Influence of Chiral Ionic Liquids on the Excited-State Properties of Naproxen Analogs
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The Department of Chemistry seeks to provide students with a foundation in the fundamentals and application of chemical theories and processes of the lab. Thus prepared they me pursue careers as teachers, industry supervisors, or research chemists in a variety of domains (governmental, academic, etc).
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The Department of Chemistry was founded in 1880.
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1880-present
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- College of Liberal Arts and Sciences (parent college)
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Abstract
The synthesis and decolorization of chiral room-temperature ionic liquids based upon 1-methyl imidazole and chloromethyl menthyl ether is reported. The excellent optical quality of these solvents permits the investigation of the effects of the two enantiomers on the excited-state photophysics of (S)-N-methyl-2-pyrrolidinemethyl 2(S)-(6-methoxy-2-naphthyl)propionate [(S,S)-NPX-PYR]. Whereas in conventional bulk polar solvents such as acetonitrile, (S,S)-NPX-PYR is known to execute excited-state intramolecular electron transfer and to form exciplexes, in these chiral solvents these nonradiative processes are absent. The chiral solvents do, however, induce a small but reproducible (∼10%) stereodifferentiation in the fluorescence lifetime of (S,S)-NPX-PYR as well as in the parent compound, (S)-naproxen. To our knowledge, this is the first example of chiral ionic liquids inducing such an effect on photophysical properties.
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Reprinted (adapted) with permission from The Journal of Physical Chemistry B, 112(5); 7555-7559. Doi: 10.1021/jp711508b. Copyright 2008 American Chemical Society.