Langmuir
Article
(17) Welton, T. Room-temperature ionic liquids. Solvents for
synthesis and catalysis. Chem. Rev. 1999, 99, 2071−2084.
(18) Rogers, R. D.; Seddon, K. R. Ionic liquids–solvents of the
future? Science 2003, 302, 792−793.
Author Contributions
§These authors contributed equally to this work.
Notes
The authors declare no competing financial interest.
(19) Moniruzzaman, M.; Nakashima, K.; Kamiya, N.; Goto, M.
Recent advances of enzymatic reactions in ionic liquids. Biochem. Eng.
J. 2010, 48, 295−314.
ACKNOWLEDGMENTS
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(20) Torimoto, T.; Tsuda, T.; Okazaki, K.; Kuwabata, S. New
frontiers in materials science opened by ionic liquids. Adv. Mater.
2010, 22, 1196−1221.
We thank Prof. Zhonghua Wu for the kind help with
synchrotron SAXS measurements and the SAXS station with
the Beijing Synchrotron Radiation Facility (BSRF) in China are
acknowledged. We are thankful for the financial support from
the National Natural Science Foundation of China (20773080,
20973104, and 21033005) and Shandong Provincial Science
Fund (2009ZRB01147).
(21) Armand, M.; Endres, F.; MacFarlane, D. R.; Ohno, H.; Scrosati,
B. Ionic-liquid materials for the electrochemical challenges of the
future. Nat. Mater. 2009, 8, 621−629.
(22) Prasad, V.; Kale, R. R.; Kumar, V.; Tiwari, V. K. Carbohydrate
chemistry and room temperature ionic liquids (RTILs): recent trends,
opportunities, challenges and future perspectives. Curr. Org. Synth.
2010, 7, 506−531.
(23) Li, Z. H.; Jia, Z.; Luan, Y. X.; Mu, T. C. Ionic liquids for
synthesis of inorganic nanomaterials. Curr. Opin. Solid State Mater. Sci.
2008, 12, 1−8.
(24) Greaves, T. L.; Drummond, C. J. Ionic liquids as amphiphile
self-assembly media. Chem. Soc. Rev. 2008, 37, 1709−1726.
(25) Walden, P. Molecular weights and electrical conductivity of
several fused salts. Bull. Acad. Imp. Sci. St. Petersburg 1914, 8, 405−422.
(26) Evans, D. F.; Chen, S. H.; Schriver, G. W.; Arnett, E. M.
Thermodynamics of solution of nonpolar gases in a fused salt.
Hydrophobic bonding behavior in a nonaqueous system. J. Am. Chem.
Soc. 1981, 102, 481−482.
(27) Mirejovsky, D.; Arnett, E. M. Heat capacities of solution for
alcohols in polar solvents and the new view of hydrophobic effects. J.
Am. Chem. Soc. 1983, 105, 1112−1117.
(28) Evans, D. F.; Yamauchi, A.; Wei, G. J.; Bloomfield, V. A. Micelle
size in ethylammonium nitrate as determined by classical and quasi-
elastic light scattering. J. Phys. Chem. 1983, 87, 3537−3541.
(29) Evans, D. F.; Kaler, E. W.; Benton, W. J. Liquid crystals in a
fused salt: β,γ-distearoylphosphatidylcholine in N-ethylammonium
nitrate. J. Phys. Chem. 1983, 87, 533−535.
(30) Araos, M. U.; Warr, G. G. Self-Assembly of Nonionic
Surfactants into Lyotropic Liquid Crystals in Ethylammonium Nitrate,
a Room-Temperature Ionic Liquid. J. Phys. Chem. B 2005, 109,
14275−14277.
(31) Greaves, T. L.; Weerawardena, A.; Fong, C.; Drummond, C. J.
Many protic ionic liquids mediate hydrocarbon-solvent interactions
and promote amphiphile self-assembly. Langmuir 2007, 23, 402−404.
(32) Greaves, T. L.; Weerawardena, A.; Fong, C.; Drummond, C. J.
Formation of amphiphile self-assembly phases in protic ionic liquids. J.
Phys. Chem. B 2007, 111, 4082−4088.
REFERENCES
■
(1) Menger, F. M.; Linau, C. A. Gemini-sufactants: synthesis and
properties. J. Am. Chem. Soc. 1991, 113, 1451−1452.
(2) Zana, R. Dimeric and oligomeric sufactants. Behavior at interfaces
and in aqueous solution: a review. Adv. Colloid Interface Sci. 2002, 97,
203−251.
(3) Zana, R.; Xia, J. Gemini surfactant: synthesis, interfacial and
solution-phase behaviour, and applications; Marcel Dekker, Inc.: New
York, 2004.
(4) Menger, F. M.; Keiper, J. S. Gemini sufactants. Angew. Chem., Int.
Ed. 2000, 39, 1906−1920.
(5) Han, Y. C.; Wang, Y. L. Aggregation behavior of gemini
surfactants and their interaction with macromolecules in aqueous
solution. Phys. Chem. Chem. Phys. 2011, 13, 1939−1956.
(6) Bombekki, C.; Giansanti, L.; Luciani, P.; Mancini, G. Gemini
surfactant based carriers in drug and gene delivery. Curr. Med. Chem.
2009, 16, 171−183.
(7) Bakshi, M. S.; Thakur, P.; Khullar, P.; Kaur, G.; Banipal, T. S.
Surface activity of highly hydrophobic surfactants and platelike PbSe
and CuSe nanoparticles. Cryst. Growth Des. 2010, 10, 1813−1822.
(8) Borde, C.; Nardello, V.; Wattebled, L.; Laschewsky, A.; Aubry, M.
J. A gemini amphiphilic phase transfer catalyst for dark singlet
oxygenation. J. Phys. Org. Chem. 2008, 21, 652−658.
́ ́
́ ́ ́ ́
(9) Pahi, A. B.; Kiraly, Z.; Mastalir, A.; Dudas, J.; Puskas, S.; A., V.
Thermodynamics of micelle formation of the counterion coupled
gemini surfactant bis(4-(2-dodecyl)benzenesulfonate)-Jeffamine salt
and its dynamic adsorption on sandstone. J. Phys. Chem. B 2008, 112,
15320−15326.
(10) Oda, R.; Huc, I.; Candau, S. J. Gemini surfactants, the effect of
hydrophobic chain length and dissymmetry. Chem. Commun. 1997,
2105−2106.
(11) Oda, R.; Huc, I.; Homo, J. C.; Heinrich, B.; Schmutz, M.;
Candau, S. J. Elongated aggregates formed by cationic gemini
surfactants. Langmuir 1999, 15, 2384−2390.
(12) Sikiric, M.; Primozic, I.; Talmon, Y.; Filipovic-Vincekovic, N.
Effect of the spacer length on the association and adsorption behavior
of dissymmetric gemini surfactants. J. Colloid Interface Sci. 2005, 281,
473−481.
(13) Bai, G. Y.; Wang, J. B.; Wang, Y. L.; Yan, H. K.
Thermodynamics of hydrophobic interaction of dissymmetric gemini
surfactants in aqueous solutions. J. Phys. Chem. B 2002, 106, 6614−
6616.
(33) Zhao, M. W.; Gao, Y. A.; Zheng, L. Q. Liquid crystalline phases
of the amphiphilic ionic liquid N-hexadecyl-N-methylpyrrolidinium
bromide formed in the ionic liquid ethylammonium nitrate and in
water. J. Phys. Chem. B 2010, 114, 11382−11389.
(34) Zhang, G. D.; Chen, X.; Zhao, Y. R.; Ma, F. M.; Jing, B.; Qiu, H.
Y. Lyotropic liquid-crystalline phases formed by Pluronic P123 in
ethylammonium nitrate. J. Phys. Chem. B 2008, 112, 6578−6584.
(35) Ma, F. M.; Chen, X.; Zhao, Y. R.; Wang, X. D.; Li, Q. H.; Lv, C.;
Yue, X. A nonaqueous lyotropic liquid crystal fabricated by a
polyoxyethylene amphiphile in protic ionic liquid. Langmuir 2010,
26, 7802−7807.
(36) Zhao, Y. R.; Chen, X.; Wang, X. D. Liquid crystalline phases
self-organized from a surfactant-like ionic liquid C16mimCl in
ethylammonium nitrate. J. Phys. Chem. B 2009, 113, 2024−2030.
(37) Wang, X. D.; Chen, X.; Zhao, Y. R.; Yue, X.; Li, Q. H.; Li, Z. H.
Nonaqueous lyotropic liquid-crystalline phases formed by Gemini
surfactants in aprotic ionic liquid. Langmuir 2012, 28, 2476−2484.
(38) Evans, D. F.; Yamauchi, A. Micelle formation in ethyl-
ammonium nitrate, a low-melting fused salt. J. Colloid Interface Sci.
1982, 88, 89−96.
(14) Wang, X. Y.; Wang, J. B.; Wang, Y. L.; Ye, J. P.; Yan, H. K.;
Thomas, R. K. Micellization of a series of dissymmetric gemini
surfactants in aqueous solution. J. Phys. Chem. B 2003, 107, 11428−
11432.
(15) Fan, Y. R.; Li, Y. J.; Cao, M. W.; Wang, J. B.; Wang, Y. L.;
Thomas, R. K. Micellization of dissymmetric cationic gemini
surfactants and their interaction with dimyristoylphosphatidylcholine
vesicles. Langmuir 2007, 23, 11458−11464.
(16) Sun, Y. H.; Feng, Y. J.; Dong, H. W.; Chen, Z. Adsorption of
dissymmetric cationic gemini surfactants at silica/water interface. Surf.
Sci. 2007, 601, 1988−1995.
(39) Zhang, G. D.; Chen, X.; Zhao, Y. R.; Xie, Y. Z.; Qiu, H. Y.
Effects of alcohols and counterions on the phase behavior of 1-octyl-3-
G
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