Synthesis and Properties of Pyridofluoranthenes

Abstract

A series of N‐doped Benzo[b]fluoranthenes was synthesized. Specifically varying the position of the Nitrogen atom in all four positions of the bottom ring. In the last reaction step the five‐membered ring of the unsubstituted core structure is formed by palladium catalyzed CH‐activation. This synthetic approach allows for the selective introduction of heteroatoms into the core structure and leads to four regioisomeric products. Subsequently the optical and electrochemical properties of these polyaromatic heterocycles were compared. DFT/TD‐DFT and NICS calculations were performed to further analyze, how the position of Nitrogen impacts the overall characteristics of the molecules. This composes a thorough study on the chemical behavior of N‐doped Benzo[b]fluoranthenes.