Journal
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY
Volume 137, Issue 34, Pages 10946-10949Publisher
AMER CHEMICAL SOC
DOI: 10.1021/jacs.5b07345
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Funding
- National Science Foundation [CHE 1300313]
- Arnold and Mabel Beckman Foundation for Beckman Institute Postdoctoral Fellowship
- Division Of Chemistry
- Direct For Mathematical & Physical Scien [1300313] Funding Source: National Science Foundation
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Mechanical activation of a beta-lactam mechanophore using ultrasound induces a formal [2 + 2] cycloelimination reaction producing ketene and imine functional groups-the reverse reaction of the Staudinger cycloaddition. This transformation is predicted by computational modeling and verified by kinetics and UV-vis absorption measurements as well as polymer end-group analysis using H-1 and C-13 NMR spectroscopy. Addition of the beta-lactam motif to the current repertoire of covalent mechanophores coupled with the diverse reactivity of the ketene functional group provides a promising new platform for achieving materials capable of autonomic self-healing behavior in response to external forces.
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