Citation: Zhao Baojing, Li Lan, Wang Yuting, Zhou Zhiming. Preparation of polar group derivative β-cyclodextrin bonded hydride silica chiral stationary phases and their chromatography separation performances[J]. Chinese Chemical Letters, ;2019, 30(3): 643-649. doi: 10.1016/j.cclet.2018.10.013 shu

Preparation of polar group derivative β-cyclodextrin bonded hydride silica chiral stationary phases and their chromatography separation performances

Zhao Baojing ^a ,
Li Lan ^a ,
Wang Yuting ^a ,
Zhou Zhiming ^a,b,*,

a.
School of Chemistry and Chemical Engineering, Beijing Institute of Technology, Beijing 100081, China
b.
State Key Laboratory of Explosion Science & Technology, Beijing Institute of Technology, Beijing 100081, China

zzm@bit.edu.cn

Received Date: 8 August 2018
Revised Date: 11 October 2018
Accepted Date: 11 October 2018
Available Online: 12 March 2018

Figures(4)

Three novel β-cyclodextrin compounds derived with piperidine which is flexible, L-proline containing a chiral center, ionic liquid with 3, 5-diamino-1, 2, 4-triazole as the cation were designed and synthesized as chiral selectors for enantiomer separation, whose name were (mono-6-deoxy-6-(piperidine)-β-cyclodextrin, mono-6-deoxy-6-(L-proline)-β-cyclodextrin, mono-6-deoxy-6-(3, 5-diamino-1, 2, 4-triazole)-β-cyclodextrin, multi-substituted 3, 5-diamino-1, 2, 4-triazole-(p-toluenesulfonic)-β-cyclodextrin), respectively. In addition, to enhance the polarity of chiral stationary phases, hydrosilylation and silylation reactions were implemented to derive ordinary silica, the common used selector carrier, to hydride silica, whose surface is covered with proton. 31 pyrrolidine compounds and some chiral drugs were tested in both polar organic mobile phase mode and normal mobile phase mode. 6-Deoxy-6-Lproline-β-cyclodextrin-CSP showed satisfactory separations in polar organic mobile phase mode and exihibited a strong separation capability in different pH values; multi-substituted 3, 5-diamino-1, 2, 4- triazole-(p-toluenesulfonic)-β-cyclodextrin-CSP can separate pyrrolidine compounds in both mobile phase modes with high resolutions and separation efficiency compared to commercially available CSPs, making it to be the most valuable object to study. The composition of mobile phase, type of stationary phase as well as the peak problem of chromatograms was discussed deeply.
- β-Cyclodextrin,
- Polar group,
- Hydride silica,
- Stationary phase,
- Separation performance
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