Aggregation behavior of alkyl triphenyl phosphonium bromides in aprotic and protic ionic liquids

Lü, Fei; Shi, Lijuan; Gu, Yingqiu; Yang, Xiujie; Zheng, Liqiang

doi:10.1007/s00396-013-2986-x

Cited by 20 publications

(6 citation statements)

References 47 publications

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“…A comparison of the micellization of alkyltriphenyl phosphonium bromide surfactants in EAN and in BMIm BF 4 showed that both were enthalpy driven, with lower CMC values and a stronger solvophobic effect in EAN. The EA cations were observed to intercalate with the surfactant molecules, whereas the BMIm cations were located in the head group region only …”

Section: Amphiphile Self-assemblymentioning

confidence: 99%

Protic Ionic Liquids: Evolving Structure–Property Relationships and Expanding Applications

2015

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Section: Amphiphile Self-assemblymentioning

confidence: 99%

Protic Ionic Liquids: Evolving Structure–Property Relationships and Expanding Applications

2015

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“…It is evident that the cmc values increase as the temperature rises, and the increasing tendency can fit a second-order polynomial, similar to the tendencies of traditional ionic surfactants in water or ionic liquid. 22,46 It is well-known that when the temperature increases the order structure of water molecules surrounding the hydrophobic domain is destroyed, which is unfavorable to micellization, and then cmc increases. An analogous mechanism 23 Steady-State Fluorescence Measurement in Water.…”

Section: = −mentioning

confidence: 99%

Self-Aggregation of New Alkylcarboxylate-Based Anionic Surface Active Ionic Liquids: Experimental and Theoretical Investigations

Cheng

Wang

et al. 2014

J. Phys. Chem. B

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Halogen-free and low-cost alkylcarboxylate-based anionic surface active ionic liquids (SAILs), namely, 1-butyl-3-methylimidazolium alkylcarboxylates ([C4mim][C(n)H(2n-1)O2], n = 8, 10, 12), were first synthesized through the neutralization of imidazolium hydroxide by alkylcarboxylic acids. A systematic study of their self-aggregation behavior in water was investigated by surface tension, electrical conductivity, steady-state fluorescence quenching, and (1)H NMR. The micellar properties of this series of SAILs in ethylammonium nitrate (EAN) were also studied by surface tensiometry for comparison. A set of surface active parameters and thermodynamic parameters of these compounds in water and EAN was obtained. Surface tension results show that the surface activity of [C4mim][C(n)H(2n-1)O2] in EAN is inferior to that in water. They exhibit a higher ability to aggregate in water than the traditional anionic surfactants, sodium alkylcarboxylates (SAC), and anionic SAILs, 1-butyl-3-methylimidazolium alkylsulfates ([C4mim][C(n)H(2n+1)SO4]) with the same hydrocarbon chain length. This demonstrates that the incorporation of carboxylate group and [C4mim](+) cation favors micelle formation. To understand the discrepancy in the surface activity of alkylsulfate- and alkylcarboxylate-based SAILs, theoretical calculations were performed to give electrostatic potential of the corresponding anions. The higher surface activity of [C4mim][C12H23O2] mainly originates from the lower electronegativity of its anion. Density functional theory (DFT) calculations manifest that the interaction energy of binary combination SAILs-EAN is larger than that of SAILs-H2O, implying the stronger interaction of the former. Consequently, it is more difficult for [C4mim][C(n)H(2n-1)O2] to self-aggregate in EAN than in H2O. This work is expected to be of practical value for the environmentally friendly alkylcarboxylate-based SAILs in some potential applications, including nanomaterials synthesis and phase separation, among others.

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“…24 Later, the aggregation behavior of the alkyl triphenylphosphonium bromides, C n TPB, in aprotic and protic ILs was also investigated, where a stronger solvophobic effect between C n TPB and protic EAN was evidenced than aprotic [Bmim][BF 4 ]. 25 It can be inferred from these reports that the higher protonation ability of EAN is the extra driving force for surfactant molecules to form ordered aggregates. However, this has to be further verified for different self-assembling systems.…”

Section: Introductionmentioning

confidence: 99%

“…The effects of ILs on the aggregation properties, critical micellar concentration (cmc), and hydration behavior of different kinds of surfactants have been reported in several studies and found to be important for fine-tuning the surfactant properties for specific applications. − Yue et al had employed aprotic 1-butyl-3-methylimidazolium tetrafluoroborate ([Bmim]BF 4 ) and protic ethylammonium nitrate (EAN) to investigate the aggregation behavior of phytosterolethoxylate surfactant (BPS-10), which showed a higher effectiveness of EAN over [Bmim]BF 4 in promoting nonionic BPS-10 aggregation . Later, the aggregation behavior of the alkyl triphenylphosphonium bromides, C n TPB, in aprotic and protic ILs was also investigated, where a stronger solvophobic effect between C n TPB and protic EAN was evidenced than aprotic [Bmim][BF 4 ] . It can be inferred from these reports that the higher protonation ability of EAN is the extra driving force for surfactant molecules to form ordered aggregates.…”

Section: Introductionmentioning

confidence: 99%

Understanding Differential Interaction of Protic and Aprotic Ionic Liquids inside Molecular Confinement

et al. 2017

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Considering the contemporary interests of water-free reverse micelles (RMs) in the field of organic reaction medium and potential drug delivery carrier, we synthesized two different classes of ionic liquids (ILs), protic N-methyl-2-pyrrolidonium hexanoate, [NMP][Hex], and aprotic choline hexanoate, [Chl][Hex], and subsequently incorporated them in a mixture of polyoxyethylene (20) sorbitan monooleate (Tween-80) and cyclohexane. In order to understand the differential nature of interinterionic interaction of two ILs, we performed DFT calculations on pure ILs to correlate with experimental results. The formation of IL-in-oil RMs was confirmed from phase behavior and DLS studies. Interestingly, [NMP][Hex]-based systems showed a larger monophasic region and droplet size along with higher shear viscosity compared to [Chl][Hex]-based systems. Stronger interaction between [NMP] and Tween-80 due to their protic nature might be the driving force for such observations which supported the resonance stabilization energy [E] and charge population analysis by NBO calculation. Smaller E values along with lesser NBO charges on atoms involved in H-bonding in pure [NMP][Hex] than [Chl][Hex] corroborated with the experimental observations. This primary hypothesis was further confirmed from FTIR and time-resolved fluorescence studies. These systems showed efficient thermal stability. Taking all of the results together, we anticipate that these RMs could be used as efficient delivery systems and for nanomaterial synthesis.

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Aggregation behavior of alkyl triphenyl phosphonium bromides in aprotic and protic ionic liquids

Cited by 20 publications

References 47 publications

Protic Ionic Liquids: Evolving Structure–Property Relationships and Expanding Applications

Protic Ionic Liquids: Evolving Structure–Property Relationships and Expanding Applications

Self-Aggregation of New Alkylcarboxylate-Based Anionic Surface Active Ionic Liquids: Experimental and Theoretical Investigations

Understanding Differential Interaction of Protic and Aprotic Ionic Liquids inside Molecular Confinement

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