Mechanically axially chiral catenanes and noncanonical mechanically axially chiral rotaxanes

John R.J. Maynard, Peter Gallagher, David Lozano, Patrick Butler, Stephen M. Goldup*

*Corresponding author for this work

Research output: Contribution to journalArticlepeer-review

4 Citations (Scopus)

Abstract

Chirality typically arises in molecules because of a rigidly chiral arrangement of covalently bonded atoms. Less generally appreciated is that chirality can arise when molecules are threaded through one another to create a mechanical bond. For example, when two macrocycles with chemically distinct faces are joined to form a catenane, the structure is chiral, although the rings themselves are not. However, enantiopure mechanically axially chiral catenanes in which the mechanical bond provides the sole source of stereochemistry have not been reported. Here we re-examine the symmetry properties of these molecules and in doing so identify a straightforward route to access them from simple chiral building blocks. Our analysis also led us to identify an analogous but previously unremarked upon rotaxane stereogenic unit, which also yielded to our co-conformational auxiliary approach. With methods to access mechanically axially chiral molecules in hand, their properties and applications can now be explored. [Figure not available: see fulltext.]

Original languageEnglish
Pages (from-to)1038-1044
Number of pages7
JournalNature Chemistry
Volume14
Issue number9
Early online date27 Jun 2022
DOIs
Publication statusPublished - Sept 2022

Bibliographical note

Funding Information:
S.M.G. thanks the ERC (agreement no. 724987) and the Royal Society for a Wolfson Research Fellowship (RSWF\FT\180010). P.B. thanks the University of Southampton for a Presidential Scholarship. P.G. thanks the University of Southampton for funding.

Publisher Copyright:
© 2022, The Author(s), under exclusive licence to Springer Nature Limited.

ASJC Scopus subject areas

  • General Chemistry
  • General Chemical Engineering

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