Fluoropolymers are widely used in many different industries due to the desirable physical properties of these polymers, such as high melting points and high electrical and chemical resistance. The inert nature of carbon-fluorine bonds surrounding the carbon backbone is what gives these materials their outstanding properties, but also make the resulting materials difficult to characterize and manipulate into functional products. The reaction conditions to generate many of these fluoropolymers involve high pressure with toxic and highly reactive gases, and the resulting polymers are troublesome to modify, with ionizing radiation being a common method. We have developed a mild and scalable method to produce fluorinated polymers through step-growth polymerization of a diiodoperfluoroalkane with a diene or diyne. The resulting polymers are highly tuneable, as functional groups can be placed within the diene/diyne monomers and the length of the fluorous block can be readily adjusted. Furthermore, this polymerization generates alkyl/vinyl iodine across the polymer backbone which is a superb molecular handle for displacement, reduction, elimination, cross-couplings, and cycloaddition post-polymerization modifications. Collectively, this new methodology sets the stage for the creation of functional fluorous materials.

Mild polymerization methods for the synthesis of modular fluoropolymers

2019 Fall National Meeting

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