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

Contributors

Wallabregue, Antoine

Directors

Lacour, Jérôme

Defense date

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 dyes
  • Cationic diazahelicenes
  • Triangulenes
  • Azobenzene
  • BODIPY
  • Aziridine
  • Sulfoximine

UNIGE affiliation entities

UNIGE 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

Main files (1)

Thesis

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Technical informations

Creation

13/10/2015 17:35:00

First validation

13/10/2015 17:35:00

Update

14/03/2023 23:42:38

Status update

14/03/2023 23:42:37

Last indexation

13/05/2025 16:51:33
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