Switchable enantioseparation based on macromolecular memory of a helical polyacetylene in the solid state
Switchable enantioseparation based on macromolecular memory of a helical polyacetylene in the solid state
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DOI：
10.1038/nchem.1916
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发表时间：
2014-05-01
期刊：
影响因子：
21.8
通讯作者：
Maeda, Katsuhiro
中科院分区：
文献类型：
--
作者：
Shimomura, Kouhei;Ikai, Tomoyuki;Maeda, Katsuhiro
在对映体的色谱分离中，洗脱顺序由混合物组分与手性固定相之间的非对映体相互作用的强度决定。对于分析目的，理想的是先洗脱次要组分，而在制备模式中，期望更快洗脱主要组分。在这里，我们描述了一种由带有2，2 '-双酚衍生侧链的聚乙炔构成的固定相，其中手性可以在使用前在固态下进行切换。聚合物主链的大分子螺旋性和侧链的轴向手性都可以通过与手性醇的相互作用在固态下切换，但重要的是，由于记忆效应，在去除手性醇后保持不变。用所制备的手性固定相对氧化二苯乙烯对映体进行了分离，对映体的洗脱顺序由预分离处理决定。
In the chromatographic separation of enantiomers the order of elution is determined by the strength of diasteromeric interactions between the components of the mixture and a chiral stationary phase. For analytical purposes, it is ideal to have the minor component elute first, whereas in the preparative mode a faster elution of the major component is desirable. Here we describe a stationary phase constructed from a polyacetylene that bears 2,2'-bisphenol-derived side chains in which chirality can be switched in the solid state prior to use. Both the macromolecular helicity of the polymer backbone and the axial chirality of the side chains can be switched in the solid state by interaction with a chiral alcohol, but importantly are maintained after removal of the chiral alcohol because of a memory effect. The chiral stationary phase thus prepared was used to separate the enantiomers of trans-stilbene oxide with the enantiomer elution order determined by the preseparation treatment.