N,O‑Chelated Organoboron Complexes with Seven-Membered Rings

Organoboron complexes have gained considerable attention owing to their versatile chemical structures and excellent optical properties. Nevertheless, stable seven-membered organoboron complexes have rarely been reported because of their challenging synthesis. Herein, seven-membered N,O-boron-chelate...

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Bibliographic Details
Published in:Journal of organic chemistry 2022-06, Vol.87 (12), p.7712-7719
Main Authors: Yang, Jie, Gai, Lizhi, Chen, Xiaoyang, Liu, Yanfei, Wu, Shengmei, Feng, Jiao, Sui, Xinbing, Lu, Hua
Format: Article
Language:English
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Summary:Organoboron complexes have gained considerable attention owing to their versatile chemical structures and excellent optical properties. Nevertheless, stable seven-membered organoboron complexes have rarely been reported because of their challenging synthesis. Herein, seven-membered N,O-boron-chelated dyes, whose photophysical properties have been thoroughly studied via spectroscopic tests and theoretical calculations, were synthesized from commercially available materials via a facile method. Single-crystal X-ray diffraction studies provided evidence of their seven-membered ring N,O-boron-chelated skeleton. These complexes produced singlet oxygen species under laser irradiation, endowing them with potential application as a photosensitizer to treat superficial tumors (B16 cells). Our study provided a new skeleton to construct versatile organoboron compounds and offered a strategy to design heavy-atom-free photosensitizers.
ISSN:0022-3263
1520-6904
DOI:10.1021/acs.joc.2c00269