Advertisement

Microchimica Acta

, Volume 183, Issue 7, pp 2197–2203 | Cite as

An eco-friendly molecularly imprinted fluorescence composite material based on carbon dots for fluorescent detection of 4-nitrophenol

  • Tongfan Hao
  • Xiao Wei
  • Yijing Nie
  • Yeqing Xu
  • Yongsheng YanEmail author
  • Zhiping Zhou
Original Paper

Abstract

We on report an eco-friendly molecularly imprinted material based on carbon dots (C-dots) via a facile and efficient sol–gel polymerization for selective fluorescence detection of 4-nitrophenol (4-NP). The amino-modified C-dots were firstly synthesized by a hydrothermal process using citric acid as the carbon source and poly(ethyleneimine) as the surface modifier, and then after a sol–gel molecular imprinting process, the molecularly imprinted fluorescence material was obtained. The material (MIP-C-dots) showed strong fluorescence from C-dots and high selectivity due to the presence of a molecular imprint. After the detection conditions were optimized, the relative fluorescence intensity (F0/F) of MIP-C-dots presented a good linearity with 4-NP concentrations in the linear range of 0.2 − 50 μmol L-1 with a detection limit (3σ/k) of 0.06 μmol L-1. In addition, the correlation coefficient was 0.9978 and the imprinting factor was 2.76. The method was applicable to the determination of trace 4-NP in Yangtze River water samples and good recoveries from 92.6–107.3 % were obtained. The present study provides a general strategy to fabricate materials based on C-dots with good fluorescence property for selective fluorescence detection of organic pollutants.

Graphical Abstract

An eco-friendly molecularly imprinted fluorescence sensor based on carbon dots (C-dots) (poly(ethyleneimine) (PEI) as the surface modifier) was prepared via a facile and efficient sol–gel polymerization (3-aminopropyltriethoxysilane (APTES) as the functional monomer and tetramethoxysilane (TEOS) as the cross linker) for selective fluorescence detection of 4-nitrophenol (4-NP).

Keywords

Molecular imprinting Sol–gel Eco-friendly material Quenching Stern-Volmer plot Selective recognition 

Notes

Acknowledgments

This work was financially supported by the National Natural Science Foundation of China (No. 21277063, No. 21407057 and No. 21407064), National Basic Research Program of China (973 Program, 2012CB821500), Natural Science Foundation of Jiangsu Province (No. BK20140535), National Postdoctoral Science Foundation (No. 2014 M561595), Postdoctoral Science Foundation funded Project of Jiangsu Province (No. 1401108C).

Compliance with ethical standards

The author(s) declare that they have no competing interests

Supplementary material

604_2016_1851_MOESM1_ESM.doc (250 kb)
ESM 1 (DOC 250 kb)

References

  1. 1.
    Yin H, Zhou Y, Han R, Qiu Y, Ai S, Zhu L (2012) Electrochemical oxidation behavior of 2,4-dinitrophenol at hydroxylapatite film-modified glassy carbon electrode and its determination in water samples. J Solid State Electrochem 16:75–82CrossRefGoogle Scholar
  2. 2.
    Hu S, Xu C, Wang G, Cu D (2001) Voltammetric determination of 4-nitrophenol at a sodium montmorillonite-anthraquinone chemically modified glassy carbon electrode. Talanta 54:115–123CrossRefGoogle Scholar
  3. 3.
    Li S, Du D, Huang J, Tu H, Yang Y, Zhang A (2013) One-step electrodeposition of a molecularly imprinting chitosan/phenyltrimethoxysilane/AuNPs hybrid film and its application in the selective determination of p-nitrophenol. Analyst 138:2761–2768CrossRefGoogle Scholar
  4. 4.
    Liu X, Ji Y, Zhang Y, Zhang H, Liu M (2007) Oxidized multiwalled carbon nanotubes as a novel solid-phase microextraction fiber for determination of phenols in aqueous samples. J Chromatogr A 1165:10–17CrossRefGoogle Scholar
  5. 5.
    Guo XF, Wang ZH, Zhou SP (2004) The separation and determination of nitrophenol isomers by high-performance capillary zone electrophoresis. Talanta 64:135–139CrossRefGoogle Scholar
  6. 6.
    Valizadeh A, Mikaeili H, Samiei M, Farkhani SM, Zarghami N, Kouhi M, Akbarzadeh A, Davaran S (2012) Quantum dots: synthesis, bioapplications, and toxicity. Nanoscale Res Lett 7:480CrossRefGoogle Scholar
  7. 7.
    Yuan C, Zhang K, Zhang Z, Wang S (2012) Highly selective and sensitive detection of mercuric ion based on a visual fluorescence method. Anal Chem 84:9792–9801CrossRefGoogle Scholar
  8. 8.
    Xu X, Ray R, Gu Y, Ploehn HJ, Gearheart L, Raker K, Scrivens WA (2004) Electrophoretic analysis and purification of fluorescent single-walled carbon nanotube fragments. J Am Chem Soc 126:12736–12737CrossRefGoogle Scholar
  9. 9.
    Baker SN, Baker GA (2010) Luminescent carbon nanodots: emergent nanolights. Angew Chem Int Ed 49:6726–6744CrossRefGoogle Scholar
  10. 10.
    Zuo PL, Lu XH, Sun ZG, Guo YH, He H (2016) A review on syntheses, properties, characterization and bioanalytical applications of fluorescent carbon dots. Microchim Acta 183(2):519–542CrossRefGoogle Scholar
  11. 11.
    Yan X, Cui X, Li B, Li L (2010) Large, solution-processable graphene quantum dots as light absorbers for photovoltaics. Nano Lett 10:1869–1873CrossRefGoogle Scholar
  12. 12.
    Lu WB, Qin XY, Liu S, Chang GH, Zhang YW, Luo YL, Asiri AM, Al-Youbi AO, Sun XP (2012) Economical, green synthesis of fluorescent carbon nanoparticles and their use as probes for sensitive and selective detection of Mercury(II) ions. Anal Chem 84:5351–5357CrossRefGoogle Scholar
  13. 13.
    Huang H, Li CG, Zhu SJ, Wang HL, Chen CL, Wang ZR, Bai TY, Shi Z, Feng SH (2014) Histidine-derived nontoxic nitrogen-doped carbon dots for sensing and bioimaging applications. Langmuir 30:13542–13548CrossRefGoogle Scholar
  14. 14.
    Gao ZH, Lin ZZ, Chen XM, Lai ZZ, Huang ZY (2016) Carbon dots-based fluorescent probe for trace Hg2+ detection in water sample. Sens Actuat B: Chem 222:965–971CrossRefGoogle Scholar
  15. 15.
    Chen LX, Xu SF, Li JH (2011) Recent advances in molecular imprinting technology: current status, challenges and highlighted applications. Chem Soc Rev 40:2922–2942CrossRefGoogle Scholar
  16. 16.
    Alexander C, Andersson HS, Andersson LI, Ansell RJ, Kirsch N, Nicholls IA, O’Mahony J, Whitcombe MJ (2006) Molecular imprinting science and technology: a survey of the literature for the years up to and including 2003. J Mol Recognit 19:106–180CrossRefGoogle Scholar
  17. 17.
    Ye L, Haupt K (2004) Molecularly imprinted polymers as antibody and receptor mimics for assays, sensors and drug discovery. Anal Bioanal Chem 378:1887–1897CrossRefGoogle Scholar
  18. 18.
    Li Y, Ding MJ, Wang S, Wang RY, Wu XL, Wen TT, Yuan LH, Dai P, Lin YH, Zhou XM (2011) Preparation of imprinted polymers at surface of magnetic nanoparticles for the selective extraction of tadalafil from medicines. ACS Appl Mater Interfaces 3:3308–3315CrossRefGoogle Scholar
  19. 19.
    Yin JF, Cui Y, Yang GL, Wang HL (2010) Molecularly imprinted nanotubes for enantioselective drug delivery and controlled release. Chem Commun 46:7688–7690CrossRefGoogle Scholar
  20. 20.
    Xu SF, Chen LX, Li JH, Qin W, Ma J (2011) Molecularly imprinted core-shell nanoparticles for determination of trace atrazine by reversible addition-fragmentation chain transfer surface imprinting. J Mater Chem 21:12047–12053CrossRefGoogle Scholar
  21. 21.
    Alizadeh T, Zare M, Ganjali MR, Norouzi P, Tavana B (2010) A new molecularly imprinted polymer (MIP)-based electrochemical sensor for monitoring 2,4,6-trinitrotoluene (TNT) in natural waters and soil samples. Biosens Bioelectron 25:1166–1172CrossRefGoogle Scholar
  22. 22.
    Orozco J, Cortés A, Cheng GZ, Sattayasamitsathit S, Gao W, Feng XM, Shen YF, Wang J (2013) Molecularly imprinted polymer-based catalytic micromotors for selective protein transport. J Am Chem Soc 135:5336–5339CrossRefGoogle Scholar
  23. 23.
    Liu HL, Fang GZ, Li CM, Pan MF, Liu CC, Fan C, Wang S (2012) Molecularly imprinted polymer on ionic liquid-modified C-dotse/ZnS quantum dots for the highly selective and sensitive optosensing of tocopherol. J Mater Chem 22:19882–19887CrossRefGoogle Scholar
  24. 24.
    Wei X, Zhou ZP, Hao TF, Li HJ, Dai JD, Gao L, Zheng XD, Wang JX, Yan YS (2015) Simple synthesis of thioglycolic acid-coated CdTe quantum dots as probes for Norfloxacin lactate detection. J Lumin 161:47–53CrossRefGoogle Scholar
  25. 25.
    Wei X, Zhou ZP, Hao TF, Li HJ, Yan YS (2015) Molecularly imprinted polymer nanospheres based on Mn-doped ZnS QDs via precipitation polymerization for room-temperature phosphorescence probing of 2,6-dichlorophenol. RSC Adv 5:19799–19806CrossRefGoogle Scholar
  26. 26.
    Wei X, Zhou ZP, Hao TF, Li HJ, Xu YQ, Lu K, Wu YL, Dai JD, Pan JM, Yan YS (2015) Highly-controllable imprinted polymer nanoshell at the surface of silica nanoparticles based room-temperature phosphorescence probe for detection of 2,4-dichlorophenol. Anal Chim Acta 870:83–91CrossRefGoogle Scholar
  27. 27.
    Wei X, Hao TF, Xu YQ, Lu K, Li HJ, Yan YS, Zhou ZP (2015) Swelling technique inspired synthesis of fluorescence composite sensor for highly selective detection of Bifenthrin. RSC Adv 5:79511–79518CrossRefGoogle Scholar
  28. 28.
    Wei X, Hao TF, Xu YQ, Lu K, Li HJ, Yan YS, Zhou ZP (2016) Facile polymerizable surfactant inspired synthesis of fluorescent molecularly imprinted composite sensor via aqueous CdTe quantum dots for highly selective detection of λ-cyhalothrin. Sens Actuat B: Chem 224:315–324CrossRefGoogle Scholar
  29. 29.
    Wei X, Zhou ZP, Hao TF, Xu YQ, Li HJ, Lu K, Dai JD, Zheng XD, Gao L, Wang JX, Yan YS, Zhu YZ (2015) Specific recognition and fluorescent determination of aspirin by using core-shell CdTe quantum dot-imprinted polymers. Microchim Acta 182:1527–1534CrossRefGoogle Scholar
  30. 30.
    Rounaghi G, Kakhki RM, Azizi-toupkanloo H (2012) Voltammetric determination of 4-nitrophenol using a modified carbon paste electrode based on a new synthetic crown ether/silver nanoparticles. Mat Sci Eng C-Mater 32:172–177CrossRefGoogle Scholar
  31. 31.
    Gu YE, Zhang Y, Zhang F, Wei J, Wang C, Du Y, Ye W (2010) Investigation of photoelectrocatalytic activity of Cu2O nanoparticles for p-nitrophenol using rotating ring-disk electrode and application for electrocatalytic determination. Electrochimi Acta 56:953–958CrossRefGoogle Scholar
  32. 32.
    Xiao W, Xiao D, Yuan H (2007) A functionalized mesoporous silica sensor for the determination of p-nitrophenol or 2,4-dinitrophenol based on fluorescence quenching. Sens Lett 5:445–449CrossRefGoogle Scholar
  33. 33.
    Moraes FC, Tanimoto ST, Salazar-Banda GR, Machado SAS, Mascaro LH (2009) A new indirect electroanalytical method to monitor the contamination of natural waters with 4-nitrophenol using multiwall carbon nanotubes. Electroanalysis 21:1091–1098CrossRefGoogle Scholar
  34. 34.
    Yin H, Zhou Y, Ai S, Liu X, Zhu L, Lu L (2010) Electrochemical oxidative determination of 4-nitrophenol based on a glassy carbon electrode modified with a hydroxyapatite nanopowder. Microchim Acta 169:87–92CrossRefGoogle Scholar
  35. 35.
    Ahmed GHG, Laíño RB, Calzón JAG, García MED (2015) Highly fluorescent carbon dots as nanoprobes for sensitive and selective determination of 4-nitrophenol in surface waters. Microchim Acta 182:51–59CrossRefGoogle Scholar

Copyright information

© Springer-Verlag Wien 2016

Authors and Affiliations

  • Tongfan Hao
    • 1
  • Xiao Wei
    • 1
  • Yijing Nie
    • 1
  • Yeqing Xu
    • 2
  • Yongsheng Yan
    • 2
  • Zhiping Zhou
    • 1
  1. 1.School of Material Science and EngineeringJiangsu UniversityZhenjiangChina
  2. 2.School of Chemistry and Chemical EngineeringJiangsu UniversityZhenjiangChina

Personalised recommendations