Title

Altering Fundamental Trends in the Emission of Xanthene Dyes

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.

Description

Copyright © 2019 American Chemical Society

DOI

10.1021/acs.joc.8b03030

Persistent Identifier

https://archives.pdx.edu/ds/psu/28035

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