Expanded Porphyrins and Other Synthetic Polypyrrole Macrocycles

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This renewal project is focused on the chemistry of expanded porphyrins and related polypyrrolic macrocycles. Emphasis will be placed on compounds that are likely to i) demonstrate unusual cation coordinating properties, ii) show liquid crystalline behavior, or iii) display interesting theoretical, spectroscopic, or optical properties. The proposed work is expected to provide further insights into the basic "ground rules" that govern the chemistry of polypyrrole macrocycles, namely how are intrinsic structural properties, such as macrocycle size, shape, and aromaticity (or lack thereof), translated into observable chemical features, including substrate recognition selectivity, metal complex stability, and liquid crystallinity. New synthetic methods, including those based on oxidative coupling, sulfur bridging, and nitrogen linking, will be developed to complement known methodologies, such as Heck couplings and olefin metathesis, that have yet to receive much attention in the expanded porphyrin or oligopyrrole macrocycle areas.With this renewal award, the Organic and Macromolecular Chemistry Program is supporting the research of Professor Jonathon L. Sessler, of the Department of Chemistry and Biochemistry at the University of Texas at Austin. Professor Sessler is exploring methods for the synthesis of novel organic compounds related to the so-called porphyrin unit that forms the basis of the oxygen transport and storage proteins, hemoglobin and myoglobin. The resulting systems are expected to give rise to new catalysts, sensors, and light modulating devices. Work in the synthetic porphyrin analogue area is highly interdisciplinary, involving aspects of organic synthesis, inorganic coordination chemistry, spectroscopy, optics, materials science, catalysis, and theoretical analysis. It thus provides an excellent training for young researchers who are then able to work effectively in a variety of research settings, including academe, industry, and government. Work in this area also contributes directly to the development of our technological infrastructure.