Synthesis and Evaluation of Pyrrole-Modified Porphyrins

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With this new award, the Organic and Macromolecular Chemistry Program supports the work of Professor Christian Bruckner of the Department of Chemistry at the University of Connecticut. The research project centers on the synthesis and evaluation of pyrrole-modified porphyrins. Pyrrole-modified porphyrins are macrocycles derived from porphyrins by formally replacing at least one pyrrolic building block with a different heterocyclic ring. The guiding hypothesis of the work is that these modifications will result in molecules with drastically altered electronic properties as compared to porphyrins, particularly with respect to their photophysical properties such as ultra violet-visible and two photon absorbance, emission, and resonance Raman spectra. The photophysical properties of the newly synthesized porphyrins will be correlated with their structural parameters such as the degree of non-planarity and conformational flexibility. An understanding of these relationships will allow the synthesis of porphyrins with designed photophysical properties.This project, which will result in expansion of the synthetic methodologies used in the porphyrin field, will facilitate the synthesis of a variety of novel materials. These substances, with their unique photophysical properties, are likely to have application as sensors and in the biomedical field as photo-therapeutics and photodiagnostic imaging agents. The program involves multidisciplinary training for undergraduate and graduate students in organic synthesis, coordination chemistry, and spectroscopic structure determination. Year-round undergraduate research projects will be part of this project. The research will be facilitated by international collaborations in Germany and Great Britain and by a collaboration with a local undergraduate institution.