Altering Fundamental Trends in the Emission of Xanthene Dyes
Sponsor
This work was supported by the National Institutes of Health (R15EB016870).
Published In
The Journal of Organic Chemistry
Document Type
Citation
Publication Date
3-5-2019
Abstract
Fluorescent small molecules enable researchers and clinicians to visualize biological events in living cells, tissues, and organs in real time. Herein, the focus is on the structure and properties of the relatively rare benzo[ a]xanthenes that exhibit enhanced steric and electronic interactions due to their annulated structures. Three types of fluorophores were synthesized: (i) pH- and solvent-dependent seminaphthorhodafluors, (ii) pH- and solvent-independent seminaphthorhodafluors, and (iii) pH-independent but solvent-sensitive seminaphthorhodamines. The probes exhibited promising far-red to near-infrared (NIR) emission, large Stoke shifts, broad full width at half-maximum (fwhm), relatively high quantum yields, and utility in immunofluorescence staining. Deviation of the π-system from planarity due to changes in the fluorophore ionization state resulted in fluorescence properties that are atypical of common xanthene dyes.
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DOI
10.1021/acs.joc.8b03030
Persistent Identifier
https://archives.pdx.edu/ds/psu/28035
Citation Details
Wang, L. G., Munhenzva, I., Sibrian-Vázquez, M., Escobedo, J. O., Kitts, C. H., Fronczek, F. R., & Strongin, R. M. (2019). Altering Fundamental Trends in the Emission of Xanthene Dyes. The Journal of organic chemistry.
Description
Copyright © 2019 American Chemical Society