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Issue 4, 2017
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Design of a thermally controlled sequence of triazolinedione-based click and transclick reactions

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Abstract

The reaction of triazolinediones (TADs) and indoles is of particular interest for polymer chemistry applications, as it is a very fast and irreversible additive-free process at room temperature, but can be turned into a dynamic covalent bond forming process at elevated temperatures, giving a reliable bond exchange or ‘transclick’ reaction. In this paper, we report an in-depth study aimed at controlling the TAD–indole reversible click reactions through rational design of modified indole reaction partners. This has resulted in the identification of a novel class of easily accessible indole derivatives that give dynamic TAD-adduct formation at significantly lower temperatures. We further demonstrate that these new substrates can be used to design a directed cascade of click reactions of a functionalized TAD moiety from an initial indole reaction partner to a second indole, and finally to an irreversible reaction partner. This controlled sequence of click and transclick reactions of a single TAD reagent between three different substrates has been demonstrated both on small molecule and macromolecular level, and the factors that control the reversibility profiles have been rationalized and guided by mechanistic considerations supported by theoretical calculations.

Graphical abstract: Design of a thermally controlled sequence of triazolinedione-based click and transclick reactions

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Publication details

The article was received on 10 Jan 2017, accepted on 15 Feb 2017 and first published on 16 Feb 2017


Article type: Edge Article
DOI: 10.1039/C7SC00119C
Citation: Chem. Sci., 2017,8, 3098-3108
  • Open access: Creative Commons BY license
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    Design of a thermally controlled sequence of triazolinedione-based click and transclick reactions

    H. A. Houck, K. De Bruycker, S. Billiet, B. Dhanis, H. Goossens, S. Catak, V. Van Speybroeck, J. M. Winne and F. E. Du Prez, Chem. Sci., 2017, 8, 3098
    DOI: 10.1039/C7SC00119C

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