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Synthèse et étude de nouveaux cucurbiturils pour l’encapsulation de gaz

Abstract : The cucurbituril family (CBn) constitutes a group of recent synthetic host-molecules. These compounds are formed by n glycoluril units and, since the beginning of the 2000’s, they have found their interest in multiple domains such as biology, chemistry and physics. They have joined the large group of synthetic receptors comprising cyclodextrins, calixarens, cryptophanes, carcerands and hemicarcerands. Gaz encapsulation in this family of compounds is misunderstood. In these PhD works, our interest concerned gaz complexation, especially xenon, into cucurbiturils.First, the synthesis of new hydrosoluble cucurbiturils to study their ability to encapsulate noble gaz and small alcans such as methan and ethan is described. Our final goal will be to define new rules concerning gaz encapsulation by cucurbiturils. Noble gaz from helium to krypton have been studied. Among these noble gaz, xenon is particularly interesting in the domain of biosensing, for the design of new diagnostic methods by MRI.In this manuscript, the synthesis of a family of hydrosoluble cyclohexylcucurbiturils and their ability to encapsulate xenon is described. Another new cucurbituril constituted by five glycoluril units and one glycoluril unit forming a six-membered ring, has also been prepared. The first two parts of the manuscript present the gaz encapsulation and the cucurbituril family. The third part describes our results concerning the new synthetized cucurbiturils. In the fourth part, we have developped a method based on metathesis reactions (ROM-CM) for preparing some precursors of acyclic congeneers of cucurbiturils. Lastly, the fifth part concerns results about gaz encapsulation. All of this study has been driven in collaboration with Laboratoire de Structure et Dynamique par Résonance Magnétique (CEA Saclay).
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Véronique Lewin. Synthèse et étude de nouveaux cucurbiturils pour l’encapsulation de gaz. Autre. Université Paris Sud - Paris XI, 2011. Français. ⟨NNT : 2011PA112261⟩. ⟨tel-00640091⟩

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