Bulletin of the Korean Chemical Society

Korean Chemical Society (대한화학회)
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Synthesis, Self-assembly, and Catalytic Activity of 1H-Imidazole Amphiphiles

  • Park, Jun-Ha (Department of Materials Science and Engineering, College of Engineering, Seoul National University) ;
  • Kim, Min-Soo (Department of Materials Science and Engineering, College of Engineering, Seoul National University) ;
  • Seo, Sang-Hyuk (Department of Materials Science and Engineering, College of Engineering, Seoul National University) ;
  • Chang, Ji-Young (Department of Materials Science and Engineering, College of Engineering, Seoul National University)
  • Received : 2011.04.15
  • Accepted : 2011.05.10
  • Published : 2011.07.20
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Abstract

We prepared polycatenar 1H-imidazole amphiphiles having a structure in which a 1H-imidazole head was connected through a benzene ring to a pheny group having two or three oligo(ethylene glycol) chains and studied their supramolecular assembly by fluorescence spectroscopy, transmission electron microscopy (TEM) and atomic force microscopy (AFM). When the aqueous solutions of the amphiphiles ($5{\times}10^{-5}M{\sim}10^{-3}M$) were deposited onto a carbon-coated copper grid and dried, twisted structures with diameters of ~200-300 nm were imaged by TEM and AFM. We presume that the structures comprised a chain of the amphiphile dimers formed via successive hydrogen bonding between the 1H of the imidazole group and 3N of the neighboring one. In a solution of pH 4, entangled fibers with diameters of several nanometers were observed by TEM. In a pH 10 solution, film-like aggregates formed exclusively. The 1H-imidazole amphiphiles hydrolyzed tetraethoxysilane to induce gelation to form fibrous and spherical silica structures at neutral pH in aqueous solutions. No silica was formed when imidazole was used instead of the amphiphiles, suggesting that the selfassembled aggregates of the amphiphiles were responsible for the gelation.

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References

  1. Percec, V.; Dulcey, A. E.; Balagurusamy, V. S. K.; Miura, Y.; Smidrkal, J.; Peterca, M.; Nummelin, S.; Edlund, U.; Hudson, S. D.; Heiney, P. A.; Duan, H.; Magonov, S. N.; Vinogradov, S. A. Nature 2004, 430, 764. https://doi.org/10.1038/nature02770
  2. Roy, S.; Dey, J. Langmuir 2005, 21, 10362. https://doi.org/10.1021/la051206m
  3. Breslow, R. Acc. Chem. Res. 1991, 24, 317. https://doi.org/10.1021/ar00011a001
  4. Chaudhary, M.; Pareek, D.; Pareek, P. K.; Kant, R.; Ojha, K. G.; Pareek, A. Bull. Korean Chem. Soc. 2011, 32, 131. https://doi.org/10.5012/bkcs.2011.32.1.131
  5. Lee, S.; Lee, S. J.; Ahn, A.; Kim, Y.; Min, A.; Choi, M. Y.; Miller, R. E. Bull. Korean Chem. Soc. 2011, 32, 885. https://doi.org/10.5012/bkcs.2011.32.3.885
  6. Seo, S. H.; Tew, G. N.; Chang, J. Y. Soft Matter 2006, 2, 886. https://doi.org/10.1039/b606870g
  7. Seo, S. H.; Chang, J. Y. Chem. Mater. 2005, 17, 3249. https://doi.org/10.1021/cm048025a
  8. Seo, S. H.; Park, J. H.; Tew, G. N.; Chang, J. Y. Tetrahedron Lett. 2007, 48, 6839. https://doi.org/10.1016/j.tetlet.2007.07.187
  9. Hafkamp, R. J. H.; Feiters, M. C.; Nolte, R. J. M. Angew. Chem. Int. Ed. 1994, 33, 986. https://doi.org/10.1002/anie.199409861
  10. Sommerdijk, N. A. J. M.; Lembermon, M. H. L.; Feiters, M. C.; Nolte, R. J. M.; Zwaneburg, B. Chem. Commun. 1997, 455.
  11. Sommerdijk, N. A. J. M.; Lembermon, M. H. L.; Feiters, M. C.; Nolte, R. J. M.; Zwaneburg, B. Chem. Commun. 1997, 1423.
  12. Flakus, H. R.; Bryk, A. Journal of Molecular Structures 1995, 372, 215. https://doi.org/10.1016/0022-2860(95)08990-X
  13. Song, X.-J.; McDermott, A. E. Magn. Reson. Chem. 2001, 39, S37. https://doi.org/10.1002/mrc.957
  14. Katrusiak, A. Journal of Molecular Structures 1999, 474, 125. https://doi.org/10.1016/S0022-2860(98)00566-3
  15. Brzezinski, B. Zundel, G. Journal of Molecular Structures 1998, 446, 199. https://doi.org/10.1016/S0022-2860(98)00281-6
  16. Massiah, M. A.; Viragh, C.; Reddy, P. M.; Kovach, I. M.; Johnson, J.; Rosenberry, T. L.; Mildvan, A. S. Biochemistry 2001, 40, 5682. https://doi.org/10.1021/bi010243j
  17. Cha, J. N.; Shimizu, K.; Zhou, Y.; Christiansen, S. C.; Chmelka, B. F.; Stucky, G. D.; Morse, D. E. Proc. Natl. Acad. Sci. 1999, 96, 361. https://doi.org/10.1073/pnas.96.2.361
  18. Voronkov, M. G.; Mileshkevich, V. P.; Yuzhelevski, Y. A. The Siloxane Bond; Consultants Bureau: New York, 1978.
  19. Jia, M.; Seifert, A.; Thiel, W. R. Chem. Mater. 2003, 15, 2174. https://doi.org/10.1021/cm021380l
  20. Lauter, U.; Meyer, W. H.; Wegner, G. Macromolecules 1997, 30, 2092. https://doi.org/10.1021/ma961098y

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