Linkage control between molecular and supramolecular chirality in 21-helical hydrogen-bonded networks using achiral components

Toshiyuki Sasaki, Ichiro Hisaki, Tetsuya Miyano, Norimitsu Tohnai, Kazuya Morimoto, Hisako Sato, Seiji Tsuzuki and Mikiji Miyata ()
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Toshiyuki Sasaki: Graduate School of Engineering, Osaka University
Ichiro Hisaki: Graduate School of Engineering, Osaka University
Tetsuya Miyano: Graduate School of Engineering, Osaka University
Norimitsu Tohnai: Graduate School of Engineering, Osaka University
Kazuya Morimoto: Graduate School of Science and Engineering, Ehime University
Hisako Sato: Graduate School of Science and Engineering, Ehime University
Seiji Tsuzuki: Research Initiative of Computational Sciences (RICS), Nanosystem Research Institute, National Institute of Advanced Industrial Science and Technology (AIST)
Mikiji Miyata: Graduate School of Engineering, Osaka University

Nature Communications, 2013, vol. 4, issue 1, 1-7

Abstract: Abstract Chiral molecules preferentially form one-handed supramolecular assemblies that reflect the absolute configuration of the molecules. Under specific conditions, however, the opposite-handed supramolecular assemblies are also obtained because of flexibility in the bond length and reversibility of non-covalent interactions. The mechanism of the handedness selectivity or switching phenomenon remains ambiguous, and most phenomena are observed by chance. Here we demonstrate the construction of chiral hydrogen-bonded twofold helical assemblies with controlled handedness in the crystalline state based on crystallographic studies. Detailed investigation of the obtained crystal structures enabled us to clarify the mechanism, and the handedness of the supramolecular chirality was successfully controlled by exploiting achiral factors. This study clearly reveals a connection between molecular chirality and supramolecular chirality in the crystalline state.

Date: 2013
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DOI: 10.1038/ncomms2756

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