Molecular Design of Donor­Acceptor­Type Organic Photocatalysts for Metal­free Aromatic C­C Bond Formations under Visible Light

Title
Molecular Design of Donor­Acceptor­Type Organic Photocatalysts for Metal­free Aromatic C­C Bond Formations under Visible Light
Authors
변지혜Lei WangRun LiWei HuangKai A. I. Zhang
Issue Date
2018-11
Publisher
Advanced synthesis & catalysis
Citation
VOL 360, NO 22-4318
Abstract
Metal-free and photocatalytic radical-mediated aromatic C-C bond formations offer a promising alternative pathway to the conventional transition metal-catalyzed cross-coupling reactions. However, the formation of aryl radicals from common precursors such as aryl halides is highly challenging due to their extremely high reductive potential. Here, we report a structural design strategy of donor-acceptor-type organic photocatalysts for visible light-driven C-C bond formations through the reductive dehalogenation of aryl halides. The reduction potential of the photocatalysts could be systematically aligned to be -2.04 V vs. SCE via a simple heteroatom engineering of the donor-acceptor moieties. The high reductive potential of the molecular photocatalyst could reduce various aryl halides into aryl radicals to form the C-C bond with heteroarenes. The designability of the molecular photocatalyst further allowed the synthesis of a high LUMO (lowest unoccupied molecular orbital) polymer photocatalyst by a self-initiated free radical polymerization without compromising its LUMO level.
URI
http://pubs.kist.re.kr/handle/201004/70701
ISSN
1615-4150
Appears in Collections:
KIST Publication > Article
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