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Title: Effects of Aromaticity in Cations and Their Functional Groups on the Low-Frequency Spectra and Physical Properties of Ionic Liquids

Abstract

We investigate the temperature dependence of low-frequency spectra in the frequency range of 0.3–200 cm-1 for ionic liquids (ILs) whose cations possess two systematically different cyclic groups, using femtosecond Raman-induced Kerr effect spectroscopy. The target ILs are bis(trifluoromethylsulfonyl)amide [NTf2]– salts of 1-cyclohexylmethyl-1-methylpyrrolidinium [CHxmMPyrr]+, 1-cyclohexylmethyl-3-methylimidazolium [CHxmMIm]+, N-cyclohexylmethylpyridinium [CHxmPy]+, 1-benzyl-1-methylpyrrolidinium [BzMPyrr]+, 1-benzyl-3-methylimidazolium [BzMIm]+, and N-benzylpyridinium [BzPy]+ cations. The aim of this study is to better understand the effects of aromaticity in the cations’ constituent groups on the temperature-dependent low-frequency spectral features of the ILs. The low-frequency spectra of these ILs are temperature dependent, but the temperature-dependent spectrum of [CHxmMPyrr][NTf2] is different from that of other ILs. While [CHxmMPyrr][NTf2] shows spectral changes with temperature in the low-frequency region below 50 cm-1, the other ILs also show spectral changes in the high-frequency region above 80 cm-1 (above 50 cm-1 in the case of [BzMPyrr][NTf2]). We conclude that the spectral change in the low-frequency region is due to both the cation and anion, while the change in the high-frequency region is attributed to the red shift of the aromatic ring librations. On the basis of the plots of the first moment of the spectra vs. temperature, we found that the first moment of the low-frequencymore » spectrum of the IL whose cation does not have an aromatic ring is less temperature dependent than that of the other ILs. However, the intrinsic first moment, the first moment at 0 K, of the low-frequency spectrum is governed by the absence or presence of a charged aromatic group, while a neutral aromatic group does not have much influence on determining the intrinsic first moment.« less

Authors:
 [1];  [2];  [2];  [3]
+ Show Author Affiliations
  1. Chiba Univ. (Japan). Dept. of Nanomaterial Science
  2. Brookhaven National Lab. (BNL), Upton, NY (United States). Chemistry Dept.
  3. Chiba Univ. (Japan). Dept. of Chemistry
Publication Date:
Research Org.:
Brookhaven National Laboratory (BNL), Upton, NY (United States)
Sponsoring Org.:
USDOE Office of Science (SC), Basic Energy Sciences (BES)
OSTI Identifier:
1425020
Report Number(s):
BNL-200000-2018-JAAM
Journal ID: ISSN 1520-6106; TRN: US1802003
Grant/Contract Number:  
SC0012704
Resource Type:
Accepted Manuscript
Journal Name:
Journal of Physical Chemistry. B, Condensed Matter, Materials, Surfaces, Interfaces and Biophysical Chemistry
Additional Journal Information:
Journal Volume: 119; Journal Issue: 29; Journal ID: ISSN 1520-6106
Publisher:
American Chemical Society
Country of Publication:
United States
Language:
English
Subject:
37 INORGANIC, ORGANIC, PHYSICAL AND ANALYTICAL CHEMISTRY; ionic; liquids

Citation Formats

Kakinuma, Shohei, Ramati, Sharon, Wishart, James F., and Shirota, Hideaki. Effects of Aromaticity in Cations and Their Functional Groups on the Low-Frequency Spectra and Physical Properties of Ionic Liquids. United States: N. p., 2014. Web. doi:10.1021/jp509412z.
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Kakinuma, Shohei, Ramati, Sharon, Wishart, James F., & Shirota, Hideaki. Effects of Aromaticity in Cations and Their Functional Groups on the Low-Frequency Spectra and Physical Properties of Ionic Liquids. United States. https://doi.org/10.1021/jp509412z
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Kakinuma, Shohei, Ramati, Sharon, Wishart, James F., and Shirota, Hideaki. Mon . "Effects of Aromaticity in Cations and Their Functional Groups on the Low-Frequency Spectra and Physical Properties of Ionic Liquids". United States. https://doi.org/10.1021/jp509412z. https://www.osti.gov/servlets/purl/1425020.
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@article{osti_1425020,
title = {Effects of Aromaticity in Cations and Their Functional Groups on the Low-Frequency Spectra and Physical Properties of Ionic Liquids},
author = {Kakinuma, Shohei and Ramati, Sharon and Wishart, James F. and Shirota, Hideaki},
abstractNote = {We investigate the temperature dependence of low-frequency spectra in the frequency range of 0.3–200 cm-1 for ionic liquids (ILs) whose cations possess two systematically different cyclic groups, using femtosecond Raman-induced Kerr effect spectroscopy. The target ILs are bis(trifluoromethylsulfonyl)amide [NTf2]– salts of 1-cyclohexylmethyl-1-methylpyrrolidinium [CHxmMPyrr]+, 1-cyclohexylmethyl-3-methylimidazolium [CHxmMIm]+, N-cyclohexylmethylpyridinium [CHxmPy]+, 1-benzyl-1-methylpyrrolidinium [BzMPyrr]+, 1-benzyl-3-methylimidazolium [BzMIm]+, and N-benzylpyridinium [BzPy]+ cations. The aim of this study is to better understand the effects of aromaticity in the cations’ constituent groups on the temperature-dependent low-frequency spectral features of the ILs. The low-frequency spectra of these ILs are temperature dependent, but the temperature-dependent spectrum of [CHxmMPyrr][NTf2] is different from that of other ILs. While [CHxmMPyrr][NTf2] shows spectral changes with temperature in the low-frequency region below 50 cm-1, the other ILs also show spectral changes in the high-frequency region above 80 cm-1 (above 50 cm-1 in the case of [BzMPyrr][NTf2]). We conclude that the spectral change in the low-frequency region is due to both the cation and anion, while the change in the high-frequency region is attributed to the red shift of the aromatic ring librations. On the basis of the plots of the first moment of the spectra vs. temperature, we found that the first moment of the low-frequency spectrum of the IL whose cation does not have an aromatic ring is less temperature dependent than that of the other ILs. However, the intrinsic first moment, the first moment at 0 K, of the low-frequency spectrum is governed by the absence or presence of a charged aromatic group, while a neutral aromatic group does not have much influence on determining the intrinsic first moment.},
doi = {10.1021/jp509412z},
journal = {Journal of Physical Chemistry. B, Condensed Matter, Materials, Surfaces, Interfaces and Biophysical Chemistry},
number = 29,
volume = 119,
place = {United States},
year = {Mon Dec 01 00:00:00 EST 2014},
month = {Mon Dec 01 00:00:00 EST 2014}
}
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https://doi.org/10.1021/jp509412z
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Figures / Tables:

TABLE I TABLE I: Fit parameters for the temperature dependence of the first moment $M$1 of the broad, low-frequency spectral band for each ionic liquid.
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    Works referencing / citing this record:

    Preface: Special Topic on Chemical Physics of Ionic Liquids
    journal, May 2018

    • Perkin, Susan; Kirchner, Barbara; Fayer, Michael D.
    • The Journal of Chemical Physics, Vol. 148, Issue 19
    • DOI: 10.1063/1.5039492

    Novel cis-[(NHC) 1 (NHC) 2 (L)Cl]platinum( ii ) complexes – synthesis, structures, and anticancer activities
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    • Rehm, Tobias; Rothemund, Matthias; Muenzner, Julienne K.
    • Dalton Transactions, Vol. 45, Issue 39
    • DOI: 10.1039/c6dt02350a

    Effects of aromaticity in cations and their functional groups on the temperature dependence of low-frequency spectrum
    journal, May 2018

    • Kakinuma, Shohei; Ramati, Sharon; Wishart, James F.
    • The Journal of Chemical Physics, Vol. 148, Issue 19
    • DOI: 10.1063/1.5010066

    Structural analysis of ionic liquids with symmetric and asymmetric fluorinated anions
    journal, August 2019

    • Zhao, Man; Wu, Boning; Lall-Ramnarine, Sharon I.
    • The Journal of Chemical Physics, Vol. 151, Issue 7
    • DOI: 10.1063/1.5111643
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      TABLE I (p. 26)table
      FIG. 1 (p. 29)figure
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      FIG. 4 (p. 32)figure
      FIG. 5 (p. 33)figure
      FIG. 6 (p. 34)figure
      FIG. 7 (p. 35)figure
      Supplemental Material A (p. 37)figure
      Supplemental Material A (Continued) (p. 38)figure
      Supplemental Material B (p. 39)figure
      Supplemental Material B (Continued) (p. 40)figure
      Supplemental Material C (p. 41)figure
      Supplemental Material C (Continued) (p. 42)figure
      Supplemental Material C (Continued) (p. 43)figure
      Supplemental Material C (Continued) (p. 44)figure
      Supplemental Material D (p. 45)figure
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