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Modular synthesis and applications of chiral Tunable Dyes and Fluorophores

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Defense Thèse de doctorat : Univ. Genève, 2015 - Sc. 4831 - 2015/09/25
Abstract The goal of this PhD was to explore the reactivity of a novel N-aminoacridinium salt. This derivative has been used for the preparation of pH-sensitive and fluorescent diaza [4]helicene dyes thanks to particularly facile N-N bond cleavage reactions. This compound has also been used as nitrogen source for the stereospecific aziridination and sulfoximination of unfunctionalized olefins and sulfoxides under metal-free oxidative conditions respectively. The corresponding NH aziridines and sulfoximines were then obtained using mild photoreductive conditions. Moreover, N-aminoacridinium salt was utilized for the preparation of the fisrt small fluorophore (pKa 5.3) which specifically stains for late endosome compartments (pH 4.8-6) and for the synthesis of chiral (helical) BODIPY and azobenzene derivatives.
Keywords PH-sensitive dyesCationic diazahelicenesTriangulenesAzobenzeneBODIPYAziridineSulfoximine
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URN: urn:nbn:ch:unige-761582
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Research group Groupe Lacour
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WALLABREGUE, Antoine. Modular synthesis and applications of chiral Tunable Dyes and Fluorophores. Université de Genève. Thèse, 2015. https://archive-ouverte.unige.ch/unige:76158

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Deposited on : 2015-10-14

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