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Fluorophores serve many applications today such as fluorescent tagging of biomolecules, pesticide detection, and chemical probes. They contain highly conjugated pi systems that re-emit light at longer wavelengths. Organic synthesis can be done to modify the properties of coumarins. These properties can improve fluorophore ion detection and produce new fluorescent capabilities. Current organic synthesis is focused on synthesizing aminofluorophores. Aminofluorophores provide increased photostability, red shifted emission, and better pH sensitivity. Their high demand and excessive costs have chemists looking for a fast, efficient way for the synthesis of aminofluorophores. Current methods consist of a Buchwald Hartwig reaction, which requires metal catalysis and harsh conditions. This work proposes an alternative, less harsh approach in the conversion of hydroxyfluorophores to aminofluorophores via the Smiles Rearrangement.
Lippe, Daniel, "Effects of the Amide Linker on the Smiles Rearrangement of Coumarin Fluorophores" (2019). Chemistry Summer Fellows. 30.