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Synthesis of Rhodamines and Rosamines Using 3,6-Difluoroxanthone as a Common Intermediate.

Rhodamines and structurally similar rosamines are some of the most highly utilized tools for molecular imaging experiments. We report a general and high-yielding route to produce 18 examples of rhodamines and rosamines, including tetramethylrhodamine, rhodamine B, and Janelia Fluor 549, from a single xanthone intermediate, 3,6-difluoroxanthone. Spectroscopic studies revealed trends in fluorophore efficiency based on substitution patterns at the 3'-, 6'-, and 9'-positions, providing insights to aid future designs of rhodamines/rosamines.