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Journal of Fluorescence

, Volume 29, Issue 4, pp 945–952 | Cite as

Triazole-Coupled Benzimidazole-Based Fluorescent Sensor for Silver, Bromide, and Chloride Ions in Aqueous Media

  • Yoon Gun Ko
  • Won Sik Na
  • Mayank
  • Narinder SinghEmail author
  • Doo Ok JangEmail author
ORIGINAL ARTICLE
  • 185 Downloads

Abstract

A triazole-coupled benzimidazole-based fluorescent probe S1 with nitrogen and oxygen binding sites was synthesized and its properties as a probe for cations were investigated. Probe S1 was found to be highly selective toward Ag+ ions in aqueous media. The fluorescence intensity of S1 was quenched as a function of the concentration of Ag+ ions in the presence of potential interfering cations with a detection limit of 2.70 μM. The resulting S1-Ag+ complex was subsequently studied for its anion recognition abilities and found to recognize Br and Cl ions, revealing the concentration-dependent fluorescence enhancement with detection limits of 22.2 and 23.0 μM, respectively. Revival of the fluorescence profile of probe S1 indicated that Ag+ ion was released from the S1-Ag+ complex. Probe S1 is a sensor that can be single-handedly utilized for the qualitative and quantitative determination of Ag+, Br, and Cl ions in aqueous media.

Keywords

Triazole Benzimidazole Fluorescence Sensor 

Notes

Acknowledgements

This research was supported partially by the Basic Science Research Program through the National Research Foundation of Korea (NRF) funded by the Ministry of Education (NRF-2018R1D1A1B07041198).

Compliance with Ethical Standards

Conflict of Interest

The authors declare no conflict of interest.

Supplementary material

10895_2019_2407_MOESM1_ESM.docx (2.1 mb)
ESM 1 (DOCX 2112 kb)

References

  1. 1.
    Quang DT, Kim JS (2010) Fluoro- and chromogenic chemodosimeters for heavy metal ion detection in solution fluorescent and biospecimens. Chem Rev 110:6280–6281CrossRefGoogle Scholar
  2. 2.
    Kim JS, Quang DT (2007) Calixarene-derived fluorescent probes. Chem Rev 107:3780–3789CrossRefGoogle Scholar
  3. 3.
    Nolan EM, Lippard SJ (2008) Tools and tactics for the optical detection of mercuric ion. Chem Rev 108:3443–3480CrossRefGoogle Scholar
  4. 4.
    Kim HN, Guo Z, Zhu W, Yoon J, Tian JH (2011) Recent progress on polymer-based fluorescent and colorimetric chemosensors. Chem Soc Rev 40:79–83CrossRefGoogle Scholar
  5. 5.
    Xu Z, Kim SK, Yoon J (2010) Revisit to imidazolium receptors for the recognition of anions: highlighted research during 2006–2009. Chem Soc Rev 39:1457–1466CrossRefGoogle Scholar
  6. 6.
    Szmacinski H, Gryczynski HI, Lakowicz JR (1993) Calcium-dependent fluorescence lifetimes of Indo-1 for one- and two-photon excitation of fluorescence. Photochem Photobiol 58:341–345CrossRefGoogle Scholar
  7. 7.
    Duke RM, Veale EB, Pfeffer FM, Kruger PE, Gunnlaugsson T (2010) Colorimetric and fluorescent anion sensors: an overview of recent developments in the use of 1,8-naphthalimide-based chemosensors. Chem Soc Rev 39:3936–3953CrossRefGoogle Scholar
  8. 8.
    Turro NJ, Bolt JD, Kuroda Y, Tabushi I (1982) A study of the kinetics of inclusion of halonaphthalenes with ß-cyclodextrin via time correlated phosphorescence. Photochem Photobiol 35:69–72CrossRefGoogle Scholar
  9. 9.
    Ko YG, Mayank SN, Jang DO (2018) Single chemosensor for sensing multiple analytes: selective fluorogenic detection of Cu2+ and Br. Tet Lett 59:3839–3844CrossRefGoogle Scholar
  10. 10.
    Barriada JL, Tappin AD, Evans EH, Achterberg EP (2007) Dissolved silver measurements in seawater. Trends Anal Chem 26:809–817CrossRefGoogle Scholar
  11. 11.
    Ratte HT (1988) Bioaccumulation and toxicity of silver compounds: a review. Environ Toxicol Chem 18:89–108CrossRefGoogle Scholar
  12. 12.
    Singh N, Billing BK, Singh J, Agnihotri PK (2016) Thiourea based dipodal receptor development for electrochemical detection of Br ion in an aqueous medium. Electroanalysis 28:718–723CrossRefGoogle Scholar
  13. 13.
    Yasri S, Wiwanitkit SV (2016) Bromide contamination in rice, cancer risk for consumer. South Asian J Cancer 5:62CrossRefGoogle Scholar
  14. 14.
    Takashima I, Kanegae A, Sugimoto M, Ojida A (2014) Aza-crown-ether-appended xanthene: selective ratiometric fluorescent probe for silver(I) ion based on arene-metal ion interaction. Inorg Chem 53:7080–7082CrossRefGoogle Scholar
  15. 15.
    Hou J-T, Zhang Q-F, Xu B-Y, Lu Q-S, Liu Q, Zhang J, Yu X-Q (2011) A novel BINOL-based cyclophane via click chemistry: synthesis and its applications for sensing silver ions. Tetrahedron Lett 52:4927–4930CrossRefGoogle Scholar
  16. 16.
    He XP, Song Z, Wang ZZ, Shi XX, Chen K, Chen GR (2011) Creation of 3,4-bis-triazolocoumarin-sugar conjugates via flourogenic dual click chemistry and their quenching specificity with silver(I) in aqueous media. Tetrahedron 67:3343–3347CrossRefGoogle Scholar
  17. 17.
    Swamy KMK, Kim HN, Soh JH, Kim Y, Kim S-J, Yoon J (2009) Manipulation of fluorescent and colorimetric changes of fluorescein derivatives and applications for sensing silver ions. Chem Commun (10):1234–1236Google Scholar
  18. 18.
    Praveen Kumar PP, Kathuria L, Haridas V (2016) Cysteine-based silver nanoparticles as dual colorimetric sensors for cations and anions. New J Chem 40:8382–8389CrossRefGoogle Scholar
  19. 19.
    Omran OA, Elgendy FA, Nafady A (2016) Fabrication and applications of potentiometric sensors based on p-tert-butylthiacalix[4]arene comprising two triazole rings ionophore for silver ion detection. Int J Electrochem Sci 11:4729–4742CrossRefGoogle Scholar
  20. 20.
    Kang JH, Chae JB, Kim C (2018) A multi-functional chemosensor for highly selective ratiometric fluorescent detection of silver(I) ion and dual turn-on fluorescent and colorimetric detection of sulfide. R Soc Open Sci 5:180293CrossRefGoogle Scholar
  21. 21.
    Singh A, Singh A, Singh N, Jang DO (2016) Selective detection of hg(II) with benzothiazole-based fluorescent organic cation and the resultant complex as a ratiometric sensor for bromide in water. Tetrahedron 72:3535–3541CrossRefGoogle Scholar
  22. 22.
    Li Y, Flood AH (2008) Pure C–H hydrogen bonding to chloride ions: a preorganized and rigid macrocyclic receptor. Angew Chem Int Ed Engl 47:2649–2652CrossRefGoogle Scholar
  23. 23.
    Lee S, Hua Y, Park H, Flood AH (2010) Intramolecular hydrogen bonds preorganize an aryl-triazole receptor into a crescent for chloride binding. Org Lett 12:2100–2102CrossRefGoogle Scholar
  24. 24.
    Howe ENW, Bhadbhade M, Thordarson P (2014) Cooperativity and complexity in the binding of anions and cations to a tetratopic ion-pair host. J Am Chem Soc 136:7505–7516CrossRefGoogle Scholar
  25. 25.
    Mahoney JM, Beatty AM, Smith BD (2001) Selective recognition of an alkali halide contact ion-pair. J Am Chem Soc 123:5847–5848CrossRefGoogle Scholar
  26. 26.
    Kaushik R, Ghosh A, Jose DA (2017) Recent progress in hydrogen sulphide (H2S) sensors by metal displacement approach. Coord Chem Rev 347:141–157CrossRefGoogle Scholar
  27. 27.
    Kaur R, Kaur N (2017) A novel cation ensembled fluorescent organic nanoparticle for selective detection of organophosphorus insecticides. Dyes Pigments 139:310–317CrossRefGoogle Scholar
  28. 28.
    Goh H, Nam TK, Singh A, Singh N, Jang DO (2017) Dipodal colorimetric sensor for ag+ and its resultant complex for iodide sensing using a cation displacement approach in water. Tet Lett 58:1040–1045CrossRefGoogle Scholar
  29. 29.
    Atwood JL, Gokel GW, Barbour L (2017) Comprehensive supramolecular chemistry II. Elsevier ScienceGoogle Scholar
  30. 30.
    Zhou Y, Yang M, Pang S, Zhu K, Padture NP (2016) Exceptional morphology-preserving evolution of formamidinium lead triiodide perovskite thin films via organic-cation displacement. J Am Chem Soc 138:5535–5538CrossRefGoogle Scholar
  31. 31.
    Weerasinghe AJ, Oyeamalu AN, Abebe FA, Venter AR, Sinn E (2016) Rhodamine based turn-on sensors for Ni2+ and Cr3+ in organic media: detecting CN via the metal displacement approach. J Fluoresc 26:891–898CrossRefGoogle Scholar
  32. 32.
    Kaushik R, Ghosh A, Jose DA (2016) Simple terpyridine based cu(II)/Zn(II) complexes for the selective fluorescent detection of H2S in aqueous medium. J Lumin 171:112–117CrossRefGoogle Scholar
  33. 33.
    Cao W, Zheng X-J, Fang D-C, Jin L-P (2014) A highly selective and sensitive Zn(II) complex-based chemosensor for sequential recognition of cu(II) and cyanide. Dalton Trans 43:7298–7303CrossRefGoogle Scholar
  34. 34.
    Tang L, Cai M, Zhou P, Zhao J, Zhong K, Hou S, 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 3:16802–16809CrossRefGoogle Scholar
  35. 35.
    Saluja P, Kaur N, Kang J, Singh N, Jang DO (2013) Benzimidazole-based chromogenic chemosensor for the recognition of oxalic acid via counter ion displacement assay in semi-aqueous medium. Tetrahedron 69:9001–9006CrossRefGoogle Scholar
  36. 36.
    Wang J-N, Qi Q, Zhang L, Li S-H (2012) Turn-on luminescent sensing of metal cations via quencher displacement: rational design of a highly selective chemosensor for chromium(III). Inorg Chem 51:13103–13107CrossRefGoogle Scholar
  37. 37.
    Hau SC, Cheng P-S, Mak TC (2015) Assembly of organosilver(I) frameworks with terminal ethynide and ethenyl groups on separate pendent arms attached to an aromatic ring. Polyhedron 52:992–1008CrossRefGoogle Scholar
  38. 38.
    Sasikala R, Rani SK, Easwaramoorthy D, Karthikeyan K (2015) Lanthanum loaded CuO nanoparticles: synthesis and characterization of a recyclable catalyst for the synthesis of 1,4-disubstituted 1,2,3-triazoles and propargylamines. RSC Adv 5:56507–56517CrossRefGoogle Scholar
  39. 39.
    Dutta S, Sarkar S, Sen AK (2013) A facile one-pot route for the general synthesis of triazole linked chiral 2-substituted benzimidazoles. J Het Chem 50:689–695CrossRefGoogle Scholar
  40. 40.
    De Silva AP, Moody TS, Wright GD (2009) Fluorescent PET (photoinduced electron transfer) sensors as potent analytical tools. Analyst 134:2385–2393CrossRefGoogle Scholar
  41. 41.
    Long GL, Winefordner JD (1983) Limit of detection. A closer look at the IUPAC definition. Anal Chem 55:712A–724ACrossRefGoogle Scholar
  42. 42.
    Job P (1928) Formation and stability of inorganic complexes in solution. Ann Chim 9:113–203Google Scholar
  43. 43.
    Benesi H, Hildebrand HJ (1948) A spectrophotometric investigation of the interaction of iodine with aromatic hydrocarbons. J Am Chem Soc 71:2703–2707CrossRefGoogle Scholar
  44. 44.
    Becke AD (1993) Density-functional thermochemistry. III. The role of exact exchange. J Chem Phys 98:5648–5652CrossRefGoogle Scholar
  45. 45.
    Lee C, Yang W, Parr RG (1988) Development of the Colle-Salvetti correlation-energy formula into a functional of the electron density. Phys Rev B 37:785–789CrossRefGoogle Scholar

Copyright information

© Springer Science+Business Media, LLC, part of Springer Nature 2019

Authors and Affiliations

  1. 1.Department of ChemistryYonsei UniversityWonjuRepublic of Korea
  2. 2.Department of Chemistry, Indian Institute of Technology RoparRupnagarIndia

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