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Highly Selective Molecularly Imprinted Overoxidized Polypyrrole Colloids: One-Step Preparation Technique

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Abstract

A convenient “one step” preparation process of molecularly imprinted overoxidized-polypyrrole (oPPy) colloids by chemical polymerization and their high uptake ability and enantioselectivity are described. Since an oxidizing agent gives a different standard redox potential and rate of polymerization, the property of the resulting oPPy colloid can be controlled by the kind and concentration of the oxidizing agent. At higher concentrations of (NH4)2S2O8 (0.3 M), the overoxidation of PPy colloid automatically occurred. The extraction of l-lactate as a dopant has created a shape-complementary cavity on the surface of the oPPy colloid through overoxidation following polymerization. The oPPy colloid exhibited an excellent selectivity not only on the alanine enantiomer but also on the difference in the side-chain size of amino acids. The uptake of oPPy colloid towards l-alanine over D-alanine was 11.3 µmol/g-colloid against 3.6 µmol/g. The molecularly imprinted cavity can also recognize the existences of the OH or CH3 substituents.

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References

  1. M. J. Whitecombe, M. E. Rodriguez, P. Villar, and E. N. Vulfson, J. Am. Chem. Soc., 1995, 117, 7105.

    Article  Google Scholar 

  2. J. Damen and D. C. Neckers, Tetrahedron Lett., 1980, 21, 1913.

    Article  CAS  Google Scholar 

  3. G. Wulff, J. Vietmeyer, and H.-G. Poll, Makromol. Chem., 1987, 188, 741.

    Article  CAS  Google Scholar 

  4. M. T. Muldoon and L. H. Stanker, Anal. Chem., 1997, 69, 803.

    Article  CAS  Google Scholar 

  5. M. Kemp and K. Mosbach, J. Chromatogr. A, 1995, 691, 314.

    Google Scholar 

  6. B. Sellergren, Anal. Chem., 1994, 66, 1578.

    Article  CAS  Google Scholar 

  7. J. Matsui, Y. Miyoshi, O. D. Dier, and T. Takeuchi, Anal. Chem., 1995, 67, 4404.

    Article  CAS  Google Scholar 

  8. K. Mosbach, K. Haupt, X.-C. Liu, P. A. G. Cormack, and O. Ramstrom, in “Molecular and Ionic Recognition with Imprinted Polymers”, ed. R. A. Bartsch and M. Maeda, 1998, Chap. 3, ACS, Washington, D.C.

  9. E. M. Genies, M. Lapkowski, C. Santier, and E. Viel, Synth. Met., 1987, 18, 631.

    Article  CAS  Google Scholar 

  10. B. Deore, Z. Chen, and T. Nagaoka, Anal. Chem., 2000, 72, 3989.

    Article  CAS  Google Scholar 

  11. H. Shiigi, R. C. Patil, M. Nakayama, T. Tonosaki, and K. Ogura, Recent Res. Devel. Electrochem., 1999, 2, 217.

    CAS  Google Scholar 

  12. H. Shiigi, T. Oho, T. Tonosaki, and K. Ogura, Electrochemistry, 2001, 69, 216.

    Article  Google Scholar 

  13. A. Cadogan, Z. Gao, A. Lewenstam, A. Ivaska, and A. Diamond, Anal. Chem., 1992, 64, 2496.

    Article  CAS  Google Scholar 

  14. A. Hulanicki and A. Michalska, Electroanalysis, 1995, 7, 692.

    Article  CAS  Google Scholar 

  15. M. Farrington and J. M. Slater, Electroanalysis, 1997, 9, 843.

    Article  CAS  Google Scholar 

  16. Z. Gao, M. Zi, and B. Chen, J. Electroanal. Chem., 1994, 373, 141.

    Article  CAS  Google Scholar 

  17. B. Deore, Z. Chen, and T. Nagaoka, Anal. Sci., 1999, 15, 827.

    Article  CAS  Google Scholar 

  18. Z. Chen, A. Okimoto, T. Kiyonaga, and T. Nagaoka, Anal. Chem., 1999, 71, 1834

    Article  CAS  Google Scholar 

  19. Z. Chen, Y. Takei, B. Deore, and T. Nagaoka, Analyst, 2000, 125, 2249.

    Article  CAS  Google Scholar 

  20. D. Y. Kim, J. Y. Lee, D. K. Moon, and C. Y. Kim, Synth. Met., 1995, 69, 471.

    Article  CAS  Google Scholar 

  21. T. Osaka, T. Momma, S. Komada, and H. Kanagawa, J. Electroanal. Chem., 1994, 372, 201.

    Article  CAS  Google Scholar 

  22. L. J. Bellamy, “The Infrared Spectra of Complex Molecules”, 3rd ed., 1975, Chapman and Hall, London.

    Book  Google Scholar 

  23. P. A. Christensen and A. Hamnett, Electrochim. Acta, 1991, 36, 1263.

    Article  CAS  Google Scholar 

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Authors and Affiliations

  1. Faculty of Engineering, Department of Applied Chemistry, Yamaguchi University, Tokiwadai, Ube, 755-8611, Japan

    Hiroshi Shiigi, Masayoshi Kishimoto, Hidetaka Yakabe, Bhavana Deore & Tsutomu Nagaoka

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  1. Hiroshi Shiigi
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  2. Masayoshi Kishimoto
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  3. Hidetaka Yakabe
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  4. Bhavana Deore
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  5. Tsutomu Nagaoka
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Correspondence to Tsutomu Nagaoka.

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Shiigi, H., Kishimoto, M., Yakabe, H. et al. Highly Selective Molecularly Imprinted Overoxidized Polypyrrole Colloids: One-Step Preparation Technique. ANAL. SCI. 18, 41–44 (2002). https://doi.org/10.2116/analsci.18.41

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  • DOI: https://doi.org/10.2116/analsci.18.41

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