Synthesis of Axially Chiral Cationic Benzo[c]phenanthridinium Derivatives

Cationic polycyclic aromatic compounds containing one or more nitrogen atom(s), also known as azonia polycyclic aromatic compounds, form a valuable class of molecules because of 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 of some axially chiral cationic benzo[c]phenanthridinium derivatives. The structural and optical properties of some of these molecules were determined. Their chirality was evidenced experimentally by single-crystal X-ray diffraction and H-1 NMR spectroscopy, and their conformational behavior was examined by computational DFT methods.

Automated summary

A class of cationic polycyclic aromatic compounds containing nitrogen atoms, known as azonia polycyclic aromatic compounds, were synthesized and their structural, optical, and conformational properties were studied using experimental and computational methods.