TY - JOUR
T1 - Altering Fundamental Trends in the Emission of Xanthene Dyes
AU - Wang, Lei G.
AU - Munhenzva, Ian
AU - Sibrian-Vazquez, Martha
AU - Escobedo, Jorge O.
AU - Kitts, Catherine H.
AU - Fronczek, Frank R.
AU - Strongin, Robert M.
N1 - Publisher Copyright:
© 2019 American Chemical Society.
PY - 2019/3/1
Y1 - 2019/3/1
N2 - 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.
AB - 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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U2 - 10.1021/acs.joc.8b03030
DO - 10.1021/acs.joc.8b03030
M3 - Article
C2 - 30719911
AN - SCOPUS:85062359209
SN - 0022-3263
VL - 84
SP - 2585
EP - 2595
JO - Journal of Organic Chemistry
JF - Journal of Organic Chemistry
IS - 5
ER -