ArticleChemistry (Weinheim an der Bergstrasse, Germany)2026
Twisted 1- and 2-Azaperopyrenes: Synthesis, Structure, and Properties.
Article in Chemistry (Weinheim an der Bergstrasse, Germany), 2026. The graph could read no effect estimate from its abstract, so it casts no vote on the map. Cited by 1 paper.
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1 citing paper in PubMed.
- Twisted 1- and 2-Azaperopyrenes: Synthesis, Structure, and Properties.Chemistry (Weinheim an der Bergstrasse, Germany) · 2026Article
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5 authors.
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Abstract
A synthesis of hitherto unknown 1- and 2-azaperopyrenes, twisted nitrogen-doped peropyrenes, is reported. The synthesis is based on a Brønsted acid-mediated benzannulation of alkynes. Key alkyne intermediates are synthesized via two complementary routes, including a Pd/C-catalyzed, copper- and amine-free Sonogashira-type coupling of (hetero)aryl chlorides, enabling access to both carbo- and heteroatom-substituted peropyrene frameworks. X-ray crystallography reveals twisted conformations with bay and end-to-end twist angles ranging between 10.0-19.9° and 5.5-25.0°, respectively, as well as unprecedented conformational isomorphism. The influence of regioselective single N-doping within the twisted peropyrene framework on the photophysical and electrochemical properties were elucidated by combined experimental and computational studies and compared with those of the carbon congener.
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