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

Chong Tian, Stephen D. P. Fielden, George F. S. Whitehead, Iñigo J. Vitorica-Yrezabal and David A. Leigh ()
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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

Nature Communications, 2020, vol. 11, issue 1, 1-10

Abstract: 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.

Date: 2020
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DOI: 10.1038/s41467-020-14576-7

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