Synthesis reveals electrochemical features and diradical character in a pyrrole-fused aza-nanographene, indicating unique properties.
A fused octapyrrolylanthracene, representing a nonplanar pyrrole-fused aza-nanographene with two deep gulf-edge regions, was readily synthesized and found to exhibit a ladder-shaped bent structure. Electrochemical studies revealed reversible multielectron oxidation up to four electrons. Stepwise oxidation with AgPF6 or I2 afforded a singlet diradical dication and a closed-shell aromatic tetracation. ESR spectroscopy indicated thermally populated diradical character, while NMR and ACID/NICS calculations confirmed global aromaticity in the tetracation.
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Matsunaga et al. (2025) studied this question.
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