Harnessing the orthogonality of fluorine for advanced biomaterials and biotechnologies

Perfluorination imparts unique, abiotic properties to molecules and materials. The unifying goal of our work is exploiting these properties to enhance therapeutics, diagnostics, and create new chemical tools. In one approach, we capitalize on the inverse quadrapole moment imparted by perfluorination of aromatics. We design cyclophane host molecules that can recognize perfluorinated aromatic compounds in living systems through arene-perfluoroarene interactions as well as secondary non-covalent or covalent interactions. Ultimately, we aim to apply these novel host–guest complexes to the detection and/or treatment of diseases with a metabolic signature, such as cancer, inflammation, and drug-resistant infection. A different area employs perfluoroalkyl compounds, more commonly referred to as perfluorocarbons, which phase separate from aqueous and organic solution. The perfluorocarbons can be stabilized as droplets in water by using surfactant to create perfluorocarbon nanoemulsions. We view perfluorocarbon nanoemulsions as bioorthogonal, nano, reaction vessels and develop methods to load an array of payloads, control their biodistribution, and trigger their disassembly. The major goal of this work is to create a versatile nanomaterial scaffold that can be tailored toward many different diseases in a personalized manner. Additionally, we continue our fruitful collaboration with the Camp às group who have developed the first methods to measure mechanical forces in tissue by capitalizing on the orthogonality of perfluorocarbons. This method involves the microinjection of a droplet of perfluorocarbon containing a surfactant and fluorophore. The surfactant controls the interfacial tension of the droplet and the fluorophore allows for visualization by confocal microscopy. As the cells exert forces on the droplet, the droplet deforms. The deformation can be observed by microscopy and, if the interfacial tension is known, correlated back to forces. We employ our expertise in fluorous fluorophore and amphiphile synthesis to create custom components for the droplet measurements, expanding the range of forces and scope of animals in which these measurements can be performed.