Characterizations for Vinylimidazolium Based Ionic Liquid Polymer Stationary Phases for Capillary Gas Chromatography

Hsieh, Yu Nung; Horng, Richard S.; Ho, Wen Yueh; Huang, Ping; Hsu, Ching Yun; Whang, Thou Jen; Kuei, Chun‐Hsiung

doi:10.1365/s10337-008-0531-8

Cited by 69 publications

(34 citation statements)

References 37 publications

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“…As the alkyl substituent length increased, the thermal stability decreased, presumably due to degradation of the alkylene substituents, contrary to previous literature. [ 30 ] Decreases in the onset of weight loss with varying alkyl substituents suggested a degradation process similar to a Hofmann elimination for ammonium-containing species. [ 31 ] However, a twostep degradation did not occur for the imidazolium homopolymers suggesting rapid backbone degradation following onset of weight loss.…”

Section: Methodsmentioning

confidence: 99%

Alkyl‐Substituted N‐Vinylimidazolium Polymerized Ionic Liquids: Thermal Properties and Ionic Conductivities

Green

Cruz

et al. 2011

Macro Chemistry & Physics

146

189

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Structure-property relationships for polymerized ionic liquids (PILs) relate chemical structure to ionic conductivity and reveal the importance of glass transition temperature ( T g ) and the energy associated with an ion-hopping mechanism for ion conduction for a series of alkyl-substituted vinylimidazolium PILs. The alkyl-substituted vinylimidazolium-based PILs with varying lengths of n -alkyl substituents provide diverse precursors with exchangeable anions to further enhance thermal stability and ionic conductivity. As the anion size increases, regardless of alkyl substituent length, T g decreases and the onset of weight loss, T D , increases. As the length of the alkyl substituent increases, T g decreases for PILs with Br − and BF 4 − counteranions. Ionic conductivity increases over an order of magnitude upon exchange of the counteranion from TfO − < Tf 2 N − . due to their unique combination of physical properties including high thermal stability, wide electrochemical window, negligible vapor pressure, and potentially high ionic conductivities. [3][4][5][6][7] Two particular classes of ILs are polymerizable ILs (PILs) that contain polymerizable functional groups and room temperature ILs (RTILs) with melting temperatures at or below room temperature. [ 8 ] Potential applications have included electrolytes in electromechanical transducers, artifi cial muscle fabrication, and non-volatile solvents for a myriad of chemical reactions. [ 9 ] Chen and Elabd investigated the solution properties and subsequent formation of electrospun fi bers of an imidazolium-containing methacrylate-based PIL. [ 10 ] This study revealed solution properties similar to polyelectrolyte solutions, and electrospun fi bers formed with intermediate fi ber diameters and onset of fi ber formation between polyelectrolyte and neutral polymers. The fi brous mats exhibited promising ionic conductivities at room temperature, and upon swelling with a RTIL, ionic conductivities were on the order of 10 mS cm − 1 . Long and co-workers also investigated the impact of counteranion on the solution and thermal properties of ammoniumbased polyelectrolytes. [ 11 ] Our study revealed the important infl uence of anion selection on the T g of the polyelectrolyte, and we observed polyelectrolyte electrospinning

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Section: Methodsmentioning

confidence: 99%

Alkyl‐Substituted N‐Vinylimidazolium Polymerized Ionic Liquids: Thermal Properties and Ionic Conductivities

Green

Cruz

et al. 2011

Macro Chemistry & Physics

146

189

View full text Add to dashboard Cite

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“…[59][60][61][62] In going from mono-to dianions, the thermal stability seems to be affected by both the nature of the charged head and the spacer. Indeed, among dianions, the naphthalenedisulfonate salt 2d shows the highest thermal stability, possibly …”

Section: Tga Measurementsmentioning

confidence: 99%

Solution and thermal behaviour of novel dicationic imidazolium ionic liquids

et al. 2013

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A new class of functionalised dicationic ionic liquids, containing a central cationic unit capped by a basic functionality (imidazole), has been synthesised. These salts have been characterised in isotropic solution using proton and 2D-NMR spectroscopy, and their thermal stability has been studied by DSC and TGA. All these novel salts contain the 1-(1-imidazolylmethyl)-3,5-di{1-(3'-octylimidazolylmethyl)}-benzene cation as a defining structural motif. Salts of both singly and doubly charged anions were prepared and, in particular, the selected monoanions (Br − , [BF 4 ] − , or [NTf 2 ] − ) differ in size, shape and hydrogenbonding ability, whereas the dianions differ in the nature of the spacer, such as 1,4-benzenedicarboxylate, 2,6-naphthalenedicarboxylate, 1,5-and 2,6-naphthalenedisulfonate, 1,4-butanedicarboxylate, and 1,6-hexanedicarboxylate. These ionic liquids exhibit the presence of different conformers in solution, whose distribution is affected by the nature of the anion. The nature of the anion also affects their thermal stability.

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“…The structures of these GILs are shown in Table II. The synthesis of BBMIB-NTf2, BBMIB-BF4, BBMIB-PF6, and BMMIB-NTf2 was completed following the procedure [3,17,25] with some variations. Firstly, BBMIB-Cl or BMMIB-Cl was synthesized by refluxing the mixture of 1-butylimidazole (10 mmol) and α,α′-dichloro-p-xylene (5 mmol) or 1-methylimidazole (10 mmol) and α,α′-dichloro-p-xylene (5 mmol) in tetrahydrofuran at 60 °C for 6 h and then cooled to room temperature.…”

Section: Synthesis Of Gils Stationary Phasesmentioning

confidence: 99%

“…The aforementioned unique properties allow ionic liquids to be widely applied in various analytical applications including gas chromatography [2][3][4], high-performance liquid chromatography [5], solvent-based microextraction [6], sorption-based extractions [7,8], capillary electrophoresis [9,10], mass spectrometry [11], and electrochemical sensing systems [12].…”

Section: Introductionmentioning

confidence: 99%

Capillary column coated with geminal ionic liquids as stationary phases for gas chromatographic separation

Jiang¹,

Liu²,

Yang³

et al. 2017

Acta Chromatographica

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Summary. Four geminal ionic liquids (GILs), namely, 1,4-bis(1,1′-butyl-3,3′-methylene-imidazolium)-benzene bis[(trifluoromethyl)sulfonyl]imide (BBMIB-NTf2), 1,4-bis(1,1′-butyl-3,3′-methylene-imidazolium)-benzene tetrafluoroborate (BBMIB-BF4), 1,4-bis(1,1′-butyl-3,3′-methylene-imidazolium)-benzene hexafluophosphate (BBMIB-PF6), and 1,4-bis(1,1′-methyl-3,3′-methylene-imidazolium)-benzene bis[(trifluoromethyl) sulfonyl]imide (BMMIB-NTf2), were synthesized. They were statically coated onto the inner walls of fused-silica capillary columns and used as stationary phases for gas chromatography. The evaluation of BBMIB-NTf2, BBMIB-BF4, BBMIB-PF6, and BMMIB-NTf2 as stationary phases is reported here for the first time. These new stationary phases exhibit efficiencies of at least 2.3 × 10 3 plates per meter. Abraham solvation parameter model was used to evaluate the solvation characteristics. The system constants indicated that the dipolarity/polarizability and the hydrogen-bond basicity play a major role among five molecular interactions between stationary phases and solute molecules. A fundamental understanding into the solvation characteristics of these GILs can be used as a guide to choosing the appropriate geminal ionic liquids for specific applications in various fields. The chromatographic separation performance was evaluated by a Grob test mixture, n-alkanes, alcohols, and aromatic isomers. Furthermore, the thermal stability was tested. The present results demonstrate that these geminal ionic liquids stationary phases possess excellent chromatographic separation performance and good thermal stability (at least up to 270 °C) and may be applicable as gas chromatography stationary phases for more application.

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Characterizations for Vinylimidazolium Based Ionic Liquid Polymer Stationary Phases for Capillary Gas Chromatography

Cited by 69 publications

References 37 publications

Alkyl‐Substituted N‐Vinylimidazolium Polymerized Ionic Liquids: Thermal Properties and Ionic Conductivities

Alkyl‐Substituted N‐Vinylimidazolium Polymerized Ionic Liquids: Thermal Properties and Ionic Conductivities

Solution and thermal behaviour of novel dicationic imidazolium ionic liquids

Capillary column coated with geminal ionic liquids as stationary phases for gas chromatographic separation

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