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Photoswitchable dynamic conjugate addition-elimination reactions as a tool for light-mediated click and clip chemistry

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  • Hanwei Lu

    (Fujian Institute of Research on the Structure of Matter, Chinese Academy of Sciences
    University of Chinese Academy of Sciences)

  • Hebo Ye

    (Fujian Institute of Research on the Structure of Matter, Chinese Academy of Sciences)

  • Meilan Zhang

    (Fujian Institute of Research on the Structure of Matter, Chinese Academy of Sciences)

  • Zimu Liu

    (Fujian Institute of Research on the Structure of Matter, Chinese Academy of Sciences)

  • Hanxun Zou

    (Fujian Institute of Research on the Structure of Matter, Chinese Academy of Sciences)

  • Lei You

    (Fujian Institute of Research on the Structure of Matter, Chinese Academy of Sciences
    University of Chinese Academy of Sciences
    Fujian Science & Technology Innovation Laboratory for Optoelectronic Information of China)

Abstract

Phototriggered click and clip reactions can endow chemical processes with high spatiotemporal resolution and sustainability, but are challenging with a limited scope. Herein we report photoswitchable reversible covalent conjugate addition-elimination reactions toward light-addressed modular covalent connection and disconnection. By coupling between photochromic dithienylethene switch and Michael acceptors, the reactivity of Michael reactions was tuned through closed-ring and open-ring forms of dithienylethene, allowing switching on and off dynamic exchange of a wide scope of thiol and amine nucleophiles. The breaking of antiaromaticity in transition states and enol intermediates of addition-elimination reactions provides the driving force for photoinduced change in kinetic barriers. To showcase the versatile application, light-mediated modification of solid surfaces, regulation of amphiphilic assemblies, and creation/degradation of covalent polymers on demand were achieved. The manipulation of dynamic click/clip reactions with light should set the stage for future endeavors, including responsive assemblies, biological delivery, and intelligent materials.

Suggested Citation

  • Hanwei Lu & Hebo Ye & Meilan Zhang & Zimu Liu & Hanxun Zou & Lei You, 2023. "Photoswitchable dynamic conjugate addition-elimination reactions as a tool for light-mediated click and clip chemistry," Nature Communications, Nature, vol. 14(1), pages 1-11, December.
    • Handle: RePEc:nat:natcom:v:14:y:2023:i:1:d:10.1038_s41467-023-39669-x
    DOI: 10.1038/s41467-023-39669-x
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    1. Anne Fuhrmann & Robert Göstl & Robert Wendt & Julia Kötteritzsch & Martin D. Hager & Ulrich S. Schubert & Kerstin Brademann-Jock & Andreas F. Thünemann & Ulrich Nöchel & Marc Behl & Stefan Hecht, 2016. "Conditional repair by locally switching the thermal healing capability of dynamic covalent polymers with light," Nature Communications, Nature, vol. 7(1), pages 1-7, December.
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