Triazolinediones enable ultrafast and reversible click chemistry for the design of dynamic polymer systems

S Billiet, K De Bruycker, F Driessen, H Goossens… - Nature …, 2014 - nature.com
Nature chemistry, 2014nature.com
With its focus on synthetic reactions that are highly specific and reliable,'click'chemistry has
become a valuable tool for many scientific research areas and applications. Combining the
modular, covalently bonded nature of click-chemistry linkages with an ability to reverse
these linkages and reuse the constituent reactants in another click reaction, however, is a
feature that is not found in most click reactions. Here we show that triazolinedione
compounds can be used in click-chemistry applications. We present examples of simple and …
Abstract
With its focus on synthetic reactions that are highly specific and reliable, ‘click’ chemistry has become a valuable tool for many scientific research areas and applications. Combining the modular, covalently bonded nature of click-chemistry linkages with an ability to reverse these linkages and reuse the constituent reactants in another click reaction, however, is a feature that is not found in most click reactions. Here we show that triazolinedione compounds can be used in click-chemistry applications. We present examples of simple and ultrafast macromolecular functionalization, polymer–polymer linking and polymer crosslinking under ambient conditions without the need for a catalyst. Moreover, when triazolinediones are combined with indole reaction partners, the reverse reaction can also be induced at elevated temperatures, and the triazolinedione reacted with a different reaction partner, reversibly or irreversibly dependent on its exact nature. We have used this ‘transclick’ reaction to introduce thermoreversible links into polyurethane and polymethacrylate materials, which allows dynamic polymer-network healing, reshaping and recycling.
nature.com
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