Journal
CHEMICAL PHYSICS
Volume 373, Issue 3, Pages 153-158Publisher
ELSEVIER
DOI: 10.1016/j.chemphys.2010.06.007
Keywords
Intramolecular intermolecular photoreduction triplet
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The photoprocesses of nifedipine, a 4-(2-nitrophenyl)-1,4-dihydropyridine, and nimodipine and nitrendipine, two 3-nitrophenyl Hantzsch-type analogues, were studied by steady-state and time-resolved methods. The intramolecular photoreduction of nifedipine into its nitrosophenyl product takes place within a few ns. The quantum yield of conversion is Phi(red) = 0.3 and does not depend significantly on the oxygen concentration and solvent properties. Formation of the fully reduced 4-(2-aminophenyl)-1,4-dihydropyridine as minor product is indicated by fluorescence spectroscopy. The photoreduction of nimodipine and nitrendipine is inefficient, Phi(red) = 0.002 in acetonitrile, but markedly enhanced in the presence of donors such as triethylamine (TEA) and 2-propanol, e. g. for TEA Phi(red) is up to 0.03. The triplet states of nimodipine and nitrendipine were characterized. They react intermolecularly with TEA and 2-propanol, forming radicals as intermediates and eventually several reduction products. (C) 2010 Elsevier B. V. All rights reserved.
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