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- Title
Synthesis and Properties of Azadibenzo[a,e]pyrenes.
- Authors
Khomutetckaia, Aleksandra; Ehlers, Peter; Villinger, Alexander; Langer, Peter
- Abstract
Four different isomeric azadibenzo[a,e]pyrenes (benzo[4,10]anthra[9,1‐gh]isoquinolines and benzo[4,10]anthra[1,9‐fg]isoquinolines) were prepared by combination of Pd‐catalyzed Sonogashira and Suzuki cross‐coupling, Brønsted acid mediated cycloisomerization and Pd‐catalysed CH‐activation reactions. The optical properties have been studied by steady‐state absorption and emission spectroscopy in different solvents and during acid titration. Trifluoroacetic acid protonation strongly affects absorption and emission properties, with variations depending on the position of the nitrogen atom of the specific compound. Electrochemical analysis showed distinct oxidation and reduction potentials. DFT calculations provided further insights into electronic properties.
- Subjects
SUZUKI reaction; ISOQUINOLINE synthesis; EMISSION spectroscopy; ELECTROCHEMICAL analysis; TRIFLUOROACETIC acid; BRONSTED acids; REDUCTION potential
- Publication
European Journal of Organic Chemistry, 2024, Vol 27, Issue 12, p1
- ISSN
1434-193X
- Publication type
Article
- DOI
10.1002/ejoc.202301299