1-Acylaminoanthraquinones serve as models for biological systems with intramolecular hydrogen bonds between adjacent carbonyl and amino groups.  We seek to gain a fundamental understanding of the impact of structure and solvent environment on photochemistry in these systems. Updated syntheses were applied to make the compounds, providing easier sample purification relative to past methods.  The acyl substituent is varied to tune the extent of excited state proton transfer observed, ranging from a nearly complete charge transfer to no charge transfer.  The proton transfer is traced through fluorescence spectroscopy, as both the locally excited state and charge transfer tautomer are fluorescent.  Temperature-dependent fluorescence spectroscopy is used to evaluate the reaction thermodynamics in a series of solvents to assess the impact of solvent interactions upon the proton transfer. The results are correlated with kinetics studies providing a more complete understanding of factors that impact the photochemical properties.

Solvent and substituent effects on the photochemistry of 1-acylaminoanthraquinones

243rd National Meeting (2012)

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