Silica nanoparticles grafted with poly(methyl acrylate) (PMA) chains anchored by a maleimideanthracene cycloadduct were synthesized to demonstrate mechanochemically selective activation of mechanophores at heterogeneous interfaces. By quantifying the anthracene-containing cleaved PMA polymers, which are generated via retro-[4 + 2] cycloaddition reactions, the first-order kinetic coefficient was determined. Activation characteristics of mechanophores anchored to a nanoparticle exhibit behavior similar to mechanophore-linked polymers, e.g., threshold molecular weight and linear increase in rate coefficient with molecular weight above the threshold. This model system is thus valuable as a probe to test stress activation of interfacially bonded mechanophores relevant to the design of fiber-reinforced polymer composites.