Aggregation behavior of non-cytotoxic ester functionalized morpholinium based ionic liquids in aqueous media

Chauhan, Vinay; Kamboj, Raman; Rana, Suraj Prakash Singh; Kaur, Taranjeet; Kaur, Gurcharan; Singh, Sukhprit; Kang, Tejwant Singh

doi:10.1016/j.jcis.2015.01.044

Cited by 48 publications

(45 citation statements)

References 55 publications

(106 reference statements)

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“…Surface tension of the aqueous C 8 EMorphBr solution as a function of concentration is plotted in Figure SI‐1 along with the published literature values of (i) imidazolium and pyridinium based ester functionalized ionic liquid based surfactant (ILBS) with C 8 alkyl chain length, C 8 EMeImBr and C 8 EPyrBr and (ii) conventional cationic surfactant with C 8 alkyl chain length, i. e. C 8 TABr at 25 °C in aqueous medium . The idea was to observe the impact of head group on surface activity and also to compare the data with the conventional surfactant.…”

Section: Resultsmentioning

confidence: 99%

“…4‐methyl‐4‐(2‐(octyloxy)‐2‐oxoethyl)morpholin‐4‐ium bromide, C 8 EMorphBr with molecular formula C 15 H 30 BrNO 3 and molecular weight of 352.31 g/mole was synthesized in our laboratory following the two steps procedure . Briefly, in the first step, the octyl‐2‐bromoacetate was synthesized by mixing n‐octanol (10 mmol, 16 mL) and bromoacetic acid (12 mmol, 8.63 mL) at a volume ratio of 1 : 1.2.…”

Section: Methodsmentioning

confidence: 99%

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Sodium Salicylate Mediated Ionic Liquid Based Catanionic Coacervates as Membrane‐Free Microreactors for the Selective Sequestration of Dyes and Curcumin

et al. 2019

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Designing artificial protocells to sequester the biomolecules within its compartments is a challenging task and can be achieved through the use of surfactant-based coacervates. Surfactant structures could be tailored to achieve the highest sequestration through coacervate droplets, irrespective of the polarity, charge and type of the analytes. Herein, we designed a morpholinium-based ester-functionalized ionic-liquid-based surfactant (ILBS) with a higher surface activity than its analogous conventional surfactant to form complex catanionic coacervates over the broad range of sodium salicylate (NaSal) concentrations. The spherically shaped micellar aggregates of the investigated ILBS are transformed into cylindrical shapes and again in the spherically shaped micellar aggregates depending on the NaSal concentration, which forms the coacervate droplets. The complex catanionic coacervates have been studied for their stability in the presence of mono and divalent cations, pH, temperature, viscosity and with respect to time. The microfluidic channel of 100 μm internal diameter was designed to obtain coacervate droplets with a maximum size of 100 μm. The coacervates were designed based on the NaSal concentration; cationic, neutral and anionic to exhibit selective and non-selective encapsulation of the model charged dyes. We speculate that the strategically designed coacervate droplets could mimic membrane-free protocells, which are applicable in multiple biomimetic operations.[a] A.

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Section: Resultsmentioning

confidence: 99%

Section: Methodsmentioning

confidence: 99%

Sodium Salicylate Mediated Ionic Liquid Based Catanionic Coacervates as Membrane‐Free Microreactors for the Selective Sequestration of Dyes and Curcumin

et al. 2019

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“…Besides the imidazolium family, other types of SAILs have also been investigated, namely ammonium-, [35][36][37][38] phosphonium-, [23] morpholinium-, [38][39][40][41] and guanidinium-based SAILs. [42][43][44] Brown et al [35] reported a series of IL-based surfactants composed of tetraalkylammonium cations and common surfactant anions (derived from dodecyl sulfate and aerosol-OT) as alternatives to imidazolium-based systems, being claimed as cheaper and environmentally more benign.…”

Section: Introductionmentioning

confidence: 99%

Synthesis and Characterization of Surface‐Active Ionic Liquids Used in the Disruption of Escherichia Coli Cells

et al. 2019

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Twelve surface‐active ionic liquids (SAILs) and surface‐active derivatives, based on imidazolium, ammonium, and phosphonium cations and containing one, or more, long alkyl chains in the cation and/or the anion, were synthetized and characterized. The aggregation behavior of these SAILs in water, as well as their adsorption at solution/air interface, were studied by assessing surface tension and conductivity. The CMC values obtained (0.03–6.0 mM) show a high propensity of these compounds to self‐aggregate in aqueous media. Their thermal properties were also characterized, namely the melting point and decomposition temperature by using DSC and TGA, respectively. Furthermore, the toxicity of these SAILs was evaluated using the marine bacteria Aliivibrio fischeri (Gram‐negative). According to the EC50 values obtained (0.3–2.7 mg L−1), the surface‐active compounds tested should be considered “toxic” or “highly toxic”. Their ability to induce cell disruption of Escherichia coli cells (also Gram‐negative), releasing the intracellular green fluorescent protein (GFP) produced, was investigated. The results clearly evidence the capability of these SAILs to act as cell disruption agents.

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“…In order to further fine‐tune the properties of the ILBSs, recently a new concept of incorporating various functionalities such as hydroxyl, vinyl, ester, amine, ether or amide in the structure of ILBSs has been materialized ,. It is reported that incorporating functionality influences the interfacial and micellar properties significantly.…”

Section: Introductionmentioning

confidence: 99%

“…It is reported that incorporating functionality influences the interfacial and micellar properties significantly. For example, ester or amide functionalized ILBSs with imidazolium, pyridinium or morpholinium cations exhibit better surface activity than the homologous traditional cationic surfactants and non‐functionalized ILBSs ,. Recently, we reported the improved interfacial and micellar properties of the vinylfunctionalized ILBSs compared to their saturated analogous ILBS and conventional surfactant .…”

Section: Introductionmentioning

confidence: 99%

Salt‐Induced Microstructural Transitions in Aqueous Dispersions of Ionic‐Liquids‐Based Surfactants

et al. 2018

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Applicability and performance ability of the surfactants are controlled through their aggregation behavior, which are modulated by employing external additives. In order to achieve favorable shape and sized nano‐aggregates, we have investigated the role of structure making hydrotop; sodium salicylate (NaSal) on the micellar transition of the functionalized and non‐functionalized ionic liquid based surfactants (ILBSs) (1‐hexadecyl‐3‐vinylimidazolium bromide and 1‐hexadecyl‐3‐methylimidazolium bromide) in aqueous medium. The micelle to vesicle transitions in the studied systems is explored using viscosity, dynamic light scattering and transmission electron microscopy measurements. For the first time we report the nano and micro‐structural aggregates of the vinylfunctionalized ILBSs with respect to the composition, and concentration of the additives; alkyl chain length and head group of ILBSs. Transmissions electron microscopy (TEM) revealed the formation of vesicles at high concentration of NaSal (∼1000 mM) for the vinylfunctionalized ILBS.

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Aggregation behavior of non-cytotoxic ester functionalized morpholinium based ionic liquids in aqueous media

Cited by 48 publications

References 55 publications

Sodium Salicylate Mediated Ionic Liquid Based Catanionic Coacervates as Membrane‐Free Microreactors for the Selective Sequestration of Dyes and Curcumin

Sodium Salicylate Mediated Ionic Liquid Based Catanionic Coacervates as Membrane‐Free Microreactors for the Selective Sequestration of Dyes and Curcumin

Synthesis and Characterization of Surface‐Active Ionic Liquids Used in the Disruption of Escherichia Coli Cells

Salt‐Induced Microstructural Transitions in Aqueous Dispersions of Ionic‐Liquids‐Based Surfactants

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