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

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Defense Thèse de doctorat : Univ. Genève, 2017 - Sc. 5063 - 2017/03/23
Abstract 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.
Keywords HeliceneCationic dyesFluorophoresCyanine dyes
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URN: urn:nbn:ch:unige-946617
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Thesis (17.9 MB) - document accessible for UNIGE members only Limited access to UNIGE (until 2019-05-15)
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Research group Groupe Lacour
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LABRADOR BELTRAN, Maria Géraldine. Synthesis, late-stage functionalization and properties of cationic [6]helicenes chromophores. Université de Genève. Thèse, 2017. https://archive-ouverte.unige.ch/unige:94661

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Deposited on : 2017-06-07

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