Mechanochemical reactions are reactions that are driven by the application of a mechanical force. Often, these reactions yield reaction paths and products that are unexpected because when force is applied, the underlying potential energy surface of the reaction is deformed. The goal of this project is to determine a relationship between the molecular structure of the force-responsive molecule, the mechanophore, and the deformations to the underlying potential energy surface (PES). In order to establish this structure-deformation relationship, a new class of mechanophores, fulgides/fulgamides, will be examined using quantum chemical simulations and Growing String Method. While the mechanochemical reactivity of fulgides and fulgamides had not yet been explored, these photo-active molecules are shown to be promising mechanophores. In order to understand how molecular geometry biases the mechanochemical reaction path, a series of electronic substitutions are made at a key location on the mechanophore. Changing the mechanophore structure from a fulgide to a fulgamide is expected to affect the reaction pathway and PES in different ways.

Functionalization of indolylfulgide/fulgamide mechanophores using quantum chemical simulations

ACS Fall 2021

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