Skip to main content

Simultaneous detection and removal of metal ions based on a chemosensor composed of a rhodamine derivative and cyclodextrin-modified magnetic nanoparticles

Journal of Materials Science volume 50, pages 168–175 (2015)Cite this article

Abstract

A variety of chemosensors have been reported for detection of metal ions. However, the metal ions could not be separated and removed at the same time for the goal of water purification. This paper presents to detect and remove metal ions from aqueous solution simultaneously by a fluorescence chemosensor and functional magnetic nanoparticles. A novel probe adamantyl (AD)–maleic anhydride (MAH)–rhodamine B (RhB) was designed and synthesized from RhB, ethylene diamine, MAH, and AD. AD–MAH–RhB showed high selectivity and sensitivity to metal ions in aqueous solution. The sensing mechanism was explored by FTIR and mass spectra. The results suggested that AD–MAH–RhB could conjugate with metal ions and form the binding complexes with various stoichiometries of probe and metal ions. Moreover, β-cyclodextrin-modified magnetic nanoparticles (CD-MNP) were fabricated and used as host materials to form inclusion complex of CD-MNP and AD–MAH–RhB-metal ions. Then, the metal ions could be removed by an outer magnet, which were confirmed by fluorescent spectrum. The probe and CD-MNP had the great potential application for sewage treatment.

This is a preview of subscription content, access via your institution.

Access options

Buy single article

Instant access to the full article PDF.

USD 39.95

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

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

References

  1. Prodi L, Bargossi C, Montalti M, Zaccheroni N, Su N, Bradshaw JS, Izatt RM, Savage PB (2000) An effective fluorescent chemosensor for mercury ions. J Am Chem Soc 122:6769–6770

    Article  Google Scholar 

  2. Kim HN, Ren WX, Kim JS, Yoon J (2012) Fluorescent and colorimetric sensors for detection of lead, cadmium, and mercury ions. Chem Soc Rev 41:3210–3244

    Article  Google Scholar 

  3. Yean LP, Ahmad ZA (2012) Effect of low Fe3+ doping on characteristics, sonocatalytic activity and reusability of TiO2 nanotubes catalysts for removal of Rhodamine B from water. Hazardous Mater 235–236:326–335

    Google Scholar 

  4. Xu JH, Hou YM, Ma QJ, Wu XF, Wei XJ (2013) A highly selective fluorescent sensor for Fe3+ based on covalently immobilized derivative of naphthalimide. Spectrochim Acta A112:116–124

    Article  Google Scholar 

  5. Ho JA, Chang HC, Su WT (2012) DOPA-mediated reduction allows the facile synthesis of fluorescent gold nanoclusters for use as sensing probes for ferric ions. Anal Chem 84:3246–3253

    Article  Google Scholar 

  6. Li YN, Huang H, Li Y, Su XG (2013) Highly sensitive fluorescent sensor for mercury (II) ion based on layer-by-layer self-assembled films fabricated with water-soluble fluorescent conjugated polymer. Sensor Actuat B 188:772–777

    Article  Google Scholar 

  7. Li JF, Wu YZ, Song FY, Wei G, Cheng YX, Zhu CJ (2012) A highly selective and sensitive polymer-based OFF–ON fluorescent sensor for Hg2+ detection incorporating salen and perylenyl moieties. J Mater Chem 22:478–482

    Article  Google Scholar 

  8. Wan XJ, Yao S, Liu HY, Yao YW (2013) Selective fluorescence sensing of Hg2+ and Zn2+ ions through dual independent channels based on the site-specific functionalization of mesoporous silica nanoparticles. J Mater Chem A 1:10505–10512

    Article  Google Scholar 

  9. Kyzas GZ, Travlou NA, Deliyanni EA (2014) The role of chitosan as nanofiller of graphite oxide for the removal of toxic mercury ions. Colloids Surf B 113:467–476

    Article  Google Scholar 

  10. Zhang D, Zou RY, Wan M, Chai MM, Wang XB, Ye Y, Zhao YF (2013) Novel series colorimetric and Off–On fluorescent chemosensors for Fe3+ based on Rhodamine B derivative. J Fluoresc 23:13–19

    Article  Google Scholar 

  11. Chai MM, Zhang D, Wang M, Hong HJ, Yong Y, Zhao YF (2012) Four rhodamine B-based fluorescent chemosensor for Fe3+ in aqueous solution. Sensor Actuat B 174:231–236

    Article  Google Scholar 

  12. Zhang LB, Li T, Li BL, Li J, Wang EK (2010) Carbon nanotube–DNA hybrid fluorescent sensor for sensitive and selective detection of mercury(II) ion. Chem Commun 46:1476–1478

    Article  Google Scholar 

  13. Kim I, Kim D, Sambasivan S, Ahn KH (2012) Synthesis of π-extended coumarins and evaluation of their precursors as reactive fluorescent probes for mercury ions. Asian J Org Chem 1:60–64

    Article  Google Scholar 

  14. Mu HL, Gong R, Ma Q (2007) A novel colorimetric and fluorescent chemosensor: synthesis and selective detection for Cu2+ and Hg2+. Tetrahedron Lett 48:5525–5529

    Article  Google Scholar 

  15. Jk Ni, Li QY, Li B, Zhang LM (2013) A novel fluorescent probe based on Rhodamine B derivative for highly selective and sensitive detection of mercury(II) ion in aqueous solution. Sensor Actuat B 186:278–285

    Article  Google Scholar 

  16. Wu C, Bian QN, Zhang BG, Cai X, Zhang SD, Zheng H, Yang SY, Jiang YB (2012) Ring expansion of spiro-thiolactam in rhodamine scaffold: switching the recognition preference by adding one atom. Org Lett 4:4198–4201

    Article  Google Scholar 

  17. Wang W, Zhang Y, Yang QB, Sun MD, Fei XL, Song Y, Zhang YM, Li YX (2013) Fluorescent and colorimetric magnetic microspheres as nanosensors for Hg2+ in aqueous solution prepared by a sol–gel grafting reaction and host–guest interaction. Nanoscale 5:4958–4965

    Article  Google Scholar 

  18. Luo J, Jiang SS, Qin SH, Wu HQ, Wang Y, Jiang JQ, Liu XY (2011) Highly sensitive and selective turn-on fluorescent chemosensor for Hg2+ in pure water based on a rhodamine containing water-soluble copolymer. Sensor Actuat B 160:1191–1197

    Article  Google Scholar 

  19. Yang H, Zhou ZG, Huang KW, Yu MX, Li FY, Yi T, Huang CH (2007) Multisignaling optical-electrochemical sensor for Hg2+ based on a rhodamine derivative with a ferrocene unit. Org Lett 9:4729–4732

    Article  Google Scholar 

  20. Wu DY, Huang W, Lin ZH, Duan CY, He C, Wu S, Wang DH (2008) Highly sensitive multiresponsive chemosensor for selective detection of Hg2+ in natural water and different monitoring environments. Inorg Chem 47:7190–7201

    Article  Google Scholar 

  21. Barman S, Sadhukhan M (2012) Facile bulk production of highly blue fluorescent graphitic carbon nitride quantum dots and their application as highly selective and sensitive sensors for the detection of mercuric and iodide ions in aqueous media. J Mater Chem 22:21832–21837

    Article  Google Scholar 

  22. Abbaspour A, Noori A (2011) A cyclodextrin host-guest recognition approach to an electrochemical sensor for simultaneous quantification of serotonin and dopamine. Biosens Bioelectron 26:4674–4680

    Article  Google Scholar 

  23. Badruddoza AZM, Rahman MT, Ghosh S, Hossain MZ, Shi JZ, Hidajat K, Uddin MS (2013) Beta-cyclodextrin conjugated magnetic, fluorescent silica core–shell nanoparticles for biomedical applications. Carbohyd Polym 95:449–457

    Article  Google Scholar 

  24. Liu JC, Liu R, Jiang JQ, Liu XY (2013) Design and synthesis of water-soluble photosensitive cyclodextrin and its application in dispersing carbon nanotubes. J Appl Polym Sci 130:2588–2593

    Article  Google Scholar 

  25. Xu MY, Wu SZ, Zeng F, Yu CM (2010) Cyclodextrin supramolecular complex as a water-soluble ratiometric sensor for ferric ion sensing. Langmuir 26:4529–4534

    Article  Google Scholar 

  26. Wang YP, Ma N, Wang ZQ, Zhang X (2007) Photocontrolled reversible supramolecular assemblies of an azobenzene-containing surfactant with alpha-cyclodextrin. Angew Chem Int Ed 46:2823–2826

    Article  Google Scholar 

  27. Xie J, Yin YX, Jin GL, He MX, Diao GW (2011) Theoretical study on the inclusion complex of β-cyclodextrin and nitrobenzene. Chinese J Struc Chem 30:706–716

    Google Scholar 

  28. Wu YP, Zuo F, Zheng ZH, Ding XB, Peng YX (2009) A novel approach to molecular recognition surface of magnetic nanoparticles based on host–guest effect. Nanoscale Res Lett 4:738–747

    Article  Google Scholar 

  29. Ghosh S, Badruddoza AZM, Uddin MS, Hidajat K (2011) Adsorption of chiral aromatic amino acids onto carboxymethyl-β-cyclodextrin bonded Fe3O4/SiO2 core–shell nanoparticles. J Colloid Interface Sci 354:483–492

    Article  Google Scholar 

  30. Huan XY, Wang DL, Dong RJ, Tu CL, Zhu BS, Yan DY, Zhu XY (2012) Supramolecular ABC miktoarm star terpolymer based on host–guest inclusion complexation. Macromolecules 45:5941–5947

    Article  Google Scholar 

  31. Ma LJ, Li Y, Li L, Wu YQ, Buchet R, Ding YH (2009) Larification of the binding model of lead(II) with a highly sensitive and selective fluoroionophore sensor by spectroscopic and structural study. Spectrochim Acta A 72:306–311

    Article  Google Scholar 

  32. Berezovskaya Y, Armstrong CT, Boyle AL, Porrini M, Woolfson DN, Barran PE (2011) Metal binding to a zinc-finger peptide: a comparison between solution and the gas phase. Chem Commun 47:412–414

    Article  Google Scholar 

  33. Qin W, Zou B, Zhang Y, Yi XH, Pan ZH (2013) UV–VIS, fluorescence and mass spectrometry investigation on the transition metal ion chelation of two bioisosteres of resveratrol. Asian J Chem 25:2185–2188

    Google Scholar 

  34. Yang XF, Liu P, Wang LP, Zhao ML (2008) A chemosensing ensemble for the detection of cysteine based on the inner filter effect using a Rhodamine B spirolactam. J Fluoresc 18:453–459

    Article  Google Scholar 

  35. Bhalla V, Tejpal R, Kumar M (2010) Rhodamine appended terphenyl: a reversible “off–on” fluorescent chemosensor for mercury ions. Sensor Actuat B 151:180–185

    Article  Google Scholar 

Download references

Acknowledgements

This study was supported by the National Natural Science Foundation of China (No. 21004029), MOE & SAFEA for the 111 Project (B13025) and Jiangsu Key Laboratory of Advanced Functional Polymer Design and Application (Soochow University, KJS1141).

Author information

Authors and Affiliations

  1. The Key Laboratory of Food Colloids and Biotechnology, Ministry of Education, School of Chemical and Material Engineering, Jiangnan University, Wuxi, 214122, People’s Republic of China

    Dongjian Shi, Ming Ni, Jinfeng Zeng, Jin Ye, Xiaoya Liu & Mingqing Chen

  2. Jiangsu Key Laboratory of Advanced Functional Polymer Design and Application, Soochow University, Suzhou, 215123, People’s Republic of China

    Dongjian Shi & Peihong Ni

Authors
  1. Dongjian Shi
    View author publications

    You can also search for this author in PubMed Google Scholar

  2. Ming Ni
    View author publications

    You can also search for this author in PubMed Google Scholar

  3. Jinfeng Zeng
    View author publications

    You can also search for this author in PubMed Google Scholar

  4. Jin Ye
    View author publications

    You can also search for this author in PubMed Google Scholar

  5. Peihong Ni
    View author publications

    You can also search for this author in PubMed Google Scholar

  6. Xiaoya Liu
    View author publications

    You can also search for this author in PubMed Google Scholar

  7. Mingqing Chen
    View author publications

    You can also search for this author in PubMed Google Scholar

Corresponding author

Correspondence to Mingqing Chen.

Electronic supplementary material

Below is the link to the electronic supplementary material.

Supplementary material (DOC 2583 kb)

Rights and permissions

Reprints and Permissions

About this article

Verify currency and authenticity via CrossMark

Cite this article

Shi, D., Ni, M., Zeng, J. et al. Simultaneous detection and removal of metal ions based on a chemosensor composed of a rhodamine derivative and cyclodextrin-modified magnetic nanoparticles. J Mater Sci 50, 168–175 (2015). https://doi.org/10.1007/s10853-014-8576-6

Download citation

  • Received:

  • Accepted:

  • Published:

  • Issue Date:

  • DOI: https://doi.org/10.1007/s10853-014-8576-6

Keywords

  • Inclusion Complex
  • Attenuate Total Reflection
  • Maleic Anhydride
  • Adamantyl
  • Carbon Nitride