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Benzo[1,2-d:4,5-d′]bisimidazoles as a Convenient Platform Towards Dyes that are Capable of Excited-State Intramolecular Proton Transfer and of Two-Photon Absorption

Authors

  • Dr. Mariusz Tasior,

    1. Institute of Organic Chemistry, Polish Academy of Sciences, Kasprzaka 44/52, 01-224 Warsaw (Poland), Fax: (+48) 226326681
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  • Vincent Hugues,

    1. Université de Bordeaux, ISM (UMR5255 CNRS), F 33400, Bordeaux (France)
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  • Dr. Mireille Blanchard-Desce,

    Corresponding author
    1. Université de Bordeaux, ISM (UMR5255 CNRS), F 33400, Bordeaux (France)
    • Mireille Blanchard-Desce, Université de Bordeaux, ISM (UMR5255 CNRS), F 33400, Bordeaux (France)

      Daniel T. Gryko, Institute of Organic Chemistry, Polish Academy of Sciences, Kasprzaka 44/52, 01-224 Warsaw (Poland), Fax: (+48) 226326681

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  • Prof. Daniel T. Gryko

    Corresponding author
    1. Institute of Organic Chemistry, Polish Academy of Sciences, Kasprzaka 44/52, 01-224 Warsaw (Poland), Fax: (+48) 226326681
    2. Warsaw University of Technology, Faculty of Chemistry, Noakowskiego 3, 00-664 Warsaw (Poland)
    • Mireille Blanchard-Desce, Université de Bordeaux, ISM (UMR5255 CNRS), F 33400, Bordeaux (France)

      Daniel T. Gryko, Institute of Organic Chemistry, Polish Academy of Sciences, Kasprzaka 44/52, 01-224 Warsaw (Poland), Fax: (+48) 226326681

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Abstract

New, strongly fluorescent benzo[1,2-d:4,5-d′]bisimidazoles have been prepared by the reaction of Bandrowski′s base with various aldehydes. Their structures were carefully designed to achieve efficient excited-state intramolecular proton transfer and good two-photon-absorption (2PA) cross-sections. Functional dyes that possessed both high fluorescence quantum yields and large Stokes shifts were prepared. A π-expanded D-A-D derivative that possessed Φfl=50 % and σ2=230 GM in the spectroscopic area of interest for biological imaging is an excellent candidate as a fluorescent probe. Thanks to the presence of two reactive amino groups, such compounds can be easily transformed into probes for bioconjugation. All of these benzo[1,2-d:4,5-d′]bisimidazoles were also strongly fluorescent in the solid state.

Abstract

W wyniku reakcji odpowiednio podstawionych aldehydów z zasadą Bandrowskiego otrzymano nowe, silnie fluoryzujące benzobisimidazole. Ich struktura została starannie zoptymalizowana pod kątem uzyskania wydajnego przeniesienia protonu w stanie wzbudzonym, następującego w wyniku jednoczesnej absorpcji dwóch fotonów. Dzięki obecności dwóch reaktywnych grup aminowych zsyntetyzowane związki dają możliwości dalszych modyfikacji i użycia w dwufotonowej mikroskopii fluorescencyjnej.

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