Journal
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
Volume 61, Issue 40, Pages -Publisher
WILEY-V C H VERLAG GMBH
DOI: 10.1002/anie.202209085
Keywords
Acridine; Decarboxylation; Degradation; Photocatalysis; Polymers
Categories
Funding
- National Science Foundation [NSF DMR-1904631]
- DoD through the ARO [W911NF-17-1-0326]
- University of Florida
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Visible light-mediated direct decarboxylation is a versatile technique for the synthesis of functional materials with tailored compositions and properties. This process allows for the generation of carbon-centered radicals in polymer chains without the need for preactivation of acid groups. It can be used to obtain challenging copolymers and trigger degradation of polymer backbones.
Visible light-mediated direct decarboxylation of carboxylic acids with an acridine photocatalyst is a convenient and powerful method to generate carbon-centered radicals in polymer chains. Advantageously, this process proceeds under mild conditions, without preactivation of the acid groups. We utilize decarboxylation in the presence of a hydrogen atom donor to form statistical acrylate-ethylene and acrylate-propylene copolymers, which are challenging to obtain by direct polymerization. We additionally show that decarboxylation of methacrylic acid units within polymethacrylates can trigger degradation of the polymer backbones. Moreover, a dual catalytic approach, which combines the function of an acridine photocatalyst with that of a cobaloxime catalyst, is leveraged to furnish unique copolymers with pendent alkenes. Our work indicates that direct decarboxylation is a versatile technique for the synthesis of functional materials with tailored compositions and properties.
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