Skip to main content
SpringerLink
Log in

A multiple target chemosensor for the sequential fluorescence detection of Zn2+ and S2− and the colorimetric detection of Fe3+/2+ in aqueous media and living cells

  • PAPER
  • Published:
Photochemical & Photobiological Sciences Aims and scope Submit manuscript

Abstract

A novel multiple target sensor, (E)-5-((4-(diethylamino)-2-hydroxybenzyldene)amino)-1H-imidazole-4-carboxamide (DHIC), was synthesized for fluorescence detection of Zn2+ and S2− and colorimetric detection of Fe3+/2+ in aqueous media. DHIC can operate as a turn “on-off” sequential fluorescent sensor for Zn2+ and S2−. Detection limits (1.59 μM and 8.03 μM) for Zn2+ and S2− are below the WHO standards (76.0 μM and 14.7 μM). The DHIC-Zn2+ complex could be reversibly reused with ethylenediaminetetra-acetic acid. Importantly, DHIC could image sequentially Zn2+ and S2− in living cells. Moreover, DHIC displayed a discriminatory color change from pale yellow to orange yellow to Fe3+/2+. The detection limit of DHIC for Fe3+/2+ (0.73 μM and 1.11 μM) is far below the EPA drinking water standard (5.37 μM). The sensor DHIC could be applied to analyze Fe3+ in real 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.

Similar content being viewed by others

References

  1. J. Zhu, Y. Zhang, Y. Chen, T. Sun, Y. Tang, Y. Huang, Q. Yang, D. Ma, Y. Wang and M. Wang, A Schiff base fluorescence probe for highly selective turn-on recognition Zn2+, Tetrahedron Lett., 2017, 58, 365–370.

    Article  CAS  Google Scholar 

  2. S. Yin, J. Zhang, H. Feng, Z. Zhao, L. Xu, H. Qiu and B. Tang, Zn2+-selective fluorescent turn-on chemosensor based on terpyridine-substituted siloles, Dyes Pigm., 2012, 95, 174–179.

    Article  CAS  Google Scholar 

  3. D. Maity and T. Govindaraju, A differentially selective sensor with fluorescence turn-on response to Zn2+ and dual-mode ratiometric response to Al3+ in aqueous media, Chem. Commun., 2012, 48, 1039–1041.

    Article  CAS  Google Scholar 

  4. A. Helal, M. Harun, O. Rashid, C. Choi and H. Kim, New regioisomeric naphthol-substituted thiazole based ratiometric fluorescence sensor for Zn2+ with a remarkable red shift in emission spectra, Tetrahedron, 2012, 68, 647–653.

    Article  CAS  Google Scholar 

  5. J. M. Jung, S. Y. Lee, E. Nam, M. H. Lim and C. Kim, A highly selective turn-on chemosensor for Zn2+ in aqueous media and living cells, Sens. Actuators, B, 2017, 244, 1045–1053.

    Article  CAS  Google Scholar 

  6. D. Jeyanthi, M. Iniya, K. Krishnaveni and D. Chellappa, Charge transfer based “turn-on” chemosensor for Zn2+ ion recognition using new triaryl pyrazoline derivative, Spectrochim. Acta, Part A, 2016, 159, 231–237.

    Article  CAS  Google Scholar 

  7. K. T. Kim, S. A. Yoon, J. Ahn, Y. Choi, M. H. Lee, J. H. Jung and J. Park, Chemical Synthesis of fluorescent naphthali-mide-functionalized Fe3O4 nanoparticles and their application for the selective detection of Zn2+ present in contaminated soil, Sens. Actuators, B, 2017, 243, 1034–1041.

    Article  CAS  Google Scholar 

  8. X. Chen, S. Nam, G.-H. Kim, N. Song, Y. Jeong, I. Shin, S. K. Kim, J. Kim, S. Park and J. Yoon, A near-infrared fluorescent sensor for detection of cyanide in aqueous solution and its application for bioimaging, Chem. Commun., 2010, 46, 8953–8955.

    Article  CAS  Google Scholar 

  9. N. Narayanaswamy, D. Maity and T. Govindaraju, Reversible fluorescence sensing of Zn2+ based on pyridine-constrained bis(triazole-linked hydroxyquinoline) sensor, Supramol. Chem., 2011, 23, 703–709.

    Article  CAS  Google Scholar 

  10. A. Bhattacharyya, S. Ghosh, S. C. Makhal and N. Guchhait, Hydrazine bridged coumarin-pyrimidine conjugate as a highly selective and sensitive Zn2+ sensor: Spectroscopic unraveling of sensing mechanism with practical application, Spectrochim. Acta, Part A, 2017, 183, 306–311.

    Article  CAS  Google Scholar 

  11. K. Wang, Z. Jin, H. Shang, C. Lv, Q. Zhang, S. Chen and Z. Hu, A highly selective fluorescent chemosensor for Zn2+ based on the rhodamine derivative incorporating coumarin group, J. Fluoresc., 2017, 27, 629–633.

    Article  CAS  PubMed  Google Scholar 

  12. R. Singh, A. Gogoi and G. Das, Benzothiazole based multianalyte sensor for selective sensing of Zn2+ and Cd2+ and subsequent sensing of inorganic phosphates (Pi) in mixed aqueous medium, RSC Adv., 2016, 6, 112246–112252.

    Article  CAS  Google Scholar 

  13. F. Yu, X. Guo, X. Tian and L. Jia, A ratiomeric fluorescent sensor for Zn2+ based on N,N'-Di(quinolin-8-yl)oxalamide, J. Fluoresc., 2017, 27, 723–728.

    Article  CAS  PubMed  Google Scholar 

  14. S. Goswami, A. Manna, S. Paul, A. K. Maity, P. Saha, C. K. Quah and H. Fun, FRET based ‘red-switch’ for Al3+ over ESIPT based ‘green-switch’ for Zn2+: dual channel detection with live-cell imaging on a dyad platform, RSC Adv., 2014, 4, 34572–34576.

    Article  CAS  Google Scholar 

  15. Z. Xu, G. Kim, S. Jung, M. Jung, C. Lee, I. Shin and J. Yoon, An NBD-based colorimetric and fluorescent chemosensor for Zn2+ and its use for detection of intracellular zinc ions, Tetrahedron, 2009, 65, 2307–2312.

    Article  CAS  Google Scholar 

  16. L. Li, S. Yun, Z. Yuan-Hui, M. Lan, Z. Xi, C. Redshaw and W. Gang, A single chemosensor for multiple analytes: Fluorogenic and ratiometric absorbance detection of Zn2+, Mg2+ and F-, and its cell imaging, Sens. Actuators, B, 2016, 226, 279–288.

    Article  CAS  Google Scholar 

  17. Z. Xu, K. Baek, H. N. Kim, J. Cui, X. Qian, D. R. Spring, I. Shin and J. Yoon, Zn2+-Triggered Amide Tautomerization Produces a Highly Zn2+-Selective, Cell-Permeable, and Ratiometric Fluorescent Sensor, J. Am. Chem. Soc., 2010, 132, 601–610.

    Article  CAS  PubMed  Google Scholar 

  18. A. Helal, S. H. Kim and H. Kim, Thiazole sulfonamide based ratiometric fluorescent chemosensor with a large spectral shift for zinc sensing, Tetrahedron, 2010, 66, 9925–9932.

    Article  CAS  Google Scholar 

  19. L. He, X. Yang, Y. Liu and W. Lin, Colorimetric and ratiometric fluorescent probe for hydrogen sulfide using a coumarin-pyronine FRET dyad with a large emission shift, Anal. Methods, 2016, 8, 8022–8027.

    Article  CAS  Google Scholar 

  20. Y. Wang, X. Lv and W. Guo, A reaction-based and highly selective fl uorescent probe for hydrogen sulfide, Dyes Pigm., 2017, 139, 482–486.

    Article  CAS  Google Scholar 

  21. B. Deng, M. Ren, J. Wang, K. Zhou and W. Lin, A mitochondrial-targeted two-photon fluorescent probe for imaging hydrogen sulfide in the living cells and mouse liver tissues, Sens. Actuators, B, 2017, 248, 50–56.

    Article  CAS  Google Scholar 

  22. R. Zhang, X. Yu, Y. Yin, Z. Ye, G. Wang and J. Yuan, Development of a heterobimetallic Ru(II)-Cu(II) complex for highly selective and sensitive luminescence sensing of sulfide anions, Anal. Chim. Acta, 2011, 691, 83–88.

    Article  CAS  PubMed  Google Scholar 

  23. S. M. Kim, M. Kang, I. Choi, J. J. Lee and C. Kim, A highly selective colorimetric chemosensor for cyanide and sulfide in aqueous solution: experimental and theoretical studies, New J. Chem., 2016, 40, 7768–7778.

    Article  CAS  Google Scholar 

  24. X. Feng, T. Zhang, J. Liu, J. Miao and B. Zhao, A new ratiometric fluorescent probe for rapid, sensitive and selective detection of endogenous hydrogen sulfide in mitochondria, Chem. Commun., 2016, 52, 3131–3134.

    Article  CAS  Google Scholar 

  25. P. Wang, J. Wu, P. Su, C. Xu, Y. Ge, D. Liu, W. Liu and Y. Tang, Fluorescence ‘on-off-on’ peptide-based chemosensor for the selective detection of Cu2+ and S2- and its application in living cell bioimaging, Dalton Trans., 2016, 45, 16246–16254.

    Article  CAS  PubMed  Google Scholar 

  26. S. Chen, H. Li and P. Hou, A novel imidazo[1,5-a]pyridine-based fluorescent probe with a large stokes shift for imaging hydrogen sulfide, Sens. Actuators, B, 2017, 1–7.

    Google Scholar 

  27. M. G. Choi, S. Cha, H. Lee, H. L. Jeon and S. K. Chang, Sulfide-selective chemosignaling by a Cu2+ complex of dipicolylamine appended fluorescein, Chem. Commun., 2009, 7390–7392.

    Google Scholar 

  28. K. Zheng, W. Lin, L. Tan and D. Cheng, A two-photon fluorescent probe with a large turn-on signal for imaging hydrogen sulfide in living tissues, Anal. Chim. Acta, 2015, 853, 548–554.

    Article  CAS  PubMed  Google Scholar 

  29. P. Zhang, J. Li, B. Li, J. Xu, F. Zeng, J. Lv and S. Wu, A logic gate-based fluorescent sensor for detecting H2S and NO in aqueous media and inside live cells, Chem. Commun., 2015, 51, 4414–4416.

    Article  CAS  Google Scholar 

  30. Y. Jiang, Q. Wu and X. Chang, A ratiometric fluorescent probe for hydrogen sulfide imaging in living cells, Talanta, 2014, 121, 122–126.

    Article  CAS  PubMed  Google Scholar 

  31. B. Gu, W. Su, L. Huang, C. Wu, X. Duan, Y. Li, H. Xu, Z. Huang, H. Li and S. Yao, Real-time tracking and selective visualization of exogenous and endogenous hydrogen sulfide by a near-infrared fluorescent probe, Sens. Actuators, B, 2018, 255, 2347–2355.

    Article  CAS  Google Scholar 

  32. J. Zhang, R. Wang, Z. Zhu, L. Yi and Z. Xi, A FRET-based ratiometric fluorescent probe for visualizing H2S in lysosomes, Tetrahedron, 2015, 71, 8572–8576.

    Article  CAS  Google Scholar 

  33. S. N. Karuk Elmas, F. Ozen, K. Koran, I. Yilmaz, A. O. Gorgulu and S. Erdemir, Coumarin Based Highly Selective “off-on-off” Type Novel Fluorescent Sensor for Cu2+ and S2- in Aqueous Solution, J. Fluoresc., 2017, 27, 463–471.

    Article  CAS  PubMed  Google Scholar 

  34. J. Li, C. Yin and F. Huo, Chromogenic and fluorogenic chemosensors for hydrogen sulfide: Review of detection mechanisms since the year 2009, RSC Adv., 2015, 5, 2191–2206.

    Article  CAS  Google Scholar 

  35. Q. Meng, Y. Shi, C. Wang, H. Jia, X. Gao, R. Zhang, Y. Wang and Z. Zhang, NBD-based fluorescent chemosensor for the selective quantification of copper and sulfide in an aqueous solution and living cells, Org. Biomol. Chem., 2015, 13, 2918–2926.

    Article  CAS  PubMed  Google Scholar 

  36. Q. Meng, R. Zhang, H. Jia, X. Gao, C. Wang, Y. Shi, A. V. Everest-Dass and Z. Zhang, A reversible fluorescence chemosensor for sequentially quantitative monitoring copper and sulfide in living cells, Talanta, 2015, 143, 294–301.

    Article  CAS  PubMed  Google Scholar 

  37. K. B. Kim, H. Kim, E. J. Song, S. Kim, I. Noh and C. Kim, A cap-type Schiff base acting as a fluorescence sensor for zinc(II) and a colorimetric sensor for iron(II), copper(II), and zinc(II) in aqueous media, Dalton Trans., 2013, 42, 16569–16577.

    Article  CAS  PubMed  Google Scholar 

  38. H. Jung, N. Singh and D. Ok, Highly Fe3+ selective ratiometric fluorescent probe based on imine-linked benzimidazole, Tetrahedron Lett., 2008, 49, 2960–2964.

    Article  CAS  Google Scholar 

  39. S. Das, K. Aich, S. Goswami, C. K. Quah and H. Fun, FRETbased fluorescence ratiometric and colorimetric sensor to discriminate Fe3+ from Fe2+, New J. Chem., 2016, 40, 6414–6420.

    Article  CAS  Google Scholar 

  40. N. Narayanaswamy and T. Govindaraju, Aldazine-based colorimetric sensors for Cu2+ and Fe3+, Sens. Actuators, B, 2012, 161, 304–310.

    Article  CAS  Google Scholar 

  41. H. Jia, X. Gao, Y. Shi, N. Sayyadi, Z. Zhang, Q. Zhao, Q. Meng and R. Zhang, Fluorescence detection of Fe3+ ions in aqueous solution and living cells based on a high selectivity and sensitivity chemosensor, Spectrochim. Acta, Part A, 2015, 149, 674–681.

    Article  CAS  Google Scholar 

  42. US EPA, Secondary drinking water standards: Guidance for Nuisance Chemicals.

  43. V. K. Bhardwaj, P. Saluja, G. Hundal, M. S. Hundal, N. Singh and D. O. Jang, Benzthiazole-based multifunctional chemosensor: Fluorescent recognition of Fe3+ and chromogenic recognition of HSO4-, Tetrahedron, 2013, 69, 1606–1610.

    Article  CAS  Google Scholar 

  44. Z. Chi, X. Ran, L. Shi, J. Lou, Y. Kuang and L. Guo, Molecular characteristics of a fluorescent chemosensor for the recognition of ferric ion based on photoresponsive azobenzene derivative, Spectrochim. Acta, Part A, 2017, 171, 25–30.

    Article  CAS  Google Scholar 

  45. Y. S. Kim, J. J. Lee, S. Y. Lee, T. G. Jo and C. Kim, A highly sensitive benzimidazole-based chemosensor for the colorimetric detection of Fe(II) and Fe(III) and the fluorometric detection of Zn(II) in aqueous media, RSC Adv., 2016, 6, 61505–61515.

    Article  CAS  Google Scholar 

  46. S. Goswami, S. Das, K. Aich, D. Sarkar, T. K. Mondal, C. K. Quah and H. K. Fun, CHEF induced highly selective and sensitive turn-on fluorogenic and colorimetric sensor for Fe3+, Dalton Trans., 2013, 42, 15113–15119.

    Article  CAS  PubMed  Google Scholar 

  47. M. Zhao, X. Zhou, J. Tang, Z. Deng, X. Xu, Z. Chen, X. Li, L. Yang and L. Ma, Pyrene excimer-based fluorescent sensor for detection and removal of Fe3+ and Pb2+ from aqueous solutions, Spectrochim. Acta, Part A, 2017, 173, 235–240.

    Article  CAS  Google Scholar 

  48. Y. Liu, R. Shen, J. Ru, X. Yao, Y. Yang, H. Liu, X. Tang, D. Bai, G. Zhang and W. Liu, A reversible rhodamine 6G-based fluorescence turn-on probe for Fe3+ in water and its application in living cell imaging, RSC Adv., 2016, 6, 111754–111759.

    Article  CAS  Google Scholar 

  49. J. Jun Lee, G. Jin Park, Y. Sung Kim, S. Young Lee, H. Ji Lee, I. Noh and C. Kim, A water-soluble carboxylic-functionalized chemosensor for detecting Al3+ in aqueous media and living cells: Experimental and theoretical studies, Biosens. Bioelectron., 2015, 69, 226–229.

    Article  CAS  PubMed  Google Scholar 

  50. M. Hosseini, Z. Vaezi, M. R. Ganjali, F. Faridbod, S. D. Abkenar, K. Alizadeh and M. Salavati-Niasari, Fluorescence ‘turn-on’ chemosensor for the selective detection of zinc ion based on Schiff-base derivative, Spectrochim. Acta, Part A, 2010, 75, 978–982.

    Article  CAS  Google Scholar 

  51. M. Hosseini, A. Ghafarloo, M. R. Ganjali, F. Faridbod, P. Norouzi and M. S. Niasari, A turn-on fluorescent sensor for Zn2+ based on new Schiff’s base derivative in aqueous media, Sens. Actuators, B, 2014, 198, 411–415.

    Article  CAS  Google Scholar 

  52. Y. W. Choi, G. R. You, M. M. Lee, J. Kim, K. D. Jung and C. Kim, Highly selective recognition of mercury ions through the ‘naked-eye’, Inorg. Chem. Commun., 2014, 46, 43–46.

    Article  CAS  Google Scholar 

  53. Y. J. Na, Y. W. Choi, J. Y. Yun, K. M. Park, P. S. Chang and C. Kim, Dual-channel detection of Cu2+ and F- with a simple Schiff-based colorimetric and fluorescent sensor, Spectrochim. Acta, Part A, 2015, 136, 1649–1657.

    Article  CAS  Google Scholar 

  54. Y. Wang, H. Q. Wu, J. H. Sun, X. Y. Liu, J. Luo and M. Q. Chen, A novel chemosensor based on rhodamine derivative for colorimetric and fluorometric detection of Cu2+ in aqueous solution, J. Fluoresc., 2012, 22, 799–805.

    Article  CAS  PubMed  Google Scholar 

  55. S. Sarkar, T. Mondal, S. Roy, R. Saha, A. K. Ghosh and S. S. Panja, A multi-responsive thiosemicarbazone-based probe for detection and discrimination of group 12 metal ions and its application in logic gates, New J. Chem., 2018, 42, 15157–15169.

    Article  CAS  Google Scholar 

  56. Y. K. La, J. A. Hong, Y. J. Jeong and J. Lee, A 1,8-naphthali-mide-based chemosensor for dual-mode sensing: Colorimetric and fluorometric detection of multiple analytes, RSCAdv., 2016, 6, 84098–84105.

    CAS  Google Scholar 

  57. W. H. Ding, D. Wang, X. J. Zheng, W. J. Ding, J. Q. Zheng, W. H. Mu, W. Cao and L. P. Jin, A turn-on fluorescence chemosensor for Al3+, F- and CN- ions, and its application in cell imaging, Sens. Actuators, B, 2015, 209, 359–367.

    Article  CAS  Google Scholar 

  58. K. Liu, X. Zhao, Q. Liu, J. Huo, Z. Li and X. Wang, A novel multifunctional BODIPY-derived probe for the sequential recognition of Hg2+ and I-, and the fluorometric detection of Cr3+, Sens. Actuators, B, 2017, 239, 883–889.

    Article  CAS  Google Scholar 

  59. K. Krishnaveni, M. Iniya, D. Jeyanthi, A. Siva and D. Chellappa, A new multifunctional benzimidazole tagged coumarin as ratiometric fluorophore for the detection of Cd2+/F- ions and imaging in live cells, Spectrochim. Acta, Part A, 2018, 205, 557–567.

    Article  CAS  Google Scholar 

  60. M. Iniya, D. Jeyanthi, K. Krishnaveni and D. Chellappa, A bifunctional chromogenic and fluorogenic probe for Fand Al3+ based on azo-benzimidazole conjugate, J. Lumin., 2015, 157, 383–389.

    Article  CAS  Google Scholar 

  61. H. A. Benesi and J. H. Hildebrand, A Spectrophotometric Investigation of the Interaction of Iodine with Aromatic Hydrocarbons, J. Am. Chem. Soc., 1949, 71, 2703–2707.

    Article  CAS  Google Scholar 

  62. Y. W. Choi, G. R. You, J. J. Lee and C. Kim, Turn-on fluorescent chemosensor for selective detection of Zn2+ in an aqueous solution: Experimental and theoretical studies, Inorg. Chem. Commun., 2016, 63, 35–38.

    Article  CAS  Google Scholar 

  63. Y. Liu, Q. Fei, H. Shan, M. Cui, Q. Liu, G. Feng and Y. Huan, A novel fluorescent ‘off-on-off’ probe for relay recognition of Zn2+ and Cu2+ derived from N,N-bis(2-pyri-dylmethyl)amine, Analyst, 2014, 139, 1868–1875.

    Article  CAS  PubMed  Google Scholar 

  64. J. Y. Yun, T. G. Jo, J. Han, H. J. Jang, M. H. Lim and C. Kim, A highly sensitive and selective fluorescent chemosensor for the sequential recognition of Zn2+ and S2- in living cells and aqueous media, Sens. Actuators, B, 2018, 255, 3108–3116.

    Article  CAS  Google Scholar 

  65. Guidelines for drinking-water quality. Vol. 2, Health criteria and other supporting information: addendum, World Health Organization, Geneva, 2nd edn, 1998.

  66. G. Grynkiewicz, M. Poenie and R. Y. Tsien, A new generation of Ca2+ indicators with greatly improved fluorescence properties, J. Biol. Chem., 1985, 260, 3440–3450.

    Article  CAS  PubMed  Google Scholar 

Download references

Acknowledgements

This work was kindly supported by the National Research Foundation of Korea (Grant No. NRF-2018R1A2B6001686 and NRF-2017R1A2B3002585).

Author information

Authors and Affiliations

  1. Depart. of Fine Chem., SNUT (Seoul National Univ. ofSci. and Tech.), Seoul, 01188, Korea

    Jin Yeong Yun, Ju Byeong Chae & Cheal Kim

  2. Department ofChemistry, Ulsan National Institute of Science and Technology (UNIST), Ulsan, 44919, Korea

    Mingeun Kim

  3. Department of Chemistry, Korea Advanced Institute of Science and Technology (KAIST), Daejeon, 34141, Korea

    Mingeun Kim & Mi Hee Lim

Authors
  1. Jin Yeong Yun
    View author publications

    You can also search for this author in PubMed Google Scholar

  2. Ju Byeong Chae
    View author publications

    You can also search for this author in PubMed Google Scholar

  3. Mingeun Kim
    View author publications

    You can also search for this author in PubMed Google Scholar

  4. Mi Hee Lim
    View author publications

    You can also search for this author in PubMed Google Scholar

  5. Cheal Kim
    View author publications

    You can also search for this author in PubMed Google Scholar

Corresponding author

Correspondence to Cheal Kim.

Rights and permissions

Reprints and permissions

About this article

Check for updates. Verify currency and authenticity via CrossMark

Cite this article

Yun, J.Y., Chae, J.B., Kim, M. et al. A multiple target chemosensor for the sequential fluorescence detection of Zn2+ and S2− and the colorimetric detection of Fe3+/2+ in aqueous media and living cells. Photochem Photobiol Sci 18, 166–176 (2019). https://doi.org/10.1039/c8pp00408k

Download citation

  • Received:

  • Accepted:

  • Published:

  • Issue Date:

  • DOI: https://doi.org/10.1039/c8pp00408k

Search

Navigation