Paper- Restricted to Campus Access
Ryan R. Walvoord
Fluorophores, such as fluorescein, are economical and can be applied to many fields such as biochemical research, to label and track cells or to diagnose infections, environmental sciences, to track water movements in groundwater as well as plants, and aid in oil leaks. The conversion of hydroxycoumarins to aminocoumarins through Smiles rearrangement gives a new method to build aminocoumarins, which have more desirable optical properties such as brightness, larger working pH range, and longer wavelength. Research regarding the conversion of hydroxyfluorophores to aminofluorophores is limited to complex, multi-step synthesistypically utilizing metals as a catalyst. Previously, our lab group has developed a method for a one-pot synthesis for the alkylation and rearrangement of hydroxycoumarins. Now we would like to explore if this method can be applied to different fluorophores such as fluorescein and resorufin. By systematically studying the rearrangement of fluorescein derivatives through NMR monitoring, we hope to optimize this method to expand to other fluorophore scaffolds. This research will also aid in advancing the field on the conversion of phenols to anilines, as well as how structural changes such as sterics and electronics affect the optical properties of these fluorophores.
D'Elia, Paige, "Direct Amination of Hydroxyfluorophores via One-Pot Smiles Rearrangement Hydrolysis" (2021). Chemistry Summer Fellows. 39.
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