Syntheses and Applications of Nonplanar Polycyclic Aromatic Compounds

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This project involves the use of the cascade cyclization reactions of the highly unsaturated benzannulated enyne-allenes as a key step for the synthesis of bowl-shaped (buckybowls) and basket-like (buckybaskets) polycyclic aromatic compounds. The overall strategy involves first constructing precursors containing multiple tetrahedral sp3-hybridized carbons. The presence of these tetrahedral sp3-hybridized carbons causes several parts of the molecules to be in close proximity to one another, allowing further connections to form carbon-carbon bonds by mild solution-phase chemistry leading to buckybowls and buckybaskets. A success of the proposed synthetic schemes would provide easy access to a variety of such compounds not readily accessible by other methods. In addition, helical heteroaromatic compounds will also be synthesized for helical supramolecular assemblies and asymmetric catalysis.With this award the Organic and Macromolecular Chemistry Program is supporting the research of Professor Kung K. Wang of the Department of Chemistry at West Virginia University. Professor Wang's research efforts have focused on the use of unsaturated systems for the construction of nonplanar organic molecules having unusual architectures. Many of these molecules could possess interesting material properties or biological activities. Successful development of the synthetic methodology will have an impact on the manufacturing processes of the chemical and pharmaceutical industries.