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

ABSTRACT: 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.

SUBMITTER: Tang Q

PROVIDER: S-EPMC9132079 | biostudies-literature | 2022 May

REPOSITORIES: biostudies-literature

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

Tang Qi Q Li Shi-Jun SJ Ye Xiaohan X Yuan Teng T Zhao Kai K He Ying Y Shan Chuan C Wojtas Lukasz L Richardson David D Lan Yu Y Shi Xiaodong X

Chemical science 20220418 20

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 coordi ...[more]

PMID: 35685813

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