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Fluorescent damage reporters that use mechanochemical activation of a covalent bond to elicit an optical signal are emerging tools in material mechanics as a means to access the nanoscale distribution of forces inside materials under stress. A promising class of damage reporters are tetraaryl succinonitriles (TASN), whose mechanical activation results in stable fluorescent radical species. However, in-depth insights into the molecular mechanics of TASN activation are absent, precluding their use as quantitative mechanoprobes. Here we perform single-molecule force spectroscopy experiments to provide these insights. We use a bridged version of the TASN unit, embedded in multi-mechanophore polymer, to enable multiplexed mechanochemical measurements at the single-molecule level. Our experiments reveal that TASN activates at surprisingly low forces and short time scales compared to other covalent mechanophores. These results establish TASN as a promising candidate for reporting the lower end of relevant forces in material mechanics.