Synthesis and Photophysics of a New Family of Fluorescent 9‐Alkyl‐Substituted Xanthenones |
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Authors: | Ángela Martínez‐Peragón Dr. Delia Miguel Rocío Jurado Dr. José Justicia Prof. José M. Álvarez‐Pez Dr. Juan M. Cuerva Dr. Luis Crovetto |
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Affiliation: | 1. Department of Organic Chemistry, University of Granada, Fuentenueva Campus, 18071 Granada (Spain), Fax: (+34)?958248437;2. Department of Physical Chemistry, University of Granada, Cartuja Campus, 18071 Granada (Spain), Fax: (+34)?958244090 |
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Abstract: | 9‐Alkyl xanthenones with different aliphatic pendant groups have been easily prepared by means of nucleophilic addition of the corresponding Grignard derivative to a tert‐butyldimethylsilyl ether (TBDMS)‐protected 3,6‐dihydroxy‐xanthenone. The photophysical behavior of the new dyes has been explored by using absorption, steady‐state‐, and time‐resolved fluorescence measurements. We determined the equilibrium constants, visible spectral characteristics, fluorescence quantum yield, and decay times. Remarkably, they retain similar fluorescent properties of fluorescein including the characteristic phosphate‐mediated excited‐state proton‐transfer (ESPT) reaction. 6‐Hydroxy‐9‐isopropyl‐3H‐xanthen‐3‐one ( 5 ) was investigated in living cells; it presented a good permeability and efficient accumulation inside the cytosol. For the first time, we reported that the requirement of an aryl group at C‐9 is no longer needed and new fluorescent sensors can be therefore easily developed. |
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Keywords: | biosensors dyes/pigments fluorescence photochemistry photophysics |
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