Center for Molecular Modeling - F. Driessen

Triazolinediones enabling ultrafast and reversible click chemistry for facile design of healable and reshapable polymers

michel — Fri, 27 Jun 2014 13:56:44 +0000

S. Billiet, K. De Bruycker, F. Driessen, H. Goossens, V. Van Speybroeck, J. Winne, F. Du Prez

Nature Chemistry

6 (9), 815-821

2014

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.

DOI

http://dx.doi.org/10.1038/nchem.2023

Private attachment

14_NatureChemistry_6(9)815_Billiet.pdf

Click/transclick reactions in combination with CRP: 'TAD's the spirit'

samuel — Thu, 06 Feb 2020 09:46:32 +0000

F. Du Prez, S. Billiet, K. De Bruycker, F. Driessen, H. Goossens, V. Van Speybroeck, J. Winne

ISBN/ISSN:

Talk

Conference / event / venue

248th National Meeting of the American-Chemical-Society (ACS 2014 )

San Francisco, CA

Sunday, 10 August, 2014 to Thursday, 14 August, 2014

Triazolinediones enabling click and transclick reactions

wim — Mon, 13 Oct 2014 07:13:00 +0000

H. Goossens, S. Billiet, K. De Bruycker, F. Driessen, J.M. Winne, F. Du Prez, V. Van Speybroeck

ISBN/ISSN:

Talk

Conference / event / venue

WATOC 2014

Santiago de Chile, Chile

Sunday, 5 October, 2014 to Friday, 10 October, 2014

Abstract (private)

Abstract_WATOC_2014_HG.pdf

Conference reference

WATOC 2014

Triazolinediones for Irreversible and Reversible Linking in polymers: Theoretical Rationalization

wim — Thu, 26 Sep 2013 13:14:44 +0000

H. Goossens, S. Billiet, K. De Bruycker, F. Driessen, J.M. Winne, F. Du Prez, V. Van Speybroeck

ISBN/ISSN: -

Poster

Conference / event / venue

Annual IAP Meeting

Ghent, Belgium

Wednesday, 18 September, 2013

Conference reference

Annual IAP Meeting (2013)