BNB-doped phenalenyls - aromaticity switch upon one-electron reduction

Fully aromatic, luminescent, and highly robust BNB-doped phenalenyls have been prepared, which are isoelectronic to the phenalenyl cation. B-Fluoromesityl-substitution leads to fluorescence in an extremely narrow range and significant increase in the reduction potential. Detailed theoretical investigations revealed an intramolecular aromaticity switch upon one-electron reduction.

Automated summary

The synthesis of fully aromatic, luminescent, and highly robust BNB-doped phenalenyls, isoelectronic to the phenalenyl cation, was successfully achieved. B-Fluoromesityl-substitution resulted in fluorescence within a narrow range and a significant increase in reduction potential. Detailed theoretical investigations unveiled an intramolecular aromaticity switch upon one-electron reduction.