Hetero-Substituted αβ-Fused BODIPY |
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Authors: | Dr Fabien Ceugniet Dr Quentin Huaulmé Alexandra Sutter Dr Denis Jacquemin Dr Nicolas Leclerc Dr Gilles Ulrich |
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Institution: | 1. Institut de Chimie et Procédés pour l'Énergie l'Environnement et la Santé (ICPEES), UMR CNRS 7515 École Européenne de Chimie, Polymères et Matériaux (ECPM), 25 Rue Becquerel, 67087 Strasbourg Cedex 02, France;2. Université de Nantes, CEISAM UMR 6230, CNRS, 44000 Nantes, France |
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Abstract: | Here, we report the synthesis and properties of heterosubtituted αβ-fused BODIPY fluorophores. The compounds were obtained in good yields by sequential and selective Stille cross-coupling reactions from 2,3,5,6-tetrahalo-BODIPY, allowing the introduction of different substituents at the 3,5 and 2,6 positions of the BODIPY ring. The final fused compounds were synthesized using oxidative cyclisation with ferrous chloride. The fully fused compounds show a strong bathochromically shifted emission along with a hyperchromic shift of the absorption maxima. The fluorescence quantum yields remain relatively large for compounds emitting in this wavelength range. Computational studies have been carried out to fully understand the photophysical behaviour of these dyes. |
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Keywords: | BODIPY dyes pigments fluorescence TD-DFT |
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