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Theses

Synthèse d'engrenages moléculaires

Abstract : Considerable progress has been made in the field of molecular machines in which the by a Nobel Prize was awarded in 2016. Multiple examples of molecular machines capable of providing controllable movement via chemical, light or electrical sources have been reported. In our group, a motor with a unidirectional and reversible motion has previously been synthesized. This molecular motor is a ruthenium (II) complex in which the whose rotation of the mobile part, the rotor, is controlled by the tunneling microscope tip. This motor raises new questions: are we able to transfer this movement to other molecules? If it takes place, what is the limit of the transfer of movement? What are the prerequisites for the transfer of motion? This thesis is part of the demonstration of the control of the rotation of a molecular motor. To find answers to these new questions a whole series of molecular gears, integrating the design of the molecular engine already studied in the team, and introducing 1D or 2D paddles have been synthesised. This thesis firstly describes the optimization and the synthesis of the different pentabrominated and pentaiodinated precursors as well the results of the observation of the pentabrominated precursor by tunneling microscopy. The later chapters are devoted to the optimization of the coupling conditions (Suzuki, Sonogashira, ...), to the coupling leading to a 1D functionalized symmetric gear with ferrocenes or aryl groups and to other couplings leading to the functionalized 2D gears with carbazole groups, BODIPY or porphyrins. The X-ray elucidated structure of a 1D symmetrical gear will also be discussed. The last chapter presents the synthesis of asymmetrical gears to demonstrate the rotation by tunneling microscopy.
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Guillaume Erbland. Synthèse d'engrenages moléculaires. Génie chimique. Université Paul Sabatier - Toulouse III, 2019. Français. ⟨NNT : 2019TOU30112⟩. ⟨tel-02868080⟩

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