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 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

Publication History

Received: 31 March 2022

Accepted after revision: 06 May 2022

Accepted Manuscript online:
06 May 2022

Article published online:
20 June 2022

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