In biological systems, various stimuli and energies are transduced into membrane potentials via ion transport or binding. The application of this concept to artificial devices may result in biomimetic signal transmitters and energy harvesters. In this study, we investigated the mechanical control of fluoride anion recognition with naphthalenediimide (NDI) monolayers at the air-water interface. Similar to the mechanosensitive ion channels in biological membranes, mechanical stimuli modulated the packing manner of the NDI monolayers, which reproducibly triggered anion binding and concomitant shifts in the membrane potential. Furthermore, mechanical stimuli resulted in anion binding or release, depending on the structure of the alkyl side chains attached to the NDI core, which was explained by the difference in the packing manner of the NDI monolayers. These findings provide insights into the development of novel mechanoelectrical transduction systems that mimic biological processes.