In various embodiments, the present invention provides an organoboronate nanoparticle. The nanoparticle includes a polymer, which includes a repeating unit that includes at least one organoboronate functional group. Various embodiments provide compositions including the nanoparticles, surface functionalized nanoparticles, nanoparticles including an encapsulant, methods of making the nanoparticles, and methods of using the nanoparticles, such as methods of stimuli-responsive release of encapsulants.