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Enantio-selective transportation of natural small chiral molecules via discrete access-controllable nanotubes based on pillararene

通过基于柱芳烃的离散访问可控纳米管对天然小手性分子进行对映选择性传输

基本信息

批准号：
21K14612
负责人：
FA SHIXIN
金额：
$ 3万
依托单位：
Kyoto University
依托单位国家：
日本
项目类别：
Grant-in-Aid for Early-Career Scientists
财政年份：
2021
资助国家：
日本
起止时间：
2021-04-01 至 2022-03-31
项目状态：
已结题

来源：
https://kaken.nii.ac.jp/en/grant/KAKENHI-PROJECT-21K14612/
关键词：
Pillar[5]arene Chirality Molecular Tube Ionic Interaction Assembly self-assemblies pillararenes artificial channels chirality nanotubes

项目摘要

Selectively transporting hydrophilic natural molecules with chirality through artificial channels is of crucial importance. However, this work is challenging due to the sophisticated molecular design and standing low efficiency. To achieve this goal, the construction of channels with chiral information is the primary task.Taking advantage of the controllable planar-chiral properties of pillar[n]arenes, we started the project with a rim-differentiated pillar[5]arene bearing stereogenic centers on one rim and benzoic acids on the other rim. An diastereomeric excess of the pillar[5]arene was produced through the host-guest interaction with achiral linear guests. The trimeric nanotubes with specific helicity and stability were synthesized through the ionic interaction of the pre-regulated rim-differentiated pillar[5]arene with an amino pillar[5]arene.Another strategy on construction of helical trimeric nanochannels was also practiced. An acidic rim-differentiated pillar[5]arene without stereogenic centers was isolated into two enantiomers firstly, and interacted with the amino pillar[5]arene to produce enantiomeric nanochannels. The constructed channels possessed pure left- and right-handed helicity.These trimeric nanotubes were expected to work as artificial channels enabling enantio-selective transportation of natural small chiral molecules, because previous work has revealed the enantio-selective recognition of pillar[5]arenes.

通过人工通道选择性地转运具有手性的亲水性天然分子是至关重要的。然而，由于复杂的分子设计和长期的低效率，这项工作具有挑战性。为了实现这一目标，构建具有手性信息的通道是首要任务，我们利用柱[n]芳烃的可控平面手性性质，开始了一个在一个边缘上带有立体中心的边缘分化的柱[5]芳烃和在另一个边缘上带有苯甲酸的项目。非对映体过量的柱[5]芳烃通过与非手性线性客体的主客体相互作用产生。通过预调控的边缘分化柱[5]芳烃与氨基柱[5]芳烃的离子相互作用，合成了具有特定螺旋度和稳定性的三聚体纳米管，并提出了构建螺旋状三聚体纳米通道的另一种策略。首先将一种不含立体异构中心的酸性边缘分化柱[5]芳烃分离为两种对映体，并与氨基柱[5]芳烃相互作用形成对映体纳米通道。所构建的通道具有纯的左旋和右旋螺旋性，这些三聚体纳米管有望作为人工通道实现天然手性小分子的对映选择性运输，因为先前的工作已经揭示了柱[5]芳烃的对映选择性识别。