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Influence of Chiral Ionic Liquids on the Excited-State Properties of Naproxen Analogs
The Journal of Physical Chemistry B
  • Ramkrishna Adhikary, Iowa State University
  • Sayantan Bose, Iowa State University
  • Prasun Mukherjee, Iowa State University
  • Aniket Thite, Iowa State University
  • George A. Kraus, Iowa State University
  • Aruna B. Wijeratne, University of Texas
  • Pritesh S. Sharma, University of Texas
  • Daniel W. Armstrong, University of Texas
  • Jacob W. Petrich, Iowa State University
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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.

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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American Chemical Society
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Ramkrishna Adhikary, Sayantan Bose, Prasun Mukherjee, Aniket Thite, et al.. "Influence of Chiral Ionic Liquids on the Excited-State Properties of Naproxen Analogs" The Journal of Physical Chemistry B Vol. 112 Iss. 25 (2008) p. 7555 - 7559
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