Some of the oldest and most widely utilized fluorophores are anthracene-based molecules such as fluorescein, pyronins, and 3,6-diaminoacridines (1). This popularity is due to many attractive properties such as the ability of Acridine orange (AO), a 3,6-diaminoacridine, and pyronins to intercalate with nucleic acids such as dsDNA and ssRNA. Although these compounds have attractive properties, they may lack in several areas, as seen in the photobleaching rate constant of 0.154 s-1 of AO, which is relatively high in comparison to commonly used fluorophores such as fluorescein isothiocyanate at 0.007 s-1. Additionally, Pyronin Y and B also have low quantum yields in aqueous solvents (0.48 for Y and 0.47 for B in EtOH) and are susceptible to photobleaching. Prior studies by Dr. Woydziak and his associates were able to demonstrate that the substitution of aryl positions 2 and 7 with fluorine atoms improved overall photophysical properties of fluorescein derivatives. Using a similar approach, this project describes a scalable, novel, four-step synthetic route to develop a small library of 2,7-difluoro-(3,6-diaminoacridine/pyronin) analogues. A total of eight pyronins and four acridines have been synthesized and characterized thus far. UV/Vis and fluorescence spectrophotometry were used to determine the excitation/emission wavelengths. Quantum yields, 1H NMR, 13C NMR, MS and photobleaching measurements were also obtained for most fluorophores.

Synthesis of novel anthracene-based fluorophores

Macromolecular Chemistry: The Second Century

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ACS Spring 2020 National Meeting & Expo

The official archive and repository for all ACS Meetings & Expositions abstracts and select posters or presentations.