期刊
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
卷 59, 期 9, 页码 3609-3617出版社
WILEY-V C H VERLAG GMBH
DOI: 10.1002/anie.201912902
关键词
covalent adaptable networks; cross-linking; Michael addition; thioacetals; thiol-yne
资金
- Research Foundation-Flanders (Fonds Wetenschappelijk Onderzoek-Vlaanderen)
- UGent
- Ghent University
- FWO
- Flemish Government-department EWI
- UGent funding (BOF-GOA)
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.
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