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Title: Discrete chiral organic nanotubes by stacking pillar[5]arenes using covalent linkages
Authors: Shi, Tan-Hao
Fa, Shixin
Nagata, Yuuya
Wada, Keisuke
Ohtani, Shunsuke
Kato, Kenichi  kyouindb  KAKEN_id  orcid https://orcid.org/0000-0001-5348-5521 (unconfirmed)
Ogoshi, Tomoki  kyouindb  KAKEN_id  orcid https://orcid.org/0000-0002-4464-0347 (unconfirmed)
Author's alias: 和田, 圭介
大谷, 俊介
加藤, 研一
生越, 友樹
Keywords: organic nanotube
pillar[5]arene
chirality
host-guest interaction
dynamic covalent bond
Issue Date: Dec-2022
Publisher: Elsevier BV
Journal title: Cell Reports Physical Science
Volume: 3
Issue: 12
Thesis number: 101173
Abstract: 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 and pS, pS), and hetero-CON, consisting of the meso form (pR, pS). These CONs show negative allosteric binding affinities toward guest molecules, which are not observed in individual pillar[5]arenes.
Rights: © 2022 The Author(s).
This is an open access article under the CC BY-NC-ND license.
URI: http://hdl.handle.net/2433/286871
DOI(Published Version): 10.1016/j.xcrp.2022.101173
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