Supramolecular architectures of symmetrical dicationic ionic liquid based systems

Tadesse, Haregewine; Blake, Alexander J.; Champness, Neil R.; Warren, John E.; Rizkallah, P.J.; Licence, Peter

doi:10.1039/c2ce25106j

Cited by 21 publications

(18 citation statements)

References 54 publications

(60 reference statements)

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“…Each of the nine dicationic compounds (DC1–DC9, Fig. ) investigated in this work was prepared using reported literature methods . All of the dicationic compounds except DC3 were synthesised with bromide anions, whereas DC3 was synthesised with bis[(trifluoromethane)sulfonyl]imide anions ([NTf 2 ] – ); the molecular structures of the DC2 and DC3 dications were the same.…”

Section: Methodsmentioning

confidence: 99%

The use of dicationic ion-pairing compounds to enhance the ambient detection of surface lipids in positive ionization mode using desorption electrospray ionisation mass spectrometry

Rao

Mitchell

Licence

2014

Rapid Commun. Mass Spectrom.

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RATIONALE:Lipids are typically analysed in negative ionisation mode in desorption electrospray ionisation mass spectrometry (DESI-MS), which can result in reduced sensitivity. In this study we examine the use of dicationic compounds as reactive DESI-MS agents to detect a range of lipid standards from the surface in positive ionisation mode. METHODS: Nine dicationic compounds were tested for their ability to detect seven representative lipid species (palmitoleic acid, linoleic acid, phosphatidic acid (34:1), phosphoethanolamine (34:2), phosphatidylglycerol (34:1), phosphatidylserine (36:1), and phosphoinositol (34:2)) with a 2D DESI source on hydrophobic surfaces. Two different solvent systems (methanol/chloroform (1:1) and methanol) were tested with each dicationic compound, with the DESI-MS analysis performed in the positive ionisation mode. RESULTS: Most of the dications tested were able to form stable ion-pairs with the negatively charged lipid species when analysed from the surface with DESI-MS, and were detected readily in positive ionisation electrospray mode as singly charged species. The optimal solvent system was found to be methanol. The dicationic compound [C 6 (C 1 Pyrr) 2 ][Br] 2 was found to enhance the detection of palmitoleic acid (638%), linoleic acid (304%) and phosphoethanolamine (269%) compared with the negative ionisation mode. CONCLUSIONS: We demonstrate the first successful application of dicationic compounds in DESI-MS for the ambient surface detection of model lipids in positive electrospray ionisation mode. Dicationic compounds could potentially be used as reactive DESI-MS agents to improve the ambient detection of a number of negatively charged analytes.

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Section: Methodsmentioning

confidence: 99%

The use of dicationic ion-pairing compounds to enhance the ambient detection of surface lipids in positive ionization mode using desorption electrospray ionisation mass spectrometry

Rao

Mitchell

Licence

2014

Rapid Commun. Mass Spectrom.

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“…C 2 (MIm) 2 Br 2 , C 3 (MIm) 2 Br 2 , C 4 (MIm) 2 Br 2 , C 6 (MIm) 2 Br 2 and C 8 (MIm) 2 Br 2 were synthesized following the same procedure [8] , [14] , [15] . A three-necked round bottom flask fitted with reflux condenser and pressure equation funnel was filled with a solution of 30 mmol of 1,2-dibromoethane, 1,3-dibromopropane, 1,4-dibromobutane, 1,6-dibromohexane or 1,8-dibromooctane in 12 mL of methanol.…”

Section: Synthesis and Characterization Of Ilsmentioning

confidence: 99%

Synthesis and characterization data of monocationic and dicationic ionic liquids or molten salts

2018

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Data presented in this article are related with the research paper entitled “Ecotoxicity assessment of dicationic versus monocationic ionic liquids as a more environmentally friendly alternative” [1]. The present article describes the synthesis steps and characterization data of a set of twenty-six imidazolium, pyrrolidinium and pyridinium-based ionic liquids (ILs) or molten salts: nine monocationic and seventeen dicationic. Specifically, the chemical structure of the compounds was confirmed by 1H NMR, 13C NMR and 19F NMR spectroscopy and mass spectrometry (MS). Other data such as physical state at room temperature, melting point temperature (for solids at room temperature) and thermal decomposition temperature (when melting was not reached before decomposition) of the ILs or molten salts are also reported here.

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“…To this end, Licence et al have recently reported data about supramolecular architectures detected in the solid phase for some diimidazolium/[Br – ]‐based DOSs 1 (R = CH 3 , n = 6, 10) and dimethylimidazolium/[Br – ]‐ and dimethylimidazolium/[BF 4 – ]‐based DOSs 2 (R = CH 3 , n = 6) 32. Data collected by single‐crystal X‐ray diffraction gave evidence of the significant influence of the different lengths of the alkyl spacers and the nature of the anions.…”

Section: Physicochemical Properties and Structurementioning

confidence: 99%

Di‐ and Tricationic Organic Salts: An Overview of Their Properties and Applications

D’Anna¹,

Noto²

2014

Eur J Org Chem

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During recent years growing interest has been devoted to the synthesis and applications of polycationic organic salts. Among them, di‐ and tricationic organic salts can be considered the natural evolution of monocationic ones. These last have given rise to the large class of ionic liquids. In the cases of di‐ and tricationic organic salts, the potential to change their structural features simply by varying the properties either of the charged heads or of the spacers separating them provides the opportunity to obtain materials suitable for different applications. This review article highlights recent progress in the study of the properties of di‐ and tricationic organic salts, as well as in some of their uses as solvent systems, receptors for anion recognition, ionic liquid crystals, low‐molecular‐weight gelators, additives for dye‐sensitized solar cells, and so on.

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Supramolecular architectures of symmetrical dicationic ionic liquid based systems

Cited by 21 publications

References 54 publications

The use of dicationic ion-pairing compounds to enhance the ambient detection of surface lipids in positive ionization mode using desorption electrospray ionisation mass spectrometry

The use of dicationic ion-pairing compounds to enhance the ambient detection of surface lipids in positive ionization mode using desorption electrospray ionisation mass spectrometry

Synthesis and characterization data of monocationic and dicationic ionic liquids or molten salts

Di‐ and Tricationic Organic Salts: An Overview of Their Properties and Applications

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