Citation: Wei-wei Chen, Mei-chun Ding, Mei Zhang, Jin-ming Zhang, Xia Gao, Jia-song He, Jun Zhang. Chiral Separation Abilities of Homogeneously Synthesized Cellulose 3,5-Dimethylphenylcarbamates:Influences of Degree of Substitution and Molecular Weight[J]. Chinese Journal of Polymer Science, ;2015, 33(12): 1633-1639. doi: 10.1007/s10118-015-1695-y shu

Chiral Separation Abilities of Homogeneously Synthesized Cellulose 3,5-Dimethylphenylcarbamates:Influences of Degree of Substitution and Molecular Weight

Wei-wei Chen ^1,2,3 ,
Mei-chun Ding ^1,2,3 ,
Mei Zhang ⁴ ,
Jin-ming Zhang ⁵ ,
Xia Gao ⁴ ,
Jia-song He ⁵ ,
Jun Zhang ⁵

1.
1. Beijing National Laboratory for Molecular Sciences, CAS Key Laboratory of Engineering Plastics, Institute of Chemistry, Chinese Academy of Sciences(CAS), Beijing 100190, China
2.
2. University of Chinese Academy of Sciences, Beijing 100049, China
3.
4.
Beijing Center for Physical and Chemical Analysis, Beijing Key Laboratory of Organic Materials Testing Technology &
5.
Beijing National Laboratory for Molecular Sciences, CAS Key Laboratory of Engineering Plastics, Institute of Chemistry, Chinese Academy of Sciences(CAS), Beijing 100190, China

Received Date: 27 April 2015
Revised Date: 14 May 2015

Fund Project: This work was financially supported by the National Natural Science Foundation of China(Nos.51103167, 21174151 and 51425307).

A series of cellulose 3,5-dimethylphenylcarbamates(CDMPCs) with different degrees of substitution(DS) and degrees of polymerization(DP) were homogeneously synthesized in 1-allyl-3-methylimidazolium chloride(AmimCl). Then, the CDMPCs were coated on silica gel and used as chiral stationary phases(CSPs), and their chiral recognition abilities for seven racemates were evaluated by high performance liquid chromatography. The results showed that DS and DP of CDMPCs had a great influence on chiral recognition abilities of the CSPs. The CSPs with the DS1 gives a low chiral recognition to most racemates. On the contrast, the CSPs with the DS2 exhibited high chiral separation abilities. For example, six racemates could be separated on the CSP with CDMPC of DS2(CSP-2). Especially, for the enantioseparation of 1-(2-naphthyl) ethanol and Trger's base, CSP-2 gave the highest separation ability in all of CSPs. On the other hand, when the DP of cellulose was in a range from 39 to 220, the chiral separation abilities of CDMPCs increased as the DP increased. This work demonstrates that the structure of cellulose esters such as DS and DP has important effect on their chiral separation ability, and therefore provides a practical method to design and prepare desirable CSPs for different racemates.
- Cellulose phenylcarbamate,
- Ionic liquid,
- Degree of substitution,
- Degree of polymerization,
- Chiral separation
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