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 co-conformations. This result represents an unprecedented example of chiral molecular recognition and can disclose innovative approaches to enantioselective sensing and catalysis.

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

Corra, Stefano;de Vet, Christiaan;Groppi, Jessica;La Rosa, Marcello;Silvi, Serena;Baroncini, Massimo
;
Credi, Alberto
2019

Abstract

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 co-conformations. This result represents an unprecedented example of chiral molecular recognition and can disclose innovative approaches to enantioselective sensing and catalysis.
Corra, Stefano; de Vet, Christiaan; Groppi, Jessica; La Rosa, Marcello; Silvi, Serena; Baroncini, Massimo; Credi, Alberto
File in questo prodotto:
File Dimensione Formato  
jacs.9b00941.pdf

accesso aperto

Tipo: Versione (PDF) editoriale
Licenza: Licenza per accesso libero gratuito
Dimensione 1.45 MB
Formato Adobe PDF
1.45 MB Adobe PDF Visualizza/Apri

I documenti in IRIS sono protetti da copyright e tutti i diritti sono riservati, salvo diversa indicazione.

Utilizza questo identificativo per citare o creare un link a questo documento: http://hdl.handle.net/11585/688074
Citazioni
  • ???jsp.display-item.citation.pmc??? 19
  • Scopus 60
  • ???jsp.display-item.citation.isi??? 61
social impact