Analytical and Bioanalytical Chemistry

, Volume 405, Issue 26, pp 8597–8605 | Cite as

Carprofen-imprinted monolith prepared by reversible addition–fragmentation chain transfer polymerization in room temperature ionic liquids

  • Lu Ban
  • Xu Han
  • Xian-Hua WangEmail author
  • Yan-Ping Huang
  • Zhao-Sheng LiuEmail author
Research Paper


To obtain fast separation, ionic liquids were used as porogens first in combination with reversible addition–fragmentation chain transfer (RAFT) polymerization to prepare a new type of molecularly imprinted polymer (MIP) monolith. The imprinted monolithic column was synthesized using a mixture of carprofen (template), 4-vinylpyridine, ethylene glycol dimethacrylate, [BMIM]BF4, and chain transfer agent (CTA). Some polymerization factors, such as template-monomer molar ratio, the degree of crosslinking, the composition of the porogen, and the content of CTA, on the column efficiency and imprinting effect of the resulting MIP monolith were systematically investigated. Affinity screening of structurally similar compounds with the template can be achieved in 200 s on the MIP monolith due to high column efficiency (up to 12,070 plates/m) and good column permeability. Recognition mechanism of the imprinted monolith was also investigated.


Carprofen Molecularly imprinted polymers (MIP) Monolith Ionic liquids Reversible addition-fragmentation chain transfer 



This work was supported by the Hundreds Talents Program of the Chinese Academy of Sciences and the National Natural Science Foundation of China (grant no. 21075090).


  1. 1.
    Wulff G (1995) Angew Chem Int Ed Engl 34:1812–1832CrossRefGoogle Scholar
  2. 2.
    Haupt K, Linares AV, Bompart M, Bui BT (2012) Top Curr Chem 325:1CrossRefGoogle Scholar
  3. 3.
    Wulff G, Liu J (2012) Acc Chem Res 45:239–247CrossRefGoogle Scholar
  4. 4.
    Haginaka J (2009) J Sep Sci 32:1548–1565CrossRefGoogle Scholar
  5. 5.
    Moreno-Bondi MC, Benito-Peña ME, Urraca JL, Orellana G (2012) Top Curr Chem 325:111–164CrossRefGoogle Scholar
  6. 6.
    Puoci F, Cirillo G, Curcio M, Parisi OI, Iemma F, Picci N (2011) Expert Opin Drug Deliv 8:1379–1393CrossRefGoogle Scholar
  7. 7.
    Yin JF, Yang GL, Chen Y (2005) J Chromatogr A 1090:68–75CrossRefGoogle Scholar
  8. 8.
    Ou J, Kong L, Pan C, Su X, Lei X, Zou H (2006) J Chromatogr A 1117:163–169CrossRefGoogle Scholar
  9. 9.
    Mu LN, Wang XH, Zhao L, Huang YP, Liu ZS (2011) J Chromatogr A 1218:9236–9243CrossRefGoogle Scholar
  10. 10.
    Kim H, Guiochon G (2005) Anal Chem 77:93–102CrossRefGoogle Scholar
  11. 11.
    Liu JX, Deng QL, Yang KG, Zhang LH, Liang Z, Zhang YK (2010) J Sep Sci 33:2757–2770CrossRefGoogle Scholar
  12. 12.
    Liu HN, Zhuang XL, Turson M, Zhang M, Dong XC (2008) J Sep Sci 31:1694–1701CrossRefGoogle Scholar
  13. 13.
    Sun HW, Qiao FX, Liu GY (2006) J Chromatogr A 1134:194–200CrossRefGoogle Scholar
  14. 14.
    Huang YP, Zhang SJ, Wu X, Zhang QW, Liu ZS (2009) Chromatographia 70:691–698CrossRefGoogle Scholar
  15. 15.
    Yan H, Row KH (2008) Biomed Chromatogr 22:487–493CrossRefGoogle Scholar
  16. 16.
    Sun XL, He J, Cai GR, Lin AQ, Zheng WJ, Liu X, Chen LX, He XW, Zhang YK (2010) J Sep Sci 33:3786–3793CrossRefGoogle Scholar
  17. 17.
    Huang YP, Zhang SJ, Zhao L, Zhang QW, Liu ZS (2010) Chromatographia 71:559–569CrossRefGoogle Scholar
  18. 18.
    Otsu T (2000) J Polym Sci Part A: Polym Chem 38:2121–2136CrossRefGoogle Scholar
  19. 19.
    Hawker CJ, Bosman AW, Harth E (2001) Chem Rev 101:3661–3688CrossRefGoogle Scholar
  20. 20.
    Matyjaszewski K, Xia J (2001) Chem Rev 101:2921–2990CrossRefGoogle Scholar
  21. 21.
    Kamigaito M, Ando T, Sawamoto M (2001) Chem Rev 101:3689–3745CrossRefGoogle Scholar
  22. 22.
    Moad G, Rizzardo E, Thang SH (2008) Polymer 49:1079–1131CrossRefGoogle Scholar
  23. 23.
    Debuigne A, Poli R, Jerome C, Jerome R, Detrembleur C (2009) Prog Polym Sci 34:211–239CrossRefGoogle Scholar
  24. 24.
    Semsarilar M, Perrier S (2010) Nat Chem 2:811–820CrossRefGoogle Scholar
  25. 25.
    Susan MA, Kaneko T, Noda A, Watanabe M (2005) J Am Chem Soc 127:4976–4983CrossRefGoogle Scholar
  26. 26.
    Ma HY, Wan XH, Zhou QF (2003) J Polym Sci Pol Chem 41:143–151CrossRefGoogle Scholar
  27. 27.
    Booker K, Bowyer MC, Holdsworth CI, McCluskey A (2006) Chem Commun 11:1730–1732CrossRefGoogle Scholar
  28. 28.
    Lin LQ, Li YC, Fu Q (2006) Polymer 47:3792–3798CrossRefGoogle Scholar
  29. 29.
    Ban L, Zhao L, Deng BL, Huang YP, Liu ZS (2013) Anal Bioanal Chem 405:2245–2253CrossRefGoogle Scholar
  30. 30.
    Li H, Liu Y, Zhang Z, Liao H, Nie L, Yao S (2005) J Chromatogr A 1098:66–74CrossRefGoogle Scholar
  31. 31.
    Sellergren B (1994) Anal Chem 66:1678–1582CrossRefGoogle Scholar
  32. 32.
    Seebach A, Seidel A (2007) Anal Chim Acta 591:57–62CrossRefGoogle Scholar
  33. 33.
    Zhao L, Ban L, Zhang QW, Huang YP, Liu ZS (2011) J Chromatogr A 1218:9071–9079CrossRefGoogle Scholar
  34. 34.
    Sellergren B (1989) Makromol Chem 190:2703–2711CrossRefGoogle Scholar
  35. 35.
    Sellergren B (2001) J Chromatogr A 906:227–252CrossRefGoogle Scholar
  36. 36.
    Chen Y, Kele M, Quinones I, Sellergren B, Guiochon G (2001) J Chromatogr A 927:1–17CrossRefGoogle Scholar
  37. 37.
    Nicholls IA, Ramström O, Mosbach K (1995) J Chromatogr A 691:349–353CrossRefGoogle Scholar
  38. 38.
    Haginaka J, Kagawa C (2004) Anal Bioanal Chem 378:1907–1912CrossRefGoogle Scholar
  39. 39.
    Sun R, Yu H, Luo H, Shen Z (2004) J Chromatogr A 1055:1–9CrossRefGoogle Scholar
  40. 40.
    Piletsky SA, Piletska EV, Karim K, Freebairn KW, Legge CH, Turner APF (2002) Macromolecules 35:7499–7504CrossRefGoogle Scholar
  41. 41.
    Sellergren B, Shea KJ (1995) J Chromatogr A 690:29–39CrossRefGoogle Scholar
  42. 42.
    Holroyd SE, Groves P, Searle MS, Gerhard U, Williams DH (1993) Tetrahedron 49:9171–9182CrossRefGoogle Scholar
  43. 43.
    Searle MS, Williams DH (1992) J Am Chem Soc 114:10690–10697CrossRefGoogle Scholar

Copyright information

© Springer-Verlag Berlin Heidelberg 2013

Authors and Affiliations

  1. 1.Tianjin Key Laboratory on Technologies Enabling Development of Clinical Therapeutics and Diagnostics (Theranostics), School of PharmacyTianjin Medical UniversityTianjinChina

Personalised recommendations