Non-Metal Based Perfluoroalkoxides for New Fluoropolymeric Materials, Theranostics, Pharmaceuticals, and Catalysts

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NATURE OF THE WORK: Fluorinated salts- usually known as perfluorinated alkoxides (PFAs)-are believed to be difficult to prepare, thus inhibiting their use in many research fields. In 2013, our group developed a simple reaction that bridges this gap in fluorine chemistry. The properties and many applications of PFAs can now be studied. We have discovered a route to readily form anhydrous tetra-alkylammonium PFAs in a single step using inexpensive, safe, and easy-to-use reagents. In particular, we have found that hydrofluoroethers (HFEs; i.e. commercial refrigerants) react with amines to generate PFAs. WHY AND TO WHOM THE RESEARCH IS IMPORTANT: PFAs are expected to have an impact in four important industries: A) The fluoropolymer industry requires building blocks (fluoromonomers with at least two reactive functional groups) which can be incorporated into biodegradable polymers to improve performance yet maintain environmental balance. With our techniques we will synthesize PFAs for producing polymers which are suitable as protective coatings, surfactants, and devices to recycle precious metals. B) The medical industry has a need for better diagnostic and therapeutic drug delivery devices (i.e. theranostics) for personalized patient care and lipophilic drugs. With PFA's exacting control, we will create polymeric tools to be applied to this important area of patient care. New methods in late-stage incorporation of PFAs in lipophilic drug manufacturing are desirable. Having useable PFAs expands options in drug design and makes the process cheaper (40% of current drugs contain fluorine). C) The electronic industry chemically vapor-deposits metals in layers for semiconductors (photovoltaics/integrated circuits). PFA could be used to volatilize metals as well as forming materials for non-flammable lithium batteries. D) The energy industry has a need to diversify fuel sources. PFAs bound to transition metals could generate new catalysts.  These new catalysts can impact the petroleum reformation processes (converting material from low octane to high octane fuels) or fuel generation (polymerization of natural plant products to make bio-polymers or fuels). ANTICIPATED OUTCOMES: In our research for the next six years, we will: A) Develop new HFEs which can be used to generate difunctional fluoropolymers (telechelic perfluoropolyalkylethers, PFPAEs) for new materials; B) Understand the stability of PFAs as a ligand with transition metals for catalyst formation; C) Attach PFAs to aromatics for advancing late-stage fluorination in drug design. In summary, we will develop new PFAs with targeted properties for new materials, industrial processes, and pharmaceuticals.