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

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

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

摘要: 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.

关键词:

English

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

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
Available Online: 05 December 2015
Fund Project:
This work was financially supported by the National Natural Science Foundation of China(Nos.51103167, 21174151 and 51425307).

Abstract: 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.

Key words:

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

English

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

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通讯作者: 陈斌, bchen63@163.com

中国化学会秘书处

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

English

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

CCS Chemistry：嵌段共聚物自组装成 “三明治”二维有机材料，实现纳米级压力传感功能

CCS Chemistry：颜徐州、鲍哲南： 你的皮肤可能是一片SPMs

CCS Chemistry：工作高效不疲劳，只须让催化剂动起来

CCS Chemistry：静电组装导向聚合- 聚电解质纳米凝胶量化制备新策略

CCS Chemistry：金黄色葡萄球菌醛基脱氢酶是如何识别特异性底物的？

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