Crown-ether enclosure generated by ionic liquid components—synthesis, crystal structure and Raman spectra of compounds of imidazolium based salts and 18-crown-6

Gjikaj, Mimoza; Brockner, W.; Namyslo, Jan C.; Adam, Arnold

doi:10.1039/b708724c

Cited by 18 publications

(14 citation statements)

References 80 publications

(28 reference statements)

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“…[117][118][119][120] The use of ILs for co-crystallization as inclusion compounds has also been reported. 121,122 Calixarene derivatives and 18-crown-6 molecules have been tested as selective ion pair receptors for ionic liquids. Inclusion compounds containing pyridinium and imidazolium ionic liquids have been isolated and crystallographically analysed for insight into the stacking, intermolecular interactions and ionic conformation in each compound (Fig.…”

Section: Ionic Liquid Clathrates Complexes and Inclusion Compoundsmentioning

confidence: 99%

Structural analysis of low melting organic salts: perspectives on ionic liquids

Dean

Pringle

MacFarlane

2010

Phys. Chem. Chem. Phys.

124

121

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Ionic liquid-forming salts often display low melting points (a lack of crystallisation at ambient temperature and pressure) as a result of decreased lattice energies in the crystalline state. Intermolecular interactions between the anion and cation, and the conformational states of each component of the salt, are of significant interest as many of the distinctive properties ascribed to ionic liquids are determined to a large extent by these interactions. Crystallographic analysis provides a direct insight into the spatial relationship between the cations and anions and provides a basis for an enhanced understanding of the physico-chemical relationship of the ionic liquids. This perspective article examines the crystallographic studies of relevance to ionic liquid-forming organic salts as a basis for the rational design and synthesis of novel ionic liquids.

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Section: Ionic Liquid Clathrates Complexes and Inclusion Compoundsmentioning

confidence: 99%

Structural analysis of low melting organic salts: perspectives on ionic liquids

Dean

Pringle

MacFarlane

2010

Phys. Chem. Chem. Phys.

124

121

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“…In this work is reported the cocrystallisation of imidazolium based salt with 18-crown-6. Comparable compounds have been synthesized very recently by Bates and Gale [6][7][8] …”

Section: Discussionmentioning

confidence: 99%

Crystal structure of bis(1,3-dimethylimidazolium hydrogen sulfate) — 18-crown-6 (2:1), [C5H9N2]2[HSO4]2 · C12H24O6

Gjikaj¹

2008

Zeitschrift Für Kristallographie - New Crystal Structures

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“…Ethyleneoxy polymers often have very low glass transition temperatures and thus are liquids at room temperature. ,,− Ethyleneoxy moieties are believed to stabilize the imidazolium cation and encourage the separation and transport of the counterion away from it. Indeed, there are many examples of complexes of imidazolium cations with polyethers, both cyclic (crown ethers) and linear, e.g., poly(ethylene glycol)s. − The ethyleneoxy moieties provide an electron-rich environment via the multiple lone pairs associated with the oxygen atoms, which stabilizes the cationic species and allows for ion pair dissociation, yielding more “free” or less tightly bound anions necessary for charge transport. , …”

Section: Introductionmentioning

confidence: 99%

Ion Conducting ROMP Monomers Based on (Oxa)norbornenes with Pendant Imidazolium Salts Connected via Oligo(oxyethylene) Units and with Oligo(ethyleneoxy) Terminal Moieties

et al. 2019

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A matrix of 22 two-armed norbornene-based imidazolium TFSI monomers (8) was synthesized to determine the optimal structure in terms of single ion conductivity. For the chain tethering the imidazolium ring to the norbornene ring three or four oxyethylene units are optimal. A terminal group of two ethyleneoxy units was optimal. NMR studies indicated that both the tether oxyethylene units and the terminal ethyleneoxy units interact with the imidazolium cation via hydrogen bonding. 8r (X = 4, Y = 2) exhibited a conductivity of 9.57 × 10–5 S/cm at 25 °C and a T g of −46 °C. Low T g values do not correlate with higher conductivity as a result of the H-bonding interactions. Stability toward autopolymerization and reasonable conductivities provide an acceptable platform for ion conducting ROMP polymers. Four one-armed norbornene-based imidazolium TFSI monomers (15) were prepared with tetra(ethyleneoxy) linkers/spacers and variable terminal groups. All of these exhibited low T gs (<−55 °C) and room temperature conductivities >10–4 S/cm, the highest being 4.39 × 10–4 S/cm for 15c (T g = −69 °C), the analogue of 8r, providing hope for outstanding polymers. Three oxanorbornene-based two-armed imidazolium TFSI monomers (18) were prepared with varied linkers and terminal groups. 18b possesses a room temperature conductivity of 1.2 × 10–4 S/cm, again augering well for polymers derived therefrom by ROMP.

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Crown-ether enclosure generated by ionic liquid components—synthesis, crystal structure and Raman spectra of compounds of imidazolium based salts and 18-crown-6

Cited by 18 publications

References 80 publications

Structural analysis of low melting organic salts: perspectives on ionic liquids

Structural analysis of low melting organic salts: perspectives on ionic liquids

Crystal structure of bis(1,3-dimethylimidazolium hydrogen sulfate) — 18-crown-6 (2:1), [C5H9N2]2[HSO4]2 · C12H24O6

Ion Conducting ROMP Monomers Based on (Oxa)norbornenes with Pendant Imidazolium Salts Connected via Oligo(oxyethylene) Units and with Oligo(ethyleneoxy) Terminal Moieties

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