Please use this identifier to cite or link to this item: https://doi.org/10.1038/s41467-020-14576-7
Title: Weak functional group interactions revealed through metal-free active template rotaxane synthesis
Authors: Tian, Chong 
Fielden, Stephen DP
Whitehead, George FS
Vitorica-Yrezabal, Inigo J
Leigh, David A
Keywords: Science & Technology
Multidisciplinary Sciences
Science & Technology - Other Topics
INTERLOCKED MOLECULES
CROWN-ETHER
AMINOLYSIS
COMPLEXES
18-CROWN-6
MECHANISM
CATALYSIS
KINETICS
CATENANES
TRANSPORT
Issue Date: 6-Feb-2020
Publisher: NATURE PUBLISHING GROUP
Citation: Tian, Chong, Fielden, Stephen DP, Whitehead, George FS, Vitorica-Yrezabal, Inigo J, Leigh, David A (2020-02-06). Weak functional group interactions revealed through metal-free active template rotaxane synthesis. NATURE COMMUNICATIONS 11 (1). ScholarBank@NUS Repository. https://doi.org/10.1038/s41467-020-14576-7
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.
Source Title: NATURE COMMUNICATIONS
URI: https://scholarbank.nus.edu.sg/handle/10635/241763
ISSN: 2041-1723
DOI: 10.1038/s41467-020-14576-7
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