Chemical On/Off Switching of Mechanically Planar Chirality and Chiral Anion Recognition in a [2]Rotaxane Molecular Shuttle

We exploit a reversible acid–base triggered molecular shuttling process to switch an appropriately designed rotaxane between prochiral and mechanically planar chiral forms. The mechanically planar enantiomers and their interconversion, arising from ring shuttling, have been characterized by NMR spec...

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Bibliographic Details
Published inJournal of the American Chemical Society Vol. 141; no. 23; pp. 9129 - 9133
Main Authors Corra, Stefano, de Vet, Christiaan, Groppi, Jessica, La Rosa, Marcello, Silvi, Serena, Baroncini, Massimo, Credi, Alberto
Format Journal Article
LanguageEnglish
Published WASHINGTON American Chemical Society 12.06.2019
Amer Chemical Soc
Subjects
Chemistry
Chemistry, Multidisciplinary
Communication
Physical Sciences
Science & Technology
DRIVEN
MOTORS
ROTAXANES
RESOLUTION
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Summary:We exploit a reversible acid–base triggered molecular shuttling process to switch an appropriately designed rotaxane between prochiral and mechanically planar chiral forms. The mechanically planar enantiomers and their interconversion, arising from ring shuttling, have been characterized by NMR spectroscopy. We also show that the supramolecular interaction of the positively charged rotaxane with optically active anions causes an imbalance in the population of the two enantiomeric coconformations. This result represents an unprecedented example of chiral molecular recognition and can disclose innovative approaches to enantioselective sensing and catalysis.
ISSN:0002-7863
1520-5126
DOI:10.1021/jacs.9b00941