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Effect of supermolecular structure of cellulosic materials on chiral discrimination

纤维素材料超分子结构对手性辨别的影响

基本信息

批准号：
14560130
负责人：
KASUYA Natsuki
金额：
$ 1.92万
依托单位：
National University Corporation Tokyo University of Agriculture and Technology
依托单位国家：
日本
项目类别：
Grant-in-Aid for Scientific Research (C)
财政年份：
2002
资助国家：
日本
起止时间：
2002 至 2003
项目状态：
已结题

来源：
https://kaken.nii.ac.jp/en/grant/KAKENHI-PROJECT-14560130/
关键词：
cellulose chiral HPLC structure キラル分離液晶性

项目摘要

Studies on the hysteretic effect of coating were investigated using cellulose triphenylcarbamate as a chiral separating phase of chiral support for HPLC. According to the previous paper by Shibata et al., the different kinds of coating solvent resulted in the different elution order of enantiomers with the use of cellulose acetate as a chiral separating phase. For further investigations of the relationship between coating solvents and chiral selecting polymers, we have selected the combination of cellulose trhiphenylcarbamate and its organic solvents reported to from alyotropic liquid crystal.Firstly, we have synthesized cellulose triphenylcarbamate according to the method of Schroeder and his coworker, dissolved it in the organic solvent such as methylpropylketone (MPK), diglyme, and e.t.c., and checked if the system forms a cholesteric liquid crystal. Because the resultant solution of cellulose derivative seemed to show a poor cholesteric nature, we repeated the synthetic reaction fo … More r the already derivatized cellulosic material and obtained typical cholesteric liquid crystals. Degree of polymerization could have changed during the repeated reaction. Cholesteric nature was recognized by observations using polarizing microscope, and the measurements of spectrum of UV, ORD.Then, the dilute solution (10wt%) of cellulose triphenylcarbamate either in MPK or in diglyme was poured onto porous silica gel (mean particle size 7 μm and mean pore diameters 100 nm), and the solvent was removed. The evaporation of the solvent was performed ether in a draft chamber for the MPK or in a vacuum oven at 30℃ for the diglyme, and the duration required for the evaporation was more than 1weeks for both solvents. After obtaining the chiral support, we prepared the laboratory-made columns for optical resolution by packing it into stain-less steel columns, and estimated their chiral recognizing ability.The chiral resolving column prepared by using MPK as a coating solvent showed a prominent resolving power and comparable to the commercial column in terms of resolution factors (α) and theoretical plate numbers, although the other column showed poor results due to the insufficient evaporation of the coating solvent. The order of elution for enantiomer was found to be the same among the tested colums. Less

以纤维素三苯基氨基甲酸酯为手性分离相，研究了涂层的滞后效应。根据柴田等人先前的论文，以醋酸纤维素为手性分离相，不同的包被溶剂导致对映体的洗脱顺序不同。为了进一步研究涂层溶剂与手性选择性聚合物之间的关系，我们选择了纤维素三苯基氨基甲酸酯及其有机溶剂的组合作为不溶致液晶，首先按照Schroeder等人的方法合成了纤维素三苯基氨基甲酸酯，将其溶于甲基丙基酮（MPK）、二甘醇二甲醚等有机溶剂中，并检查系统是否形成双折射液晶。由于所得纤维素衍生物的溶液似乎显示出差的溶解性，我们重复了合成反应， ...更多信息 R已经衍生化的纤维素材料，并获得典型的双折射液晶。聚合度在重复反应过程中可能发生变化。然后将纤维素三苯基氨基甲酸酯在MPK或二甘醇二甲醚中的稀溶液（10wt%）倒在多孔硅胶（平均粒径7 μm，平均孔径100 nm）上，除去溶剂。对于MPK，在通风室中进行溶剂蒸发，对于二甘醇二甲醚，在30℃的真空烘箱中进行溶剂蒸发，两种溶剂的蒸发时间均超过1周。得到手性载体后，将其装入不锈钢柱中，制备了实验室自制的光学拆分柱，并对其手性识别能力进行了评价，结果表明，以MPK为涂层溶剂制备的手性拆分柱在分离因子（α）和理论塔板数方面与市售色谱柱相当，尽管另一个柱由于涂布溶剂的蒸发不充分而显示出差的结果。对映异构体的洗脱顺序在检测色谱柱中相同。少