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Synthesis of Axially Chiral Cationic Benzo[c]phenanthridinium Derivatives

Résumé

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.

Domaines

Chimie organique

Dates et versions

hal-03856925 , version 1 (17-11-2022)

Licence

Domaine public

Identifiants

  • HAL Id : hal-03856925 , version 1

Citer

Brian Castro Agudelo, Florian Rigoulet, Michel Giorgi, Babak Sayah, Jean Rodriguez, et al.. Synthesis of Axially Chiral Cationic Benzo[c]phenanthridinium Derivatives. France. 2022. ⟨hal-03856925⟩
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