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Imidazolium-based ionic liquids with large weakly coordinating anions

Imidazolium-based ionic liquids with large weakly coordinating anions
Imidazolium-based ionic liquids with large weakly coordinating anions
Eight imidazolium-based salts with the weakly-coordinating anions [BArF]− and [Al(OtC4F9)4]− ([BArF]− = tetrakis{3,5-bis(trifluoromethyl)phenyl}borate) have been synthesized. Characterization by 1H NMR spectroscopy shows that the salts are fully dissociated in solution. Six examples have been further characterized by X-ray crystallography, revealing that weak hydrogen bonds do occur in the solid phase between the imidazolium cations and weakly coordinating anions. Comparison with the bulky [IDiPPH] imidazolium cation (IDiPPH = 1,3-bis{2,6-bis(diisopropyl)phenyl}imidazolium) shows that large steric bulk close to the imidazolium protons can preclude hydrogen bonds from forming. Differential scanning calorimetry of the salts reveal that all are thermally stable up to 200 °C which renders them as potentially suitable background electrolytes for electrochemical processes which take place at elevated temperatures.
1144-0546
1677-1686
Levason, William
e7f6d7c7-643c-49f5-8b57-0ebbe1bb52cd
Pugh, David
9ec61267-ae4d-40d8-bebf-0d603e2588d3
Reid, Gillian
37d35b11-40ce-48c5-a68e-f6ce04cd4037
Levason, William
e7f6d7c7-643c-49f5-8b57-0ebbe1bb52cd
Pugh, David
9ec61267-ae4d-40d8-bebf-0d603e2588d3
Reid, Gillian
37d35b11-40ce-48c5-a68e-f6ce04cd4037

Levason, William, Pugh, David and Reid, Gillian (2017) Imidazolium-based ionic liquids with large weakly coordinating anions. New Journal of Chemistry, 41, 1677-1686. (doi:10.1039/C6NJ03674K).

Record type: Article

Abstract

Eight imidazolium-based salts with the weakly-coordinating anions [BArF]− and [Al(OtC4F9)4]− ([BArF]− = tetrakis{3,5-bis(trifluoromethyl)phenyl}borate) have been synthesized. Characterization by 1H NMR spectroscopy shows that the salts are fully dissociated in solution. Six examples have been further characterized by X-ray crystallography, revealing that weak hydrogen bonds do occur in the solid phase between the imidazolium cations and weakly coordinating anions. Comparison with the bulky [IDiPPH] imidazolium cation (IDiPPH = 1,3-bis{2,6-bis(diisopropyl)phenyl}imidazolium) shows that large steric bulk close to the imidazolium protons can preclude hydrogen bonds from forming. Differential scanning calorimetry of the salts reveal that all are thermally stable up to 200 °C which renders them as potentially suitable background electrolytes for electrochemical processes which take place at elevated temperatures.

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NJ-ART-11-2016-003674 - Accepted Manuscript
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Accepted/In Press date: 13 January 2017
e-pub ahead of print date: 16 January 2017
Published date: 21 February 2017

Identifiers

Local EPrints ID: 412501
URI: http://eprints.soton.ac.uk/id/eprint/412501
ISSN: 1144-0546
PURE UUID: 074d3d7c-8651-4a96-a634-861ee7c92cbc
ORCID for William Levason: ORCID iD orcid.org/0000-0003-3540-0971
ORCID for Gillian Reid: ORCID iD orcid.org/0000-0001-5349-3468

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Date deposited: 17 Jul 2017 14:00
Last modified: 18 Feb 2021 16:34

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Author: William Levason ORCID iD
Author: David Pugh
Author: Gillian Reid ORCID iD

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