In this project funded by the Chemical Synthesis Program of the Chemistry Division, Professor Timothy D. Lash of the Department of Chemistry at Illinois State University will explore the synthesis, characterization, and reactivity of porphyrin-like macrocycles, including neo-confused porphyrins and other carbaporphyrinoid systems. Specifically, syntheses of heterobenziporphyrins and heteropyriporphyrins will be developed using a "3 + 1" strategy. The chemistry of previously prepared monocarbaporphyrins will also be studied. A strategy for synthesizing carbaporphyrins and carbachlorins from a cyclopentene dialdehyde and a new route to benzocarbaporphyrins from 6-methoxyazulene will be developed. General approaches to the synthesis of a new class of porphyrin isomers known as neo-confused porphyrins will be investigated. In addition to dicarbaporphyrinoids, tri- or tetracarbaporphyrinoid systems will be studied.
This work will not only lead to more efficient routes to carbaporphyrinoid systems but will also allow access to new classes of porphyrin analogues. This project is important to improve our basic understanding of fundamental chemistry concepts such as aromaticity. It also has practical applications for the synthesis of fine chemicals, since the target compounds can be used to construct catalysts for chemical synthesis. In addition, the target compounds are important in medicines, as they have potential applications in photodynamic therapy. These projects not only provide an excellent environment for training undergraduates and master level graduate students in the field of organic synthesis, but they also expose them to the multidisciplinary nature of modern scientific research.
