The development of mechanophores that are both highly mechanosensitive and capable of permanently recording mechanical activation events could enhance the study of nanoscale mechanical processes. Recently, our group introduced a diarylethene configurational mechanophore (Figure ) that undergoes a noncovalent-yet-chemical conversion of atropisomer stereochemistry upon mechanical stimulation, transitioning from a parallel form to its antiparallel diastereomers. This stereochemical conversion permanently alters molecular symmetry and turns on chemical reactivity toward a subsequent photochemical electrocyclization reaction. Density-functional theory (DFT) calculations using the constrained geometries simulate external force (CoGEF) method estimated its peak force Fmax at 0.6 nN, significantly lower than is typical of mechanically induced covalent chemical reactions that have been evaluated using CoGEF. This mechanophore also showed faster activation rates in solution-phase ultrasonication experiments compared to a benchmark anthracene-maleimide mechanophore. These initial findings underscore the force-stereochemistry coupling as a promising mechanism for developing high-sensitivity mechanochemical transformations, but a quantitative measure of the transition force required to drive the stereochemical conversion at given rate has yet to be determined.