Correlation between Excited-State Intramolecular Proton-Transfer and Singlet-Oxygen Quenching Activities in 1-(Acylamino)anthraquinones
2015
Nagaoka, Shin-ichi | Endo, Hikaru | Ohara, Keishi | Nagashima, Umpei
Excited-state intramolecular proton-transfer (ESIPT) and singlet-oxygen (¹O₂) quenching activities of intramolecularly hydrogen-bonded 1-(acylamino)anthraquinones have been studied by means of static and laser spectroscopies. The ESIPT shows a substituent effect, which can be explained in terms of the nodal-plane model. The ESIPT activity positively and linearly correlates with their ¹O₂ quenching activity. The reason for this correlation can be understood by considering ESIPT-induced distortion of their ground-state potential surface and their encounter complex formation with ¹O₂. Intramolecularly hydrogen-bonded hydroxyanthraquinones found in aloe also show a similar positive and linear correlation, which can be understood in the same way.
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