Abstract

Antiaromatic moieties fused in polycyclic π-conjugated molecules usually exhibit strong localized antiaromaticiy. Herein, we reported the synthesis and properties of a bisazapentalene dication (BAP2+) obtained from in situ two-electron oxidation of neutral species 8. Noteworthily, it possesses global aromaticity and an open-shell singlet ground state. This study underlines the importance of heteroatoms in determining the delocalization of π-electrons and the aromaticity of molecules in their oxidized states.

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