Doctoral thesis
Open access

Synthesis, late-stage functionalization and properties of cationic [6]helicenes chromophores

Defense date2017-03-23

The goal of this PhD was to explore a new synthetic protocol for the synthesis, resolution and late stage functionalization of cationic [6]helicenes. The replacement of oxygen by nitrogen atom at bridge position is favorable due to the better charge stabilization brought by the electron-donating groups. The transformation from dioxa into azaoxa and diaza [6]helicenes is achieved in milder conditions. The enantiomers of the cationic [6]helicenes were separated using CSP-HPLC conditions in neutral or cationic derivatives and their chiroptical properties and racemization barriers were studied. In addition, an oxidative coupling between the more electrophilic dioxa [6]helicene and indoles or indoline was achieved on the naphthyl rings. This regioselective functionalization led to donor-acceptor dyes with interesting optical properties. Further tuning of the electronic properties was achieved through the addition of electron-donating or electron-withdrawing substituents at the periphery of diaza [6]helicene. Highly efficient luminophores or far-red absorbers are now accessible.

  • Helicene
  • Cationic dyes
  • Fluorophores
  • Cyanine dyes
Research group
Citation (ISO format)
LABRADOR BELTRAN, Maria Géraldine. Synthesis, late-stage functionalization and properties of cationic [6]helicenes chromophores. 2017. doi: 10.13097/archive-ouverte/unige:94661
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Technical informations

Creation05/15/2017 9:32:00 PM
First validation05/15/2017 9:32:00 PM
Update time03/15/2023 1:44:59 AM
Status update03/15/2023 1:44:58 AM
Last indexation10/19/2023 3:53:42 AM
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