Citation: WANG Litao, DONG Shuqing, ZHANG Zhixin, WANG Yangjun, ZHANG Xiaoli, ZHANG Xia, ZHANG Pengyun, ZHAO Liang. Preparation and enantioseparation performance of β-cyclodextrin-silica hybrid chiral stationary phases[J]. Chinese Journal of Chromatography, ;2016, 34(1): 89-95. doi: 10.3724/SP.J.1123.2015.06036 shu

Preparation and enantioseparation performance of β-cyclodextrin-silica hybrid chiral stationary phases

  • Corresponding author: ZHAO Liang, 
  • Received Date: 20 June 2015

    Fund Project: 国家自然科学基金项目(21405162,21405161) (21405162,21405161)乌鲁木齐市科技局重点项目(Y141320007) (Y141320007)

  • A simple preparation method for β-cyclodextrin-silica hybrid chiral stationary phases was developed. Firstly, the β-cyclodextrin-silica derivative was synthesized by the reaction of 3-aminopropyltriethoxysilane and monochlorotriazinyl β-cyclodextrin under weak base condition. Spherical β-cyclodextrin-silica hybrid materials with β-cyclodextrin in the surface of pores by covalent bonding were prepared using 1,2-bis(triethoxysilyl) ethane and the β-cyclodextrin-silica derivative under the alkaline condition by one-step polymerization reaction. The β-Cyclodextrin-silica hybrid chiral stationary phases could be directly used as high performance liquid chromatographic packings after the template removal. The hybrid materials prepared in this paper possessed regular spherical morphology, good monodispersion, high specific surface area, good mechanical property, high chemical stability and simple preparation process. It combined the chiral recognition performance of β-cyclodextrin and the outstanding performance of organic-inorganic hybrid material. The effect of the composition, ratio and pH of mobile phase on chiral separation was investigated, and the best chiral separation conditions had been optimized. The baseline chiral separations for five chiral compounds were obtained under the optimal conditions. The results of enantioseparation showed that the hybrid chiral stationary phases had favorable chiral recognition ability. Compared with the traditional preparation process of chiral stationary phases, a new thought for new type of chiral stationary phase is provided by the present method in this paper.
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    1. [1]

      [1] Lorenz H, Seidel-Morgenstern A. Angew Chem Int Ed, 2014, 53(5): 1218  

    2. [2]

      [2] Tu H S, Fan J, Zhang W G, et al. Chinese Journal of Chromatography, 2014, 32(5): 452 涂鸿盛, 范军, 章伟光, 等. 色谱, 2014, 32(5): 452

    3. [3]

      [3] Xiao Y, Ng S C, Tan T T Y, et al. J Chromatogr A, 2012, 1269: 52  

    4. [4]

      [4] Ward T J, Ward K D. Anal Chem, 2012, 84(2): 626  

    5. [5]

      [5] Wang Y, Chen H, Xiao Y, et al. Nat Protoc, 2011, 6(7): 935  

    6. [6]

      [6] Lai X, Tang W, Ng S C. J Chromatogr A, 2011, 1218: 5597  

    7. [7]

      [7] Chen X, Zou H, Zhang Q, et al. J Chromatogr Sci, 2002, 40(6): 315  

    8. [8]

      [8] Wang R Q, Ong T T, Ng S C. Tetrahedron Lett, 2012, 53(18): 2312  

    9. [9]

      [9] Nicole L, Laberty-Robert C, Rozes L, et al. Nanoscale, 2014, 6(12): 6267  

    10. [10]

      [10] Sanchez C, Shea K J, Kitagawa S. Chem Soc Rev, 2011, 40(2): 471  

    11. [11]

      [11] Yang F, Mao J, Zhang Y K, et al. Chinese Journal of Chromatography, 2013, 31(6): 531 杨帆, 毛劼, 张玉奎, 等. 色谱, 2013, 31(6): 531  

    12. [12]

      [12] Huq R, Mercier L, Kooyman P J. Chem Mater, 2001, 13(12): 4512  

    13. [13]

      [13] Degoutin S, Bacquet M. J Porous Mater, 2013, 20(4): 663  

    14. [14]

      [14] Zhang Z, Wu M, Wu R A, et al. Anal Chem, 2011, 83(9): 3616  

    15. [15]

      [15] Wang L T, Dong S Q, Han F, et al. J Chromatogr A, 2015, 1383: 70  

    16. [16]

      [16] Xiao X H, Liu X, Jiang S X. Chinese Journal of Chromatography, 2002, 22(1): 61 肖小华, 刘霞, 蒋生祥. 色谱, 2002, 22(1): 61

    17. [17]

      [17] Berthod A, Chang C D, Armstrong D W. Talanta, 1993, 40(9): 1367  

    18. [18]

      [18] Lin C, Liu W, Fan J, et al. J Chromatogr A, 2013, 1283: 68  

    19. [19]

      [19] Zhang Y, Guo Z, Ye J, et al. J Chromatogr A, 2008, 1191: 188  

  • 加载中
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