Journal
JOURNAL OF PHOTOCHEMISTRY AND PHOTOBIOLOGY A-CHEMISTRY
Volume 200, Issue 2-3, Pages 325-333Publisher
ELSEVIER SCIENCE SA
DOI: 10.1016/j.jphotochem.2008.08.012
Keywords
4-Hydroxyacridine; Intermolecular proton transfer; Absorption; Fluorescence; Density Functional Theory (DFT)
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Funding
- Department of Science and Technology, India [SR/SI /PC1/2003]
- CSIR, New Delhi
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The possibility of ground and excited state proton transfer reaction across the five member intramolecular hydrogen bonded ring in 4-hydroxyacridine (4-HA) has been investigated spectroscopically and the experimental results have been correlated with quantum chemical calculations. The difference in the emissive behaviour of 4-HA in different types of solvents is due to the presence of different species in the excited state. In non-polar solvents. the species present is non-fluorescing in nature, whereas 4-HA molecule shows normal emission from intramolecularly hydrogen bonded closed conformer in polar aprotic solvents. In polar protic solvents like MeOH, EtOH, etc. (except water), a single broad emission band is attributed to the hydrogen bonded solvated form of 4-HA. However, in case of water, fluorescence from the tautomeric form of 4-HA is observed apart from emission from the solvated form. Emission from the tautomeric form may arise due to double proton transfer via a single water molecule bonded to 4-HA. Evaluation of the potential energy surfaces by quantum chemical calculations using density functional theory (DFT) and time dependent density functional theory (TDDFT), however, points towards the possibility of proton transfer-both intrinsic intramolecular as well as water mediated in the first excited state of 4-HA. (C) 2008 Elsevier B.V. All rights reserved.
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