Synthesis of Axially Chiral Cationic Benzo[c]phenanthridinium Derivatives

Abstract Cationic polycyclic aromatic compounds containing one or more nitrogen atom(s), also known as azonia compounds, form a valuable class of molecules because their fluorescent and/or medicinal properties. N-Arylated hydroisoquinoline derivatives were synthesized through an aryne aza-Diels–Alder cycloaddition/N-arylation sequence. A subsequent two-electron oxidation allowed the synthesis some axially chiral cationic benzo[c]phenanthridinium derivatives. The structural and optical properties these determined. Their chirality was evidenced experimentally by single-crystal X-ray diffraction 1H NMR spectroscopy, conformational behavior examined computational DFT methods.