"Altering Fundamental Trends in the Emission of Xanthene Dyes" by Lei G. Wang, Ian Munhenzva et al.

Faculty Publications

Title

Altering Fundamental Trends in the Emission of Xanthene Dyes

Authors

Lei G. Wang, Department of Biomedical Engineering , Oregon Health & Science University , 3181 SW Sam Jackson Park Road , Portland , Oregon 97239 , United States.
Ian Munhenzva, Department of Chemistry , Portland State University , 1719 SW 10th Avenue , Portland , Oregon 97201 , United States.
Martha Sibrian-Vazquez, Department of Chemistry , Portland State University , 1719 SW 10th Avenue , Portland , Oregon 97201 , United States.
Jorge O. Escobedo, Department of Chemistry , Portland State University , 1719 SW 10th Avenue , Portland , Oregon 97201 , United States.
Catherine H. Kitts, Department of Chemistry , Portland State University , 1719 SW 10th Avenue , Portland , Oregon 97201 , United States.
Frank R. Fronczek, Department of Chemistry , Louisiana State University , 232 Choppin Hall , Baton Rouge , Louisiana 70803 , United States.
Robert M. Strongin, Department of Chemistry , Portland State University , 1719 SW 10th Avenue , Portland , Oregon 97201 , United States.

Document Type

Article

Publication Date

3-1-2019

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.

Publication Source (Journal or Book title)

The Journal of organic chemistry

First Page

2585

Last Page

2595

Recommended Citation

Wang, L. G., Munhenzva, I., Sibrian-Vazquez, 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, 84 (5), 2585-2595. https://doi.org/10.1021/acs.joc.8b03030

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