Approaches to Diverse Fluoroorganics and Fluorinated Building Blocks

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The Chemical Synthesis Program of the NSF Chemistry Division supports the research of Professor Barbara Zajc in the Department of Chemistry at the City College of the City University of New York. Professor Zajc and her students develop novel methods for synthesis of fluorinated organic compounds. Organofluorine compounds are of importance in diverse fields, including agrochemicals and pharmaceuticals, materials sciences, and as biological probes. Approximately one in five pharmaceuticals contains a fluorine atom. Fluorine-18 (18F) labeled organofluorine compounds are often used in medicine (for positron emission tomography (PET) imaging). As an example, 2-deoxy-2-(18F)-D-glucose is commonly used in brain imaging. Organofluorine compounds are also rapidly gaining importance as Magnetic Resonance Imaging (MRI) contrast agents - also used in the diagnosis of disease. 19F MRI is being studied for brain imaging, for instance, visualizing amyloid plaque formation in Alzheimer's disease. Development of novel methods for the efficient synthesis of organofluorine compounds, which is the focus of this funded project, is therefore of strong interest. Students in Professor Zajc's research group are of diverse ethnicity and from an international community. Research projects are designed for training students at all educational levels, in order to provide experience in an area of societal relevance.The unique and valuable properties of organofluorine compounds make them important in a range of scientific areas. However, selective introduction of fluorine atoms into organic molecules continues to be challenging. This project develops novel chemical approaches to various classes of regiospecifically fluorinated compounds - those containing chiral centers. Some of the molecules developed may have a direct impact on studying neurodegenerative disorders. The approaches undertaken here focus on modular assemblies using new fluorinated building blocks. Where applicable, the role of fluorine on reactivity is studied. Due to the widespread importance of organofluorine compounds in medicinal and biological chemistry, including diagnostics such as the study of brain disorders using 19F MRI imaging, this research may have impact in areas beyond chemical synthesis. The research activities involve education and training of students from diverse ethnic groups, including those that are underrepresented in the sciences. The City College of New York has a large minority student population, and their education and training has an impact on a diversified workforce.