Journal
APPLIED SURFACE SCIENCE
Volume 546, Issue -, Pages -Publisher
ELSEVIER
DOI: 10.1016/j.apsusc.2021.149138
Keywords
Metal free; Reactive oxygen species; Imide; Photocatalysis; Hydroxylation of arylboronic acids
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Funding
- Doctor Foundation of Southwest University of Science and Technology [18zx7137]
- Opening Project of State Key Laboratory of Polymer Materials Engineering (Sichuan University) [sklpme2019-4-33]
- State Key Laboratory of Polymer Materials Engineering [sklpme2019-2-08]
- Project of State Key Laboratory of Environment-friendly Energy Materials, Southwest University of Science and Technology [20fksy17]
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A metal-free and straightforward protocol for the photocatalytic synthesis of phenols from arylboronic acids has been demonstrated using perylene-g-C3N4 polymeric semiconductors. The research revealed that internal imide functional groups within the catalyst's molecular structures can facilitate ROS generation, with O-2(center dot-) being the decisive specie in the hydroxylation. Yield can reach as high as 97% using this method.
A metal-free and straightforward protocol for the photocatalytic synthesis of phenols from arylboronic acids has been demonstrated using perylene tri-s-triazine (perylene-g-C3N4) polymeric semiconductors. Tri-s-triazine and perylene are connected through imide bonds to give catalysts P-M of high imide-bond ratio and P+M of low imide-bond ratio. The aerobic hydroxylation of arylboronic acids can be operated at room temperature and atmospheric environment under white-light LED irradiation. This research work has revealed that internal imide functional groups within the catalyst's molecular structures can facilitate the ROS (O-2(center dot-), OH center dot and O-1(2)) generation and O-2(center dot-) is the decisive specie in the hydroxylation due to the faster reaction rate compared with OH center dot and O-1(2), with yield as high as 97%. This environment-friendly method and the molecule design principle will provide a valuable strategy for developing metal-free polymeric semiconductors with specific molecular structures and deep insights into the ROS involved catalysis in photo-generated chemical transformations.
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