorescence intensity increased, and other anions had no significant effect on the probe. After treatment with cyanide in the probe solution, the solution showed a noticeable colour change, from light yellow to purple. Moreover, a fluorescence spectrophotometer can be used to observe that the fluorescence intensity of the solution is significantly enhanced. The response of the colourimetric and fluorescent dual-channel probe to CNˉ was attributed to nucleophilic addition, and the mechanism was determined by 1H NMR spectroscopy. In addition, this probe was used to detect CNˉ in actual water samples, including river water, drinking water, and tap water. The spiked CNˉ recovery rate is very high (97.2%-100.06%), and analytical precision is also very high (RSD < 2%), which shows its feasibility and reliability for detecting cyanide ions in actual 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
Scheme 2
Fig. 1
Fig. 2
Fig. 3
Fig. 4
Fig. 5
Fig. 6
Fig. 7
Fig. 8
Fig. 9
Fig. 10
Scheme 3
Fig. 11

Similar content being viewed by others

Data Availability

The data sets used and/or analyzed during the present study are available from the corresponding author on reasonable request.

References

  1. Liu C, Wei Z-L, Mu H-R, Dong W-K, Ding Y-J (2020) A novel unsymmetric bis(salamo)-based chemosensor for detecting Cu2+ and continuous recognition of amino acids. J Photochem Photobio A 397:112569

    CAS  Google Scholar 

  2. Yan L-Q, Li R-J, Ma F-L, Qi Z-J (2017) A simple salicylaldehyde-based fluorescent “turn-on” probe for selective detection of Zn2+ in water solution and its application in live cell imaging. Anal Methods 9:1119–1124

    CAS  Google Scholar 

  3. Hao J, Li X-Y, Zhang Y, Dong W-K (2018) A reversible bis(Salamo)-based fluorescence sensor for selective detection of Cd2+ in water-containing systems and food samples. Materials 11:523

    PubMed Central  Google Scholar 

  4. Chen C-Y, Zhang J-W, Zhang Y-H, Yang Z-H, Wu H-L, Pan G-L, Bai Y-C (2015) Gadolinium(III) and dysprosium(III) complexes with a Schiff base bis(N-salicylidene)-3-oxapentane-1,5-diamine: Synthesis, characterization, antioxidation, and DNA-binding studies. J Coord Chem 68:1054–1071

    CAS  Google Scholar 

  5. Pan Y-Q, Zhang Y, Yu M, Zhang Y, Wang L (2020) Newly synthesized homomultinuclear Co (II) and Cu(II) bissalamo-like complexes: Structural characterizations, Hirshfeld analyses, fluorescence and antibacterial properties. Appl Organomet Chem 34:e5441

    CAS  Google Scholar 

  6. Yun D-J, Jung J-M, Kim C (2018) A fluorescent and colourimetric chemosensor for Ga3+ and CNˉ. Inorg Chim Acta 479:154–160

    CAS  Google Scholar 

  7. Zhao H-W, Wu G, Sun X-Y, Chao J-B, Li Y-Q, Jiang L, Han H (2018) A highly selective and ratiometric molecular probe for cyanide sensing based on a phenothiazine-hemicyanine dye. J Lumin 201:474–478

    CAS  Google Scholar 

  8. Li L, Zan M-H, Qie X-W, Miao P, Yue J, Chang Z-M, Wang Z, Bai F-Q, Zhang H-X, Ferri J-K, Dong W-F (2018) A highly selective fluorescent probe for cyanide ion and its detection mechanism from theoretical calculations. Talanta 185:1–6

    PubMed  Google Scholar 

  9. Pan Y-Q, Xu X, Zhang Y, Zhang Y, Dong W-K (2020) A highly sensitive and selective bis(salamo)-type fluorescent chemosensor for identification of Cu2+ and the continuous recognition of S2–. Spectrochim Acta Part A 229:117917

    Google Scholar 

  10. Yu B, Li C-Y, Sun Y-X, Jia H-R, Guo J-Q, Li J (2017) A new azine derivative colorimetric and fluorescent dual-channel probe for cyanide detection. Spectrochim Acta Part A 184:249–254

    CAS  Google Scholar 

  11. Wang L, Wei Z-L, Chen Z-Z, Liu C, Dong W-K, Ding Y-J (2020) A chemical probe capable for fluorescent and colorimetric detection to Cu2+ and CNˉ based on coordination and nucleophilic addition mechanism. Microchem J 155:104801

    CAS  Google Scholar 

  12. Wei Z-L, Wang L, Wang J-F, Guo W-T, Zhang Y, Dong W-K (2020) Two highly sensitive and efficient salamo-like copper(II) complex probes for recognition of CNˉ. Spectrochim Acta Part A 228:117775

    CAS  Google Scholar 

  13. Liu L-Z, Wang L, Yu M, Zhao Q, Zhang Y, Sun Y-X, Dong W-K (2019) A highly sensitive and selective fluorescent “off-on-off” relay chemosensor based on a new bis(salamo)-type tetraoxime for detecting Zn2+ and CNˉ. Spectrochim Acta Part A 222:117209

    CAS  Google Scholar 

  14. Yan L-R, Yang M-P, Leng X, Zhang M, Long Y, Yang B-Q (2016) A new dual-function fluorescent probe of Fe3+ for bioimaging and probe-Fe3+ complex for selective detection of CNˉ. Tetrahedron 72:4361–4367

    CAS  Google Scholar 

  15. Xu W, Han G-J, Ma P-Y, Diao Q-P, Xu L-B, Liu X, Sun Y, Wang X-H, Song D-Q (2017) A highly selective turn-on fluorescent and chromogenic probe for CNˉ and its applications in imaging of living cells and zebrafish in vivo. Sens Actuators B Chem 251:366–373

    CAS  Google Scholar 

  16. Bhardwaj S, Maurya N, Singh A-K (2018) Chromone based fluorescent organic nanoparticles for high-precision in-situ sensing of Cu2+ and CNˉ ions in 100% aqueous solutions. Sens Actuators B Chem 260:753–762

    CAS  Google Scholar 

  17. Gonçalves A-C, Capelo J-L, Lodeiro C, Santos A-A-D (2017) A selective emissive chromogenic and fluorogenic seleno-coumarin probe for Cu2+ detection in aprotic media. Photochem Photobiol Sci 16:1174–1181

    PubMed  Google Scholar 

  18. Zhang Y, Yu M, Pan Y-Q, Zhang Y, Xu L, Dong X-Y (2020) Three rare heteromultinuclear 3d-4f salamo-like complexes constructed from auxiliary ligand 4,40-bipy: Syntheses, structural characterizations, fluorescence and antimicrobial properties. Appl Organomet Chem 4:e5442

    Google Scholar 

  19. Yu M, Zhang Y, Pan Y-Q, Wang L (2020) Two novel copper(II) salamo-based complexes: Syntheses, X-ray crystal structures, spectroscopic properties and Hirshfeld surfaces analyses. Inorg Chim Acta 509:119701

    CAS  Google Scholar 

  20. An X-X, Zhao Q, Mu H-R, Dong W-K (2019) A new half-salamo-based homo-trinuclear nickel(II) complex: Crystal structure, Hirshfeld surface analysis, and fluorescence properties. Crystals 9:101

    CAS  Google Scholar 

  21. Simon T, Shellaiah M, Srinivasadesikan V, Lin C-C, Ko F-H, Sun K-W, Lin M-C (2016) Novel anthracene- and pyridine-containing Schiff base probe for selective ‘‘off–on’’ fluorescent determination of Cu2+ ions towards live cell application. New J Chem 40:6101–6108

    CAS  Google Scholar 

  22. Saleh S-M, Ali R, Elshaarawy R-F-M (2016) A ratiometric and selective fluorescent chemosensor for Ca(II) ions based on a novel water-soluble ionic Schiff-base. RSC Adv 6:68709–68718

    CAS  Google Scholar 

  23. Yu B, Sun Y-X, Yang C-J, Guo J-Q, Li J (2017) Synthesis and crystal structures of an unexpected tetranuclear zinc(II) complex and a benzoquinone compound derived from ZnII- and CdII- promoted reactivity of Schiff base ligands. Z Anorg Allg Chem 643:689–698

    CAS  Google Scholar 

  24. Li X-Y, Kang Q-P, Liu C, Zhang Y, Dong W-K (2019) Structurally characterized homo-trinuclear ZnII and hetero-pentanuclear [ZnII4LnIII] complexes constructed from an octadentate bis(Salamo)-based ligand: Hirshfeld surfaces, fluorescence and catalytic properties. New J Chem 43:4605–4619

    CAS  Google Scholar 

  25. Liu L-Z, Yu M, Li X-Y, Kang Q-P, Dong W-K (2019) Syntheses, structures, Hirshfeld analyses and fluorescent properties of two Ni(II) and Zn(II) complexes constructed from a bis(salamo)-like ligand. Chinese J Inorg Chem 35:1283–1294

    CAS  Google Scholar 

  26. Jia H-R, Chang J, Zhang H-J, Li J, Sun Y-X (2018) Three polyhydroxyl-bridged defective dicubane tetranuclear MnIII complexes: Synthesis, crystal structures, and spectroscopic properties. Crystals 8:272

    Google Scholar 

  27. Guo J-Q, Sun Y-X, Yu B, Li J, Jia H-R (2017) Syntheses, crystal structures and spectroscopic properties of copper (II) and nickel (II) complexes with oxime-type Schiff base ligands. Chinese J Inorg Chem 33:1481–1488

    CAS  Google Scholar 

  28. Li J, Zhang H-J, Chang J, Jia H-R, Sun Y-X, Huang Y-Q (2018) Solvent-induced unsymmetric Salamo-like trinuclear NiII complexes: Syntheses, crystal structures, fluorescent and magnetic properties. Crystals 8:176

    CAS  Google Scholar 

  29. Zhang H-J, Chang J, Jia H-R, Sun Y-X (2018) Syntheses, supramolecular structures and spectroscopic properties of Cu (II) and Ni(II) complexes with Schiff base oxime group. Chinese J Inorg Chem 34:2261–2270

    CAS  Google Scholar 

  30. Zhang S-Z, Guo G, Ding W-M, Li J, Wu Y, Zhang H-J, Guo J-Q, Sun Y-X (2020) Synthesis and spectroscopic properties of two different structural Schiffbase Zn(II) complexes constructed with/without auxiliary ligands. J Mol Struct. https://doi.org/10.1016/j.molstruc.2020.129627

    Article  Google Scholar 

  31. Zhang S-Z, Chang J, Zhang H-J, Wu Y, Sun Y-X, Wang Y-B (2020) Synthesis, crystal structure and spectral properties of binuclear Ni(II) and cubane-like Cu4(µ3-O)4 cored tetranuclear Cu(II) complexes based on coumarin Schiff base. Chinese J Inorg Chem 36:503–514

    CAS  Google Scholar 

  32. Liu C, An X-X, Cui Y-F, Xie K-F, Dong W-K (2020) Novel structurally characterized hetero-bimetallic [Zn(II)2M(II)] (M = Ca and Sr) bis(salamo)-type complexes: DFT calculation, Hirshfeld analyses, antimicrobial and fluorescent properties. Appl Organomet Chem 34:e5272

    CAS  Google Scholar 

  33. Chang J, Zhang S-Z, Wu Y, Zhang H-J, Sun Y-X (2020) Three supramolecular trinuclear nickel(II) complexes based on Salamo–type chelating ligand: Syntheses, crystal structures, solvent effect, Hirshfeld surface analysis and DFT calculation. Transit Met Chem 45:279–293

    CAS  Google Scholar 

  34. Sun Y-X, Pan Y-Q, Xu X, Zhang Y (2019) Unprecedented dinuclear CuII N,O-donor complex: Synthesis, structural characterization, fluorescence property, and hirshfeld analysis. Crystals 9:607

    CAS  Google Scholar 

  35. Zhang L-W, Zhang Y, Cui Y-F, Yu M, Dong W-K (2020) Heterobimetallic [NiIILnIII] (Ln = Sm and Tb) N2O4-donor coordination polymers: Syntheses, crystal structures and fluorescence properties. Inorg Chim Acta 506:119534

    CAS  Google Scholar 

  36. Chao J-B, Xu M, Liu Y-M, Zhang Y-B, Huo F-J, Yin C-X, Wang X-L (2019) A pyrene-based turn-On fluorescence probe for CNˉ detection and its bioimaging applications. Chem Select 4:3071–3075

    CAS  Google Scholar 

  37. Zhao Q, An X-X, Liu L-Z, Dong W-K (2019) Syntheses, luminescences and Hirshfeld surfaces analyses of structurally characterized homo-trinuclear ZnII and hetero-pentanuclear ZnII-LnIII (Ln = Eu, Nd) bis(salamo)-like complexes. Inorg Chim Acta 490:6–15

    CAS  Google Scholar 

  38. Gao L, Wang F, Zhao Q, Zhang Y, Dong W-K (2018) Mononuclear Zn(II) and trinuclear Ni(II) complexes derived from a coumarin-containing N2O2 ligand: Syntheses, crystal structures and fluorescence properties. Polyhedron 139:7–16

    CAS  Google Scholar 

  39. Wang L-N, Qin W-W, Liu W-S (2014) Two highly sensitive Schiff-base fluorescent indicators for the detection of Zn2+. Anal Methods 6:1167–1173

    CAS  Google Scholar 

  40. Jia H-R, Li J, Sun Y-X, Guo J-Q, Yu B, Wen N, Xu L (2017) Two supramolecular cobalt(II) complexes: Syntheses, crystal structures, spectroscopic behaviors, and counter anion effects. Crystals 7:247

    Google Scholar 

  41. Chang J, Zhang H-J, Jia H-R, Sun Y-X (2018) Binuclear nickel (II) and zinc (II) complexes based on 2-amino-3-hydroxy-pyridine Schiff base: Syntheses, supramolecular structures and spectral properties. Chinese J Inorg Chem 34:2097–2107

    CAS  Google Scholar 

  42. Wang L, Li W-X, Zhi W-J, Huang Y, Han J, Wang Y, Ren Y-P, Ni L (2018) A new coumarin schiff based fluorescent-colorimetric chemosensor for dual monitoring of Zn2+ and Fe3+ in different solutions: Anapplication to bio-imaging. Sens Actuators B Chem 260:243–254

    CAS  Google Scholar 

  43. Niu Q-F, Sun T, Li T-D, Guo Z-R, Pang H (2018) Highly sensitive and selective colorimetric/fluorescent probe with aggregation induced emission characteristics for multiple targets of copper, zinc and cyanide ions sensing and its practical application in water and food samples. Sens Actuators B Chem 266:730–743

    CAS  Google Scholar 

  44. Cheng X-H, Tang R-L, Jia H-Z, Feng J, Qin J-G, Li Z (2012) New fluorescent and colorimetric probe for cyanide: Direct reactivity, high selectivity, and bioimaging application. ACS Appl Mater Interfaces 4:4387–4392

    CAS  PubMed  Google Scholar 

  45. Jiang D-Y, Xue X-Y, Zhu M, Zhang G-N, Wang Y-C, Feng C, Wang Z-F, Zhao H (2019) Novel rhodamine-derivated dual-responsive colorimetric fluorescent chemoprobe for the hypersensitive detection of Ga3+ and Hg2+ and biological imaging. Ind Eng Chem Res 58:18456–18467

    CAS  Google Scholar 

  46. Ravichandiran P, Subramaniyan S-A, Bella A-P, Johnson P-M, Kim A-R, Shim K-S, Dong J-Y (2019) Simple fluorescence turn-on chemosensor for selective detection of Ba2+ ion and its live cell imaging. Anal Chem 91:10095–10101

    CAS  PubMed  Google Scholar 

  47. Gao T, Huang X-Y, Huang S, Dong J, Yuan K, Feng X-P, Liu T-T, Yu K-Q, Zeng W-B (2019) A sensitive water-soluble fluorescent probe based on umpolung and aggregation-induced emission strategies for selective detection of Hg2+ in living cells and zebrafish. J Agric Food Chem 67:2377–2383

    CAS  PubMed  Google Scholar 

  48. Liu Y-J, Qiu D-L, Pan H, Li M-G, Chen H-B, Li H-M (2018) A highly selective fluorescent probe for colourimetric recognition of cyanide anion based on heptamethine cyaninetriphenylamine conjugate. J Photoch Photobio A: Chem 364:151–158

    CAS  Google Scholar 

  49. Wang F, Gao L, Zhao Q, Zhang Y, Dong W-K, Ding Y-J (2018) A highly selective fluorescent chemosensor for CNˉ based on a novel bis(salamo)-type tetraoxime ligand. Spectrochim Acta Part A 190:111–115

    CAS  Google Scholar 

  50. Liu S-Z, Yang M, Liu Y-J, Chen H-B, Li H-M (2018) A novel “turn-on” fluorescent probe based on triphenylimidazole-hemicyanine dyad for colourimetric detection of CNˉ in 100% aqueous solution. J Hazard Mater 344:875–882

    CAS  PubMed  Google Scholar 

  51. Wang Y-T, Wang J-J, Xian Q-M (2018) A highly selective fluorescent and chromogenic probe for CNˉ detection and its applications in bioimaging. Talanta 190:487–491

    CAS  PubMed  Google Scholar 

  52. Kumari N, Jha S, Bhattacharya S (2014) An efficient probe for rapid detection of cyanide in water at parts per billion levels and naked-eye detection of endogenous cyanide. Chem Asian J 9:830–837

    CAS  PubMed  Google Scholar 

  53. Gomez T, Moreno D, Grenu B-D, Fernandez A-C, Rodriguez T, Rojo J, Cuevas J-V, Torroba T (2013) Turn-on fluorogenic probes for the selective and quantitative detection of the cyanide anion from natural sources. Chem Asian J 8:1271–1278

    CAS  PubMed  Google Scholar 

  54. Zhou F, Sultanbawa Y, Feng H, Wang Y-L, Meng Q-T, Wang Y, Zhang Z-Q, Zhang R (2019) A new red-emitting fluorescence probe for rapid and effective visualisation of bisulfite in food samples and live animals. J Agric Food Chem 67:4375–4383

    CAS  PubMed  Google Scholar 

  55. Wang J-L, Hao Y-F, Wang H, Yang S-X, Tian H-Y, Sun B-G, Liu Y-G (2017) Rapidly responsive and highly selective fluorescent probe for bisulfite detection in food. J Agric Food Chem 65:2883–2887

    CAS  PubMed  Google Scholar 

Download references

Acknowledgements

This work was supported by the Science and Technology Program of Gansu Province (18YF1GA054) and the Program for the Excellent Team of Scientific Research in the Lanzhou Jiaotong University (201706), both of which are gratefully acknowledged.

Funding

This work was supported by the Science and Technology Program of Gansu Province (18YF1GA054) and the Program for the Excellent Team of Scientific Research in the Lanzhou Jiaotong University (201,706).

Author information

Authors and Affiliations

  1. School of Chemical and Biological Engineering, Lanzhou Jiaotong University, Lanzhou, 730073, People’s Republic of China

    Ya Wu, Wen-Min Ding, Juan Li, Geng Guo, Shu-Zhen Zhang, Hao-Ran Jia & Yin-Xia Sun

Authors
  1. Ya Wu
    View author publications

    You can also search for this author in PubMed Google Scholar

  2. Wen-Min Ding
    View author publications

    You can also search for this author in PubMed Google Scholar

  3. Juan Li
    View author publications

    You can also search for this author in PubMed Google Scholar

  4. Geng Guo
    View author publications

    You can also search for this author in PubMed Google Scholar

  5. Shu-Zhen Zhang
    View author publications

    You can also search for this author in PubMed Google Scholar

  6. Hao-Ran Jia
    View author publications

    You can also search for this author in PubMed Google Scholar

  7. Yin-Xia Sun
    View author publications

    You can also search for this author in PubMed Google Scholar

Contributions

All authors contributed to the study conception and design. Data collection and analysis were performed by all authors. The first draft of the manuscript was written by Ya Wu and all authors commented on previous versions of the manuscript. All authors read and approved the final manuscript.

Corresponding author

Correspondence to Yin-Xia Sun.

Ethics declarations

Conflicts of Interest/Competing Interests

The authors declare that they have no conflict of interest. 

Ethics Approval

Not applicable. 

Consent to Participate

Not applicable.

Code Availability

 Not applicable.

Additional information

Publisher’s Note

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

Rights and permissions

Reprints and permissions

About this article

Check for updates. Verify currency and authenticity via CrossMark

Cite this article

Wu, Y., Ding, WM., Li, J. et al. A Highly Selective Turn‐on Fluorescent and Naked‐eye Colourimetric Dual‐channel Probe for Cyanide Anions Detection in Water Samples. J Fluoresc 31, 437–446 (2021). https://doi.org/10.1007/s10895-020-02677-x

Download citation

  • Received:

  • Accepted:

  • Published:

  • Issue Date:

  • DOI: https://doi.org/10.1007/s10895-020-02677-x

Keywords

Search

Navigation