Issue 20, 2022

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.

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

Supplementary files

Article information

Article type
Edge Article
Submitted
21 Feb 2022
Accepted
18 Apr 2022
First published
18 Apr 2022
This article is Open Access

All publication charges for this article have been paid for by the Royal Society of Chemistry
Creative Commons BY-NC license

Chem. Sci., 2022,13, 5982-5987

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

Q. Tang, S. Li, X. Ye, T. Yuan, K. Zhao, Y. He, C. Shan, L. Wojtas, D. Richardson, Y. Lan and X. Shi, Chem. Sci., 2022, 13, 5982 DOI: 10.1039/D2SC01103D

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