Journal
JOURNAL OF ORGANIC CHEMISTRY
Volume 87, Issue 12, Pages 7712-7719Publisher
AMER CHEMICAL SOC
DOI: 10.1021/acs.joc.2c00269
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Funding
- National Natural Science Foundation of China [21801057, 21871072]
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This study synthesized dyes with stable seven-membered N,O-boron-chelated skeleton and thoroughly investigated their photophysical properties through spectroscopic tests and theoretical calculations. Single-crystal X-ray diffraction studies provided evidence of their structure. These dyes produced singlet oxygen species under laser irradiation, showing potential as photosensitizers for treating superficial tumors.
Organoboron complexes have gained considerable attention owing to their versatile chemical structures and excellent optical properties. Nevertheless, stable seven-membered organo-boron 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.
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