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Establishment of a novel surface-imprinting system for melamine recognition and mechanism of template–matrix interactions

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Abstract

A surface molecular-imprinting system was developed on polypropylene (PP) fiber for melamine (Mel) as an N-containing template. In this article, acrylic acid was introduced onto the surface of PP for template binding. Subsequently, binding sites on PP were stabilized by crosslinking with ethylene glycol diglycidyl ether in the presence of Mel. The imprinted fiber (MIF-Mel) prepared with the optimal 15 % crosslinking density showed best-imprinting effect, with an imprinting factor of 2.18 respect to nonimprinted fiber, and a relative selectivity coefficient k′ of 10.40 for Mel with respect to its structural analog 2,4-dinitroaniline. MIF-Mel showed higher affinity to Mel with the maximum adsorption capacity of 15.5 mg g−1, while that on nonimprinted fiber was only 6.9 mg g−1. Its adsorption isotherm was well described using Langmuir model. Kinetic studies showed a rapid-binding interaction and high affinity of the MIF-Mel for its template, with a 2.5 times higher in binding amount and 4.7 times faster in binding speed than those of granular molecular-imprinting polymer with the same chemical structure. High degree of fitness with pseudo-second-order model revealed chemisorption was the rate-controlling step in the template-binding process. Basic theory of matrix–template interaction in this imprinting system was clarified to be dominated by electrostatic force synergized by hydrogen bonding between deprotonated carboxyl groups and protonated N atom in the template. It suggests that extension of this novel approach or theory to other imprinting system involving nitrogenous templates is very likely.

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References

  1. Sibrian-Vazquez M, Spivak DA (2004) Molecular imprinting made easy. J Am Chem Soc 126:7827–7833

    Article  Google Scholar 

  2. Ansell R (2005) Molecularly imprinted polymers for the enantioseparation of chiral drugs. Adv Drug Deliv Rev 57:1809–1835

    Article  Google Scholar 

  3. Greene NT, Morgan SL, Shimizu KD (2004) Molecularly imprinted polymer sensor arrays. Chem Commun 10:1172–1173

    Article  Google Scholar 

  4. Ramström O, Mosbach K (1999) Synthesis and catalysis by molecularly imprinted materials. Curr Opin Chem Biol 3:759–764

    Article  Google Scholar 

  5. Wulff G (2002) Enzyme-like catalysis by molecularly imprinted polymers. Chem Rev 102:1–27

    Article  Google Scholar 

  6. Balamurugan K, Gokulakrishnan K, Prakasam T (2011) Preparation and evaluation of molecularly imprinted polymer liquid chromatography column for the separation of ephedrine enantiomers. Arab J Chem 2:77

    Google Scholar 

  7. Yang H–H, Zhang S-Q, Yang W, Chen X-L, Zhuang Z-X, Xu J-G, Wang X-R (2004) Molecularly imprinted sol–gel nanotubes membrane for biochemical separations. J Am Chem Soc 126:4054–4055

    Article  Google Scholar 

  8. Cunliffe D, Kirby A, Alexander C (2005) Molecularly imprinted drug delivery systems. Adv Drug Deliv Rev 57:1836–1853

    Google Scholar 

  9. Wei X, Li X, Husson SM (2005) Surface molecular imprinting by atom transfer radical polymerization. Biomacromolecules 6:1113–1121

    Article  Google Scholar 

  10. Kempe H, Kempe M (2004) Novel method for the synthesis of molecularly imprinted polymer bead libraries. Macromol Rapid Commun 25:315–320

    Article  Google Scholar 

  11. Ye L, Mosbach K (2001) Molecularly imprinted microspheres as antibody binding mimics. React Funct Polym 48:149–157

    Article  Google Scholar 

  12. Hirayama K, Sakai Y, Kameoka K (2001) Synthesis of polymer particles with specific lysozyme recognition sites by a molecular imprinting technique. J Appl Polym Sci 81:3378–3387

    Article  Google Scholar 

  13. Strikovsky A, Hradil J, Wulff G (2003) Catalytically active, molecularly imprinted polymers in bead form. React Funct Polym 54:49–61

    Article  Google Scholar 

  14. Lepinay S, Kham K, Millot MC, Carbonnier B (2012) In-situ polymerized molecularly imprinted polymeric thin films used as sensing layers in surface plasmon resonance sensors: mini-review focused on 2010-2011. Chem Pap 66:340–351

    Article  Google Scholar 

  15. Das K, Penelle J, Rotello VM (2003) Selective picomolar detection of hexachlorobenzene in water using a quartz crystal microbalance coated with a molecularly imprinted polymer thin film. Langmuir 19:3921–3925

    Article  Google Scholar 

  16. Huang HC, Lin CI, Joseph AK, Lee YD (1027) Photo-lithographically impregnated and molecularly imprinted polymer thin film for biosensor applications. J Chromatoge A 2004:263–268

    Google Scholar 

  17. Duffy DJ, Das K, Hsu SL, Penelle J, Rotello VM, Stidham HD (2002) Binding efficiency and transport properties of molecularly imprinted polymer thin films. J Am Chem Soc 124:8290–8296

    Article  Google Scholar 

  18. Gauczinski J, Liu Z, Zhang X, Schönhoff M (2012) Surface molecular imprinting in layer-by-layer films on silica particles. Langmuir 28:4267–4273

    Article  Google Scholar 

  19. Yan W, Gao R, Zhang Z, Wang Q, Jiang CV, Yan C (2003) Capillary electrochromatographic separation of ionizable compounds with a molecular imprinted monolithic cationic exchange column. J Sep Sci 26:555–561

    Article  Google Scholar 

  20. Schweitz L, Andersson LI, Nilsson S (1997) Capillary electrochromatography with molecular imprint-based selectivity for enantiomer separation of local anaesthetics. J Chromatoge A 792:401–409

    Article  Google Scholar 

  21. Che A-F, Wan L-S, Ling J, Liu Z-M, Xu Z-K (2009) Recognition mechanism of theophylline-imprinted polymers: two-dimensional infrared analysis and density functional theory study. J Phys Chem B 113:7053–7058

    Article  Google Scholar 

  22. Özacar M, Şengil İA (2003) Adsorption of reactive dyes on calcined alunite from aqueous solutions. J Hazard Mater 98:211–224

    Article  Google Scholar 

  23. Skorik Y (2012) Carboxyethylated polyaminostyrene for selective copper removal. Polym Bull 68:1065–1078

    Article  Google Scholar 

  24. Vorderbruggen MA, Wu K, Breneman CM (1996) Use of cationic aerosol photopolymerization to form silicone microbeads in the presence of molecular templates. Chem Mater 8:1106–1111

    Article  Google Scholar 

  25. Ran D, Wang Y, Jia X, Nie C (2012) Bovine serum albumin recognition via thermosensitive molecular imprinted macroporous hydrogels prepared at two different temperatures. Anal Chim Acta 723:45–53

    Article  Google Scholar 

  26. Rostamizadeh K, Vahedpour M, Bozorgi S (2012) Synthesis, characterization and evaluation of computationally designed nanoparticles of molecular imprinted polymers as drug delivery systems. Int J Pharm 424:67–75

    Article  Google Scholar 

  27. Ersöz A, Say R, Denizli A (2004) Ni(II) ion-imprinted solid-phase extraction and preconcentration in aqueous solutions by packed-bed columns. Anal Chim Acta 502:91–97

    Article  Google Scholar 

  28. Cao Q, Zhao H, Zeng L, Wang J, Wang R, Qiu X, He Y (2009) Electrochemical determination of melamine using oligonucleotides modified gold electrodes. Talanta 80:484–488

    Article  Google Scholar 

  29. Nityanandi D, Subbhuraam CV (2009) Kinetics and thermodynamic of adsorption of chromium(VI) from aqueous solution using puresorbe. J Hazard Mater 170:876–882

    Article  Google Scholar 

  30. Cheng HC (2004) The influence of cooperativity on the determination of dissociation constants: examination of the Cheng–Prusoff equation, the Scatchard analysis, the Schild analysis and related power equations. Pharmacol Res 50:21–40

    Article  Google Scholar 

  31. Ying X, Cheng G, Li X (2011) The imprinting induce-fit model of specific rebinding of macromolecularly imprinted polymer microspheres. J Appl Polym Sci 122:1847–1856

    Article  Google Scholar 

  32. Patachia S, Croitoru C (2011) Imprinted poly (vinyl alcohol) as a promising tool for xanthine derivatives separation. J Appl Polym Sci 122:2081–2089

    Article  Google Scholar 

  33. Tseng R-L, Wu F-C, Juang R-S (2010) Characteristics and applications of the Lagergren’s first-order equation for adsorption kinetics. J Taiwan Inst Chem E 41:661–669

    Article  Google Scholar 

  34. Ho YS, McKay G (1999) The sorption of lead(II) ions on peat. Water Res 33:578–584

    Article  Google Scholar 

  35. Ho YS, McKay G (1999) Pseudo-second order model for sorption processes. Process Biochem 34:451–465

    Article  Google Scholar 

  36. Özacar M, Şengil İA, Türkmenler H (2008) Equilibrium and kinetic data, and adsorption mechanism for adsorption of lead onto valonia tannin resin. Chem Eng J 143:32–42

    Article  Google Scholar 

  37. Li T, Chen S, Li H, Li Q, Wu L (2011) Preparation of an ion-imprinted fiber for the selective removal of Cu2+. Langmuir 27:6753–6758

    Article  Google Scholar 

  38. Chiou M-S, Li H-Y (2002) Equilibrium and kinetic modeling of adsorption of reactive dye on cross-linked chitosan beads. J Hazard Mater 93:233–248

    Article  Google Scholar 

  39. Yang H–H, Zhang S-Q, Tan F, Zhuang Z-X, Wang X-R (2005) Surface molecularly imprinted nanowires for biorecognition. J Am Chem Soc 127:1378–1379

    Article  Google Scholar 

  40. Lu C-H, Zhou W-H, Han B, Yang H–H, Chen X, Wang X-R (2007) Surface-imprinted core–shell nanoparticles for sorbent assays. Anal Chem 79:5457–5461

    Article  Google Scholar 

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Acknowledgements

The authors gratefully acknowledge the financial support provided by the National Natural Science Foundation of China (Grant No. 51173211), Science and Technology Project of Guangdong Province (2011B090400030), Science and Technology Project of Zhuhai (2010B050102024).

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Correspondence to Shuixia Chen.

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Xu, X., Chen, S., Zhuang, L. et al. Establishment of a novel surface-imprinting system for melamine recognition and mechanism of template–matrix interactions. J Mater Sci 49, 2853–2863 (2014). https://doi.org/10.1007/s10853-013-7991-4

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  • DOI: https://doi.org/10.1007/s10853-013-7991-4

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