Molécules chirales à géométrie hélicoïdale : synthèse et modulation de leurs propriétés spectroscopiques par leur environnement

Abstract : Chirality is an essential property of natural molecules, involved in many living biological mechanisms. It can be characterized by the chiroptical activity of chiral molecules, through circular dichroism, rotatory power, optical rotatory dispersion or circularly polarized luminescence. Biaryl and helicenic molecules are known for their intense chiroptical properties and they can be used for their applications in many fields, going from catalysis to optoelectronics.The research carried out during this thesis deals with the synthesis of new biaryl and helicenoid molecules and the study of their spectroscopic properties in interaction with their environment. First, different families of helicoidal molecules with extended aromatic systems have been synthesized. In order to target biological applications, their hydrosolubilization was achieved by the addition of PEG chain. Then, we focused on their spectroscopic and especially chiroptical properties and their modulation according to their structures, their interaction with protons, metals or deoxyribonucleix acid (DNA). During these studies, we experienced an unexpected photochemical reaction, which lead to a new photogenerated product revealing selective interactions with DNA G-quadruplexes. Finally, in order to exploit the controlled modularity of chiroptical properties, new chiral molecules that selectively detecting sugars by with boronic acids have been designed.
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Maëlle Mosser. Molécules chirales à géométrie hélicoïdale : synthèse et modulation de leurs propriétés spectroscopiques par leur environnement. Chimie organique. Université de Lyon, 2019. Français. ⟨NNT : 2019LYSEN024⟩. ⟨tel-02296732⟩

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