1-Acylaminoanthraquinones are a good model system for studying the effects of solvent on the photochemistry of compounds' adjacent amine and carbonyl groups. Previous work has looked into the effect of the acyl substituent of 1-AAQ derivatives and the viability of an excited state intramolecular proton transfer (ESIPT) reaction, noting increased electronegativity of the substituent group increases ESIPT. 1-Dichloroacetylaminoanthraquinone (1-DCAQ) is synthesized and analyzed in this study as another electronegative derivative that exhibits a partial ESIPT. Solvent effect on ESIPT in 1-DCAQ is investigated by quantifying emission spectra as thermodynamic data and looking for changes of the ESIPT reaction between solvents. Polar solvents were found to inhibit the formation of the tautomer, with methanol as the least favorable solvent for ESIPT. Nonpolar solvents, dichloromethane and chloroform, favored the reaction despite an initial energy barrier compared to methanol, the only solvent without an energy barrier for ESIPT.

Effect of solvent on 1-dichloroacetylaminoanthraquinone photochemistry

247th National Meeting (2014)

The official archive and repository for all ACS Meetings & Expositions abstracts and select posters or presentations.