Document Type

Paper- Restricted to Campus Access

Publication Date


Faculty Mentor

Ryan Walvoord


Fluorophores are molecules that are often utilized in biological imaging, probe sensors, and forensics to detect molecules or atoms of interest. For this study, we want to improve the capability of these fluorophores. We use a method called Smiles Rearrangement, which is an intramolecular cyclic reaction involving nitrogen and oxygen trading places. To monitor this reaction, we use a time-lapsed NMR experiment to characterize the molecule throughout the reaction. In the NMR, a sample is placed in a unidirectional magnetic field, in which pulse frequencies are administered to the sample, to produce a spectrum. In the spectrum, each signal represents a particular hydrogen in the molecule. Thus we can see the electronics and functional groups of the molecule. For our experiment, investigating the electronics throughout the reaction allows us to understand how the Smiles Rearrangement proceeds by the emergence and disappearance of certain NMR peaks. In addition to the reaction identity, we also acquire the NMR yield of the product using an internal standard, which is a nonreactive molecule in the reaction, to determine the approximate conversion to the rearranged product. This project hopes to further characterize the Smiles Rearrangement.


Presented as part of the Ursinus College Celebration of Student Achievement (CoSA) held April 23 – April 30, 2020.

The downloadable file is a poster with recorded audio commentary.


Available to Ursinus community only.