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Covalent adaptable networks with tunable exchange rates based on reversible thiol-yne cross-linking

Niels Van Herck (UGent) , Diederick Maes (UGent) , Kamil Ünal (UGent) , Marc Guerre (UGent) , Johan Winne (UGent) and Filip Du Prez (UGent)
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Abstract
The design of covalent adaptable networks (CANs) relies on the ability to trigger the rearrangement of bonds within a polymer network. Simple activated alkynes are now used as versatile reversible cross-linkers for thiols. The click-like thiol-yne cross-linking reaction readily enables network synthesis from polythiols through a double Michael addition with a reversible and tunable second addition step. The resulting thioacetal cross-linking moieties are robust but dynamic linkages. A series of different activated alkynes have been synthesized and systematically probed for their ability to produce dynamic thioacetal linkages, both in kinetic studies of small molecule models, as well as in stress relaxation and creep measurements on thiol-yne-based CANs. The results are further rationalized by DFT calculations, showing that the bond exchange rates can be significantly influenced by the choice of the activated alkyne cross-linker.
Keywords
MOLECULAR-SIZE DISTRIBUTION, MALLEABLE MATERIALS, CLICK CHEMISTRY, POLYMER, covalent adaptable networks, cross-linking, Michael addition, thioacetals, thiol-yne

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MLA
Van Herck, Niels, et al. “Covalent Adaptable Networks with Tunable Exchange Rates Based on Reversible Thiol-Yne Cross-Linking.” ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, vol. 59, no. 9, 2020, pp. 3609–17.
APA
Van Herck, N., Maes, D., Ünal, K., Guerre, M., Winne, J., & Du Prez, F. (2020). Covalent adaptable networks with tunable exchange rates based on reversible thiol-yne cross-linking. ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 59(9), 3609–3617.
Chicago author-date
Van Herck, Niels, Diederick Maes, Kamil Ünal, Marc Guerre, Johan Winne, and Filip Du Prez. 2020. “Covalent Adaptable Networks with Tunable Exchange Rates Based on Reversible Thiol-Yne Cross-Linking.” ANGEWANDTE CHEMIE-INTERNATIONAL EDITION 59 (9): 3609–17.
Chicago author-date (all authors)
Van Herck, Niels, Diederick Maes, Kamil Ünal, Marc Guerre, Johan Winne, and Filip Du Prez. 2020. “Covalent Adaptable Networks with Tunable Exchange Rates Based on Reversible Thiol-Yne Cross-Linking.” ANGEWANDTE CHEMIE-INTERNATIONAL EDITION 59 (9): 3609–3617.
Vancouver
1.
Van Herck N, Maes D, Ünal K, Guerre M, Winne J, Du Prez F. Covalent adaptable networks with tunable exchange rates based on reversible thiol-yne cross-linking. ANGEWANDTE CHEMIE-INTERNATIONAL EDITION. 2020;59(9):3609–17.
IEEE
[1]
N. Van Herck, D. Maes, K. Ünal, M. Guerre, J. Winne, and F. Du Prez, “Covalent adaptable networks with tunable exchange rates based on reversible thiol-yne cross-linking,” ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, vol. 59, no. 9, pp. 3609–3617, 2020.
@article{8658235,
  abstract     = {The design of covalent adaptable networks (CANs) relies on the ability to trigger the rearrangement of bonds within a polymer network. Simple activated alkynes are now used as versatile reversible cross-linkers for thiols. The click-like thiol-yne cross-linking reaction readily enables network synthesis from polythiols through a double Michael addition with a reversible and tunable second addition step. The resulting thioacetal cross-linking moieties are robust but dynamic linkages. A series of different activated alkynes have been synthesized and systematically probed for their ability to produce dynamic thioacetal linkages, both in kinetic studies of small molecule models, as well as in stress relaxation and creep measurements on thiol-yne-based CANs. The results are further rationalized by DFT calculations, showing that the bond exchange rates can be significantly influenced by the choice of the activated alkyne cross-linker.},
  author       = {Van Herck, Niels and Maes, Diederick and Ünal, Kamil and Guerre, Marc and Winne, Johan and Du Prez, Filip},
  issn         = {1433-7851},
  journal      = {ANGEWANDTE CHEMIE-INTERNATIONAL EDITION},
  keywords     = {MOLECULAR-SIZE DISTRIBUTION,MALLEABLE MATERIALS,CLICK CHEMISTRY,POLYMER,covalent adaptable networks,cross-linking,Michael addition,thioacetals,thiol-yne},
  language     = {eng},
  number       = {9},
  pages        = {3609--3617},
  title        = {Covalent adaptable networks with tunable exchange rates based on reversible thiol-yne cross-linking},
  url          = {http://dx.doi.org/10.1002/anie.201912902},
  volume       = {59},
  year         = {2020},
}

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