A primary aim of covalent mechanochemistry is to develop polymer bound mechanophores that undergo constructive transformations in response to otherwise destructive forces. In our group, we have extensively explored the mechanochemical electrocyclic ring opening of dihalocyclopropanes to 2,3-dihaloalkenes in polybutadiene and polynorbornene based polymers. This transformation occurs readily in solution, via pulsed ultrasound, and in the bulk. Recently, we have leveraged this transformation to demonstrate in situ stress-induced network formation, whereby new bonds are formed in response to otherwise destructive flow forces. Additionally, we have developed a class of non-scissile mechanophores based on a fused bicyclic (bicyclo[3.2.0]heptane and bicyclo[4.2.0]octane) framework, in which the cyclobutane subunit mechanochemically dissociates into tethered alkenes. This versatile platform has enabled us to develop multi-stimuli responsive polymers, expand the toolkit of mechanochemically generated reactive groups, examine stereochemical effects on mechanochemical reactivity, and probe the mechanism of ring opening. Here we will detail our progress to date developing stress-responsive polymers through mechanochemistry.

Stress-responsive polymers via mechanochemistry

247th National Meeting (2014)

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