Mechanochemistry is a branch of chemistry in which the application of mechanical force is used to drive chemical reactions. When a mechanical force is applied to a reaction, the underlying potential energy surface is deformed which can lead to unexpected reaction paths and reaction products. In order to develop an understanding of the relation between molecular structure and potential energy surface deformation, eight students in an upper-level computational chemistry course at Oglethorpe University have analyzed the effect of substitutions on mechanochemical reaction paths. Working in pairs, students wrote proposals that included their proposed series of substitutions which vary steric and/or electronic parameters, and the specific locations at which they plan to make these substitutions on a fulgide or oxanorbornadiene mechanophore framework. Quantum chemical simulations using Growing String Method were used to directly interrogate the force-biased potential energy surface. Mechanophores embedded along a polymer chain increase the functionality of polymers and can allow for the development of longer-lasting materials via provided strain relief. Understanding how to molecular geometry affects mechanical activity will allow for the tuning of the various mechanochemical properties these mechanophores provide. This presentation reports the findings of these studies and provides a glimpse into the previously unpredictable force-biased potential energy surface.

Connecting molecular geometry to force-biased potential energy surfaces in mechanochemical reactions

ACS Fall 2021

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