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Photoinduced processes of 3-substituted 6-fluoro-1,4-dihydro-4-oxoquinoline derivatives: A theoretical and spectroscopic study

Paper ID Volume ID Publish Year Pages File Format Full-Text
27995 44055 2010 12 PDF Available
Title
Photoinduced processes of 3-substituted 6-fluoro-1,4-dihydro-4-oxoquinoline derivatives: A theoretical and spectroscopic study
Abstract

Presented computational study of 3-substituted 6-fluoro-1,4-dihydro-4-oxoquinoline derivatives confirmed the existence of two tautomeric (oxo- and hydroxy-) forms of these molecules originating from the presence of 4-oxo substitution on quinoline skeleton. The computed singlet excitation energies at the time-dependent density functional theory (DFT) level and the simulated absorption spectra are in accordance with the experimental UV/vis spectra measured in aprotic solvents (1,4-dioxane, acetonitrile, dimethylsulfoxide). Measured spectra indicate the solvent capability to affect the ratio of tautomeric forms in the solution. Reaction pathways of O2− and singlet oxygen (1Δg) formation and the energetics of these processes were studied using TD-DFT including the solvent effect in terms of polarizable continuum model. EPR spectroscopy confirmed that photoinduced reactions of 3-substituted 6-fluoro-1,4-dihydro-4-oxoquinoline derivatives with molecular oxygen lead to O2− and singlet oxygen (1Δg) formation.

Keywords
ACN, acetonitrile; AEA, adiabatic electron affinity; AIP, adiabatic ionization potential; DMPO, 5,5-dimethyl-1-pyrroline N-oxide; DFT, density functional theory; DIOX, 1,4-dioxane; DMSO, dimethylsulfoxide; EPR, electron paramagnetic resonance; Hfcc, hyper
First Page Preview
Photoinduced processes of 3-substituted 6-fluoro-1,4-dihydro-4-oxoquinoline derivatives: A theoretical and spectroscopic study
Publisher
Database: Elsevier - ScienceDirect
Journal: Journal of Photochemistry and Photobiology A: Chemistry - Volume 211, Issue 1, 5 March 2010, Pages 47–58
Authors
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Subjects
Physical Sciences and Engineering Chemical Engineering Bioengineering