In the course of our investigations on new monoboronic acid saccharide sensors with C0 spacers, a series of probes 1-6 based on 1,8-naphthalenedicarboximide were synthesized. These probes display features typical of PET monoboronic acid sensors and give good selectivity to fructose. Within the series, probe 2 exhibits a novel dual emission and remarkable sensitivity for glucose relative to fructose and galactose through subtle changes in pH. To further investigate the causes of this remarkable 2-color emission, A 3 x 14 matrix of substituted N-aryl-1,8-naphthalimides was synthesized for the evaluation and discovery of dual fluorescence. The matrix library was designed to investigate the effects of heterocycles, particularly pi-escessive and pi-deficient systems. Of the 42 compounds surveyed, five displayed well-resolved two-color emission in solvents as nonpolar as hexane. Finally, a new applications of these fluorescent platforms are envisioned in the form of fluorescent small molecule proteomimetics.