Submission Date

7-23-2021

Document Type

Paper- Restricted to Campus Access

Department

Chemistry

Faculty Mentor

Ryan R. Walvoord

Comments

Presented during the 23rd Annual Summer Fellows Symposium, July 23, 2021 at Ursinus College.

Project Description

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.

Download

Restricted

Available to Ursinus community only.

Share

COinS