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 1H NMR spectroscopy, and their conformational behavior was examined by computational
DFT methods.
Key words
arynes - axial chirality - azadienes - azonia compounds - crystallography - DFT -
fluorescence - rotamers
