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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. |
| Rights: | http://creativecommons.org/licenses/by/3.0/ |
| Type: | article |
| URI: | http://hdl.handle.net/2115/60296 |
| 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)
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Submitter: 上遠野 亮
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