Abstract

For efficient enantioseparation, eight organic–inorganic hybrid bead-type chiral packing materials (CPMs) with high organic contents have been developed using cellulose tris(3,5-dimethylphenylcarbamates) bearing small amount of 3-(triethoxysilyl)propyl groups and tetraethyl orthosilicate by a modified Stöber process in the basic condition. The hybrid beads could be formed more efficiently in the basic condition without using surfactant, compared to that in the acidic condition. The preparation conditions, including type and amount of catalyst, amount of water and temperature, significantly affected the organic contents and morphology of the hybrid CPMs. Their chiral recognition properties were then examined by high-performance liquid chromatography. The obtained hybrid CPMs with a higher organic content possessed better enantioseparation ability than the traditional CPMs and previous analogue derived from the acidic condition. For some racemates, the hybrid CPMs exhibited even higher enantioselectivity than the commercial Chiralpak IB N, which is one of the most powerful immobilized-type CPMs and prepared from cellulose tris(3,5-dimethylphenylcarbamate).

Graphic abstract

中文翻译：

---

纤维素苯基氨基甲酸酯衍生的杂化珠型手性包装材料，可有效地进行手性识别

摘要

为了进行有效的对映体分离，已经开发了八种有机含量高的有机-无机杂化珠型手性包装材料（CPM），其使用的是带有少量3-（三乙氧基甲硅烷基）丙基和原硅酸四乙酯的纤维素三（3,5-二甲基苯基氨基甲酸酯）。在基本条件下改进的Stöber工艺。与在酸性条件下相比，可以在碱性条件下不使用表面活性剂更有效地形成杂化珠。制备条件，包括催化剂的类型和用量，水的量和温度，显着影响了混合CPM的有机物含量和形态。然后通过高效液相色谱法检查它们的手性识别特性。所获得的具有较高有机含量的杂化CPMs具有比传统CPMs和先前源自酸性条件的类似物更好的对映体分离能力。对于某些外消旋体，杂化CPM的对映选择性比商业Chiralpak IB N更高，后者是最强大的固定化CPM之一，由纤维素三（3,5-二甲基苯基氨基甲酸酯）制得。

图形摘要