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Synthesis and Characterization of New Fluorinated Tetrazines Displaying a High Fluorescence Yield

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Abstract

Following the case of tetrazines substituted with perfluorinated alkyl chains, separated by two methylene groups from the tetrazine core, a new series of analogous tetrazines, but featuring only one methylene group between the fluorescent core and the perfluorinated chain, have been synthesized, and their photo-physical properties investigated. Their fluorescence quantum yields in acetonitrile are in same range than chloroalkoxytetrazines, which make them interesting candidates for light emission. Surprisingly, the quantum yields are lower with one methylene group, rather than two methylene groups separating the fluorinated chain from the emitting core, in the case of unsymmetrical compounds, while they are superior in the case of symmetrical ones. This unusual observation is discussed in the article.

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Authors and Affiliations

  1. Laboratory of Organic Molecular Chemistry, ENSIT MONTFLEURY, University of Tunis, 5 Taha Hussein Avenue 1008 Montfleury, Tunis, Tunisia

    Refka Guermazi & Ahmed Hedhli

  2. PPSM, ENS Cachan, CNRS, Université Paris-Saclay, 94235, Cachan, France

    Lorna Royer, Laurent Galmiche, Gilles Clavier & Pierre Audebert

Authors
  1. Refka Guermazi
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  2. Lorna Royer
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  3. Laurent Galmiche
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  4. Gilles Clavier
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  5. Pierre Audebert
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  6. Ahmed Hedhli
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Corresponding author

Correspondence to Pierre Audebert.

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Guermazi, R., Royer, L., Galmiche, L. et al. Synthesis and Characterization of New Fluorinated Tetrazines Displaying a High Fluorescence Yield. J Fluoresc 26, 1349–1356 (2016). https://doi.org/10.1007/s10895-016-1822-3

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  • DOI: https://doi.org/10.1007/s10895-016-1822-3

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