Journal
CHEMICAL SCIENCE
Volume 13, Issue 20, Pages 5982-5987Publisher
ROYAL SOC CHEMISTRY
DOI: 10.1039/d2sc01103d
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Funding
- NSF [CHE-2054180]
- NIH [1R01GM120240-01]
- University of South Florida Interdisciplinary NMR Facility
- University of South Florida Chemical Purication, Analysis, and Screening (CPAS) Core Facility
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A new class of stable four-coordinated benzotriazole-borane compounds was developed via gold-catalyzed alkyne hydroboration. These compounds showed excellent stability, strong and tunable fluorescence emission, and easy synthesis, making them interesting new fluorescent probes for future chemical and biological applications.
A new class of stable four-coordinated benzotriazole-borane compounds was developed via gold-catalyzed alkyne hydroboration. The application of polymeric (BH2CN)(n) 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.
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