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

Chong TianStephen D P FieldenGeorge F S WhiteheadIñigo J Vitorica-YrezabalDavid A Leigh
Published in: Nature communications (2020)
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.
Keyphrases
  • solid state
  • high resolution
  • binding protein