Carbaporphyrins and other highly modified porphyrinoid systems

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This project proposes an in-depth investigation of the synthesis, characterization, and reactivity of a number of novel porphyrin-like macrocycles. It is suggested that these studies may provide fundamental insights into properties of porphyrin-type structures (e.g., aromaticity), may afford compounds with potentially useful properties (e.g., long wavelength absorbance for photodynamic therapy applications), and may facilitate the preparation of novel organometallic derivatives with interesting and potentially useful catalytic properties. Improved routes to carbaporphyrins and related porphyrinoids will be developed. Direct routes to meso-tetraarylazuliporphyrins and benzocarba-porphyrins have allowed the synthesis of novel organometallic derivatives, and future investigations will target further metalation reactions and modifications to the porphyrinoid macrocycle (e.g., with diimide or osmium tetroxide). The new molecules will be thoroughly characterized by spectroscopic methods and, where possible, X-ray crystal structures will be obtained. The chemistry and spectroscopic properties of these novel carbaporphyrinoids will provide further insights into the aromatic properties of porphyrin-type structures. Further modified structures will be prepared from 1,8-dihydroxy-naphthalene-2,7-dicarbaldehyde and 1,10-phenanthroline-2,9-dicarbaldehyde, and these macrocycles will most likely show interesting coordination chemistry.With this award, the Organic and Macromolecular Chemistry Program supports Professor Timothy D. Lash of Illinois State University whose research has important implications for the fields of heterocyclic and organometallic chemistry, and may lead to applications as diverse as catalysis and medicine. Hence, these projects not only provide an excellent environment for training undergraduates and MS level graduate students in the field of organic synthesis, but also expose them to the multidisciplinary nature of modern scientific research.