Bulletin of the Korean Chemical Society

Korean Chemical Society (대한화학회)
권호 표지
DOI QR코드

DOI QR Code

Preparation of Cucurbituril Anchored Silica Gel by Cross Polymerization and Its Chromatographic Applications

  • Cheong, Won-Jo (Department of Chemistry and Fine Nano Center, Inha University) ;
  • Go, Joung-Ho (Department of Chemistry and Fine Nano Center, Inha University) ;
  • Baik, Yoon-Suk (Department of Chemistry and Fine Nano Center, Inha University) ;
  • Kim, Sung-Soon (Department of Chemistry and Fine Nano Center, Inha University) ;
  • Nagarajan, Erumaipatty R (National Creative Research Initiative Center for Smart Supramolecules, and Department of Chemistry, Pohang University of Science and Technology (POSTECH)) ;
  • Selvapalam, Narayanan (National Creative Research Initiative Center for Smart Supramolecules, and Department of Chemistry, Pohang University of Science and Technology (POSTECH)) ;
  • Ko, Young-Ho (National Creative Research Initiative Center for Smart Supramolecules, and Department of Chemistry, Pohang University of Science and Technology (POSTECH)) ;
  • Kim, Ki-Moon (National Creative Research Initiative Center for Smart Supramolecules, and Department of Chemistry, Pohang University of Science and Technology (POSTECH))
  • Published : 2008.10.20
Download PDF
⟨ Previous Next ⟩

Abstract

A new chromatographic stationary phase has been prepared by cross polymerization between allylsilica and perallyloxycucurbit[6]uril and characterized by elemental analysis and FT-IR spectroscopy. The double endcapping has been proven to improve the separation efficiency of the cucurbituril-based stationary phase material. The first end-capping was carried out when allylsilica was made. The second end-capping was done as the final step of the whole process, and the use of a mixture of hexamethyldisilazane (HMDS) and trimethylchlorosilane (TMCS) as an end-capping reagent was found better than the use of only HMDS or TMCS. Our stationary phase has shown generally good results in separation of nonpolar and polar analytes. This phase showed even better separation performance than the commercial C18 phase for the case where hostguest chemistry was properly incorporated in solute retention.

Keywords

References

  1. Mock, W. L. Top. Curr. Chem. 1995, 175, 1-24 https://doi.org/10.1007/3-540-58800-0_16
  2. Kim, K. Chem. Soc. Rev. 2002, 31, 96-107 https://doi.org/10.1039/a900939f
  3. Kim, J.; Jung, I.-S.; Kim, S.-Y.; Lee, E.; Kang, J.-K.; Sakamoto, S.; Yamaguchi, K.; Kim, K. J. Am. Chem. Soc. 2000, 122, 540-541 https://doi.org/10.1021/ja993376p
  4. Liu, S.; Ruspic, C.; Mukhopadhyay, P.; Chakrabatri, S.; Zavalij, P. Y.; Isaacs, L. J. Am. Chem. Soc. 2005, 127, 15959-15967 https://doi.org/10.1021/ja055013x
  5. Lee, J. W.; Samal, S.; Selvapalam, N.; Kim, H. J.; Kim, K. Acc. Chem. Res. 2003, 36, 621-630 https://doi.org/10.1021/ar020254k
  6. Lagona, J.; Mukhopadhyay, P.; Chakrabarti, S.; Isaacs, L. Angew. Chem., Int. Ed. 2005, 44, 4844-4870 https://doi.org/10.1002/anie.200460675
  7. Jon, S. Y.; Selvapalam, N.; Oh, D. H.; Kang, J.-K.; Kim, S.-Y.; Jeon, Y. J.; Lee, J. W.; Kim, K. J. Am. Chem. Soc. 2003, 125, 10186-10187 https://doi.org/10.1021/ja036536c
  8. Lee, H.-K.; Park, K. M.; Jeon, Y. J.; Kim, D.; Oh, D. H.; Kim, H. S.; Park, C. K.; Kim, K. J. Am. Chem. Soc. 2005, 127, 5006-5007 https://doi.org/10.1021/ja042172s
  9. Jeon, Y. J.; Kim, H.; Jon, S.; Selvapalam, N.; Oh, D. H.; Seo, I.; Park, C.-S.; Jung, S. R.; Koh, D.-S.; Kim, K. J. Am. Chem. Soc. 2004, 126, 15944-15945 https://doi.org/10.1021/ja044748j
  10. Kim, K.; Balaji, R.; Oh, D. H.; Ko, Y. H.; Jon, S. Y. PCT WO 2004/072151 A1, 2004, KR 0008453, 2003
  11. Kim, K.; Oh, D. H.; Nagarajan, E. R.; Ko, Y. H.; Samal, S. PCT WO 2005/010058 A1, 2005, KR 0051840, 2003
  12. Liu, S. M.; Xu, L.; Wu, C. T.; Feng, Y. Q. Talanta 2004, 64, 929- 934 https://doi.org/10.1016/j.talanta.2004.04.012
  13. Nagarajan, E. R.; Oh, D. H.; Selvapalam, N.; Ko, Y. H.; Park, K. M.; Kim, K. Tetrahedron Lett. 2006, 47, 2073-2075 https://doi.org/10.1016/j.tetlet.2006.01.139
  14. Minguillon, C.; Franco, P.; Oliveros, L.; Lopez, P. J. Chromatogr. A 1996, 728, 407-414 https://doi.org/10.1016/0021-9673(95)01123-4
  15. Minguillon, C.; Franco, P.; Oliveros, L. J. Chromatogr. A 1996, 728, 415-422 https://doi.org/10.1016/0021-9673(95)01203-6
  16. Oliveros, L.; Senso, A.; Minguillon, C. Chirality 1997, 9, 145-149 https://doi.org/10.1002/(SICI)1520-636X(1997)9:2<145::AID-CHIR12>3.0.CO;2-N
  17. Kubota, T.; Yamamoto, C.; Okamoto, Y. Chirality 2003, 15, 77-82 https://doi.org/10.1002/chir.10169
  18. Kubota, T.; Yamamoto, C.; Okamoto, Y. J. Polym. Sci., Part A: Polym. Chem. 2004, 42, 4704-4710 https://doi.org/10.1002/pola.20372
  19. Kubota, T.; Yamamoto, C.; Okamoto, Y. J. Polym. Sci., Part A: Polym. Chem. 2003, 41, 3703-3712 https://doi.org/10.1002/pola.10836
  20. Chen, X.; Qin, F.; Liu, Y.; Huang, X.; Zou, H. J. Chromatogr. A 2004, 1034, 109-116 https://doi.org/10.1016/j.chroma.2004.02.007
  21. Cheong, W. J.; Seo, Y. J.; Park, S. T.; Kang, G. W. Bull. Korean Chem. Soc. 2006, 27, 1059-1062 https://doi.org/10.5012/bkcs.2006.27.7.1059
  22. Seo,Y. J.; Kang, G. W.; Park, S. T.; Moon, M.; Park, J. H.; Cheong, W. J. Bull. Korean Chem. Soc. 2007, 28, 999-1004 https://doi.org/10.5012/bkcs.2007.28.6.999
  23. Cheong, W. J. J. Chromatogr. A 2005, 1066, 231-237 https://doi.org/10.1016/j.chroma.2005.01.011

Cited by

  1. Cucurbituril as a new “host” of organic molecules in inclusion complexes vol.61, pp.7, 2012, https://doi.org/10.1007/s11172-012-0180-9
  2. Facile Syntheses of Cucurbit[6]uril-Anchored Polymers and Their Noncovalent Modification vol.46, pp.4, 2013, https://doi.org/10.1021/ma400017y
  3. Perhydroxylcucurbit[6]uril as a highly selective gas chromatographic stationary phase for analytes of wide-ranging polarity vol.38, pp.5, 2015, https://doi.org/10.1002/jssc.201400876
  4. Cucurbit(6)uril immobilized on silica: A novel high-performance liquid chromatographic stationary phase vol.38, pp.7, 2015, https://doi.org/10.1002/jssc.201401049
  5. Preparation of an allyloxy-cucurbit[6]uril-modified polymer monolithic column for microextraction of estrogens in cosmetics vol.39, pp.12, 2015, https://doi.org/10.1039/C5NJ01802A
  6. Synthesis and separation of cucurbit[n]urils and their derivatives vol.14, pp.19, 2016, https://doi.org/10.1039/C6OB00268D
  7. The fluorescence study of a styryl dye supramolecular complexes with cucurbit[6]uril and cucurbit[7]uril included in gels vol.81, pp.1, 2017, https://doi.org/10.1007/s10971-016-4183-0
  8. Complexation of Aliphatic Ammonium Ions with a Water-Soluble Cucurbit[6]uril Derivative in Pure Water: Isothermal Calorimetric, NMR, and X-ray Crystallographic Study vol.15, pp.25, 2009, https://doi.org/10.1002/chem.200900305
  9. Use of chain transfer agent attached to silica particles in preparation of polystyrene-based stationary phases vol.33, pp.4-5, 2010, https://doi.org/10.1002/jssc.200900578
  10. A New Stationary Phase with Improved Ligand Morphology Prepared by Polymerization of Styrene upon Initiator-attached Lichorsorb Silica Particles vol.30, pp.12, 2008, https://doi.org/10.5012/bkcs.2009.30.12.3127
  11. A New Stationary Phase Prepared by Polymerization of Styrene on Initiator Bonded Porous Silica vol.30, pp.3, 2009, https://doi.org/10.5012/bkcs.2009.30.3.722