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 |
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Authors: | Dr Mariusz Tasior Vincent Hugues Dr Mireille Blanchard‐Desce Prof Daniel T Gryko |
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Institution: | 1. Institute of Organic Chemistry, Polish Academy of Sciences, Kasprzaka 44/52, 01‐224 Warsaw (Poland), Fax: (+48)?226326681;2. Université de Bordeaux, ISM (UMR5255 CNRS), F 33400, Bordeaux (France);3. Warsaw University of Technology, Faculty of Chemistry, Noakowskiego 3, 00‐664 Warsaw (Poland) |
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Abstract: | New, strongly fluorescent benzo1,2‐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 benzo1,2‐d:4,5‐d′]bisimidazoles were also strongly fluorescent in the solid state. |
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Keywords: | absorption dyes/pigments fluorescence fluorescent probes nitrogen heterocycles |
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