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Fluorescent Properties of BODIPY Sensors Based on Photoinduced Electron Transfer

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Abstract

Two boron-dipyrrin (BODIPY) based dyes with dimethylaminophenyl and carboxyphenyl substituents in 8-position of dipyrrin ligand have been synthesized and characterized. Photophysical and spectral properties of the obtained compounds have been investigated in water-ethanol mixture and water-cyclohexane system with variation of pH values. The equilibria constants of the compounds were identified by classical methods of acid-base titration. BODIPY bearing dimethylaminophenyl and carboxyphenyl subunits show deprotonation/protonation dependent fluorescence off/on-switching. The change of the emission could be mechanistically explained by a PET (photoinduced electron transfer) from the 8-substituent to the fluorophore. The present study demonstrates that BODIPY-based fluorescent sensors can be used to measure the pH in the range of 2–13 extending the scope of BODIPY dyes available as pH-indicators. Investigated compounds demonstrate weak dye-dye interaction allowing their cooperative usage as indicators.

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Acknowledgments

The work was partially supported by the grants of the Russian Foundation for Basic Research (No 16-03-01028 А, No 15-33-20002 and No 15-43-03214) Grant of the President of the Russian Federation (МК-8835.2016.3).

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Authors and Affiliations

  1. Department of Inorganic Chemistry, Ivanovo State University of Chemistry and Technology, 7 Sheremetevsky av, 153000, Ivanovo, Russia

    Yu S. Marfin, M. V. Shipalova, V. O. Kurzin, K. V. Ksenofontova, A. V. Solomonov & E. V. Rumyantsev

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  1. Yu S. Marfin
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  2. M. V. Shipalova
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  3. V. O. Kurzin
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  4. K. V. Ksenofontova
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  5. A. V. Solomonov
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  6. E. V. Rumyantsev
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Correspondence to Yu S. Marfin.

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Marfin, Y.S., Shipalova, M.V., Kurzin, V.O. et al. Fluorescent Properties of BODIPY Sensors Based on Photoinduced Electron Transfer. J Fluoresc 26, 2105–2112 (2016). https://doi.org/10.1007/s10895-016-1905-1

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  • DOI: https://doi.org/10.1007/s10895-016-1905-1

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