Synthesis and Characterization of Azaborine-Boronic Acid Photoinduced Electron Transfer (PET) Fluorescence Sensor for Monosaccharides

The process of detecting monosaccharides is useful in tracking and getting fast results about the presence of sugar within a system. Over the past decades, boronic acid derivatives such as ortho-aminomethyl phenylboronic acid have been utilized in sugar sensing systems because of the strong binding affinity of boronic acids to saccharides. Here, we designed a fluorescence turn-on probe capable of detecting monosaccharides by linking ortho-aminomethyl phenylboronic acid, as a photoinduced electron transfer (PET) sensor, to an azaborine fluorophore, resulting in the intensification of the azaborine’s emission in the presence of fructose. We will investigate the binding affinity of the novel azaborine-boronic acid PET sensor with multiple monosaccharides as well as tuning the preference of the sensor to a particular monosaccharide. We will also investigate tuning the azaborine fluorophore with the addition of electron –withdrawing and –donating substituents such that the emission wavelength of the fluorophore is near the IR region