Mechanogeneration of Acid from Oxime Sulfonates

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.