Experimental and DFT studies on the aggregation behavior of imidazolium-Based surface-active ionic liquids with aromatic counterions in aqueous solution

Langmuir

Volumn 31, Issue 4, 2015, Pages 1272-1282

  Xu, Wenwen ^a,b   Wang, Tao ^c   Cheng, Ni ^a   Hu, Qiongzheng ^d   Bi, Yanhui ^a   Gong, Yanjun ^a   Yu, Li ^a,b  

^a SHANDONG UNIVERSITY   (China)

^b QUFU NORMAL UNIVERSITY   (China)

^c Sinopec   (China)

^d University of Houston   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

AGGLOMERATION; AROMATIC COMPOUNDS; AROMATIZATION; CHEMICAL BONDS; CRYSTALLINE MATERIALS; DENSITY FUNCTIONAL THEORY; ELECTRONEGATIVITY; HYDROPHOBICITY; IONS; LIQUID CRYSTALS; LIQUIDS; MOLECULES; SOLUTIONS; X RAY SCATTERING;

CONDUCTIVITY MEASUREMENTS; ELECTROSTATIC ATTRACTIONS; HYDROCARBON CHAIN LENGTH; HYDROPHOBIC INTERACTIONS; LIQUID CRYSTALLINE PHASE; LYOTROPIC LIQUID CRYSTAL; POLARIZED OPTICAL MICROSCOPY; SURFACE ACTIVE IONIC LIQUIDS;

IONIC LIQUIDS;

EID: 84922151396     PISSN: 07437463     EISSN: 15205827     Source Type: Journal    
DOI: 10.1021/la503884v     Document Type: Article

References (56)

1. Rogers, R. D.; Seddon, K. R. Ionic liquids-Solvents of the future? Science 2003, 302, 792-793
2. Welton, T. Room-temperature ionic liquids-Solvents for synthesis and catalysis Chem. Rev. 1999, 99, 2071-2083
3. Ranu, B. C.; Banerjee, S. Ionic liquid as catalyst and reaction medium. The dramatic influence of a task-specific ionic liquid, [bmim]OH, in Michael addition of active methylene compounds to conjugated ketones, carboxylic esters, and nitriles Org. Lett. 2005, 7, 3049-3052
4. Cooper, E. R.; Andrews, C. D.; Wheatley, P. S.; Webb, P. B.; Wormald, P.; Morris, R. E. Ionic liquids and eutectic mixtures as solvent and template in synthesis of zeolite analogues Nature 2004, 430, 1012-1016
5. Kuang, D. B.; Brezesinski, T.; Smarsly, B. Hierarchical porous silica materials with a trimodal pore system using surfactant templates J. Am. Chem. Soc. 2004, 126, 10534-10535
6. Endres, F.; Bukowski, M.; Hempelmann, R.; Natter, H. Electrodeposition of nanocrystalline metals and alloys from ionic liquids Angew. Chem., Int. Ed. 2003, 42, 3428-3430
7. Huddleston, J. G.; Willauer, H. D.; Swatloski, R. P.; Visser, A. E.; Rogers, R. D. Room temperature ionic liquids as novel media for "clean" liquid-liquid extraction Chem. Commun. 1998, 1765-1766
8. Anouti, M.; Jones, J.; Boisset, A.; Jacquemin, J.; Caravanier, M.C.; Lemordant, D. Aggregation behavior in water of new imidazolium and pyrrolidinium alkycarboxylates protic ionic liquids J. Colloid Interface Sci. 2009, 340, 104-111
9. Abe, M.; Uchiyama, H.; Yamaguchi, T.; Suzuki, T.; Ogino, K. Micelle formation by pure nonionic surfactants and their mixtures Langmuir 1992, 8, 2147-2151
10. Schulman, J. H.; Stoeckenius, W.; Princ, L. M. Mechanism of formation and structure of micro emulsions by electron microscopy J. Phys. Chem. 1959, 63, 1677-1680
11. Park, J. W.; Bak, C. S.; Labes, M. M. Effects of molecular complexing on the properties of binary nematic liquid crystal mixtures J. Am. Chem. Soc. 1975, 97, 4398-4400
12. Taubert, A. CuCl nanoplatelets from an ionic liquid-crystal precursor Angew. Chem., Int. Ed. 2004, 43, 5380-5382
13. Gin, D. L.; Gu, W. Q.; Pindzola, B. A.; Zhou, W. J. Polymerized lyotropic liquid crystal assemblies for materials applications Acc. Chem. Res. 2001, 34, 973-980
14. Torres, W.; Fox, M. A. Electrosynthesis of polypyrrole in a nematic liquid crystal Chem. Mater. 1992, 4, 583-588
15. Nesseem, D. I. Formulation and evaluation of itraconazole via liquid crystal for topical delivery system J. Pharm. Biomed. Anal. 2001, 26, 387-399
16. Firestone, M. A.; Dzielawa, J. A.; Zapol, P.; Curtiss, L.A.; Seifert, S.; Dietz, M. L. Lyotropic liquid-crystalline gel formation in a room-temperature ionic liquid Langmuir 2002, 18, 7258-7260
17. Zhao, Y. R.; Yue, X.; Wang, X. D.; Chen, X. Lyotropic liquid crystalline phases with a series of N -alkyl- N -methylpiperidinium bromides and water J. Colloid Interface Sci. 2013, 389, 199-205
18. 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
19. Shi, L. J.; Wei, Y.; Sun, N.; Zheng, L. Q. First observation of rich lamellar structures formed by a single-tailed amphiphilic ionic liquid in aqueous solutions Chem. Commun. 2013, 49, 11388-11390
20. Biswas, M.; Dule, M.; Samanta, P. N.; Ghosh, S.; Mandal, T. K. Imidazolium-based ionic liquids with different fatty acid anions: Phase behavior, electronic structure and ionic conductivity investigation Phys. Chem. Chem. Phys. 2014, 16, 16255-16263
21. Huang, D. D.; Chen, X.; Li, Z. H. Formation of pyrrolidinium fatty acid soap and its lyotropic liquid crystalline phase behavior Colloids Surf. A 2013, 426, 55-62
22. Cheng, N.; Hu, Q. Z.; Bi, Y. H.; Xu, W. W.; Gong, Y. J.; Yu, L. Gels and lyotropic liquid crystals: Using an imidazolium-based catanionic surfactant in binary solvents Langmuir 2014, 30, 9076-9084
23. Jiao, J. J.; Dong, B.; Zhang, H. N.; Zhao, Y. Y.; Wang, X. Q.; Wang, R.; Yu, L. Aggregation behaviors of dodecyl sulfate-based anionic surface active ionic liquids in water J. Phys. Chem. B 2012, 116, 958-965
24. Jiao, J. J.; Han, B.; Liu, M. J.; Cheng, N.; Yu, L.; Liu, M. Salt-free catanionic surface active ionic liquids 1-alkyl-3-methylimidazolium alkylsulfate: Aggregation behavior in aqueous solution J. Colloid Interface Sci. 2013, 412, 24-30
25. Jiao, J. J.; Zhang, Y. F.; Fang, L. Y.; Yu, L.; Sun, L. M.; Wang, R.; Cheng, N. Electrolyte effect on the aggregation behavior of 1-butyl-3-methylimidazolium dodecylsulfate in aqueous solution J. Colloid Interface Sci. 2013, 402, 139-145
26. Cheng, N.; Yu, P. M.; Wang, T.; Sheng, X.; Bi, Y. H.; Gong, Y. J.; Yu, L. Self-aggregation of new alkylcarboxylate-based anionic surface active ionic liquids: Experimental and theoretical investigations J. Phys. Chem. B 2014, 118, 2758-2768
27. Wang, X. Q.; Liu, J.; Yu, L.; Jiao, J. J.; Wang, R.; Sun, L. M. Surface adsorption and micelle formation of imidazolium-based zwitterionic surface active ionic liquids in aqueous solution J. Colloid Interface Sci. 2013, 391, 103-110
28. Ye, X. C.; Jin, L. H.; Caglayan, H.; Chen, J.; Xing, G. Z.; Zheng, C.; Doan-Nguyen, V.; Kang, Y. J.; Engheta, N.; Kagan, C. R.; Murray, C. B. Improved size-tunable synthesis of monodisperse gold nanorods through the use of aromatic additives ACS Nano 2012, 6, 2804-2817
29. Yu, D. F.; Huang, X.; Deng, M. L.; Lin, Y. Y.; Jiang, L. X.; Huang, J. B.; Wang, Y. L. Effects of inorganic and organic salts on aggregation behavior of cationic gemini surfactants J. Phys. Chem. B 2010, 114, 14955-14964
30. Campbell, P. S.; Yang, M.; Pitz, D.; Cybinska, J.; Mudring, A. V. Highly luminescent and color-tunable salicylate ionic liquids Chem.-Eur. J. 2014, 20, 4704-4712
31. Rosen, M. J. Surfactants and Interfacial Phenomena, 2 nd ed.; Wiley: New York, 1989.
32. Jaycock, M. J.; Parfitt, G. D. Chemistry of Interfaces; John Wiley & Sons: New York, 1981.
33. Dong, B.; Li, N.; Zheng, L.Q.; Yu, L.; Inoue, T. Surface adsorption and micelle formation of surface active ionic liquids in aqueous solution Langmuir 2007, 23, 4178-4182
34. Dong, B.; Zhao, X. Y.; Zheng, L. Q.; Zhang, J.; Li, N.; Inoue, T. Aggregation behavior of long-chain imidazolium ionic liquids in aqueous solution: Micellization and characterization of micelle microenvironment Colloids Surf. A 2008, 317, 666-672
35. Anouti, M.; Jones, J.; Boisset, A.; Jacquemin, J.; Magaly, C. C.; Lemordant, D. Aggregation behavior in water of new imidazolium and pyrrolidinium alkycarboxylates protic ionic liquids J. Colloid Interface Sci. 2009, 340, 104-111
36. 2O J. Phys. Chem. B 2005, 109, 9014-9019
37. Inoue, T.; Dong, B.; Zheng, L. Q. Phase behavior of binary mixture of 1-dodecyl-3-methylimidazolium bromide and water revealed by differential scanning calorimetry and polarized optical microscopy J. Colloid Interface Sci. 2007, 307, 578-581
38. Leigh, I. D.; McDonald, M. P.; Wood, R. M.; Tiddy, G. J. T.; Trevethan, M. A. Structure of liquid-crystalline phases formed by sodium dodecyl sulphate and water as determined by optical microscopy, X-ray diffraction and nuclear magnetic resonance spectroscopy J. Chem. Soc., Faraday Trans. 1 1981, 77, 2867-2876
39. Yamashita, Y.; Kunieda, H.; Oshimura, E.; Sakamotoa, K. Formation of intermediate micellar phase between hexagonal and discontinuous cubic liquid crystals in brine/ N -acylamino acid surfactant/ N -acylamino acid oil system J. Colloid Interface Sci. 2007, 312, 172-178
40. Wu, J. P.; Zhang, J.; Zheng, L. Q.; Zhao, X. Y.; Li, Na.; Dong, B. Characterization of lyotropic liquid crystalline phases formed in imidazolium based ionic liquids Colloids Surf. A 2009, 336, 18-22
41. Gu, Y. Q.; Shi, L. J.; Gao, H. J.; Li, J.; Zheng, L. Q. Phase behavior of didecylpyrrolidium bromide in aqueous solution Colloids Surf. A 2013, 420, 82-88
42. Cordobes, F.; Munoz, J.; Gallegos, C. Linear viscoelasticity of the direct hexagonal liquid crystalline phase for a heptane/nonionic surfactant/water system J. Colloid Interface Sci. 1997, 187, 401-417
43. Shi, L. J.; Zhao, M. W.; Zheng, L. Q. Lyotropic liquid crystalline phases formed in ternary mixtures of N- alkyl- N -methylpyrrolidinium bromide/1-decanol/water RSC Adv. 2012, 2, 11922-11929
44. Haas, S.; Hoffmann, H.; Thunig, C.; Hoinkis, E. Phase and aggregation behaviour of double-chain cationic surfactants from the class of N -alkyl- N -alkyl- N, N -dimethylammonium bromide surfactants Colloid Polym. Sci. 1999, 277, 856-867
45. Frisch, M. J.; Trucks, G. W.; Schlegel, H. B.; Scuseria, G. E.; Robb, M. A.; Cheeseman, J. R.; Scalmani, G.; Barone, V.; Mennucci, B.; Petersson, G. A.; Nakatsuji, H.; Caricato, M.; Li, X.; Hratchian, H. P.; Izmaylov, A. F.; Bloino, J.; Zheng, G.; Sonnenberg, J. L.; Hada, M.; Ehara, M.; Toyota, K.; Fukuda, R.; Hasegawa, J.; Ishida, M.; Nakajima, T.; Honda, Y.; Kitao, O.; Nakai, H.; Vreven, T.; Montgomery, J. A., Jr.; Peralta, J. E.; Ogliaro, F.; Bearpark, M.; Heyd, J. J.; Brothers, E.; Kudin, K. N.; Staroverov, V. N.; Keith, T.; Kobayashi, R.; Normand, J.; Raghavachari, K.; Rendell, A.; Burant, J. C.; Iyengar, S. S.; Tomasi, J.; Cossi, M.; Rega, N.; Millam, J. M.; Klene, M.; Knox, J. E.; Cross, J. B.; Bakken, V.; Adamo, C.; Jaramillo, J.; Gomperts, R.; Stratmann, R. E.; Yazyev, O.; Austin, A. J.; Cammi, R.; Pomelli, C.; Ochterski, J. W.; Martin, R. L.; Morokuma, K.; Zakrzewski, V. G.; Voth, G. A.; Salvador, P.; Dannenberg, J. J.; Dapprich, S.; Daniels, A. D.; Farkas, Ö.; Foresman, J. B.; Ortiz, J. V.; Cioslowski, J.; Fox, D. J. Gaussian 09, revision A.02; Gaussian, Inc.: Wallingford, CT, 2009.
46. Tanford, C. Micelle shape and size J. Phys. Chem. 1972, 76, 3020-3024
47. Weimann, M.; Fárník, M.; Suhm, M. A.; Alikhani, M. E.; Sadlej, J. Cooperative and anticooperative mixed mrimers of HCl and methanol J. Mol. Struct. 2006, 790, 18-26
48. Das, D.; Dey, J.; Chandra, A. K.; Thapa, U.; Ismail, K. Aggregation behavior of sodium dioctylsulfosuccinate in aqueous ethylene glycol medium. A case of hydrogen bonding between surfactant and solvent and its manifestation in the surface tension isotherm Langmuir 2012, 28, 15762-15769
49. Pan, A.; Mati, S. S.; Naskar, B.; Bhattacharya, S. C.; Moulik, S. P. Self-aggregation of MEGA-9 (N -nonanoyl- N -methyl- d -glucamine) in aqueous medium: Physicochemistry of interfacial and solution behaviors with special reference to formation energetics and micelle microenvironment J. Phys. Chem. B 2013, 117, 7578-7592
50. Mitchell, D. J.; Ninham, B. W. Micelles, vesicles and microemulsions J. Chem. Soc., Faraday Trans. 2 1981, 77, 601-629
51. Israelachvili, J. N.; Mitchell, D. J.; Ninham, B. W. Theory of self-assembly of hydrocarbon amphiphiles into micelles and bilayers J. Chem. Soc., Faraday Trans. 2 1976, 72, 1525-1568
52. Lin, Y. Y.; Qiao, Y.; Yan, Y.; Huang, J. B. Thermo-responsive viscoelastic wormlike micelle to elastic hydrogel transition in dual-component systems Soft Matter 2009, 5, 3047-3053
53. Wei, X. L.; Ping, A. Li.; Du, P. P.; Liu, J.; Sun, D. Z.; Zhang, Q. F.; Hao, H. G.; Yu, H. J. Formation and properties of wormlike micelles in solutions of a cationic surfactant with a 2-hydroxypropoxy insertion group Soft Matter 2013, 9, 8454-8463
54. Mishra, B. K.; Samant, S. D.; Pradhan, P.; Mishra, S. B.; Manohar, C. A new strongly flow birefringent surfactant system Langmuir 1993, 9, 894-898
55. Horbaschek, K.; Hoffmann, H.; Thunig, C. Formation and properties of lamellar phases in systems of cationic surfactants and hydroxy-naphthoate J. Colloid Interface Sci. 1998, 206, 439-456
56. Hao, J. C.; Hoffmann, H. Self-assembled structures in excess and salt-free catanionic surfactant solutions Curr. Opin. Colloid Interface Sci. 2004, 9, 279-293