Skip to main content
SpringerLink
Log in

A novel fluorescent chemosensor based on carbazate moiety for detection of Zn2+

  • Regular Article
  • Published:
Journal of Chemical Sciences Aims and scope Submit manuscript

Abstract

A novel carbazate-based fluorescent sensor BC-MS was developed for the detection of Zn2+. In the presence of Zn2+, BC-MS showed a strong fluorescence enhancement with a 1:1 stoichiometry. Significantly, BC-MS could determine the presence of Zn2+ without the inhibition of Cd2+. The detection mechanism of BC-MS toward Zn2+ was proposed through analytical tools like UV-vis spectroscopy, Job plot, ESI-MS, 1H NMR titration and theoretical calculations.

Graphical abstract

A novel carbazate-based fluorescent sensor BC-MS was developed for detection of Zn2+ BC-MS showed a strong fluorescence enhancement in the presence of Zn2+ without the inhibition of Cd2+. The detection mechanism of BC-MS to Zn2+ was supported by theoretical calculations.

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
Figure 1
Figure 2
Figure 3
Figure 4
Figure 5
Figure 6
Figure 7
Scheme 2
Figure 8

Similar content being viewed by others

References

  1. Goswami S, Manna A, Paul S, Maity A K, Saha P, Quah C K and Fun H-K 2014 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. 4 34572

  2. Nguyen M-H, Nguyen T-N, Do D-Q, Nguyen H-H, Phung Q-M, Thirumalaivasan N, Wu S-P and Dinh T-H 2020 A highly selective fluorescent anthracene-based chemosensor for imaging Zn2+ in living cells and zebrafish Inorg. Chem. Commun. 115 107882

  3. Pandith A, Uddin N, Choi C H and Kim H-S 2017 Highly selective imidazole-appended 9,10-N,N″-diaminomethylanthracene fluorescent probe for switch-on Zn2+ detection and switch-off H2PO4− and CN− detection in 80% aqueous DMSO, and applications to sequential logic gate operations Sens Actuat. B Chem. 247 840

    Article  CAS  Google Scholar 

  4. An M, Kim B-Y, Seo H, Helal A and Kim H-S 2016 Fluorescence sensor for sequential detection of zinc and phosphate ions Spectrochim. Acta A 169 87

    Article  CAS  Google Scholar 

  5. Chakraborty S, Lohar S, Dhara K, Ghosh R, Dam S, Zangrando E and Chattopadhyay P 2020 A new half-condensed Schiff base platform: structures and sensing of Zn2+ and H2PO4− ions in an aqueous medium Dalton Trans. 49 8991

    Article  CAS  Google Scholar 

  6. Tang L, Dai X, Zhong K, Wu D and Wen X 2014 A novel 2,5-diphenyl-1,3,4-oxadiazole derived fluorescent sensor for highly selective and ratiometric recognition of Zn2+ in water through switching on ESIPT Sens. Actuat. B 203 557

    Article  CAS  Google Scholar 

  7. Jang H J, Chae J B, Jung J M, So H and Kim C 2019 Colorimetric detection of Co2+, Cu2+, and Zn2+ by a multifunctional chemosensor in aqueous solution Bull. Kor. Chem. Soc. 40 650

    Article  CAS  Google Scholar 

  8. Kumar S S, Kumar R S and Kumar S K A 2020 An “Off-On-Off” type fluorescent chemosensor for the relay detection of Zn2+ and H2PO4− in aqueous environment Inorg. Chim. Acta 502 119348

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

    Article  CAS  Google Scholar 

  10. Rao K S, Balaji T, Rao T P, Babu Y and Naidu G R K 2002 Determination of iron, cobalt, nickel, manganese, zinc, copper, cadmium and lead in human hair by inductively coupled plasma-atomic emission spectrometry Spectrochim. Acta B 5 1333

    Google Scholar 

  11. Antunes G A, Santos H S, Silva Y P, Silva M M, Piatnicki C M S and Samios D 2017 Determination of iron, copper, zinc, aluminum, and chromium in biodiesel by flame atomic absorption spectrometry using a microemulsion preparation method Energy Fuel. 31 2944

    Article  CAS  Google Scholar 

  12. Sun Z, Li H, Guo D, Sun J, Cui G, Liu Y, et al. 2015 A multifunctional magnetic core-shell fibrous silica sensing probe for highly sensitive detection and removal of Zn2+ from aqueous solution J. Mater. Chem. C 3 4713

    Article  CAS  Google Scholar 

  13. Hu Y, Du L and Yang J 2020 A highly sensitive and selective chemosensors for detection of Zn2+ and its application in live cell imaging Inorg. Chim. Acta 509 119675

  14. Lin Q, Jiang X-M, Ma X-Q, Liu J, Yao H, Zhang Y-M and Wei T-B 2018 Novel bispillar[5]arene-based AIEgen and its’ application in mercury(II) detection Sens Actuat. B Chem. 272 139

    Article  CAS  Google Scholar 

  15. Ma D-L, He H-Z, Zhong H-J, Lin S, Chan D S H, Wang L, et al. 2014 Visualization of Zn2+ ions in live zebrafish using a luminescent iridium(III) chemosensor ACS Appl Mater. Interf. 6 14008

    Article  CAS  Google Scholar 

  16. Goswami S, Paul S and Manna A 2013 Selective "naked eye" detection of Al(III) and PPi in aqueous media on a rhodamine-isatin hybrid moiety RSC Adv. 3 10639

  17. Kaur R, Saini S, Kaur N, Singh N and Jang D O 2020 Rhodamine-based fluorescent probe for sequential detection of Al3+ ions and adenosine monophosphate in water Spectrochim. Acta A 225 117523

  18. Jung H J, Singh N, Lee D Y and Jang D O 2010 Single sensor for multiple analytes: chromogenic detection of I− and fluorescent detection of Fe3+ Tetrahedron Lett. 51 3962

  19. Zhang Y-M, Fang H, Zhu W, He J-X, Yao H, Wei T-B, Lin Q and Qu W-J 2020 Ratiometric fluorescent sensor based oxazolo-phenazine derivatives for detect hypochlorite via oxidation reaction and its application in environmental samples Dyes Pigm. 172 107765

  20. Wu J, Zhao X, Gao Y, Hu J and Ju Y 2015 A steroid-salen conjugate for zinc ion recognition and its applications in test-strips, living cells imaging, and cascade recognition for dihydrogen phosphate Sens. Actuat. B Chem. 221 334

    Article  CAS  Google Scholar 

  21. Ahmmed E, Lohar S, Ghatak S, Hira S K, Manna P P and Chattopadhyay P 2019 Development of a selective reaction-based turn-on fluorosensor and biomarker for hypochlorite ions in aqueous media Anal. Methods 11 2415

    Article  CAS  Google Scholar 

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

    Article  CAS  Google Scholar 

  23. Yuan C, Li S, Wu Y, Lu L and Zhu M 2017 Zn(II)-selective and sensitive fluorescent chemosensor based on steric constrains and inhibition of ESIPT Sens. Actuat. B Chem. 242 1035

    Article  CAS  Google Scholar 

  24. Park S, Lee H, Yi Y, Lim M H and Kim C 2020 A rhodanine-based fluorescent chemosensor for sensing Zn2+ and Cd2+: applications to water sample and cell imaging Inorg. Chim. Acta 513 119936

  25. Gao L-L, Li S-P, Wang Y, Wu W-N, Zhao X-L, Li H-J and Xu Z-H 2020 Quinoline-based hydrazone for colorimetric detection of Co2+ and fluorescence turn-on response of Zn2+ Spectrochim. Acta A 230 118025

  26. Tang L, Cai M, Zhou P, Zhao J, Zhong K, Hou S and Bian Y 2013 A highly selective and ratiometric fluorescent sensor for relay recognition of zinc(II) and sulfide ions based on modulation of excited-state intramolecular proton transfer RSC Adv. 3 16802

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

    Article  Google Scholar 

  28. Jang H J, Kim A, Jung J M, Lee M, Lim M H and Kim C 2018 Detection of zinc(II) by a fluorescence chemosensor based on benzofuran in aqueous media and live cells Bull. Kor. Chem. Soc. 39 1373

    Article  CAS  Google Scholar 

  29. Parveen S, Nguyen H H, Premkumar T, Puschmann H and Govindarajan S 2020 Nano spinel cobaltites and their catalytic and electrochemical properties: facile synthesis of metal (Co, Ni, and Zn) and mixed metal (Co–Ni and Co–Zn) complexes of Schiff bases prepared from α-ketoglutaric acid and ethyl carbazate New J. Chem. 44 12729

    Article  Google Scholar 

  30. Sathiyakumar S, Selvam P, Antharjanam S, Hakkim F L, Srinivasan K and Harrison W T A 2020 Mechano-chemical syntheses of new cobalt(II) complexes of alkyl 2-(pyridine-2yl-methylene) hydrazinecarboxylates: crystal structures, spectroscopic and photoluminescence properties J. Mol. Struct. 1205 127666

  31. Yang X, Wang Y, Li Z, Du J, Wang L and Zhang T 2019 Energetic transition metal complexes based on methyl carbazate and picric acid: Syntheses, structures, physicochemical properties and catalysis on the thermal decomposition of ammonium perchlorate New J. Chem. 43 14159

    Article  CAS  Google Scholar 

  32. Gatto C C, Duarte E A, Liarte G S, Silva T S, Santiago M B and Martins C H G 2020 Transition metal complexes with 2-acetylpyridine-ethylcarbazate: noncovalent interactions in their structures and antimicrobial studies J. Coord. Chem. 73 1

    Article  Google Scholar 

  33. Qiu S, Lu M, Cui S, Wang Z and Pu S 2019 A bifunctional sensor based on diarylethene for the colorimetric recognition of Cu2+ and fluorescence detection of Cd2+ RSC Adv. 9 29141

  34. Bhuvanesh N, Suresh S, Kumar P R, Mothi E M, Kannan K, Kannan V R and Nandhakumar R 2018 Small molecule “turn on” fluorescent probe for silver ion and application to bioimaging J. Photochem. Photobiol. A Chem. 360 6

    Article  CAS  Google Scholar 

  35. Lan H, Wen Y, Shi Y, Liu K, Mao Y and Yi T 2014 Fluorescence turn-on detection of Sn2+ in live eukaryotic and prokaryotic cells Analyst 139 5223

  36. Lee S Y, Bok K H, Jo T G, Kim S Y and Kim C 2017 A simple Schiff-base fluorescence probe for the simultaneous detection of Ga3+ and Zn2+ Inorg. Chim. Acta 461 127

    Article  CAS  Google Scholar 

  37. Kim S, Lee H, So H, Lee H, Kim K T and Kim C 2020 A benzyl carbazate-based fluorescent chemosensor for detecting Zn2+: application to zebrafish Spectrochim. Acta A 228 117787

  38. Chandra R, Manna A K, Sahu M, Rout K and Patra G K 2020 Simple salicylaldimine-functionalized dipodal bis Schiff base chromogenic and fluorogenic chemosensors for selective and sensitive detection of Al3+ and Cr3+ Inorg. Chim. Acta 499 119192

  39. Chandra R, Sahu M, Manna A K, Rout K, Chowdhury S and Patra G K 2020 Ether based flexible bis Schiff base fluorescent colorimetric chemosensors for selective and sensitive detection of HF2− ion J. Photochem. Photobiol. A Chem. 389 112179

  40. Manigandan S, Muthusamy A, Nandhakumar R and Immanuel C D 2020 Recognition of Fe3+ by a new azine-based fluorescent “turn-off” chemosensor and its binding mode analysis using DFT J. Mol. Struct. 1208 127834

  41. Li X, Sun Y, Chen J, Wu Z, Cheng P, Li Q, et al. 2019 Enhanced fluorescence quantum yield of syndiotactic side-chain TPE polymers via Rh-catalyzed carbene polymerization: influence of the substitution density and spacer length Polym. Chem. 10 1575

    Article  Google Scholar 

  42. Kim C and Chae J B 2018 A highly selective fluorescent chemosensor for detecting indium(III) with a low detection limit and its application J. Fluoresc. 28 1363

    Article  CAS  Google Scholar 

  43. Frisch M J, Trucks G W, Schlegel H B, Scuseria G E, Robb M A, Cheeseman J R, Scalmani G, Barone V, Petersson G A, Nakatsuji H, Li X, Caricato M, Marenich A V, Bloino J, Janesko B G, Gomperts R, Mennucci B, Hratchian H P, Ortiz J V, Izmaylov A F, Sonnenberg J L, Williams-Young D, Ding F, Lipparini F, Egidi F, Goings J, Peng B, Petrone A, Henderson T, Ranasinghe D, Zakrzewski V G, Gao J, Rega N, Zheng G, Liang W, Hada M, Ehara M, Toyota K, Fukuda R, Hasegawa J, Ishida M, Nakajima T, Honda Y, Kitao O, Nakai H, Vreven T, Throssell K, Montgomery J A, Jr., Peralta J E, Ogliaro F, Bearpark M J, Heyd J J, Brothers E N, Kudin K N, Staroverov V N, Keith T A, Kobayashi R, Normand J, Raghavachari K, Rendell A P, Burant J C, Iyengar S S, Tomasi J, Cossi M, Millam J M, Klene M, Adamo C, Cammi R, Ochterski J W, Martin R L, Morokuma K, Farkas O, Foresman J B, and Fox D J, Gaussian, Inc., Wallingford C T, 2016.

  44. Becke A D 1993 Density‐functional thermochemistry. III. The role of exact exchange J. Chem. Phys. 98 5648

  45. Lee C, Yang W and Parr R G 1988 Development of the Colle-Salvetti correlation-energy formula into a functional of the electron density Phys. Rev. B 37 785

    Article  CAS  Google Scholar 

  46. Hariharan P C and Pople J A 1973 The influence of polarization functions on molecular orbital hydrogenation energies Theor. Chim. Acta 28 213

    Article  CAS  Google Scholar 

  47. Francl M M, Pietro W J, Hehre W J, Binkley J S, Gordon M S, DeFrees D J and Pople J A 1982 Self-consistent molecular orbital methods. XXIII. A polarization-type basis set for second-row elements J. Chem. Phys. 77 3654

  48. Hay P J and Wadt W R 1985 Ab initio effective core potentials for molecular calculations. Potentials for the transition metal atoms Sc to Hg J. Chem. Phys. 82 270

  49. Wadt W R and Hay P J 1985 Ab initio effective core potentials for molecular calculations. Potentials for main group elements Na to Bi J. Chem. Phys. 82 284

  50. Hay P J and Wadt W R 1985 Ab initio effective core potentials for molecular calculations. Potentials for K to Au including the outermost core orbitale J. Chem. Phys. 82 299

  51. Klamt A, Moya C and Palomar J 2015 A comprehensive comparison of the IEFPCM and SS(V)PE continuum solvation methods with the COSMO approach J. Chem. Theor. Comput. 11 4220

    Article  CAS  Google Scholar 

  52. Benesi H A and Hildebrand J H 1949 A spectrophotometric inverstigation of the interaction of iodine with aromatic hydrocarbons Nature 164 963

    Google Scholar 

  53. Mukhopadhyay M, Banerjee D, Koll A, Mandal A, Filarowski A, Fitzmaurice D, et al. 2005 Excited state intermolecular proton transfer and caging of salicylidine-3,4,7-methyl amine in cyclodextrins J. Photochem. Photobiol. A Chem. 175 94

    Article  CAS  Google Scholar 

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

    Article  CAS  Google Scholar 

Download references

Acknowledgements

This study was supported by the Advanced Research Project funded by the SeoulTech (Seoul National University of Science and Technology).

Author information

Authors and Affiliations

  1. Department of Fine Chemistry, Seoul National University of Science and Technology, Seoul, 136-742, Korea

    Donghwan Choe & Cheal Kim

Authors
  1. Donghwan Choe
    View author publications

    You can also search for this author in PubMed Google Scholar

  2. Cheal Kim
    View author publications

    You can also search for this author in PubMed Google Scholar

Corresponding author

Correspondence to Cheal Kim.

Supplementary Information

Below is the link to the electronic supplementary material.

Supplementary file1 (PDF 506 kb)

Rights and permissions

Reprints and permissions

About this article

Check for updates. Verify currency and authenticity via CrossMark

Cite this article

Choe, D., Kim, C. A novel fluorescent chemosensor based on carbazate moiety for detection of Zn2+. J Chem Sci 133, 115 (2021). https://doi.org/10.1007/s12039-021-01984-5

Download citation

  • Received:

  • Revised:

  • Accepted:

  • Published:

  • DOI: https://doi.org/10.1007/s12039-021-01984-5

Keywords

Search

Navigation