Mechanogeneration of Acid from Oxime Sulfonates

Chikkannagari Nagamani; Huiying Liu; Jeffrey S. Moore

doi:10.1021/jacs.6b00097

Mechanogeneration of Acid from Oxime Sulfonates

Chikkannagari Nagamani, Huiying Liu, Jeffrey S. Moore

Research output: Contribution to journal › Article › peer-review

Abstract

The generation of acid under mechanical force is potentially useful for initiating proton-catalyzed changes in polymeric materials. Here we demonstrate that oxime sulfonates - known photoacid generators - are also acid generators when activated mechanically. NMR analysis of products suggests that the ultrasound-induced mechanochemical scission of the oxime sulfonate mechanophore also generates a ketone functional moiety, in addition to acid. Both acid and ketone moieties are useful for developing stress-responsive polymeric materials for autonomous self-healing applications.

Original language	English (US)
Pages (from-to)	2540-2543
Number of pages	4
Journal	Journal of the American Chemical Society
Volume	138
Issue number	8
DOIs	https://doi.org/10.1021/jacs.6b00097
State	Published - Mar 2 2016

ASJC Scopus subject areas

Catalysis
Chemistry(all)
Biochemistry
Colloid and Surface Chemistry

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10.1021/jacs.6b00097

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AB - The generation of acid under mechanical force is potentially useful for initiating proton-catalyzed changes in polymeric materials. Here we demonstrate that oxime sulfonates - known photoacid generators - are also acid generators when activated mechanically. NMR analysis of products suggests that the ultrasound-induced mechanochemical scission of the oxime sulfonate mechanophore also generates a ketone functional moiety, in addition to acid. Both acid and ketone moieties are useful for developing stress-responsive polymeric materials for autonomous self-healing applications.

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Mechanogeneration of Acid from Oxime Sulfonates

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