Nitrogen-Doped Dehydrobenzoannulene as an Electron Acceptor Enabling Trace Epinephrine Analysis.

Herein, utilizing dehydrobenzoannulene and azadehydrobenzoannulene as the acceptor, three electron donor-acceptor architectures were divergently synthesized. Intriguingly, benefiting from the nitrogen-doped skeleton, the corresponding aza derivative exhibited striking red-shifted fluorescence and enhanced bipolar electrochemiluminescence. Furthermore, their intramolecular charge transfer properties were disclosed by solvent-dependent fluorescence and density functional theory calculations. Finally, an azadehydrobenzoannulene-based sensor for the epinephrine assay was constructed, which provided a sensitive analytical system for early diagnosis of neurodegenerative diseases.