Real-time chirality transfer monitoring from statistically random to discrete homochiral nanotubes

Shixin Fa, Tan-hao Shi, Suzu Akama, Keisuke Adachi, Keisuke Wada, Seigo Tanaka, Naoki Oyama, Kenichi Kato, Shunsuke Ohtani, Yuuya Nagata, Shigehisa Akine and Tomoki Ogoshi ()
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Shixin Fa: Kyoto University
Tan-hao Shi: Kyoto University
Suzu Akama: Kyoto University
Keisuke Adachi: Kyoto University
Keisuke Wada: Kyoto University
Seigo Tanaka: Kyoto University
Naoki Oyama: Kyoto University
Kenichi Kato: Kyoto University
Shunsuke Ohtani: Kyoto University
Yuuya Nagata: Hokkaido University
Shigehisa Akine: Kanazawa University
Tomoki Ogoshi: Kyoto University

Nature Communications, 2022, vol. 13, issue 1, 1-10

Abstract: Abstract 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.

Date: 2022
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DOI: 10.1038/s41467-022-34827-z

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