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Chromophores pentacycliques azotés fluorescents : nouvelle cascade diastéréosélective pallado-catalysée et exploration de leurs propriétés biologiques

Abstract : The aim of this work concerns the synthesis of a new family of aza-pentacyclic chromophore whose fluorescence properties can be modulated according to the functional groups present in the molecule. These chromophores were obtained through a cascade process between 2-formylbenzene boronic acid and 2,5-dihalopyridines. The cascade process is initiated by a palladium-catalyzed cross-coupling reaction and is followed by two successive nucleophilic cyclizations; the first cyclization performed on the pyridine nitrogen and the second occurred regioselectively on the adjacent carbon atom. This new cascade reaction allowed the formation of a pentacycle as a single regioisomer with four new bonds and two contiguous stereocenters with trans relationships. In addition, preliminary studies have shown that these polycyclic compounds have excellent fluorescence properties as well as biological properties that should enable us to extend the scope of these new chromophores to the medical field and molecular electronics
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https://hal.univ-lorraine.fr/tel-01749238
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Zein El Abidine Chamas. Chromophores pentacycliques azotés fluorescents : nouvelle cascade diastéréosélective pallado-catalysée et exploration de leurs propriétés biologiques. Autre. Université de Lorraine, 2012. Français. ⟨NNT : 2012LORR0079⟩. ⟨tel-01749238⟩

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