title: Synthesis of Highly Functionalized BOPHY Chromophores Displaying Large Stokes Shifts.
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)).
authors.affiliation: †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.
authors.forename: Quentin
authors.initials: Q
authors.lastname: Huaulmé
authors.affiliation: †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.
authors.forename: Antoine
authors.initials: A
authors.lastname: Mirloup
authors.affiliation: ‡Institut de Chimie des Substances Naturelles (ICSN), CNRS, Avenue de la Terrasse, 91198 Gif Sur Yvette Cedex, France.
authors.forename: Pascal
authors.initials: P
authors.lastname: Retailleau
authors.affiliation: †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.
authors.forename: Raymond
authors.initials: R
authors.lastname: Ziessel
mesh_terms: D001372:Aza Compounds / Q000138:chemical synthesis* / Q000737:chemistry; D001896:Boron Compounds / Q000138:chemical synthesis* / Q000737:chemistry; D005456:Fluorescent Dyes / Q000138:chemical synthesis* / Q000737:chemistry; D015394:Molecular Structure; D010165:Palladium / Q000737:chemistry; D010569:Perylene / Q000737:chemistry*; D013050:Spectrometry, Fluorescence
chemical_list: D001372:Aza Compounds; D001896:Boron Compounds; D005456:Fluorescent Dyes; D010569:Perylene; D010165:Palladium