Gold-catalyzed bidirectional access to planar heptacyclic benzobispyrido(1,2-α)indoles and benzobispyrrolo(1,2-α)quinolines for materials science

• Verfasst von: Heckershoff, Robin [VerfasserIn]
• Verfasst von: Eberle, Lukas [VerfasserIn]
• Verfasst von: May, Garrett [VerfasserIn]
• Verfasst von: Krämer, Petra [VerfasserIn]
• Verfasst von: Rominger, Frank [VerfasserIn]
• Verfasst von: Rudolph, Matthias [VerfasserIn]
• Verfasst von: Hashmi, A. Stephen K. [VerfasserIn]
• Titel: Gold-catalyzed bidirectional access to planar heptacyclic benzobispyrido(1,2-α)indoles and benzobispyrrolo(1,2-α)quinolines for materials science
• Verf.angabe: Robin Heckershoff, Lukas Eberle, Garrett May, Petra Krämer, Frank Rominger, Matthias Rudolph, and A. Stephen K. Hashmi
• E-Jahr: 2022
• Jahr: October 18, 2022
• Umfang: 8 S.
• Illustrationen: Illustrationen
• Fussnoten: First published: 06 September 2022 ; Gesehen am 20.12.2022
• Titel Quelle: Enthalten in: Advanced synthesis & catalysis
• Ort Quelle: Weinheim : Wiley-VCH, 2001
• Jahr Quelle: 2022
• Band/Heft Quelle: 364(2022), 20 vom: Okt., Seite 3559-3566
• ISSN Quelle: 1615-4169
• DOI: doi:10.1002/adsc.202200708
• Datenträger: Online-Ressource
• Sprache: eng
• Sach-SW: Gold catalysis
• Sach-SW: Materials science
• Sach-SW: Nitrogen heterocycles
• Sach-SW: Organic semiconductors
• Sach-SW: Photophysics
• K10plus-PPN: 1828152005
• K10plus-PPN:
  Universitätsbibliothek
• Lokale URL UB: Zum Volltext

Abstract

Our recently developed gold-catalyzed synthesis of indolo[1,2-a]quinolines was successfully expanded towards bidirectional approaches, enabling access to two heptacyclic structural motifs. In the case of benzobispyrido[1,2-a]indoles, previously inaccessible modifications of the only known representative were made possible. In addition, the synthesis of a new class of nitrogen-containing heptacycles - namely benzobispyrrolo[1,2-a]quinolines - was achieved by applying alkynylated benzodipyrrole derivatives as starting materials. All new compounds alongside with their corresponding precursors were fully characterized and their properties were investigated by X-ray crystallography, photophysical measurements and computational methods. The study revealed important structure-effect relationships between the solid-state structures and the observed photophysical properties, e. g. aggregation-induced emission and solid-state fluorescence.