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Synthesis and Photophysical Properties of Azaarene-Substituted Hypocrellin B Derivatives
Tian Liu1,2, Xiuli Zheng1,2, Tong Mu1,2
1Key Laboratory of Photochemical Conversion and Optoelectronic Materials, Technical Institute of Physics and Chemistry, Chinese Academy of Sciences, Beijing 100190, China.
Abstract:
Azaarenes have been widely used in the field of organic synthesis due to their unique electronic structures, bonding characteristics, and functional performances. In this work, three azaarene-substituted hypocrellin B (HB) derivatives were prepared through C-N coupling at position 13 by a radical pathway. In the presence of triethylamine, the complex of HB and fluoroboron (HB-2BF) could form an anion radical, which easily reacts with azaarene at position 13. Acting as a precursor for the anion radical, HB-2BF could synthesize azaarene-substituted HB derivatives with excellent properties, such as the 2-pyridone-modified HB derivative (HBPD), which functions as a 1O2-responsive "off-on-off" photosensitizer for phototherapy.
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