Open AccessChemical On/Off Switching of Mechanically Planar Chirality and Chiral Anion Recognition in a [2]Rotaxane Molecular Shuttle
Author(s) -
Stefano Corrà,
Christiaan de Vet,
Jessica Groppi,
Marcello La Rosa,
Serena Silvi,
Massimo Baroncini,
Alberto Credi
Publication year - 2019
Publication title -
journal of the american chemical society
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 7.115
H-Index - 612
eISSN - 1520-5126
pISSN - 0002-7863
DOI - 10.1021/jacs.9b00941
Subject(s) - rotaxane , chemistry , supramolecular chemistry , enantioselective synthesis , chirality (physics) , enantiomer , molecular recognition , planar , planar chirality , molecular switch , population , molecule , stereochemistry , combinatorial chemistry , catalysis , organic chemistry , chiral symmetry breaking , physics , computer graphics (images) , demography , quantum mechanics , sociology , computer science , nambu–jona lasinio model , quark
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.
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