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Facile synthesis of magnetic molecularly imprinted polymers for caffeine via ultrasound-assisted precipitation polymerization

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Abstract

Facile method for preparation of magnetic molecularly imprinted polymers was developed via ultrasound-assisted precipitation polymerization using caffeine as the model template. Magnetic iron oxide powder was incorporated into the imprinted polymer matrix containing methacrylic acid and ethyleneglycol dimethacrylate as a functional monomer and a crosslinker, respectively. The amount of Fe3O4 and sonication time were varied and the recognition properties of the produced magnetic polymers were investigated. It was found that the developed method allow up to 41.4 % inclusion of iron oxide into the polymer beads in single step. Surface functionalization of the magnetic core and the use of additive surfactant or stabilizer were unnecessary. Under the optimum conditions, highly selective magnetic caffeine-imprinted polymer was produced in moderate yield with comparable recognition properties relative to the previously reported imprinted non-magnetic material.

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References

  1. Cormack PAG, Elorza AZ (2004) Molecularly imprinted polymers: synthesis and characterisation. J Chromatogr B 804(1):173–182

    Article  CAS  Google Scholar 

  2. Chen L, Xu S, Li J (2011) Recent advances in molecular imprinting technology: current status, challenges and highlighted applications. Chem Soc Rev 40(5):2922–2942

    Article  CAS  Google Scholar 

  3. Díaz-Díaz G, Antuña-Jiménez D, Carmen Blanco-López M, Jesús Lobo-Castañón M, Miranda-Ordieres AJ, Tuñón-Blanco P (2012) New materials for analytical biomimetic assays based on affinity and catalytic receptors prepared by molecular imprinting. Trends Anal Chem 33:68–80

    Article  Google Scholar 

  4. Deng F, Li Y, Luo X, Dong R, Tu X, Wang M (2011) Preparation and research progress of magnetic molecularly imprinted polymers. Polym Mater Sci Eng 27(4):171–174

    CAS  Google Scholar 

  5. Weihai Y, Wu Y, Zhang Y, Wei C, Yan S, Wang Q (2010) Preparation and application of core-shell magnetic molecularly imprinted polymer microspheres. Prog Chem 22(9):1819–1825

    Google Scholar 

  6. Jie Z, Xiwen H (1999) Study of the nature of recognition in molecularly imprinted polymer selective for 2-aminopyridine. Anal Chim Acta 381(1):85–91

    Article  CAS  Google Scholar 

  7. Wang X, Ding X, Zheng Z, Hu X, Cheng X, Peng Y (2006) Magnetic molecularly imprinted polymer particles synthesized by suspension polymerization in silicone oil. Macromol Rapid Commun 27(14):1180–1184

    Article  CAS  Google Scholar 

  8. Zhang Z, Tan W, Hu Y, Li G, Zan S (2012) Microwave synthesis of gibberellin acid 3 magnetic molecularly imprinted polymer beads for the trace analysis of gibberellin acids in plant samples by liquid chromatography-mass spectrometry detection. Analyst 137(4):968–977

    Article  CAS  Google Scholar 

  9. Luo X, Deng F, Luo S, Tu X, Yang L (2011) Grafting of molecularly imprinted polymers from the surface of Fe3O4 nanoparticles containing double bond via suspension polymerization in aqueous environment: a selective sorbent for theophylline. J Appl Polym Sci 21(4):1930–1937

    Article  Google Scholar 

  10. Ji Y, Yin J, Xu Z, Zhao C, Huang H, Zhang H, Wang C (2009) Preparation of magnetic molecularly imprinted polymer for rapid determination of bisphenol A in environmental water and milk samples. Anal Bioanal Chem 395(4):1125–1133

    Article  CAS  Google Scholar 

  11. 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(9):3308–3315

    Article  CAS  Google Scholar 

  12. Ansell RJ, Mosbach K (1998) Magnetic molecularly imprinted polymer beads for drug radioligand binding assay. Analyst 123(7):1611–1616

    Article  CAS  Google Scholar 

  13. Zhang Y, Liu R, Hu Y, Li G (2009) Microwave heating in preparation of magnetic molecularly imprinted polymer beads for trace triazines analysis in complicated samples. Anal Chem 81(3):967–976

    Article  CAS  Google Scholar 

  14. Hu Y, Li Y, Liu R, Tan W, Li G (2011) Magnetic molecularly imprinted polymer beads prepared by microwave heating for selective enrichment of β-agonists in pork and pig liver samples. Talanta 84(2):462–470

    Article  CAS  Google Scholar 

  15. Jing T, Xia H, Guan Q, Lu W, Dai Q, Niu J, Lim JM, Hao Q, Lee YI, Zhou Y, Mei S (2010) Rapid and selective determination of urinary lysozyme based on magnetic molecularly imprinted polymers extraction followed by chemiluminescence detection. Anal Chim Acta 692(1–2):73–79

    Google Scholar 

  16. Men HF, Liu HQ, Zhang ZL, Huang J, Zhang J, Zhai YY, Li L (2011) Synthesis, properties and application research of atrazine Fe3O4@SiO2 magnetic molecularly imprinted polymer. Environ Sci Pollut 19:2271–2280

    Google Scholar 

  17. Gonzato C, Courty M, Pasetto P, Haupt K (2011) Magnetic molecularly imprinted polymer nanocomposites via surface-initiated RAFT polymerization. Adv Funct Mater 21(20):3947–3953

    Article  CAS  Google Scholar 

  18. Xia X, Lai EPC, Ormeci B (2012) Ultrasonication-assisted synthesis of molecularly imprinted polymer-encapsulated magnetic nanoparticles for rapid and selective removal of 17β-estradiol from aqueous environment. Polym Eng Sci. doi:10.1002/pen.23126

    Google Scholar 

  19. Jin Y, Row KH (2006) Molecularly imprinted solid-phase extraction of caffeine from green tea. J Ind Eng Chem 12:494–499

    CAS  Google Scholar 

  20. Wang D, Hong SP, Yang G, Row KH (2003) Caffeine molecular imprinted microgel spheres by precipitation polymerization. Korean J Chem Eng 20(6):1073–1076

    Article  CAS  Google Scholar 

  21. Price GJ (1996) Ultrasonically enhanced polymer synthesis. Ultrason Sonochem 3(3):S229–S238

    Article  CAS  Google Scholar 

  22. Suslick KS, Price GJ (1999) Applications of ultrasound to materials chemistry. Annu Rev Mater Sci 29:295–326

    Article  CAS  Google Scholar 

  23. Zeng H, Lai Q, Liu X, Wen D, Ji X (2007) Factors influencing magnetic polymer microspheres prepared by dispersion polymerization. J Appl Polym Sci 106:3474–3480

    Article  CAS  Google Scholar 

  24. Ashjari M, Mahdavian AR, Ebrahimi NG, Mosleh Y (2010) Efficient dispersion of magnetite nanoparticles in the polyurethane matrix through solution mixing and investigation of the nanocomposite properties. J Inorg Organomet Polym 20:213–219

    Article  CAS  Google Scholar 

  25. Yoshimatsu K, Reimhult K, Krozer A, Mosbach K, Sode K, Ye L (2007) Uniform molecularly imprinted microspheres and nanoparticles prepared by precipitation polymerization: the control of particle size suitable for different analytical applications. Anal Chim Acta 584(1):112–121

    Article  CAS  Google Scholar 

  26. Kan X, Geng Z, Zhao Y, Wang Z, Zhu JJ (2009) Magnetic molecularly imprinted polymer for aspirin recognition and controlled release. Nanotechnology 20(16):1–7

    Article  Google Scholar 

  27. Villamena FA, De La Cruz AA (2001) Caffeine selectivity of divinylbenzene crosslinked polymers in aqueous media. J Appl Polym Sci 82(1):195–205

    Article  CAS  Google Scholar 

  28. Yan S, Fang Y, Yao W, Gao Z (2007) Characterization and quality assessment of binding properties of the monocrotophos molecularly imprinted microspheres prepared by precipitation polymerization in toluene. Polym Eng Sci 47:1302–1308

    Article  CAS  Google Scholar 

  29. García-Calzón JA, Díaz-García ME (2007) Characterization of binding sites in molecularly imprinted polymers. Sens Actuators B 123(2):1180–1194

    Article  Google Scholar 

  30. Theodoridis G, Manesiotis P (2002) Selective solid-phase extraction sorbent for caffeine made by molecular imprinting. J Chromatogr A 948(1–2):163–169

    CAS  Google Scholar 

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Acknowledgments

This research was supported by the grant under the program Strategic Scholarships for Frontier Research Network for the Ph.D. Program Thai Doctoral degree from the Commission on Higher Education (CHE), Thailand (to N. Phutthawong). The authors also gratefully acknowledge the National Research University Project under Thailand’s Office of the Higher Education Commission and the Center of Excellence for Innovation in Chemistry (PERCH-CIC) for financial support of this research.

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  1. Department of Chemistry and Center of Excellence for Innovation in Chemistry, Faculty of Science, Chiang Mai University, Chiang Mai, 50200, Thailand

    Nathaporn Phutthawong & Mookda Pattarawarapan

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  1. Nathaporn Phutthawong
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  2. Mookda Pattarawarapan
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Correspondence to Mookda Pattarawarapan.

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Phutthawong, N., Pattarawarapan, M. Facile synthesis of magnetic molecularly imprinted polymers for caffeine via ultrasound-assisted precipitation polymerization. Polym. Bull. 70, 691–705 (2013). https://doi.org/10.1007/s00289-012-0836-5

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  • DOI: https://doi.org/10.1007/s00289-012-0836-5

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