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Disabling Photoinduced Electron Transfer in 4,4-Difluoro-8(-4′-hydroxyphenyl)-1,3,5,7-tetramethyl-4-bora-3a,4a-diaza-s-indacene by Phosphorylation

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Abstract

The synthesis and photophysical characterization of the phosphorylated Bodipy dye 5 are reported and compared to those of its hydroxyphenyl counterpart 1. Conversion of the latter by three methods of phosphorylation yields the strongly fluorescent dye 5 which exhibits similar steady-state spectra like 1 but an approximately five times prolonged fluorescence lifetime τFl. We attribute this distinct change from τFl = 0.7 ns for 1 to τFl = 3.7 ns for 5 to the suppression of photoinduced electron transfer in 5. This photochemical reaction was previously held responsible for fluorescence quenching in 1. Fluorescence correlation spectroscopy reveals that 5 can be detected by single-molecule methods and that uncaging of phosphate in 5 is a minor problem.

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Acknowledgement

Financial support is provided by the German Science Foundation (DFG, JU-650/2-2). We are indebted to Benjamin Hötzer, Babette Hinkeldey, Michael Schmitt and Rolf Hempelmann for assistance and support.

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  1. Biophysical Chemistry, Saarland University, Building B2 2, Campus, 66123, Saarbruecken, Germany

    Michaela Jacob, Alexander Schmitt & Gregor Jung

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  1. Michaela Jacob
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  2. Alexander Schmitt
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  3. Gregor Jung
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Correspondence to Gregor Jung.

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Jacob, M., Schmitt, A. & Jung, G. Disabling Photoinduced Electron Transfer in 4,4-Difluoro-8(-4′-hydroxyphenyl)-1,3,5,7-tetramethyl-4-bora-3a,4a-diaza-s-indacene by Phosphorylation. J Fluoresc 18, 639–644 (2008). https://doi.org/10.1007/s10895-008-0373-7

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  • DOI: https://doi.org/10.1007/s10895-008-0373-7

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