Effect on aggregation behavior of long-chain spacers of dicationic imidazolium-based ionic liquids in aqueous solution

Colloids and Surfaces A: Physicochemical and Engineering Aspects

Volumn 468, Issue , 2015, Pages 285-294

  Frizzo, Clarissa P ^a   Gindri, Izabelle M ^a   Bender, Caroline R ^a   Tier, Aniele Z ^a   Villetti, Marcos A ^a   Rodrigues, Danieli C ^b   Machado, Giovanna ^c   Martins, Marcos A P ^a  

^a FEDERAL UNIVERSITY OF SANTA MARIA   (Brazil)

^b UNIVERSITY OF TEXAS AT DALLAS   (United States)

^c Laboratory of Nanotechnology   (Brazil)

Author keywords

Aggregate; Ionic liquid; Micelles; Surface activity; TEM

Indexed keywords

AGGLOMERATION; AGGREGATES; CHAINS; DIFFERENTIAL SCANNING CALORIMETRY; DYNAMIC LIGHT SCATTERING; LIGHT SCATTERING; LIQUIDS; MICELLES; SCANNING ELECTRON MICROSCOPY; SOLUTIONS; SURFACE TENSION; TRANSMISSION ELECTRON MICROSCOPY;

AGGREGATION BEHAVIOR; CRITICAL AGGREGATION CONCENTRATION; IMIDAZOLIUM-BASED IONIC LIQUID; SPACER CHAIN LENGTH; STRUCTURED PACKINGS; SURFACE ACTIVITIES; SURFACE TENSION MEASUREMENTS; SURFACTANT PROPERTIES;

IONIC LIQUIDS;

BENZOPHENONE; CATION; DICATIONIC IMIDAZOLIUM BASED IONIC LIQUID; DICATIONIC LIQUID; IMIDAZOLE DERIVATIVE; IONIC LIQUID; PYRENE; SURFACTANT; UNCLASSIFIED DRUG;

AQUEOUS SOLUTION; ARTICLE; CHEMICAL PHENOMENA; CONDUCTANCE; DIFFERENTIAL SCANNING CALORIMETRY; FLUORESCENCE; IONIC LIQUID AGGREGATION; LIGHT SCATTERING; MORPHOLOGICAL TRAIT; MORPHOLOGY; PRIORITY JOURNAL; SURFACE PROPERTY; SURFACE TENSION; TRANSMISSION ELECTRON MICROSCOPY;

EID: 84921419442     PISSN: 09277757     EISSN: 18734359     Source Type: Journal    
DOI: 10.1016/j.colsurfa.2014.12.029     Document Type: Article

References (51)

1. Bermúdez M.-D., Jiménez A.-E., Sanes J., Carrión F.-J. Ionic liquids as advanced lubricant fluids. Molecules 2009, 14:2888-2908. 10.3390/molecules14082888.
2. Zhou F., Liang Y., Liu W. Ionic liquid lubricants: designed chemistry for engineering applications. Chem. Soc. Rev. 2009, 38:2590-2599. 10.1039/b817899m.
3. Smirnova N.A., Safonova E.A. Micellization in solutions of ionic liquids. Colloid J. 2012, 74:254-265. 10.1134/S1061933X12020123.
4. Kunz W., Zemb T., Harrar A. Using ionic liquids to formulate microemulsions: current state of affairs. Curr. Opin. Colloid Interface Sci. 2012, 17:205-211. 10.1016/j.cocis.2012.03.002.
5. Qiu Z., Texter J. Ionic liquids in microemulsions. Curr. Opin. Colloid Interface Sci. 2008, 13:252-262. 10.1016/j.cocis.2007.10.005.
6. Vollmer C., Janiak C. Naked metal nanoparticles from metal carbonyls in ionic liquids: easy synthesis and stabilization. Coord. Chem. Rev. 2011, 255:2039-2057. 10.1016/j.ccr.2011.03.005.
7. Moniruzzaman M., Kamiya N., Goto M. Activation and stabilization of enzymes in ionic liquids. Org. Biomol. Chem. 2010, 8:2887-2899. 10.1039/b926130c.
8. Santos C.I.M., Barata J.F.B., Faustino M.A.F., Lodeiro C., Neves M.G.P.M.S. Revisiting Heck-Mizoroki reactions in ionic liquids. RSC Adv. 2013, 3:19219. 10.1039/c3ra43493a.
9. Yan H., Wang H. Recent development and applications of dispersive liquid-liquid microextraction. J. Chromatogr. A 2013, 1295:1-15. 10.1016/j.chroma.2013.04.053.
10. Trujillo-Rodríguez M.J., Rocío-Bautista P., Pino V., Afonso A.M. Ionic liquids in dispersive liquid-liquid microextraction. Trends Anal. Chem. 2013, 51:87-106. 10.1016/j.trac.2013.06.008.
11. Domínguez de María P. Recent trends in (ligno)cellulose dissolution using neoteric solvents: switchable, distillable and bio-based ionic liquids. J. Chem. Technol. Biotechnol. 2014, 89:11-18. 10.1002/jctb.4201.
12. Kohno Y., Ohno H. Ionic liquid/water mixtures: from hostility to conciliation. Chem. Commun. (Camb.) 2012, 48:7119-7130. 10.1039/c2cc31638b.
13. Wang H., Gurau G., Rogers R.D. Ionic liquid processing of cellulose. Chem. Soc. Rev. 2012, 41:1519-1537. 10.1039/c2cs15311d.
14. Williams H.D., Sahbaz Y., Ford L., Nguyen T.-H., Scammells P.J., Porter C.J.H. Ionic liquids provide unique opportunities for oral drug delivery: structure optimization and in vivo evidence of utility. Chem. Commun. (Camb.) 2014, 50:1688-1690. 10.1039/c3cc48650h.
15. Ding Y.-S., Zha M., Zhang J., Wang S.-S. Synthesis, characterization and properties of geminal imidazolium ionic liquids. Colloid Surf. A: Physicochem. Eng. Asp. 2007, 298:201-205. 10.1016/j.colsurfa.2006.10.063.
16. Moulik S.P., Paul B.K. Structure, dynamics and transport properties of microemulsions. Adv. Colloid Interface Sci. 1998, 78:99-195. 10.1016/S0001-8686(98)00063-3.
17. Paul B.K., Mitra R.K. Water solubilization capacity of mixed reverse micelles: effect of surfactant component, the nature of the oil, and electrolyte concentration. J. Colloid Interface Sci. 2005, 288:261-279. 10.1016/j.jcis.2005.02.088.
18. Leodidis E.B., Hatton T.A. Amino acids in AOT reversed micelles. 2. The hydrophobic effect and hydrogen bonding as driving forces for interfacial solubilization. J. Phys. Chem. 1990, 94:6411-6420. 10.1021/j100379a047.
19. Liu Y., Yu L., Zhang S., Yuan J., Shi L., Zheng L. Dispersion of multiwalled carbon nanotubes by ionic liquid-type Gemini imidazolium surfactants in aqueous solution. Colloid Surf. A: Physicochem. Eng. Asp. 2010, 359:66-70. 10.1016/j.colsurfa.2010.01.065.
20. 2 nanoparticles coated with ionic liquids: a supramolecular approach. ACS Appl. Mater. Interfaces 2014, 6:11536-11543. 10.1021/am5022107.
21. Zhang B., Yan N. Towards rational design of nanoparticle catalysis in ionic liquids. Catalysts 2013, 3:543-562. 10.3390/catal3020543.
22. Steudte S., Bemowsky S., Mahrova M., Bottin-Weber U., Tojo-Suarez E., Stepnowski P., et al. Toxicity and biodegradability of dicationic ionic liquids. RSC Adv. 2014, 4:5198. 10.1039/c3ra45675g.
23. Borse M., Sharma V., Aswal V.K., Goyal P.S., Devi S. Effect of head group polarity and spacer chain length on the aggregation properties of Gemini surfactants in an aquatic environment. J. Colloid Interface Sci. 2005, 284:282-288. 10.1016/j.jcis.2004.10.008.
24. Liu Q., van Rantwijk F., Sheldon R.A. Synthesis and application of dicationic ionic liquids. J. Chem. Technol. Biotechnol. 2006, 81:401-405. 10.1002/jctb.1411.
25. Anderson J.L., Ding R., Ellern A., Armstrong D.W. Structure and properties of high stability geminal dicationic ionic liquids. J. Am. Chem. Soc. 2005, 127:593-604. 10.1021/ja046521u.
26. Jin C.-M., Ye C., Phillips B.S., Zabinski J.S., Liu X., Liu W., et al. Polyethylene glycol functionalized dicationic ionic liquids with alkyl or polyfluoroalkyl substituents as high temperature lubricants. J. Mater. Chem. 2006, 16:1529. 10.1039/b517888f.
27. Baltazar Q.Q., Chandawalla J., Sawyer K., Anderson J.L. Interfacial and micellar properties of imidazolium-based monocationic and dicationic ionic liquids. Colloid Surf. A: Physicochem. Eng. Asp. 2007, 302:150-156. 10.1016/j.colsurfa.2007.02.012.
28. Ao M., Huang P., Xu G., Yang X., Wang Y. Aggregation and thermodynamic properties of ionic liquid-type Gemini imidazolium surfactants with different spacer length. Colloid Polym. Sci. 2008, 287:395-402. 10.1007/s00396-008-1976-x.
29. Eastoe J., Nave S., Downer A., Paul A., Rankin A., Penfold J. Adsorption of ionic surfactants at the air-solution interface. Langmuir 2000, 4511-4518.
30. Li Z.X., Dong C.C., Thomas R.K. Neutron reflectivity studies of the surface excess of Gemini surfactants at the air-water interface. Langmuir 1999, 4392-4396.
31. Martins M.A.P., Frizzo C.P., Moreira D.N., Zanatta N., Bonacorso H.G. Ionic liquids in heterocyclic synthesis. Chem. Rev. 2008, 108:2015-2050. 10.1021/cr078399y.
32. Frizzo C.P., Tier A.Z., Gindri I.M., Buriol L., Villetti M.A., Zanatta N., et al. Nanostructure evaluation of ionic liquid aggregates by spectroscopy. Nanoscale Spectrosc. Appl. 2013, 215-278.
33. T. Edition, Principles of Fluorescence Spectroscopy, n.d.
34. Zhou L., Jiang X., Li Y., Chen Z., Hu X. Synthesis and properties of a novel class of Gemini pyridinium surfactants. Langmuir 2007, 23:11404-11408. 10.1021/la701154w.
35. Fisicaro E., Compari C., Biemmi M., Duce E., Peroni M., Barbero N., et al. Unusual behavior of the aqueous solutions of Gemini bispyridinium surfactants: apparent and partial molar enthalpies of the dimethanesulfonates. J. Phys. Chem. B 2008, 112:12312-12317. 10.1021/jp804271z.
36. Ao M., Xu G., Zhu Y., Bai Y. Synthesis and properties of ionic liquid-type Gemini imidazolium surfactants. J. Colloid Interface Sci. 2008, 326:490-495. 10.1016/j.jcis.2008.06.048.
37. Deng M., Li J., Liu J., Ma X., Wang Y. Abnormal interfacial tension behavior of alkanediyl-α,ω-bis(dodecyldimethylammonium bromide) Gemini surfactants. Colloid Surf. A: Physicochem. Eng. Asp. 2010, 356:97-103. 10.1016/j.colsurfa.2009.12.032.
38. Diamant H., Andelman D. Dimeric surfactants spacer chain conformation and specific area at the airnater interface. Langmuir 1994, 2910-2916.
39. Rosen M.J. Surfactants and Interfacial Phenomena 2004, Wiley, ISBN 0471478180, 455pp. 3rd ed.
40. Kabir-ud-Din, Sheikh M.S., Dar A.A. Interaction of a cationic Gemini surfactant with conventional surfactants in the mixed micelle and monolayer formation in aqueous medium. J. Colloid Interface Sci. 2009, 333:605-612. 10.1016/j.jcis.2009.01.041.
41. Yoshimura T., Bong M., Matsuoka K., Honda C., Endo K. Surface properties and aggregate morphology of partially fluorinated carboxylate-type anionic Gemini surfactants. J. Colloid Interface Sci. 2009, 339:230-235. 10.1016/j.jcis.2009.07.054.
42. Zana R. Ionization of cationic micelles: effect of the detergent structure. J. Colloid Interface Sci. 1980, 78:330-337.
43. Li N., Zhang S., Zheng L., Dong B., Li X., Yu L. Aggregation behavior of long-chain ionic liquids in an ionic liquid. Phys. Chem. Chem. Phys. 2008, 10:4375-4377. 10.1039/b807339b.
44. Wang J., Wang H., Zhang S., Zhang H., Zhao Y. Conductivities, volumes, fluorescence, and aggregation behavior of ionic liquids [C4mim][BF4] and [C(n)mim]Br (n=4, 6, 8, 10, 12) in aqueous solutions. J. Phys. Chem. B 2007, 111:6181-6188. 10.1021/jp068798h.
45. Liu X., Dong L., Fang Y. Synthesis and self-aggregation of a hydroxyl-functionalized imidazolium-based ionic liquid surfactant in aqueous solution. J. Surfactant Deterg. 2010, 14:203-210. 10.1007/s11743-010-1234-3.
46. Orth R.G., Dunbar R.C. Luminescent Probes for Detergent Solutions A Simple Procedure for Determination of the Mean Aggregation Number of Micelles. J. Am. Chem. Soc. 1978, 100:5949-5951.
47. Zhang S., Yuan J., Ma H., Li N., Zheng L., Inoue T. Aqueous phase behavior of ionic liquid-related Gemini surfactant revealed by differential scanning calorimetry and polarized optical microscopy. Colloid. Polym. Sci. 2010, 289:213-218. 10.1007/s00396-010-2333-4.
48. 3]: mesomorphism and aggregation. Phys. Chem. Chem. Phys. 2009, 11:4260-4268. 10.1039/b822341f.
49. Anouti M., Sizaret P.-Y., Ghimbeu C., Galiano H., Lemordant D. Physicochemical characterization of vesicles systems formed in mixtures of protic ionic liquids and water. Colloid Surf. A: Physicochem. Eng. Asp. 2012, 395:190-198. 10.1016/j.colsurfa.2011.12.030.
50. Vaghela N.M., Sastry N.V., Aswal V.K. Surface active and aggregation behavior of methylimidazolium-based ionic liquids of type [Cnmim] [X], n=4, 6, 8 and [X]=Cl-, Br-, and I-in water. Colloid Polym. Sci. 2010, 289:309-322. 10.1007/s00396-010-2332-5.
51. Gindri I.M., Siddiqui D.A., Bhardwaj P., Rodriguez L.C., Palmer K.L., Palmer C.P., et al. Dicationic imidazolium-based ionic liquids: a new strategy for non-toxic and antimicrobial materials. RSC Adv. 2014, 4:62594-62602.