Doctoral thesis
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Modular synthesis and applications of chiral Tunable Dyes and Fluorophores

Defense date2015-09-25
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 dyes
  • Cationic diazahelicenes
  • Triangulenes
  • Azobenzene
  • BODIPY
  • Aziridine
  • Sulfoximine
Research groups
Citation (ISO format)
WALLABREGUE, Antoine. Modular synthesis and applications of chiral Tunable Dyes and Fluorophores. Doctoral Thesis, 2015. doi: 10.13097/archive-ouverte/unige:76158
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Technical informations

Creation10/13/2015 7:35:00 PM
First validation10/13/2015 7:35:00 PM
Update time03/15/2023 12:42:38 AM
Status update03/15/2023 12:42:37 AM
Last indexation10/31/2024 2:33:49 AM
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