Solvate Ionic Liquids as Reaction Media for Electrocyclic Transformations

Eyckens, Daniel J.; Champion, Megan E.; Fox, Bronwyn; Yoganantharajah, Prusothman; Gibert, Yann; Welton, Tom; Henderson, Luke C.

doi:10.1002/ejoc.201501614

Cited by 32 publications

(39 citation statements)

References 36 publications

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“…The Gutmann acceptor number, based on the 31 P chemical shift of triphenylphosphine oxide, has recently been reported to be 26.5 for both numbers of [Li(G3)] NTF 2 and [Li(G4)] NTF 2 , compared with 0.2 for the glymes alone . In fact, both SILs were concluded to be more acidic than the conventional IL [C 4 C 1 im] NTf 2 .…”

Section: Resultsmentioning

confidence: 99%

“…While the structure and properties of pure SILs has received some attention, the behaviour of SILs as solvents is relatively unexplored except for our recent study of polyethylene‐oxide–SIL solutions . The first use of SILs as solvents for Diels–Alder and cycloaddition reactions has recently been reported . Determining the polarity is an important step towards understanding dissolution and reactivity in SILs, and therefore their potential beyond electrolytes.…”

Section: Introductionmentioning

confidence: 99%

“…[8] The first use of SILs as solvents for Diels-Alder and cycloaddition reactions has recently been reported. [15] Determining the polarity is an important step towards understanding dissolution and reactivity in SILs,a nd therefore their potentialbeyonde lectrolytes.…”

Section: Introductionmentioning

confidence: 99%

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Kamlet–Taft Solvation Parameters of Solvate Ionic Liquids

2016

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The Kamlet-Taft solvent parameters of solvate ionic liquids (SILs) prepared from lithium salts with glyme and glycol ligands are determined. The dipolarity/polarisibilities (π*) are high, similar to those found in conventional ionic liquids. The H-bond basicities (β) depend strongly on the anion. The H-bond acidities (α) are high in both glyme and glycol SILs, indicating that the lithium is acting as a H-bond donor site. "Poor" SILs have glyme-rich and salt-rich regions. In these liquids the π* and β values are almost identical to the parent glyme or glycol, and the α values are determined by the salt alone.

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Section: Resultsmentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

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Kamlet–Taft Solvation Parameters of Solvate Ionic Liquids

2016

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“…The typical sample masses were approximately 8 mg, which were sealed in aluminum hermetic pans. Preparation of dimethyl 4-methylcyclohexa-1,4-diene-1,2-dicarboxylate (11) [37]. Following the procedure of Smit et al [28] a mixture of dimethylacetylene dicarboxylate (3.468 g, 24.40 mmol), isoprene (14.7 mL, 146 mmol), and activated silica gel (40.13 g) was stirred at room temperature for 18 h. The reaction flask was equipped with a Findenser™ to minimize the evaporation of isoprene.…”

Section: Methodsmentioning

confidence: 99%

Phthalate plasticizers covalently linked to PVC via copper-free or copper catalyzed azide-alkyne cycloadditions

Earla

Costanzo

et al. 2017

Polymer

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Plasticization of PVC was carried out by covalently linking phthalate derivatives via copper-free (thermal) or copper catalyzed azide-alkyne cycloadditions. Di(2-ethylhexyl) phthalate derivatives (DEHPether and DEHP-ester) were synthesized and appended to PVC at two different densities. The glass transition temperatures of the modified PVC decreased with increasing content of plasticizer. PVC-DEHP-ether gave lower glass transition temperatures than PVC-DEHP-ester, reflecting the enhanced flexibility of the ether versus ester linker.

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“…38 Moreover, one may introduce a new functionality into the solvate ILs to form, for example, stimuli-responsible ILs by designing the components of the complexes. Of course, the application of the solvate ILs is not limited to electrochemical devices, but they have already been tested as reaction media for organic synthesis 39 and as the media for CO 2 capture. 40 The significant material design flexibility for solvate ILs provides infinite possibilities.…”

Section: Discussionmentioning

confidence: 99%

Categorizing Molten Salt Complexes as Ionic Liquids and Their Applications to Battery Electrolytes

Ueno

2016

Electrochemistry

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Certain stoichiometric mixtures of salts and solvents (ligands) yield a salt complex. Salt complexes that are low melting and consist of discrete complex ions and their counter ions in the molten state can together form the essence of an ionic liquid (IL). This stable complex melt can now be categorized into a new subclass of ionic liquids, "solvate (or chelate) ILs." In this paper, we describe the current criteria for this new family of ILs. Concentrated mixtures of lithium salts and oligoether solvents are useful models for these solvate ionic liquids; the effects of the ion-ion and ion-solvent interactions on their structure and properties were investigated to contrast with classical concentrated electrolyte solutions. The performance of solvate ILs as electrolytes for lithium-sulfur (Li-S) batteries is also reported. The dissolution of lithium polysulfides (i.e., reaction intermediates of the sulfur cathode) into the electrolyte, which is a serious issue for the practical application of Li-S cells, was greatly suppressed in the solvate ILs. Therefore, a stable charge-discharge with high Coulombic efficiency was achieved with the solvate IL electrolytes.

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Solvate Ionic Liquids as Reaction Media for Electrocyclic Transformations

Cited by 32 publications

References 36 publications

Kamlet–Taft Solvation Parameters of Solvate Ionic Liquids

Kamlet–Taft Solvation Parameters of Solvate Ionic Liquids

Phthalate plasticizers covalently linked to PVC via copper-free or copper catalyzed azide-alkyne cycloadditions

Categorizing Molten Salt Complexes as Ionic Liquids and Their Applications to Battery Electrolytes

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