RUI: Synthesis of Macrocyclic Polymers Using Radical Trap Assisted-Intramolecular Atom Transfer Radical Coupling

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In this project funded by the Macromolecular, Supramolecular and Nanochemistry Program of the Chemistry Division, Eric Tillman of Bucknell University will devise synthetic routes leading to macrocyclic polymers, which posses a set of properties distinct from their linear analogs and offer potential advantages in diverse areas in which polymers are used. The focus of this proposal is the addition of a radical trap, such as a nitroso group, to an end-to-end atom transfer radical coupling reaction of a dihalogenated linear precursor, creating a scenario where the halogenated chain ends no longer require simultaneous activation to undergo ring closure. This synthetic route will be applied to the synthesis of a variety of macrocyclic architectures, from cyclic diblock copolymers, chromophore-functionalized cyclic polymers, and even complex multicyclic structures. As a broader impact of the research, undergraduate and Masters-level students will gain valuable training in both synthesis and characterization of polymeric materials.Polymers are long chain organic molecules and are found in many facets of everyday life that utilize plastics, including food packaging, structural materials for automotive and aerospace transportation, and lightweight electronic devices. Cyclic polymers offer a set of properties that often differ substantially from the linear polymers from which they are derived, yet are notoriously difficult to synthesize. Cyclic polymers may be potentially useful in a variety of applications, such as electronic materials and drug delivery vehicles. This research focuses on both developing a new, straightforward route to preparing cyclic polymers and applying this strategy to prepare polymers displaying complex cyclic architectures.