New difluoro-boradiazaindacene shaped with gallate platforms |
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Authors: | Raymond Ziessel Laure Bonardi Pascal Retailleau Franck Camerel |
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Affiliation: | aLaboratoire de chimie moléculaire, ECPM, UMR 7509, CNRS—Université Louis-Pasteur, 25, rue Becquerel, 67087 Strasbourg cedex 02, France;bLaboratoire de cristallochimie, ICSN – CNRS, Bât. 27, 1, avenue de la Terrasse, F-91198 Gif-sur-Yvette, France |
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Abstract: | The present account describes the synthesis of difluoro-boradiazaindacenes (F-Bodipy) functionalized at the central 8-position by phenylamino or phenyldiamino moieties conveniently transformable into phenyl amide scaffoldings. Molecules carrying three linear or branched chains, or six linear chains were prepared and fully characterized. Four X-ray crystal structures were determined and the packing is discussed in terms of molecular interactions, a key feature for the formation of aggregates or thin films. With the exception of nitro derivatives quenched by a photo-induced reductive electron transfer and the amino-derivatives partially quenched, all dyes are highly fluorescent with quantum yields lying between 50 and 90%. The few nanosecond excited-state lifetimes and the weak Stokes shifts are in keeping with singlet excited states. Reversible reduction and oxidation processes occur around −1.34 and +0.97 V in solution and the electroactivity and photoluminescence are maintained in thin films. Interestingly, two distinct emissions are observed at 550 and 635 nm by electroluminescence of the trimethoxyphenyl-Bodipy derivative, corresponding, respectively, to the luminescence of isolated molecules and aggregates. Dispersion of the Bodipy into a fluorescent poly(N-vinylcarbazole) polymer (PVK) (approximately 3 mol% per repeating unit of PVK) by solution processing exclusively produces yellow emission due to isolated Bodipy fluorophore. |
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Keywords: | Boradiazaindacene Amides Gallate derivatives Fluorescence Redox activity Electroluminescence |
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