Modular Synthesis, Orthogonal Post-Functionalization, Absorption, and Chiroptical Properties of Cationic [6]Helicenes

Modular Synthesis, Orthogonal Post-Functionalization, Absorption, and Chiroptical Properties of Cationic [6]Helicenes

Pick and choose: Novel cationic diaza‐, azaoxo‐, and dioxo[6]helicenes are readily prepared and functionalized selectively by orthogonal aromatic electrophilic and vicarious nucleophilic substitutions (see scheme). Reductions, cross‐coupling, or condensation reactions introduce additional diversity...

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Veröffentlicht in:Angewandte Chemie International Edition 2013-02, Vol.52 (6), p.1796-1800
Hauptverfasser: Torricelli, Franck, Bosson, Johann, Besnard, Céline, Chekini, Mahshid, Bürgi, Thomas, Lacour, Jérôme
Format: Artikel
Sprache:eng
Schlagworte:
arenes
Cationic
Condensing
Enantiomers
helical structures
Modular
Picks
Reduction
Synthesis
synthetic methods
Tuning
UV/Vis spectroscopy
vicarious nucleophilic substitution
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Beschreibung
Zusammenfassung:Pick and choose: Novel cationic diaza‐, azaoxo‐, and dioxo[6]helicenes are readily prepared and functionalized selectively by orthogonal aromatic electrophilic and vicarious nucleophilic substitutions (see scheme). Reductions, cross‐coupling, or condensation reactions introduce additional diversity and allow tuning of the absorption properties up to the near‐infrared region. The diaza salts can be resolved into single enantiomers.
ISSN:1433-7851
1521-3773
DOI:10.1002/anie.201208926