Discrete chiral organic nanotubes by stacking pillar[5]arenes using covalent linkages
Discrete chiral organic nanotubes by stacking pillar[5]arenes using covalent linkages
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DOI：
10.1016/j.xcrp.2022.101173
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发表时间：
2022-12
影响因子：
8.9
通讯作者：
Tan‐Hao Shi;Shixin Fa;Yuuya Nagata;K. Wada;S. Ohtani;Kenichi Kato;Tomoki Ogoshi
中科院分区：
文献类型：
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作者：
Tan‐Hao Shi;Shixin Fa;Yuuya Nagata;K. Wada;S. Ohtani;Kenichi Kato;Tomoki Ogoshi
有机纳米管由于其独特的一维中空结构，近年来得到了广泛的研究。共价有机纳米管（CON）可以通过经由共价键堆叠结构单元如大环来制备。然而，由于不匹配的共价连接，可控合成具有清晰结构的分立CON，如侧壁和手性，是一个具有挑战性的目标。本工作通过动态共价键偶联两个柱[5]芳烃，成功地制备了具有5重对称性的、分立的、热稳定的CON。分离了三种不同的手性CON，包括由两种对映体（pR，pR和pS，pS）组成的homo-CON和由中间体（pR，pS）组成的hetero-CON。这些CON显示出对客体分子的负变构结合亲和力，这在单个柱[5]芳烃中未观察到。
Owing to their unique one-dimensional hollow structures, organic nanotubes have been widely explored in recent years. Covalent organic nanotubes (CONs) can be prepared by stacking building blocks, such as macrocycles, through covalent linkages. However, because of the mismatched covalent connections, controllable synthesis of the discrete CONs with clear structures, such as sidewall and chirality, is a challenging target. In this work, by coupling two pillar[5]arenes through dynamic covalent bonds, thermodynamically stable discrete CONs with 5-fold symmetry are successfully prepared. Three different chiral CONs are separated, including homo-CONs, consisting of two enantiomers (pR,pR andpS,pS), and hetero-CON, consisting of themesoform (pR,pS). These CONs show negative allosteric binding affinities toward guest molecules, which are not observed in individual pillar[5]arenes.