Interfacial and aggregation behavior of dicationic and tricationic ionic liquid-based surfactants in aqueous solution

Omprakash Nacham; Armide Martín-Pérez; Daniel J. Steyer; María J. Trujillo-Rodríguez; Jared L. Anderson; Verónica Pino; Ana M. Afonso

doi:10.1016/j.colsurfa.2015.01.026

Interfacial and aggregation behavior of dicationic and tricationic ionic liquid-based surfactants in aqueous solution

Omprakash Nacham, Armide Martín-Pérez, Daniel J. Steyer, María J. Trujillo-Rodríguez, Jared L. Anderson, Verónica Pino, Ana M. Afonso

Chemistry (Twin Cities)

Research output: Contribution to journal › Article › peer-review

28 Scopus citations

Abstract

The interfacial and aggregation behavior of three dicationic and two tricationic ionic liquid-based (IL) surfactants in aqueous solutions have been carried out. The studied dicationic IL-based surfactants were 1,12-di(3-butylimidazolium)dodecane bromide ((C₄Im)₂C₁₂-2Br), 1,12-di(3-decylimidazolium)dodecane bromide ((C₁₀Im)₂C₁₂-2Br), and 1,12-di(3-hexadecylimidazolium)dodecane bromide ((C₁₆Im)₂C₁₂-2Br). Two classes of trigonal tricationic surfactants containing triethylamine (Am) and 1,3,5-trimethylbenzene (Bn) cores were synthesized for first time and characterized, specifically, 3,3',3″-octyl-1,1',1″-(2-ethylamino) imidazolium bromide ((C₈Im)₃Am-3Br), and 3,3',3″-octyl-1,1',1″-(1,3,5)tris(methylene) benzene imidazolium bromide ((C₈Im)₃Bn-3Br). The critical micelle concentration (CMC) values and other aggregation parameters, including adsorption efficiency (pC₂₀), surface tension at the CMC (γ_cmc), degree of dissociation (α), and the degree of counterion binding in the micelle (β) were obtained using a variety of techniques including surface tension, conductivity, and fluorescence measurements. For the first time, the aggregation numbers (N_agg) were also obtained for this group of surfactants. A study into the influence of acetonitrile on the stability and aggregation behavior of dicationic and tricationic IL-based surfactants was also undertaken. The CMC values of the dicationic surfactants clearly decrease as a function of the side chain, when the same linker is maintained. The CMC values of the tricationic surfactants were lower than analogous linear trimeric surfactants. For the novel tricationic surfactants, the effect of sodium salts (C₆H₅COONa, NaBr, and NaI) on the surface activity was also investigated. It was also observed that the surface activity parameters (pC₂₀ and CMC/C₂₀) of tricationic surfactants increased significantly in the presence of added electrolytes.

Original language	English (US)
Pages (from-to)	224-234
Number of pages	11
Journal	Colloids and Surfaces A: Physicochemical and Engineering Aspects
Volume	469
DOIs	https://doi.org/10.1016/j.colsurfa.2015.01.026
State	Published - Mar 1 2015

Bibliographical note

Funding Information:
V.P. thanks the Spanish Ministry of Economy and Competitiveness (MINECO) for the Ramón y Cajal contract with the University of La Laguna (ULL), as well as funding from MINECO ref. MAT2013-43101-R and from the ULL ref. 2013-young researchers modality. A.M.A. acknowledges funding from a Bridge Project and a Consolidated Research Funding Project of ULL. J.L.A. acknowledges funding from the Chemical Measurement and Imaging Program in the Division of Chemistry at the National Science Foundation ( CHE-1413199 ). A.M.P. thanks his fellowship from the Environmental Service of ULL (SEMALL), and M.J.T.R. thanks her PhD fellowship from “Fundación CajaCanarias”. D.J.S. thanks the office of Undergraduate Research at The University of Toledo for funding of an undergraduate research grant.

Publisher Copyright:
© 2015 Elsevier B.V.

Keywords

Aggregation number
Cationic surfactants
Critical micelle concentration
Dicationic ionic liquids
Ionic liquid-based surfactants
Tricationic ionic liquids

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Nacham, O., Martín-Pérez, A., Steyer, D. J., Trujillo-Rodríguez, M. J., Anderson, J. L., Pino, V., & Afonso, A. M. (2015). Interfacial and aggregation behavior of dicationic and tricationic ionic liquid-based surfactants in aqueous solution. Colloids and Surfaces A: Physicochemical and Engineering Aspects, 469, 224-234. https://doi.org/10.1016/j.colsurfa.2015.01.026

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abstract = "The interfacial and aggregation behavior of three dicationic and two tricationic ionic liquid-based (IL) surfactants in aqueous solutions have been carried out. The studied dicationic IL-based surfactants were 1,12-di(3-butylimidazolium)dodecane bromide ((C4Im)2C12-2Br), 1,12-di(3-decylimidazolium)dodecane bromide ((C10Im)2C12-2Br), and 1,12-di(3-hexadecylimidazolium)dodecane bromide ((C16Im)2C12-2Br). Two classes of trigonal tricationic surfactants containing triethylamine (Am) and 1,3,5-trimethylbenzene (Bn) cores were synthesized for first time and characterized, specifically, 3,3',3″-octyl-1,1',1″-(2-ethylamino) imidazolium bromide ((C8Im)3Am-3Br), and 3,3',3″-octyl-1,1',1″-(1,3,5)tris(methylene) benzene imidazolium bromide ((C8Im)3Bn-3Br). The critical micelle concentration (CMC) values and other aggregation parameters, including adsorption efficiency (pC20), surface tension at the CMC (γcmc), degree of dissociation (α), and the degree of counterion binding in the micelle (β) were obtained using a variety of techniques including surface tension, conductivity, and fluorescence measurements. For the first time, the aggregation numbers (Nagg) were also obtained for this group of surfactants. A study into the influence of acetonitrile on the stability and aggregation behavior of dicationic and tricationic IL-based surfactants was also undertaken. The CMC values of the dicationic surfactants clearly decrease as a function of the side chain, when the same linker is maintained. The CMC values of the tricationic surfactants were lower than analogous linear trimeric surfactants. For the novel tricationic surfactants, the effect of sodium salts (C6H5COONa, NaBr, and NaI) on the surface activity was also investigated. It was also observed that the surface activity parameters (pC20 and CMC/C20) of tricationic surfactants increased significantly in the presence of added electrolytes.",

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author = "Omprakash Nacham and Armide Mart{\'i}n-P{\'e}rez and Steyer, {Daniel J.} and Trujillo-Rodr{\'i}guez, {Mar{\'i}a J.} and Anderson, {Jared L.} and Ver{\'o}nica Pino and Afonso, {Ana M.}",

note = "Funding Information: V.P. thanks the Spanish Ministry of Economy and Competitiveness (MINECO) for the Ram{\'o}n y Cajal contract with the University of La Laguna (ULL), as well as funding from MINECO ref. MAT2013-43101-R and from the ULL ref. 2013-young researchers modality. A.M.A. acknowledges funding from a Bridge Project and a Consolidated Research Funding Project of ULL. J.L.A. acknowledges funding from the Chemical Measurement and Imaging Program in the Division of Chemistry at the National Science Foundation ( CHE-1413199 ). A.M.P. thanks his fellowship from the Environmental Service of ULL (SEMALL), and M.J.T.R. thanks her PhD fellowship from “Fundaci{\'o}n CajaCanarias”. D.J.S. thanks the office of Undergraduate Research at The University of Toledo for funding of an undergraduate research grant. Publisher Copyright: {\textcopyright} 2015 Elsevier B.V.",

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T1 - Interfacial and aggregation behavior of dicationic and tricationic ionic liquid-based surfactants in aqueous solution

AU - Nacham, Omprakash

AU - Martín-Pérez, Armide

AU - Steyer, Daniel J.

AU - Trujillo-Rodríguez, María J.

AU - Anderson, Jared L.

AU - Pino, Verónica

AU - Afonso, Ana M.

N1 - Funding Information: V.P. thanks the Spanish Ministry of Economy and Competitiveness (MINECO) for the Ramón y Cajal contract with the University of La Laguna (ULL), as well as funding from MINECO ref. MAT2013-43101-R and from the ULL ref. 2013-young researchers modality. A.M.A. acknowledges funding from a Bridge Project and a Consolidated Research Funding Project of ULL. J.L.A. acknowledges funding from the Chemical Measurement and Imaging Program in the Division of Chemistry at the National Science Foundation ( CHE-1413199 ). A.M.P. thanks his fellowship from the Environmental Service of ULL (SEMALL), and M.J.T.R. thanks her PhD fellowship from “Fundación CajaCanarias”. D.J.S. thanks the office of Undergraduate Research at The University of Toledo for funding of an undergraduate research grant. Publisher Copyright: © 2015 Elsevier B.V.

PY - 2015/3/1

Y1 - 2015/3/1

N2 - The interfacial and aggregation behavior of three dicationic and two tricationic ionic liquid-based (IL) surfactants in aqueous solutions have been carried out. The studied dicationic IL-based surfactants were 1,12-di(3-butylimidazolium)dodecane bromide ((C4Im)2C12-2Br), 1,12-di(3-decylimidazolium)dodecane bromide ((C10Im)2C12-2Br), and 1,12-di(3-hexadecylimidazolium)dodecane bromide ((C16Im)2C12-2Br). Two classes of trigonal tricationic surfactants containing triethylamine (Am) and 1,3,5-trimethylbenzene (Bn) cores were synthesized for first time and characterized, specifically, 3,3',3″-octyl-1,1',1″-(2-ethylamino) imidazolium bromide ((C8Im)3Am-3Br), and 3,3',3″-octyl-1,1',1″-(1,3,5)tris(methylene) benzene imidazolium bromide ((C8Im)3Bn-3Br). The critical micelle concentration (CMC) values and other aggregation parameters, including adsorption efficiency (pC20), surface tension at the CMC (γcmc), degree of dissociation (α), and the degree of counterion binding in the micelle (β) were obtained using a variety of techniques including surface tension, conductivity, and fluorescence measurements. For the first time, the aggregation numbers (Nagg) were also obtained for this group of surfactants. A study into the influence of acetonitrile on the stability and aggregation behavior of dicationic and tricationic IL-based surfactants was also undertaken. The CMC values of the dicationic surfactants clearly decrease as a function of the side chain, when the same linker is maintained. The CMC values of the tricationic surfactants were lower than analogous linear trimeric surfactants. For the novel tricationic surfactants, the effect of sodium salts (C6H5COONa, NaBr, and NaI) on the surface activity was also investigated. It was also observed that the surface activity parameters (pC20 and CMC/C20) of tricationic surfactants increased significantly in the presence of added electrolytes.

AB - The interfacial and aggregation behavior of three dicationic and two tricationic ionic liquid-based (IL) surfactants in aqueous solutions have been carried out. The studied dicationic IL-based surfactants were 1,12-di(3-butylimidazolium)dodecane bromide ((C4Im)2C12-2Br), 1,12-di(3-decylimidazolium)dodecane bromide ((C10Im)2C12-2Br), and 1,12-di(3-hexadecylimidazolium)dodecane bromide ((C16Im)2C12-2Br). Two classes of trigonal tricationic surfactants containing triethylamine (Am) and 1,3,5-trimethylbenzene (Bn) cores were synthesized for first time and characterized, specifically, 3,3',3″-octyl-1,1',1″-(2-ethylamino) imidazolium bromide ((C8Im)3Am-3Br), and 3,3',3″-octyl-1,1',1″-(1,3,5)tris(methylene) benzene imidazolium bromide ((C8Im)3Bn-3Br). The critical micelle concentration (CMC) values and other aggregation parameters, including adsorption efficiency (pC20), surface tension at the CMC (γcmc), degree of dissociation (α), and the degree of counterion binding in the micelle (β) were obtained using a variety of techniques including surface tension, conductivity, and fluorescence measurements. For the first time, the aggregation numbers (Nagg) were also obtained for this group of surfactants. A study into the influence of acetonitrile on the stability and aggregation behavior of dicationic and tricationic IL-based surfactants was also undertaken. The CMC values of the dicationic surfactants clearly decrease as a function of the side chain, when the same linker is maintained. The CMC values of the tricationic surfactants were lower than analogous linear trimeric surfactants. For the novel tricationic surfactants, the effect of sodium salts (C6H5COONa, NaBr, and NaI) on the surface activity was also investigated. It was also observed that the surface activity parameters (pC20 and CMC/C20) of tricationic surfactants increased significantly in the presence of added electrolytes.

KW - Aggregation number

KW - Cationic surfactants

KW - Critical micelle concentration

KW - Dicationic ionic liquids

KW - Ionic liquid-based surfactants

KW - Tricationic ionic liquids

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JO - Colloids and Surfaces A: Physicochemical and Engineering Aspects

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ER -

Interfacial and aggregation behavior of dicationic and tricationic ionic liquid-based surfactants in aqueous solution

Abstract

Bibliographical note

Keywords

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