Maßgeschneiderte Aryl‐Alkyl‐substituierte ionische Flüssigkeiten (TAAILs) – die nächste Generation ionischer Flüssigkeiten

Ahrens, Sebastian; Peritz, Anke; Straßner, Thomas

doi:10.1002/ange.200903399

Cited by 23 publications

(11 citation statements)

References 7 publications

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“…The replacement of a spherical halide counterion by a calamitic sulfonimide anion indeed led to a decrease of the melting points, the effect being larger for trifluorosulfonimides 2a and 3a as compared to methylsulfonimides 2b and 3b . It should be noted that Strassner has recently introduced a different concept to tune melting points in ionic liquids by electronic effects of the aryl substituent [44–45]. However, the mesogenic sulfonimide resulted in the formation of a SmA mesophase only in the case of 3b , while ion pairs 2a , b and 3a did not show any liquid-crystalline properties.…”

Section: Resultsmentioning

confidence: 99%

Synthesis of guanidinium–sulfonimide ion pairs: towards novel ionic liquid crystals

Butschies¹,

Neidhardt²,

Mansueto³

et al. 2013

Beilstein J. Org. Chem.

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SummaryThe recently introduced concept of ionic liquid crystals (ILCs) with complementary ion pairs, consisting of both, mesogenic cation and anion, was extended from guanidinium sulfonates to guanidinium sulfonimides. In this preliminary study, the synthesis and mesomorphic properties of selected derivatives were described, which provide the first example of an ILC with the sulfonimide anion directly attached to the mesogenic unit.

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Section: Resultsmentioning

confidence: 99%

Synthesis of guanidinium–sulfonimide ion pairs: towards novel ionic liquid crystals

Butschies¹,

Neidhardt²,

Mansueto³

et al. 2013

Beilstein J. Org. Chem.

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“…Subsequent metathesis with lithium bis(trifluoromethanesulfonyl)amide (LiNTf 2 ) or potassium hexafluorophosphate (KPF 6 ) resulted in the formation of click ionic salts 4 a-4 n. Compound 4 n with mesitylimidazolium parent ring can be classified as a tunable aryl-alkyl IL and fulfils the standard for next-generation ILs. [26] The steric and electronic properties of the click ionic salts can be flexibly modified by variation of substituents (R', R'', and R''') at the imidazolium and/or triazolyl rings. Though only fourteen salts are presented herein, the powerful methodology provides a facile route for the synthesis of a variety of ionic salts and flexible structural tuning by using readily available azides and alkyne-quaternized aryl imidazolium or alkyl imidazolium compounds.…”

Section: Resultsmentioning

confidence: 99%

Click Ionic Liquids: A Family of Promising Tunable Solvents and Application in Suzuki–Miyaura Cross‐Coupling

Li¹,

Wang²,

Wu³

et al. 2012

Chemistry A European J

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A series of click ionic salts 4 a-4 n was prepared through click reaction of organic azides with alkyne-functionalized imidazolium or 2-methylimidazolium salts, followed by metathesis with lithium bis(trifluoromethanesulfonyl)amide or potassium hexafluorophosphate. All salts were characterized by IR, NMR, TGA, and DSC, and most of them can be classified as ionic liquids. Their steric and electronic properties can be easily tuned and modified through variation of the aromatic or aliphatic substituents at the imidazolium and/or triazolyl rings. The effect of anions and substituents at the two rings on the physicochemical properties was investigated. The charge and orbital distributions based on the optimized structures of cations in the salts were calculated. Reaction of 4 a with PdCl(2) produced mononuclear click complex 4 a-Pd, the structure of which was confirmed by single-crystal X-ray diffraction analysis. Suzuki-Miyaura cross-coupling shows good catalytic stability and high recyclability in the presence of PdCl(2) in 4 a. TEM and XPS analyses show formation of palladium nanoparticles after the reaction. The palladium NPs in 4 a are immobilized by the synergetic effect of coordination and electrostatic interactions with 1,2,3-triazolyl and imidazolium, respectively.

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“…[1] ILs show unique properties as solvents and reaction media as compared to conventional organic solvents, such as a large liquid range, [2] wide electrochemical windows, [3] high thermal stability, [4] easy recycling, [5] negligible volatility [6] and, above all, a very versatile naturetheir properties can be tailored by selecting a specific cationanion pair. [7] However, one of the major drawbacks in terms of their possible industrial application is their relatively high viscosity, which can hinder pumping, stirring and diffusing operations. [8] Typically, ILs exhibit viscosities ranging from tens to thousands of mPa s, which are much higher than the viscosities of traditional simple molecular solvents (MSs).…”

Section: Introductionmentioning

confidence: 99%

Viscosity Mixing Rules for Binary Systems Containing One Ionic Liquid

Tariq¹,

Altamash²,

Salavera³

et al. 2013

ChemPhysChem

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In this work the applicability of four of the most commonly used viscosity mixing rules to [ionic liquid (IL)+molecular solvent (MS)] systems is assessed. More than one hundred (IL+MS) binary mixtures were selected from the literature to test the viscosity mixing rules proposed by 1) Hind (Hi), 2) Grunberg and Nissan (G-N), 3) Herric (He) and 4) Katti and Chaudhri (K-C). The analyses were performed by estimating the average (absolute or relative) deviations, AADs and ARDs, between the available experimental data and the predicted ideal mixture viscosity values obtained by means of each rule. The interaction terms corresponding to the adjustable parameters inherent to each rule were also calculated and their trends discussed.

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Maßgeschneiderte Aryl‐Alkyl‐substituierte ionische Flüssigkeiten (TAAILs) – die nächste Generation ionischer Flüssigkeiten

Cited by 23 publications

References 7 publications

Synthesis of guanidinium–sulfonimide ion pairs: towards novel ionic liquid crystals

Synthesis of guanidinium–sulfonimide ion pairs: towards novel ionic liquid crystals

Click Ionic Liquids: A Family of Promising Tunable Solvents and Application in Suzuki–Miyaura Cross‐Coupling

Viscosity Mixing Rules for Binary Systems Containing One Ionic Liquid

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