A new class of stable four-coordinated benzotriazole-borane compounds was developed via gold-catalyzed alkyne hydroboration.  The application of polymeric (BH<sub>2</sub>CN)<sub>n</sub> reagent gave the formation of cyano-amine-boranes (CAB) complexes with less basic N-heterocyclic amines and anilines.  Various new CABs were investigated in catalytic hydroboration to synthesize N-B cycles.  The 1,2,3-benzotriazoles were identified as the only feasible N-source, giving the four coordinated borane N-B cycles (BTAB) in excellent yields (up to 90%) with good functional group tolerability.  This new class of polycyclic N-B compounds showed excellent stability toward acid, base, high temperature, and photo-irradiation.  The facile synthesis, excellent stability, strong and tunable fluorescence emission make BTAB interesting new fluorescent probes for future chemical and biological applications.

Design and synthesis of stable four-coordinated benzotriazole-borane with tunable fluorescence emission

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