Annulated borepinol 1 was designed and synthesized. Borepinol 1 exhibited aromaticity that could be controlled by coordination at the boron center. Disrupted coordination by nucleophiles resulted in blue shifts in the UV-vis spectra, and this coordination was affected by the molecular structure of the nucleophiles. Borepinol 1 appeared to selectively bind to dopamine over norepinephrine, which are normally difficult to differentiate.