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Real-time chirality transfer monitoring from statistically random to discrete homochiral nanotubes
Nature Communications ( IF 16.6 ) Pub Date : 2022-11-30 , DOI: 10.1038/s41467-022-34827-z
Shixin Fa 1, 2 , Tan-Hao Shi 1 , Suzu Akama 1 , Keisuke Adachi 1 , Keisuke Wada 1 , Seigo Tanaka 1 , Naoki Oyama 1 , Kenichi Kato 1 , Shunsuke Ohtani 1 , Yuuya Nagata 3 , Shigehisa Akine 4, 5 , Tomoki Ogoshi 1, 4
Affiliation  

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.



中文翻译:

从统计随机到离散纯手性纳米管的实时手性转移监测

实时监测手性转移过程对于更好地了解它们的动力学特性是必要的。在此,我们实时监测从统计随机分布到非对映体纯组装的理想手性转移过程。手性转移基于平面手性柱[5]芳烃的离散三聚体管状组装,通过外消旋边缘分化的柱[5]芳烃五酸之间的离子对协同作用,实现柱[5]芳烃的非对映体纯三聚体的构建在一个环上带有五个苯甲酸,在另一个环上带有五个烷基链,以及一个带有十个胺的光学分解柱 [5] 芳烃十胺。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,最初产生统计上随机的纯手性三聚体和两个异手性三聚体的混合物。在五酸单元翻转后,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非对映纯三聚体。

更新日期:2022-11-30
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