Influence of Chiral Ionic Liquids on the Excited-State Properties of Naproxen Analogs

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2008-06-10
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Adhikary, Ramkrishna
Bose, Sayantan
Mukherjee, Prasun
Thite, Aniket
Wijeratne, Aruna
Sharma, Pritesh
Armstrong, Daniel
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Kraus, George
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Petrich, Jacob
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Chemistry

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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.

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