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Controllability of dynamic double helices: quantitative analysis of the inversion of a screw-sense preference upon complexation

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Title: Controllability of dynamic double helices: quantitative analysis of the inversion of a screw-sense preference upon complexation
Authors: Katoono, Ryo Browse this author
Kawai, Shunsuke Browse this author
Fujiwara, Kenshu Browse this author
Suzuki, Takanori Browse this author
Issue Date: 10-Dec-2015
Publisher: Royal Society of Chemistry
Journal Title: Chemical science
Volume: 6
Issue: 11
Start Page: 6592
End Page: 6600
Publisher DOI: 10.1039/c5sc02614h
Abstract: We describe a quantitative analysis of the complexation-induced inversion of a screw-sense preference based on a conformationally dynamic double-helix structure in a macrocycle. The macrocycle is composed of two twisting units (terephthalamide), which are spaced by two strands (1,3-bis(phenylethynyl)benzene), and is designed to generate a double-helix structure through twisting about a C-2 axis in a conrotatory manner. The attachment of chiral auxiliaries to the twisting units induces a helical preference for a particular sense of (M)- or (P)-helicity through the intramolecular transmission of chirality to dynamic double helices. The twisting unit can also act as a binding site for capturing a guest molecule, and, in a complexed state, the preferred screw sense of the dynamic double-helix structure is reversed to exhibit the contrary preference. We quantitatively monitored the complexation-induced inversion of the screw-sense preference using H-1 NMR spectroscopy, which enabled us to observe independently two species with (M)- or (P)-helicity in both the absence and presence of a guest molecule. Inversion of the screw-sense preference was induced upon complexation with an achiral guest as well as a chiral guest.
Type: article
Appears in Collections:理学院・理学研究院 (Graduate School of Science / Faculty of Science) > 雑誌発表論文等 (Peer-reviewed Journal Articles, etc)

Submitter: 上遠野 亮

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