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

Hanwei Lu, Hebo Ye, Meilan Zhang, Zimu Liu, Hanxun Zou and Lei You ()
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Hanwei Lu: Fujian Institute of Research on the Structure of Matter, 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

Nature Communications, 2023, vol. 14, issue 1, 1-11

Abstract: 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.

Date: 2023
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DOI: 10.1038/s41467-023-39669-x

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