Unsymmetrical Dicationic Ionic Liquids: Manipulation of Physicochemical Properties Using Specific Structural Architectures

Payagala, Tharanga; Huang, Jin‐Shun; Breitbach, Zachary S.; Sharma, Pritesh S.; Armstrong, Daniel W.

doi:10.1021/cm702325a

Cited by 220 publications

(200 citation statements)

References 23 publications

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“…In this light, the operational limit for the dicationic ionic liquids ranges from 228.8°C for [2C 8 31,56 In general, our ionic liquids show a lower thermal stability with respect to dicationic pyrrolidinium and imidazolium salts having aliphatic spacers previously reported by Armstrong and co-workers. 3 The very different thermal stability could be a result of the different nature of the spacer used.…”

Section: Tga Measurementssupporting

confidence: 53%

“…1,2 Room temperature ionic liquids with dipositive cations are rare, hence their physical behaviour is not well understood. [3][4][5][6][7][8][9] Tripositive cations are even scarcer. [10][11][12] The interest in dicationic ionic liquids is largely due to their high thermal stability, higher than that normally characterising the corresponding monocationic ionic liquids.…”

Section: Introductionmentioning

confidence: 99%

“…This class of ionic liquids was hence characterised by the presence of the 1-(1-imidazolylmethyl)-3,5-di{1-(3′-octylimidazolylmethyl)}benzene cation ([2C 8 bti] 2+ , where bti indicates a benzene-tris-imidazole unit bearing two octyl alkyl chains (2C 8 ) on two different imidazole rings) (2a-i) (Scheme 1).…”

Section: Introductionmentioning

confidence: 99%

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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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Section: Tga Measurementssupporting

confidence: 53%

Section: Introductionmentioning

confidence: 99%

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Solution and thermal behaviour of novel dicationic imidazolium ionic liquids

et al. 2013

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“…The purpose of this study is to examine the effects of using a variety of different types and structures of dication reagents, and to determine whether or not their selectivity, sensitivity, and efficacy vary for different anions. Our previous efforts included extensive research in developing dicationic compounds [21][22][23][24]. Originally synthesized as ultra-stable ionic liquids [21], this research has led to the development of a wide array of dicationic compounds, including imidazolium [21,22] and phosphonium unpublished results based dications, as well as those with differing linkage chains [22,23] and even unsymmetrical species [23].…”

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confidence: 99%

Evaluation of dicationic reagents for their use in detection of anions using positive ion mode ESI-MS via gas phase ion association

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et al. 2008

J. Am. Soc. Mass Spectrom.

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Twenty-three different dications were investigated for their effectiveness in pairing with singly charged anions, thereby allowing the electrospray ionization mass spectrometry (ESI-MS) detection of anions as positively charged complexes. Nitrate, iodide, cyanate, monochloroacetate, benzenesulfonate, and perfluoro-octanoate were chosen as representative test anions as they differ in mass, size-to-charge ratio, chaotropic nature, and overall complexity. Detection limits were found using direct injection of the anion into a carrier liquid containing the dication. Detection limits are given for all six anions with each of the 23 dications. Each anion was easily detected at the ppb (g/L) and often the ppt (ng/L) levels using certain dicationic reagents. The ability of dicationic reagents to pair with anions and produce ESI-MS signals varied tremendously. Indeed, only a few dications can be considered broadly useful and able to produce sensitive results. Liquid chromatography (LC)-ESI-MS also was investigated and used to show how varying the dicationic reagent produced significantly different peak intensities. Also, the use of tandem mass spectrometry can lead to even greater sensitivity when using imidazolium based dications. (J

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“…A special class of ionic liquids have recently been synthetized using geminal imidazolium dications (Anderson et al, 2005;Payagala et al, 2007;Sun et al, 2009). This class of compounds represents an interesting variation of the cationic partner and may present several advantages over the traditional monocationic ionic liquid in their application as lubricants (Jin et al, 2006), solvents (Han & Armstrong, 2005;Xiao & Shreeve, 2005) and separation media (Anderson et al, 2005).…”

Section: An Example: Dicationic Imidazoliummentioning

confidence: 99%