Synthesis of Cycloalkanoporphyrins and Related Highly Conjugated Systems

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The focus of this research is the synthesis and origins of the porphyrins from oil shales and petroleum, including porphyrins with five- and six-membered exocyclic rings. In addition, the preparation of N-15 and deuterium labeled porphyrins needed for resonance Raman studies will be carried out. Other porphyrin systems that will be synthesized include porphyrin dimers and novel porphyrin-containing chromophores such as indenoporphyrins, naphth 2,3-b porphyrins, tetranapthoporphyrins, phenanthropor-phyrins, coronenoporphyrins and phenanthrolinoporhyrins. These latter porphyrins will be of particular interest because of their ability to bind metal cations at the external phenanthroline subunit as well as within the central porphyrin cavity. With this award, the Synthetic Organic Program is supporting the research of Dr. Timothy D. Lash of the Department of Chemistry at the Illinois State University. Professor Lash will focus his work on the synthesis of sedimentary cycloalkanoporphyrins, which are geochemical markers that help determine the origins of oil shales and petroleum, and also novel porphyrin-containing chromophores with highly conjugated systems. These later compounds will provide an important new entry into supramolecular porphyrin chemistry.