Department of Synthetic Chemistry and Biological Chemistry, Graduate School of Engineering, Kyoto University, Katsura, Nishikyo-ku, Kyoto, 615-8510, Japan.
School of Chemistry and Chemical Engineering, Northwestern Polytechnical University, Xi'an, Shaanxi, 710072, P.R. China.
Nat Commun. 2022 Nov 30;13(1):7378. doi: 10.1038/s41467-022-34827-z.
Real time monitoring of chirality transfer processes is necessary to better understand their kinetic properties. Herein, we monitor an ideal chirality transfer process from a statistically random distribution to a diastereomerically pure assembly in real time. The chirality transfer is based on discrete trimeric tubular assemblies of planar chiral pillar[5]arenes, achieving the construction of diastereomerically pure trimers of pillar[5]arenes through synergistic effect of ion pairing between a racemic rim-differentiated pillar[5]arene pentaacid bearing five benzoic acids on one rim and five alkyl chains on the other, and an optically resolved pillar[5]arene decaamine bearing ten amines. When the decaamine is mixed with the pentaacid, the decaamine is sandwiched by two pentaacids through ten ion pairs, initially producing a statistically random mixture of a homochiral trimer and two heterochiral trimers. The heterochiral trimers gradually dissociate and reassemble into the homochiral trimers after unit flipping of the pentaacid, leading to chirality transfer from the decaamine and producing diastereomerically pure trimers.
实时监测手性转移过程对于更好地了解其动力学性质是必要的。在此，我们实时监测了从统计上随机分布到手性纯组装的理想手性转移过程。手性转移基于平面手性柱状[5]芳烃的离散三聚体管状组装体，通过在一个边缘区分的外消旋的柱状[5]芳烃五酸上带有五个苯甲酸和另一个上带有五个烷基链之间的离子对协同作用，以及通过光学拆分的柱状[5]芳烃十胺，实现了手性纯的柱状[5]芳烃三聚体的构建。当十胺与五酸混合时，十胺通过十个离子对被两个五酸夹在中间，最初产生同手性三聚体和两个异手性三聚体的统计上随机混合物。在五酸的单元翻转后，异手性三聚体逐渐解离并重新组装成同手性三聚体，导致十胺的手性转移并产生手性纯三聚体。
