The recent discoveries of facile methodologies for the synthesis of corroles allowed for their utilization in various fields including the development of light harvesting molecules and as a photonic device and sensor in the diagnosis and treatment of cancer. Free-base triphenilcorrole (H3TPCor) differs from regular free-base tetraphenylporphyrin (H2TPP) because of removal of one of the meso methane carbons, resulting in a direct pyrrole-pyrrole connection. In addition, free-base corroles has three NH groups, compared to free-base porphyrin that only has two. Because of the changes in the structure of H3TPCor, the macrocycle tends to adopt a different conformation, and therefore different photophysical properties. Two different tautomeric forms of H3TPCor have been proposed, and each tautomer has different photophysical properties. Although it has been found that one tautomer exist when the corrole is dissolve in a non-polar solvent and the other one occur when it is dissolve in a polar solvent, it still is poorly understood which solvent property controls the formation of either tautomer.            In our group, we are characterizing the photophysical properties of free-base triphenylcorrole to determine which solvent properties influence the stability of each free-base corrole tautomer. We have used a series of solvents with a variety of properties that will allow us to determine which of these solvents properties dominate the transition from one tautomer to another. Our photophysical data demonstrates that in several solvents both tautomers co-exist, and we have investigated the correlation between tautomers composition and solvent properties. We are currently working in finding and increasing the number of solvent where H3TPCor tautomers co-exist and we are expanding our study to include other optical techniques and calculations. A detailed understanding of the photophysical properties of these tautomers is important in order to use free-base corroles in photonic devices.

Photophysical characterization and solvent effect on the tautomerism of free-base corrole

247th National Meeting (2014)

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