π-Expanded azaullazines: synthesis of quinolino-azaullazines by Povarov reaction and cycloisomerisation

Doping and extension of polycyclic aromatic hydrocarbons (PAHs) by simple and efficient synthetic methods is of increased demand for the development of novel and improved organic electronics. Diarylindolizino[6,5,4,3- ija ]quinolino[2,3- c ][1,6]naphthyridines (quinolino-azaullazines) were prepared...

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Bibliographic Details
Published in:Organic & biomolecular chemistry 2024-03, Vol.22 (1), p.227-242
Main Authors: Polkaehn, Jonas, Thom, Richard, Ehlers, Peter, Villinger, Alexander, Langer, Peter
Format: Article
Language:English
Subjects:
Charge transfer
Cross coupling
Cyclic compounds
Isomerization
Optical properties
Polycyclic aromatic hydrocarbons
Quinoline
Substitution reactions
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Summary:Doping and extension of polycyclic aromatic hydrocarbons (PAHs) by simple and efficient synthetic methods is of increased demand for the development of novel and improved organic electronics. Diarylindolizino[6,5,4,3- ija ]quinolino[2,3- c ][1,6]naphthyridines (quinolino-azaullazines) were prepared by combination of Pd catalyzed cross-coupling with Povarov and cycloisomerisation reactions. The products contain an electron-rich ullazine and an electron-poor quinoline moiety and show intramolecular charge transfer properties that can be tuned by the substitution pattern. The optical properties were studied experimentally and further elaborated by (TD)DFT calculations. Quinolino-azaullazines were prepared by combination of Pd catalyzed cross-coupling with Povarov and cycloisomerisation reactions. They show intramolecular charge transfer properties that can be tuned by the substitution pattern.
ISSN:1477-0520
1477-0539
1477-0539
DOI:10.1039/d4ob00091a