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Macrocycle Size Matters: “Small” Functionalized Rotaxanes in Excellent Yield Using the CuAAC Active Template Approach

Authors

  • Hicham Lahlali,

    1. School of Biological and Chemical Sciences, Queen Mary University of London, Joseph Priestley Building, Mile End Road, London, E1 4NS (UK)
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  • Kajally Jobe,

    1. School of Biological and Chemical Sciences, Queen Mary University of London, Joseph Priestley Building, Mile End Road, London, E1 4NS (UK)
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  • Michael Watkinson,

    1. School of Biological and Chemical Sciences, Queen Mary University of London, Joseph Priestley Building, Mile End Road, London, E1 4NS (UK)
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  • Dr. Stephen M. Goldup

    Corresponding author
    1. School of Biological and Chemical Sciences, Queen Mary University of London, Joseph Priestley Building, Mile End Road, London, E1 4NS (UK)
    • School of Biological and Chemical Sciences, Queen Mary University of London, Joseph Priestley Building, Mile End Road, London, E1 4NS (UK)
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  • We thank Majid Motevalli for assistance with the X-ray crystal structure of rotaxane 6. This work was supported by the Leverhulme Trust (Early Career Fellowship to S.M.G.), the Royal Society, and Q.M.U.L.. S.M.G. is a Royal Society Research Fellow. CuAAC=copper-catalyzed azide–alkyne cycloaddition.

Abstract

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By shrinking the macrocycle in the CuAAC active template reaction not only is it demonstrated to be possible to use smaller macrocycles, but, surprisingly, that smaller macrocycles lead to higher yields of rotaxane product (see scheme). The synthesis of “small” functionalized [2]rotaxanes showcases this as a method for the production of materials with potential applications in molecular electronics, drug delivery, sensing, and enantioselective catalysis.

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