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

Nat Chem. 2014 Sep;6(9):815-21. doi: 10.1038/nchem.2023. Epub 2014 Aug 11.

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.

Publication types

  • Research Support, Non-U.S. Gov't

Associated data

  • PubChem-Substance/186528314
  • PubChem-Substance/186528315
  • PubChem-Substance/186528316
  • PubChem-Substance/186528317
  • PubChem-Substance/186528318