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Synthesis and Properties of Dendrimers Possessing the Same Fluorophore(s) Located Either Peripherally or Off-Center

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journal contribution
posted on 09.11.2007, 00:00 by Grégory Franc, Serge Mazères, Cédric-Olivier Turrin, Laure Vendier, Carine Duhayon, Anne-Marie Caminade, Jean-Pierre Majoral
Two series of phosphorus dendrimers functionalized by maleimide derivatives are synthesized, as well as three new monomeric maleimide derivatives, of which two are characterized by X-ray diffraction. The first series of phosphorus dendrimers possesses maleimide derivatives as end groups (6−48, from generation 0 to generation 3). The second series of dendrimers possesses a single copy of the same maleimide derivative linked “off-center” to a cyclotriphosphazene core, leading to dissymmetrical dendrimers; this series is synthesized from generation 0 to generation 2. The fluorescence properties of both series of dendrimers and of monomers are studied, affording new information. First, the presence of labile hydrogen extinguishes the fluorescence. Second, the grafting of the fluorophore(s) directly to the core affords highly fluorescent compounds. Finally, an original influence of the branches possessing phosphorhydrazone linkages toward the fluorescence properties is shown.