Self-aggregation of ionic liquids: micelle formation in aqueous solution

Blešić, Marijana; Marques, Maria Helena Vieira Pereira; Plechkova, Natalia V.; Seddon, Kenneth R.; Rebelo, Luís Paulo N.; Lopes, António

doi:10.1039/b615406a

Cited by 551 publications

(506 citation statements)

References 30 publications

(38 reference statements)

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“…[14][15][16] A special feature of these saltssamong which imidazoliumbased ILs have received particular attentionsis that their amphiphilic character and their hydrophobicity can be tuned by varying the size of their alkyl chain length. 17 Nevertheless, in spite of their growing interest, their bulk state, structure, and dynamics on a nanoscopic scale have just started being explored. Yet, based only on simplistic considerations, a structural organization in ILs and IL solutions is expected since the imidazolium cation can be sketched as a polar head with an apolar tail (the alkyl side chains).…”

Section: Introductionmentioning

confidence: 99%

¹H NMR and Molecular Dynamics Evidence for an Unexpected Interaction on the Origin of Salting-In/Salting-Out Phenomena

et al. 2010

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By employing 1 H NMR spectroscopy and molecular simulations, we provide an explanation for recent observations that the aqueous solubilities of ionic liquids exhibit salting-out to salting-in regimes upon addition of distinct inorganic salt ions. Using a typical ionic liquid [1-butyl-3-methylimidazolium bis(trifluoromethylsulfonyl)imide], we observed the existence of preferential specific interactions between the low electrical charge density ("apolar moiety") parts of the ionic liquid cation and the inorganic salts. These a priori unexpected interactions become increasingly favorable as one moves from salting-out to salting-in effects. More specifically, this interpretation is validated by distinct aqueous solution 1 H NMR data shifts in the ionic liquid cation upon inorganic salt addition. These shifts, which are well noted in the terminal and preterminal hydrogens of the alkyl chain appended to the imidazolium ring, correlate quantitatively with solubility data, both for cases where the nature of inorganic salt is changed, at constant concentration, and for those where the concentration of a given inorganic salt is varied. Molecular simulations have also been performed permitting us to garner a broader picture of the underlying mechanism and structure of this complex solvation phenomenon. These findings can now be profitably used to anticipate solution behavior upon inorganic salt addition well beyond the specificity of the ionic liquid solutions, i.e., for a diversity of distinct solutes differing in chemical nature.

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Section: Introductionmentioning

confidence: 99%

¹H NMR and Molecular Dynamics Evidence for an Unexpected Interaction on the Origin of Salting-In/Salting-Out Phenomena

et al. 2010

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“…The blue and gray lines are the predicted EC50 lines for wild-type (with cell wall) and mutant (without cell wall) strains of Chlamydomoas reinhardtii, respectively. The green line corresponds to the RTIL critical micelle concentration (CMC) of (Blesic et al 2007). The symbols correspond to the specific morphologies as in the right image.…”

Section: Introductionmentioning

confidence: 99%

Room-temperature ionic liquids meet bio-membranes: the state-of-the-art

Benedetto

2017

Biophys Rev

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Room-temperature ionic liquids (RTIL) are a new class of organic salts whose melting temperature falls below the conventional limit of 100°C. Their low vapor pressure, moreover, has made these ionic compounds the solvents of choice of the so-called green chemistry. For these and other peculiar characteristics, they are increasingly used in industrial applications. However, studies of their interaction with living organisms have highlighted mild to severe health hazards. Since their cytotoxicity shows a positive correlation with their lipophilicity, several chemical-physical studies of their interactions with biomembranes have been carried out in the last few years, aiming to identify the molecular mechanisms behind their toxicity. Cation chain length and anion nature of RTILs have seemed to affect lipophilicity and, in turn, their toxicity. However, the emerging picture raises new questions, points to the need to assess toxicity on a case-by-case basis, but also suggests a potential positive role of RTILs in pharmacology, bio-medicine and bio-nanotechnology. Here, we review this new subject of research, and comment on the future and the potential importance of this emerging field of study.

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“…It was proposed that the short-chain [C 4 mim][BF 4 ] formed polydisperse spherical aggregates, whereas the [C 8 mim]I formed regularly sized micelles above the cmc. The micelle formation of surface active [C 2n mim] + (n = 4~8) in aqueous solution was investigated by several methods, such as surface tension, electrical conductivity measurements and fluorescence techniques et al (Blesic et al, 2007;Blesic et al, 2008;Dong et al, 2007;Dong et al, 2008a;Dong et al, 2008b;El Seoud et al, 2007;Inoue et al, 2007;Jungnickel et al, 2008;Luczak et al, 2008;Luczak et al, 2009;Modaressi et al, 2007b;Singh & Kumar, 2007Vanyur et al, 2007;Wang et al, 2008;Wang et al, 2007;Zhang et al, 2008b;Zhao et al, 2008a). Results showed that the long chain imidazolium ILs acted as ionic surfactants and stronger aggregation tendency of the ILs might be attributed to characteristic nature of imidazolium head group such as potency of H-bond formation, which is lacking in common ionic surfactants.…”

Section: Wwwintechopencommentioning

confidence: 99%

Supramolecular Structures in the Presence of Ionic Liquids

Shen¹,

Chen²,

Zhang³

et al. 2011

Ionic Liquids: Theory, Properties, New Approaches

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Self-aggregation of ionic liquids: micelle formation in aqueous solution

Cited by 551 publications

References 30 publications

¹H NMR and Molecular Dynamics Evidence for an Unexpected Interaction on the Origin of Salting-In/Salting-Out Phenomena

¹H NMR and Molecular Dynamics Evidence for an Unexpected Interaction on the Origin of Salting-In/Salting-Out Phenomena

Room-temperature ionic liquids meet bio-membranes: the state-of-the-art

Supramolecular Structures in the Presence of Ionic Liquids

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Self-aggregation of ionic liquids: micelle formation in aqueous solution

Cited by 551 publications

References 30 publications

1H NMR and Molecular Dynamics Evidence for an Unexpected Interaction on the Origin of Salting-In/Salting-Out Phenomena

1H NMR and Molecular Dynamics Evidence for an Unexpected Interaction on the Origin of Salting-In/Salting-Out Phenomena

Room-temperature ionic liquids meet bio-membranes: the state-of-the-art

Supramolecular Structures in the Presence of Ionic Liquids

Contact Info

Product

Resources

About

¹H NMR and Molecular Dynamics Evidence for an Unexpected Interaction on the Origin of Salting-In/Salting-Out Phenomena

¹H NMR and Molecular Dynamics Evidence for an Unexpected Interaction on the Origin of Salting-In/Salting-Out Phenomena