%0 Journal Article %T Synthesis of Axially Chiral Cationic Benzo[c]phenanthridinium Derivatives %+ Institut des Sciences Moléculaires de Marseille (ISM2) %+ Fédération Sciences Chimiques Marseille (FSCM) %+ Spectropôle - Aix Marseille Université (AMU SPEC) %+ Provepharm Life Solutions %A Agudelo, Brian Castro %A Rigoulet, Florian %A Giorgi, Michel %A Sayah, Babak %A Rodriguez, Jean %A Coquerel, Yoann %< avec comité de lecture %@ 0039-7881 %J Synthesis: Journal of Synthetic Organic Chemistry %I Georg Thieme Verlag %V 54 %N 22 %P 5035-5041 %8 2022 %D 2022 %R 10.1055/a-1845-3128 %K arynes %K axial chirality %K azadienes %K azonia compounds %K crystallography %K DFT %K fluorescence %K rotamers %Z Chemical Sciences/Organic chemistryJournal articles %X 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. %G English %2 https://hal.science/hal-03856921/document %2 https://hal.science/hal-03856921/file/2022S-5035.pdf %L hal-03856921 %U https://hal.science/hal-03856921 %~ CNRS %~ UNIV-AMU %~ EC-MARSEILLE %~ ISM2 %~ INC-CNRS %~ ANR %~ TEST2-HALCNRS