Synthesis and Evaluation of Pyrrole-Modified Porphyrins

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The Chemical Structure, Dynamics and Mechanisms Program in the Chemistry Division at the National Science Foundation supports Professor Christian Brueckner of the University of Connecticut, for the synthesis of pyrrole-modified porphyrins from meso-tetraarylporphyrins and the determination of structure/property relationships for this important class of organic molecule. The goal of this work is to establish connections between structural changes in one of the pyrrole sub-units of the porphyrin ring (degree of saturation, steric bulk, and conformational flexibility) and the observed electronic properties in both the ground and electronically excited states (absorption and emission wavelengths, excited state lifetimes). Structurally modified porphyrins find wide applicability in many technical fields, such as therapeutics for disease treatment, chemosensors, and biological imaging agents.Broader impacts of the research include the multidisciplinary training opportunities for students, from organic synthesis to photochemistry and photophysics. Potential applications for the synthesized molecules include photodynamic therapy agents for cancer treatment, photoacoustic imaging contrast enhancement, and monitoring the aging process in concrete. These applications will be assessed through Professor Brueckner's collaborations with researchers in the biomedical and engineering fields; this includes an international collaboration in the UK. Undergraduate participation in this research will be year-round through an established REU program at the Univeristy of Connecticut, and there is also significant involvement with a local undergraduate institution (Central Connecticut State University).