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Dérivés de s-tétrazine et de triphénylamine : du design aux applications

Abstract : This work deals with the synthesis and the spectroscopic and electrochemical studies of donor-acceptor systems which have been designed for electrofluorochromism, two-photon absorption and photovoltaics. s-Tetrazine has been chosen as the acceptor for its high electron affinity, its emission properties and its ability to structure a layer thanks to intermolecular interactions (--stacking). Triphenylamine has been selected as the donor for its low ionization potential, its spectroscopic properties (high absorption and emission) and the easy modulation of its properties by changing the substituents. Seven triphenylamine derivatives have been synthesized as well as eighteen new multichromophoric compounds based on tetrazine and triphenylamine which have five different links and various substituents. They have been characterized by electrochemistry and spectroscopy (stationary and time-resolved). The study of the modulation of the photophysic properties with the controle of the redox state has been then done. Ten compounds having a conjugating link between the tetrazine and the tetrazine have been synthesized and characterized by electrochemistry and spectroscopy. Given their properties, six of them have been tested in two-photon absorption and two of them have been selected to be used as a donor in an organic solar cell. Moreover two reactions have been examined in depth in order to explain some unexpected synthesis results.
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  • HAL Id : tel-00957915, version 1

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Cassandre Quinton. Dérivés de s-tétrazine et de triphénylamine : du design aux applications. Autre. École normale supérieure de Cachan - ENS Cachan, 2013. Français. ⟨NNT : 2013DENS0047⟩. ⟨tel-00957915⟩

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