The long term objective of this research is to develop efficient methods for the preparation of complex molecules, and develop highly versatile and efficient synthesis tools so that any desired molecule may be prepared in a practical manner. Two different approaches will be investigated: (1) iodonium compounds will be developed as new, efficient, general electrophilic cross-coupling partners; (2) coordination directed self-assembly will be explored to prepare large (nanoscale), complex abiological molecules with well defined shapes and size. Specifically, organic chemists will have new reagents for the formation of a variety of structurally demanding C-C bonds and all chemists will have conceptually new strategies for the formation (via noncovalent synthesis) of large, complex molecules via self-assembly. Abiological self-assembly strategies will provide not only valuable insights into nature's own poorly understood self-assembly phenomen, of importance in all living organisms, but will also find many useful applications in molecular recognition, selective substrate transformations, sensing, signal transduction and many other, yet unforeseen, biomedical uses. In the long term, the ready availability of new synthesis methodologies that we are developing will facilitate the production and discovery of improved and new agents for the diagnosis and treatment of medical disorders.
Specific aims for the project are: 1. Systematically investigating the use of aryl-, vinyl- and alkynyliodonium triflates in cross coupling reactions. 2. Examining the use of perfluoroalkyl and perfluoroaryl iodonium salts in cross coupling reactions. 3. Examine the simultaneous use of coordination and hydrogen bonding in the spontaneous self-assembly of unique 2D and 3D ensembles. 4. Developing new, water soluble, coordination based, self-assembly strategies.5. Preparing and characterizing new, unusual 3D molecular species via coordination. 6. Investigating molecular recognition phenomena and host-guest interactions of the above ensembles, including the possible encapsulation of biological molecules. 7. Study the process or mechanism of coordination driven self assembly. 8. Further examining the antimicrobial properties and biological activity of iodonium species. 9. Screening for biological activity, with emphasis on antitumor and anti-HIV activity, all new, stable self-assembled species. The proposed studies are based upon recent, new discoveries in our laboratories on polyvalent chemistry and a novel coordination based self-assembly paradigm.Moreover, the proposed systems have considerable potential as scaffolds for the creation of biomolecular receptors.
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