Micellization behavior of the ionic liquid lauryl isoquinolinium bromide in aqueous solution

Colloid and Polymer Science

Volumn 292, Issue 5, 2014, Pages 1111-1120

  Zhang, Xiaohong ^a   Peng, Xinying ^a   Ge, Lingling ^a   Yu, Lei ^a   Liu, Zhimin ^a   Guo, Rong ^a  

^a YANGZHOU UNIVERSITY   (China)

Author keywords

Enthalpy entropy compensation; Ionic liquids; Isoquinoline; Micellar properties; Stacking

Indexed keywords

AGGLOMERATION; CRITICAL MICELLE CONCENTRATION; ENTHALPY; ENTROPY; MICELLIZATION; NUCLEAR MAGNETIC RESONANCE SPECTROSCOPY; SOLUTIONS;

CRITICAL MICELLE CONCENTRATION (CMC); ELECTRICAL CONDUCTIVITY; ENTHALPY-ENTROPY COMPENSATION; ISOQUINOLINES; MICELLAR PROPERTIES; MICELLIZATION BEHAVIOR; NUCLEAR MAGNETIC RESONANCE(NMR); THERMODYNAMIC PARAMETER;

IONIC LIQUIDS;

1 DODECYLPYRIDINIUM BROMIDE; 2 DODECYLISOQUINOLINIUM BROMIDE; BROMINE DERIVATIVE; BUTYLISOQUINOLINIUM BROMIDE; COUNTERION; IONIC LIQUID; ISOQUINOLINE; OCTYLISOQUINOLINIUM BROMIDE; SURFACTANT; UNCLASSIFIED DRUG;

AQUEOUS SOLUTION; ARTICLE; CRITICAL MICELLE CONCENTRATION; ELECTRIC CONDUCTIVITY; ENTHALPY; ENTROPY; MICELLIZATION; PRIORITY JOURNAL; PROTON NUCLEAR MAGNETIC RESONANCE; SURFACE TENSION; TEMPERATURE; THERMODYNAMICS;

EID: 84902368503     PISSN: 0303402X     EISSN: 14351536     Source Type: Journal    
DOI: 10.1007/s00396-013-3151-2     Document Type: Article

References (49)

1. Tariq M, Freire MG, Saramago B, Coutinho JAP, Lopes JNC, Rebelo LPN (2012) Surface tension of ionic liquids and ionic liquid solutions. Chem Soc Rev 41:829-868
2. Blesic M, Marques MH, Plechkova NV, Seddon KR, Rebelo LPN, Lopes A (2007) Self-aggregation of ionic liquids: micelle formation in aqueous solution. Green Chem 9:481-4902
3. Ao MQ, Xu GY, Kang WL, Meng LW, Zhou T (2011) Surface rheological behavior of gelatin/ionic liquid-type imidazolium gemini surfactant mixed systems. Soft Matter 7:1199-1206
4. El Seoud OA, Pires PAR, Abdel-Moghny T (2007) Synthesis and micellar properties of surface-active ionic liquids: 1-alkyl-3-methylimidazolium chlorides. J Colloid Interface Sci 313:296-304 (Pubitemid 47042782)
5. Galgano PD, El Seoud OA (2010) Micellar properties of surface active ionic liquids: a comparison of 1-hexadecyl-3-methylimidazolium chloride with structurally related cationic surfactants. J Colloid Interface Sci 345:1-11
6. Galgano PD, El Seoud OA (2011) Surface active ionic liquids: study of the micellar properties of 1-(1-alkyl)-3-methylimidazolium chlorides and comparison with structurally related surfactants. J Colloid Interface Sci 361:186-194
7. Shi LJ, Zheng LQ (2012) Aggregation behavior of surface active imidazolium ionic liquids in ethylammonium nitrate: effect of alkyl chain length, cations, and counterions. J Phys Chem B 116:2162-2172
8. Bowers J, Butts CP, Martin PJ, Vergara-Gutierrez MC, Heenan RK (2004) Aggregation behavior of aqueous solutions of ionic liquids. Langmuir 20:2191-2219
9. Chhatre AS, Joshi RA, Kulkarni BD (1993) Microemulsions as media for organic synthesis: selective nitration of phenol to orthonitrophenol using dilute nitric acid. J Colloid Interface Sci 158:183-187
10. Holmberg K (2003) Organic reactions in microemulsions. Curr Opin Colloid Interface Sci 8:187-196
11. Merritt MV, Chang IW, Flannery CA, Hsieh SJ, LeeK, Yung J (1995) Micelle-induced changes in the solvation of carbocations: effect of sodium dodecyl sulfate micelles on the enantiomer-specific oxygen exchange reactions of 1-phenyl-1-ethanol and 1-phenyl-1-butanol. J Am Chem Soc 117:9791-9799
12. Cornellas A, Perez L, Comelles F, Ribosa I, Manresa A, Garcia MT (2011) Self-aggregation and antimicrobial activity of imidazolium and pyridinium based ionic liquids in aqueous solution. J Colloid Interface Sci 355:164-171
13. Bandres I, Meler S, Giner B, Cea P, Lafuente C (2009) Aggregation behavior of pyridinium-based ionic liquids in aqueous solution. J Solut Chem 38:1622-1634
14. Jiang Z, Li XF, Yang GF, Cheng L, Yang Y (2012) pH-responsive surface activity and solubilization with novel pyrrolidone-based gemini surfactants. Langmuir 28:7174-7181
15. 1H NMR chemical shifts, SANS and SAXS measurements. J Colloid Interface Sci 371:52-61
16. Dabholkar VV, Tripathi DR (2011) Synthesis and antibacterial activity of isochromene and isoquinoline derivative. J Heterocycl Chem 48:529-532
17. Lava K, Evrard Y, Van Hecke K, Van Meervelt L, Binnemans K (2012) Quinolinium and isoquinolinium ionic liquid crystals. RSC Adv 2:8061-8070
18. Visser AE, Holbrey JD, Rogers RD (2001) Hydrophobic ionic liquids incorporating N-alkylisoquinolinium cations and their utilization in liquid-liquid separations. Chem Commun 2001:2484-2485 (Pubitemid 33124097)
19. Domañska U, Zawadzki M, Paduszyñski K, Królikowski M (2012) Perturbed-chain SAFT as a versatile tool for thermodynamic modeling of binary mixtures containing isoquinolinium ionic liquids. J Phys Chem B 116:8191-8200
20. Domañska U, Zawadzki M, Lewandrowska A (2012) Effect of temperature and composition on the density, viscosity, surface tension, and thermodynamic properties of binary mixtures of Noctylisoquinolinium bis{(trifluoromethyl) sulfonyl}imide with alcohols. J Chem Thermodyn 48:101-111
21. 2] using GLC. J Chem Thermodyn 43:499-504
22. Domañska U, Zawadzki M, Królikowski M, Lewandrowska A (2012) Phase equilibria study of binary and ternary mixtures of {N-octylisoquinolinium bis{(trifluoromethyl)sulfonyl}imide + hydrocarbon, or an alcohol, r water}. J Chem Thermodyn 181:63-71
23. Jaycock MJ, Parfitt GD (1981) Chemistry of interfaces. Wiley, New York, p 26
24. Filippov A, Shah FU, Glavatskih S, Antzutkin ON (2013) NMR self-diffusion study of a phosphonium bis(mandelato)borate ionic liquid. Phys Chem Chem Phys 15:9281-9287
25. Singh T, Kumar A (2007) Aggregation behavior of ionic liquids in aqueous solutions: effect of alkyl chain length, cations, and anions. J Phys Chem B 111:7843-7851 (Pubitemid 47169696)
26. Zhao Y, Gao SJ, Wang JJ, Tang JM (2008) Aggregation of ionic liquids [Cnmim]Br (n=4, 6, 8, 10, 12) in D2O: a NMR study. J Phys Chem B 112:2031-2039 (Pubitemid 351316326)
27. Huang X, Han YH, Wang YX, Wang YL (2007) Aggregation behavior of nitrophenoxy-tailed quaternary ammonium surfactants. J Phys Chem B 111:12439-12446 (Pubitemid 350097589)
28. Rosen MJ (1989) Surfactants and interfacial phenomena, 2nd edn. Wiley, New York
29. Shi LJ, Li N, Yan H, Gao YA, Zheng LQ (2011) Aggregation behavior of long-chain N-aryl imidazolium bromide in aqueous solution. Langmuir 27:1618-1625
30. Shanks PC, Franses EI (1992) Estimation ofmicellization parameters of aqueous sodium dodecyl sulfate from conductivity data. J Phys Chem 96:1794-1805
31. Wadekar MN, Boekhoven J, Jager WF, Koper GJM, Picken SJ (2012) Micellization behavior of aromatic moiety bearing hybrid fluorocarbon sulfonate surfactants. Langmuir 28:3397-3402
32. Shi LJ, Li N, Zheng LQ (2011) Aggregation behavior of long-chain N-aryl imidazolium bromide in a room temperature ionic liquid. J Phys Chem C 115:18295-18301
33. Sugihara G, Hisatomi M (1999) Enthalpy-entropy compensation phenomenon observed for different surfactants in aqueous solution. J Colloid Interface Sci 219:31-36 (Pubitemid 29500863)
34. Chen LJ, Lin SY, Huang CC (1998) Effect of hydrophobic chain length of surfactants on enthalpy-entropy compensation of micellization. J Phys Chem B 102:4350-4356
35. Galan JJ, Rodriguez JR (2010) Thermodynamic study of the process of micellization of long chain alkyl pyridinium salts in aqueous solution. J Therm Anal Calorim 101:359-364
36. Lehanine Z, Badache L (2011) Thermodynamics of micellization of cationic surfactants based on O-alkyl and O-perfluoro- N, Ń-diisopropylisourea: effect of the counter ion nature. J Chem Thermodyn 43:1342-1348
37. Perger TM, Bester-Rogac M (2007) Thermodynamics of micelle formation of alkyltrimethylammonium chlorides from high performance electric conductivity measurements. J Colloid Interface Sci 313:288-295
38. Galan J, Gonzalez-Perez A, Del Castillo JL, Rodriguez JR (2002) Thermal parameters associated tomicellization of dodecylpyridinium bromide and chloride in aqueous solution. J Therm Anal Calorim 70: 229-234 (Pubitemid 35251104)
39. Headley AD, Kotti SRSS, Nam J, Li KY (2005) Effect of hydrophobic side-chains on the solvation of imidazolium salts. J Phys Org Chem 18:1018-1022 (Pubitemid 41311434)
40. Guin M, Patwari GN, Karthikeyan S, Kim KS (2011) Do N-heterocyclic aromatic rings prefer π-stacking? Phys Chem Chem Phys 13:5514-5525
41. 1H NMR relaxation and 2D NOESY. Colloid Polym Sci 282:280-286
42. 1H isotropic chemical shielding in certain homo- and hetero-nuclear aromatic systems. Theor Chem Accounts 131:1092
43. 1H NMR spectroscopic investigations on the conformation of amphiphilic aromatic amino acid derivatives in solution: effect of chemical architecture of amphiphiles and polarity of solvent medium. J Phys Chem B 114:13691-13702
44. Tada EB, Novaki LP, El Seoud OA (2001) Solvatochromism in cationic micellar solutions: effects of the molecular structures of the solvatochromic probe and the surfactant headgroup. Langmuir 17: 652-658 (Pubitemid 32873109)
45. Okano LT, El Seoud OA, Halstead TK (1997) A proton NMR study on aggregation of cationic surfactants in water: effects of the structure of the headgroup. Colloid Polym Sci 274:138-145 (Pubitemid 127492208)
46. Dong B, Gao YA, Su YJ, Zheng LQ, Xu JK, Inoue T (2010) Self-aggregation behavior of fluorescent carbazole-tailed imidazolium ionic liquids in aqueous solutions. J Phys Chem B 114:340-348
47. Shimizu S, El Seoud OA (2003) Synthesis and aggregation of benzyl (2-acylaminoethyl) dimethylammonium chloride surfactants. Langmuir 19:238-243
48. Zhao J, Fung BM (1993) Conformation change of hydrocarbon chains upon the formation of micelle. J Phys Chem 97:5185-5187
49. Suratkar V, Mahapatra S (2000) Solubilization site of organic perfume molecules in sodium dodecyl, sulfate micelles: new insights from proton NMR studies. J Colloid Interface Sci 225:32-38 (Pubitemid 30246737)