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The Asymmetry is Derived from Mechanical Interlocking of Achiral Axle and Achiral Ring Components –Syntheses and Properties of Optically Pure [2]Rotaxanes–

Authors :
Keiji Hirose
Masaya Ukimi
Shota Ueda
Chie Onoda
Ryohei Kano
Kyosuke Tsuda
Yuko Hinohara
Yoshito Tobe
Source :
Symmetry, Vol 10, Iss 1, p 20 (2018)
Publication Year :
2018
Publisher :
MDPI AG, 2018.

Abstract

Rotaxanes consisting of achiral axle and achiral ring components can possess supramolecular chirality due to their unique geometrical architectures. To synthesize such chiral rotaxanes, we adapted a prerotaxane method based on aminolysis of a metacyclophane type prerotaxane that had planar chirality, which is composed of an achiral stopper unit and a crown ether type ring component. The prerotaxanes were well resolved using chiral HPLC into a pair of enantiomerically pure prerotaxanes, which were transferred into corresponding chiral rotaxanes, respectively. Obtained chiral rotaxanes were revealed to have considerable enantioselectivity.

Details

Language :
English
ISSN :
20738994
Volume :
10
Issue :
1
Database :
Directory of Open Access Journals
Journal :
Symmetry
Publication Type :
Academic Journal
Accession number :
edsdoj.38ae8d7c5845450c91f9090ac7f67fd7
Document Type :
article
Full Text :
https://doi.org/10.3390/sym10010020