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

Content Provider	Europe PMC
Author	Sasaki, Toshiyuki Hisaki, Ichiro Miyano, Tetsuya Tohnai, Norimitsu Morimoto, Kazuya Sato, Hisako Tsuzuki, Seiji Miyata, Mikiji
Copyright Year	2013
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.
Journal	Nature Communications [Nat Commun]
Volume Number	4
DOI	10.1038/ncomms2756
PubMed Central reference number	PMC3644081
PubMed reference number	23653199
e-ISSN	20411723
Language	English
Publisher	Nature Publishing Group
Publisher Date	2013-01-01
Access Restriction	Open
Content Type	Text
Resource Type	Article
Subject	Chemistry Biochemistry, Genetics and Molecular Biology Physics and Astronomy