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Synthesis of Highly Functionalized BOPHY Chromophores Displaying Large Stokes Shifts
Quentin Huaulmé1, Antoine Mirloup1, Pascal Retailleau2
1†Institut de Chimie et Procédés pour l'Energie, l'Environnement et la Santé, Laboratoire de Chimie Moléculaire et Spectroscopies Avancées (ICPEES-LCOSA), UMR 7515 au CNRS, ECPM, 25 rue Becquerel, 67087 Strasbourg Cedex 02, France.
Abstract:
BOPHY dyes bearing bromo (in 5,5'-position) and iodo (in 4,4'-position) were synthesized. Double Knoevenagel reactions allow the extension of conjugation, resulting in an absorption above 625 nm. Selective cross-coupling reactions promoted by palladium(0) and microwave irradiation allow linking of a perylene module. These dyes are highly fluorescent, and the intramolecular cascade energy transfer from the perylene moiety to the BOPHY framework is almost quantitative, providing large virtual Stoke shifts (>5100 cm(-1)).
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