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Expanding and Improving the Mechanophore Toolkit for Mechanically Active Polymers
- Abstract:
This report describes work towards the development of novel mechano-responsive polymers that are potentially capable of self-strengthening and/or facile post-synthetic polymer modification. The strategy centers on the development of mechanophores: functional groups that undergo chemical transformations triggered by coupled mechanical forces. We propose first that aziridines and epoxides are potential mechanophores that might be activated to yield valuable azomethine and carbonyl ylide intermediates, respectively. Second, we propose to demonstrate a new “lever effect” strategy for enhancing the extent of mechanochemical activation in previously reported dihalocyclopropane mechanophores. Mechanophore co-polymers were synthesized via the aziridination or epoxidation of polybutadiene, and mechanical activity was subsequently investigated through the elongational shear forces associated with sonication. No evidence of mechanically induced ylide formation was observed (a result possibly attributed to the intrinsic high activation energy of the desired reactions). Ongoing work targets new polymer scaffolds in which ylide formation is stabilized both electronically and mechanically.
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