The Direct Arylation Polymerization (DArP) of Well-Defined Alternating Copolymers Based On 5,6-dicyano[2,1,3]benzothiadiazole (DCBT)

Qinqin Shi, Wesley Tatum, Junxiang Zhang, Colleen Scott, Christine K. Luscombe, Seth R. Marder, and Simon B. Blakey

Asian J. Org. Chem.,
2018, 7, 7, 1419-1425; DOI: 10.1002/ajoc.201800232

06/2018

Direct arylation polymerization (DArP) represents an ideal sustainability method that has seen recent use in material sciences. However, chemically embedded defects from DArP such as homocoupling, branching, and cross-coupling, remain difficult to identify. We isolated dimers, trimers and pentamers by coupling material related building blocks and DCBT. Analysis of 1H NMR and 13C NMR, as well as the optical and electrochemical properties of the polymers and corresponding oligomers provide evidence for the regioregular structure of the polymers. One of the polymers has been tested to show modest electron transport mobility by transistor devices.

This collaborative work from researchers in four CCHF groups successfully applied our previous palladium catalyzed C-H activation methodology on benzothiadiazole (J. Org. Chem., 2016, 81, 360-370) into copolymerization without observable structural defects.

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