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

Hannes Houck (UGent) , Kevin De Bruycker (UGent) , Stijn Billiet (UGent) , Bastiaan Dhanis (UGent) , Hannelore Goossens (UGent) , Saron Catak (UGent) , Veronique Van Speybroeck (UGent) , Johan Winne (UGent) and Filip Du Prez (UGent)
(2017) CHEMICAL SCIENCE. 8(4). p.3098-3108
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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.
Keywords
DIELS-ALDER REACTION, CHEMISTRY, POLYMER, SERVICE, ULTRAFAST, SYSTEMS, ENE

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Chicago
Houck, Hannes, Kevin De Bruycker, Stijn Billiet, Bastiaan Dhanis, Hannelore Goossens, Saron Catak, Veronique Van Speybroeck, Johan Winne, and Filip Du Prez. 2017. “Design of a Thermally Controlled Sequence of Triazolinedione-based Click and Transclick Reactions.” Chemical Science 8 (4): 3098–3108.
APA
Houck, H., De Bruycker, K., Billiet, S., Dhanis, B., Goossens, H., Catak, S., Van Speybroeck, V., et al. (2017). Design of a thermally controlled sequence of triazolinedione-based click and transclick reactions. CHEMICAL SCIENCE, 8(4), 3098–3108.
Vancouver
1.
Houck H, De Bruycker K, Billiet S, Dhanis B, Goossens H, Catak S, et al. Design of a thermally controlled sequence of triazolinedione-based click and transclick reactions. CHEMICAL SCIENCE. 2017;8(4):3098–108.
MLA
Houck, Hannes, Kevin De Bruycker, Stijn Billiet, et al. “Design of a Thermally Controlled Sequence of Triazolinedione-based Click and Transclick Reactions.” CHEMICAL SCIENCE 8.4 (2017): 3098–3108. Print.
@article{8518837,
  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.},
  author       = {Houck, Hannes and De Bruycker, Kevin and Billiet, Stijn and Dhanis, Bastiaan and Goossens, Hannelore and Catak, Saron and Van Speybroeck, Veronique and Winne, Johan and Du Prez, Filip},
  issn         = {2041-6520},
  journal      = {CHEMICAL SCIENCE},
  keyword      = {DIELS-ALDER REACTION,CHEMISTRY,POLYMER,SERVICE,ULTRAFAST,SYSTEMS,ENE},
  language     = {eng},
  number       = {4},
  pages        = {3098--3108},
  title        = {Design of a thermally controlled sequence of triazolinedione-based click and transclick reactions},
  url          = {http://dx.doi.org/10.1039/c7sc00119c},
  volume       = {8},
  year         = {2017},
}

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