Correlation between Excited-State Intramolecular Proton-Transfer and Singlet-Oxygen Quenching Activities in 1‑(Acylamino)anthraquinones

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 t...

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Published inThe journal of physical chemistry. B Vol. 119; no. 6; pp. 2525 - 2532
Main Authors Nagaoka, Shin-ichi, Endo, Hikaru, Ohara, Keishi, Nagashima, Umpei
Format Journal Article
LanguageEnglish
Published United States American Chemical Society 12.02.2015
Subjects
Anthraquinones - chemistry
Protons
Singlet Oxygen - chemistry
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Summary: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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ISSN:1520-6106
1520-5207
DOI:10.1021/jp508355k