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Chiral Near-Infrared Fluorophores by Self-Promoted Oxidative Coupling of Cationic Helicenes with Amines/Enamines
Johann Bosson1, Geraldine M Labrador1, Céline Besnard2
1Department of Organic Chemistry, University of Geneva, Quai Ernest Ansermet 30, 1211, Geneva 4, Switzerland.
Abstract:
In one pot, tertiary alkyl amines are oxidized to enamines by cationic dioxa[6]helicene, which further reacts as electrophile and oxidant to form mono or bis donor-π-acceptor coupling products. This original and convergent synthetic approach provides a strong extension of conjugation yielding chromophores that absorb intensively in far-red or NIR domains (λmax up to 791 nm) and fluoresce in the NIR as well (λmax up to 887 nm). Intense ECD properties around 790 nm with a |Δϵ| value up to 60 M-1 cm-1 are observed.
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