Developing ipso-arylative coupling routes to conjugated molecules and macromolecules

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With this award, the Macromolecular, Supramolecular and Nanochemistry Program of the Division of Chemistry is supporting Professor Robert B. Grubbs of Stony Brook University to investigate the development of methods for the preparation of semiconducting polymers for new organic electronic materials and devices. Organic electronic materials are of growing industrial importance due to their potential as low-cost, flexible, and lightweight materials with potential uses in a number of applications, notably those where they function as sensors, light-emitting materials, and materials for converting solar energy to electrical energy. These methods allow the use of stable monomers that can be polymerized with less toxic by-products than other methods, and have the potential to allow the preparation of a range of new polymer structures. This work provides training for graduate students, including students from traditionally underrepresented groups, in organic electronic materials research, and involves regular interactions with scientists at Brookhaven National Laboratory. As part of this project, participants plan to present their work at local, regional, national, and international meetings, as well as at a workshop on environmental science and sustainability for local high school teachers. Professor Grubbs and co-workers are investigating the use of palladium-catalyzed ipso-arylative coupling methods for the preparation of conjugated polymers. The key objectives of the project are to expand and optimize ipso-arylative polymerization methods to allow polymerization of a broader range of monomers and apply these conditions to the preparation of new polymer structures, including those with controlled sequences of different monomers. Developing an understanding of the effects of monomer structure and polymerization conditions on the preparation of model poly(3-hexylthiophene) systems is a key goal. The design of ipso-arylative ring-opening polymerization systems, which allows polymerization to proceed without the formation of by-products, is also a key goal. The newly developed methods are being used in the preparation of new conjugated polymers, including side-chain-functionalized polymers (by ring-opening polymerization), poly(2,6-pyridyl) derivatives, and designed sequences of conjugated oligomers. In each case, the use of ipso-arylative coupling conditions is critical to the construction of the new polymers. As new polymers are prepared and characterized, their electronic properties are to be measured in collaboration with co-workers at the Center for Functional Nanomaterials at Brookhaven National Laboratory.