Citation: YIN Chunchun, YANG Tiantian, ZHANG Jinming, ZHANG Jun. Homogeneous synthesis of cellulose phenylcarbamates and evaluation of their enantioseparation capabilities[J]. Chinese Journal of Chromatography, ;2020, 38(4): 476-483. doi: 10.3724/SP.J.1123.2019.08044 shu

Homogeneous synthesis of cellulose phenylcarbamates and evaluation of their enantioseparation capabilities

YIN Chunchun ^1,2 ,
YANG Tiantian ^1,2 ,
ZHANG Jinming ^1,, ,
ZHANG Jun ^1,2,,

1.
CAS Key Laboratory of Engineering Plastics, Institute of Chemistry, Chinese Academy of Sciences, Beijing 100190, China;
2.
University of Chinese Academy of Sciences, Beijing 100049, China

Corresponding author: ZHANG Jinming, ZHANG Jun,
Received Date: 30 August 2019

Fund Project: National Natural Science Foundation of China (Nos. 51425307, 51573196)

Understanding the structure-property relationship of polysaccharide derivatives is of great significance toward the development of novel chiral stationary phases. In this work, we used an ionic liquid, 1-allyl-3-methylimidazolium chloride (AmimCl), as the solvent and introduced phenyl isocyanates with various substituents into cellulose to obtain a series of cellulose phenylcarbamates. The effects of the degree of substitution (DS), as well as the type and position of the substituents, on the chiral separation capability of the cellulose phenylcarbamates were researched in detail. With an increase in the DS, the chiral recognition capability of the cellulose phenylcarbamates improved dramatically for most of the chiral analytes. Fully substituted cellulose phenylcarbamates showed the best enantioseparation capabilities. In addition, the type and position of the substituents on the benzene ring significantly influenced the chiral separation capabilities of the cellulose phenylcarbamates. Cellulose 3-methyl-4-chlorophenylcarbamate, 3,5-dichlorophenylcarbamate, and 2-methyl-5-chlorophenylcarbamate had better chiral recognition capabilities than cellulose 3,5-dimethylphenylcarbamate for some chiral analytes.
- enantioseparation,
- cellulose,
- cellulose phenylcarbamates,
- homogeneous synthesis
1. [1]
2. [2]
3. [3]
4. [4]
5. [5]
6. [6]
7. [7]
8. [8]
9. [9]
10. [10]
11. [11]
12. [12]
13. [13]
14. [14]
15. [15]
16. [16]
17. [17]
18. [18]
19. [19]
20. [20]
21. [21]
22. [22]
23. [23]
24. [24]
25. [25]
26. [26]
27. [27]
28. [28]
29. [29]
30. [30]
31. [31]
32. [32]
33. [33]
34. [34]
35. [35]
36. [36]
37. [37]
38. [38]
39. [39]
40. [40]
41. [41]
42. [42]
43. [43]
44. [44]
45. [45]
46. [46]
47. [47]
48. [48]
49. [49]
50. [50]
51. [51]
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