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Weak functional group interactions revealed through metal-free active template rotaxane synthesis

Author

Listed:
  • Chong Tian

    (University of Manchester)

  • Stephen D. P. Fielden

    (University of Manchester)

  • George F. S. Whitehead

    (University of Manchester)

  • Iñigo J. Vitorica-Yrezabal

    (University of Manchester)

  • David A. Leigh

    (University of Manchester)

Abstract

Modest functional group interactions can play important roles in molecular recognition, catalysis and self-assembly. However, weakly associated binding motifs are often difficult to characterize. Here, we report on the metal-free active template synthesis of [2]rotaxanes in one step, up to 95% yield and >100:1 rotaxane:axle selectivity, from primary amines, crown ethers and a range of C=O, C=S, S(=O)2 and P=O electrophiles. In addition to being a simple and effective route to a broad range of rotaxanes, the strategy enables 1:1 interactions of crown ethers with various functional groups to be characterized in solution and the solid state, several of which are too weak — or are disfavored compared to other binding modes — to be observed in typical host–guest complexes. The approach may be broadly applicable to the kinetic stabilization and characterization of other weak functional group interactions.

Suggested Citation

  • Chong Tian & Stephen D. P. Fielden & George F. S. Whitehead & Iñigo J. Vitorica-Yrezabal & David A. Leigh, 2020. "Weak functional group interactions revealed through metal-free active template rotaxane synthesis," Nature Communications, Nature, vol. 11(1), pages 1-10, December.
    • Handle: RePEc:nat:natcom:v:11:y:2020:i:1:d:10.1038_s41467-020-14576-7
    DOI: 10.1038/s41467-020-14576-7
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