Heat‐ and Light‐Responsive Materials Through Pairing Dynamic Thiol–Michael and Coumarin Chemistry

Covalent adaptable networks (CANs) based on the thiol–Michael (TM) linkages can be thermal and pH responsive. Here, a new vinyl‐sulfone‐based thiol–Michael crosslinker is synthesized and incorporated into acrylate‐based CANs to achieve stable materials with dynamic properties. Because of the reversi...

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Bibliographic Details
Published in:Macromolecular rapid communications. 2021-09, Vol.42 (18), p.e2100070-n/a
Main Authors: Chakma, Progyateg, Wanasinghe, Shiwanka V., Morley, Colleen N., Francesconi, Sebastian C., Saito, Kei, Sparks, Jessica L., Konkolewicz, Dominik
Format: Article
Language:English
Subjects:
Cans
Coumarin
covalent adaptable networks
Crosslinking
dynamic bonding
Dynamic stability
Light effects
Linkages
photochemistry
responsive materials
self‐healing materials
thiol–Michael bonding
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Summary:Covalent adaptable networks (CANs) based on the thiol–Michael (TM) linkages can be thermal and pH responsive. Here, a new vinyl‐sulfone‐based thiol–Michael crosslinker is synthesized and incorporated into acrylate‐based CANs to achieve stable materials with dynamic properties. Because of the reversible TM linkages, excellent temperature‐responsive re‐healing and malleability properties are achieved. In addition, for the first time, a photoresponsive coumarin moiety is incorporated with TM‐based CANs to introduce light‐mediated reconfigureability and postpolymerization crosslinking. Overall, these materials can be on demand dynamic in response to heat and light but can retain mechanical stability at ambient condition. This work explores the combination of temperature‐ and light‐responsive chemistries as multiresponsive dynamic materials. A new and simple thermoresponsive linker based on thiol–Michael chemistry involving sulfones is developed. Additionally, pendant coumarin groups are included to enable light responsiveness and bonding. The combination of the two responsive groups enables the materials properties to adapt to either stimulus.
ISSN:1022-1336
1521-3927
DOI:10.1002/marc.202100070