Brominated [15]Dehydrobenzoannulenes: Synthesis, Properties, and Applications

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Abstract Utilizing dehydrobenzoannulene (DBA) as a structural core, a brominated DBA molecular carbon material was concisely synthesized. To investigate the influence of substituents on the properties of such structures, four electron-donating methoxy groups were introduced onto the DBA ring. As a result, despite having a lower relative photoluminescence quantum yield compared to its tert-butyl analogue, the methoxy-substituted structure exhibited significant red shifts in both absorption and fluorescence emission spectra. Subsequently, the electrochemiluminescence (ECL) of the methoxy-substituted structure and its tert-butyl analogue were comparatively investigated, which revealed that the methoxy groups could significantly enhance the ECL emission. Finally, a dopamine sensor based on the brominated DBA was constructed, which demonstrated favorable detection performance. Through systematic comparative investigation, this work elucidated the regulatory role of methoxy substitution on the optoelectronic properties of DBA-based materials, providing a new strategy for designing high-performance molecular carbon materials for biosensing.

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