Control of dual stimuli-responsive vesicle formation in aqueous solutions of single-tailed ferrocenyl surfactant by varying pH and redox conditions

Journal of Oleo Science

Volumn 63, Issue 3, 2014, Pages 239-248

  Hata, Shinichi ^a   Takahashi, Hiro ^a   Takahashi, Yutaka ^a   Kondo, Yukishige ^a  

^a TOKYO UNIVERSITY OF SCIENCE   (Japan)

Author keywords

Ferrocene; Multistimuli responsive surfactant; pH; Redox reaction; Spontaneous vesicle formation

Indexed keywords

11 FERROCENYLUNDECYLTRIMETHYLAMMONIUM BROMIDE; 11-FERROCENYLUNDECYLTRIMETHYLAMMONIUM BROMIDE; FERROUS ION; SURFACTANT; WATER;

ARTICLE; CHEMICAL STRUCTURE; CHEMISTRY; OXIDATION REDUCTION REACTION; PH; SOLUTION AND SOLUBILITY; SYNTHESIS;

FERROUS COMPOUNDS; HYDROGEN-ION CONCENTRATION; MOLECULAR STRUCTURE; OXIDATION-REDUCTION; SOLUTIONS; SURFACE-ACTIVE AGENTS; WATER;

EID: 84894550995     PISSN: 13458957     EISSN: 13473352     Source Type: Journal    
DOI: 10.5650/jos.ess13164     Document Type: Article

References (44)

1. Kunitake, T.; Okahata, Y. A Totally synthetic bilayer membrane. J. Am. Chem. Soc. 99, 3860-3861 1977
2. Brady, J. E.; Evans, D. F.; Kachar, B.; Ninham, B. W. Spontaneous vesicles. J. Am. Chem. Soc. 106, 4279-4280 1984.
3. Kakizawa, Y.; Sakai, H.; Nishiyama, K.; Abe, M.; Shoji, H.; Kondo, Y.; Yoshino, N. Solution properties of double-tailed cationic surfactants having ferrocenyl groups in their hydrophobic moieties. Langmuir 12, 921-92 1996
4. zu Putlitz, B.; Landfester, K.; Forster, S.; Antonietti, M. Vesicle-forming single-tail hydrocarbon surfactants with sulfonium headgroup. Langmuir 16, 3003-3005 2000.
5. Kunitake, T.; Okahata, Y. Formation of stable bilayer assemblies in dilute diphenylazomethine segment diphenylazomethine segment. J. Am. Chem. Soc. 99, 549-55 1980.
6. Kunitake, T.; Okahata, Y.; Shimomura, M.; Yasunami, S; Takarabe, K. Formation of stable bilayer assemblies in water from single-chain amphiphiles. Relationship between the amphiphile structure and the aggregate morphology. J. Am. Chem. Soc. 103, 5401-5413 1981.
7. Kaler, E. W.; Murthy, A. K.; Rodriguez, B. E.; Zasadozinski, J. A. N. Spontaneous vesicle formation in aqueous mixtures of single-tailed surfactants. Science 245, 1371-137 1989.
8. Kondo, Y.; Uchiyama, H.; Yoshino, N.; Nishiyama, K.; Abe, M. Spontaneous vesicle formation from aqueous solutions of didodecyldimethylammonium bromide and sodium dodecyl sulfate mixtures. Langmuir 11, 2380-238 1995.
9. Liu, X.; Abbott, N. L. Spatial and temporal control of surfactant systems. J. Colloid Interface Sci. 339, 1-18 2009
10. Brown, P.; Butts, C. P.; Eastoe, J. Stimuli-responsive surfactants. Soft Matter 9, 2365-237 2013
11. Aydogan, N.; Abbott, N. L. Comparison of the surface activity and bulk aggregation of ferrocenyl surfactants with cationic and anionic headgroups. Langmuir 17, 5703-570 2001
12. Aydogan, N.; Abbott, N. L. Effect of electrolyte concentration on interfacial and bulk solution properties of ferrocenyl surfactants with anionic headgroups. Langmuir 18, 7826-783 2002
13. Sakai, H.; Matsumura, A.; Yokoyama, S.; Saji, T.; Abe, M. Photochemical switching of vesicle formation using an azobenzene-modified surfactant. J. Phys. Chem. B 103, 10737-1074 1999
14. Matsumura, A.; Tsuchiya, K.; Torigoe, K.; Sakai, K.; Sakai, H.; Abe, M. Photochemical control of molecular assembly formation in a catanionic surfactant system. Langmuir 27, 1610-161 2011.
15. Tsuchiya, K.; Orihara, Y.; Kondo, Y.; Yoshino, N.; Ohkubo, T.; Sakai, H.; Abe, M. Control of viscoelasticity using redox reaction. J. Am. Chem. Soc. 126, 12282-1228 2004.
16. Sakai, H.; Orihara, Y.; Kodashima, H.; Matsumura, A.; Ohkubo, T.; Tsuchiya, K.; Abe, M. Photoinduced reversible change of fluid viscosity. J. Am. Chem. Soc. 127, 13454-1345 2005
17. Sakai, H.; Imamura, H.; Kakizawa, Y.; Abe, M.; Kondo, Y.; Yoshino, N.; Harwell, J. H. Active control of vesicle formation using a redox-active surfactant. Denki Kagaku 65, 669-67 1997
18. Sakai, H.; Imamura, H.; Kondo, Y.; Yoshino, N.; Abe, M. Reversible control of vesicle formation using electro-chemical reaction. Colloid Surf. A 232, 221-228 2004.
19. Li, X.; Yang, Y.; Eastoe, J.; Dong, J. Rich self-assembly behavior from a simple amphiphile. ChemPhysChem 11, 3074-307 2010
20. Yang, Y.; Dong, J.; Li, X. Micelle to vesicle transitions of N-dodecyl-1, ω-diaminoalkanes: Effects of pH, temperature and salt. J. Colloid Interface Sci. 380, 83-89 2012.
21. Klaikherd, A.; Nagamani, C.; Thayumanavan, S. Multi- stimuli sensitive amphiphilic block copolymer assemblies. J. Am. Chem. Soc. 131, 4830-483 2009
22. Wang, X. J.; Xing, L. B.; Wang, F.; Wang, G. X.; Chen, B.; Tung, C. H.; Wu, L. Z. Multistimuli responsive micelles formed by a tetrathiafulvalene-functionalized amphiphile. Langmuir 27, 8665-867 2011.
23. Han, D.; Tong, X.; Zhao, Y. Block copolymer micelles with a dual-stimuli-responsive core for fast or slow degradation. Langmuir 28, 2327-233 2012
24. Saji, T.; Hoshino, K.; Ishii, Y.; Goto, M. Formation of or-ganic thin films by electrolysis of surfactants with the ferrocenyl moiety. J. Am. Chem. Soc. 113, 450-456 1991.
25. Yoshino, N.; Shoji, H.; Kondo, Y.; Kakizawa, Y.; Sakai, H.; Abe, M. Syntheses of cationic surfactants having two ferrocenylalkyl chains. J. Jpn. Oil Chem. Soc. 45, 769-77 1996
26. Fulmer, G. R.; Miller, A. J. M.; Sherden, N. H.; Gottlieb, H. E.; Nudelman, A.; Stoltz, B. M.; Bercaw, J. E.; Goldberg, K. I. NMR chemical shifts of trace impurities: common laboratory solvents, organics, and gases in deuterated solvents relevant to the organometallic chemist. Organometallics 29, 2176-217 2010.
27. Habich, A.; Qiao, G. G.; Ducker, W. Enantioselective adsorption of surfactants monitored by ATR-FTIR. Langmuir 26, 13944-1395 2010.
28. Zander, F.; Finkelmann, H. State of order of the cross- linker in main-chain liquid crystalline elastomers. Macromol. Chem. Phys. 211, 1167-117 2010.
29. Pizzey, C. L.; Jewell, C. M.; Hays, M. E.; Lynn, D. M.; Abbott, N. L.; Kondo, Y.; Golan, S.; Tahnon, Y. Characterization of the nanostructure of complexes formed by a redox-active cationic lipid and DNA. J. Phys. Chem. B 113, 5849-585 2008.
30. Aytar, B. S.; Muller, J. P. E.; Golan, S.; Hata, S.; Takahashi, H.; Kondo, Y.; Talmon, Y.; Abbott, N. L.; Lynn, D. M. Addition of ascorbic acid to the extracellular environment activates lipoplexes of a ferrocenyl lipid and promotes cell transfection. J. Control. Release 157, 249-25 2012.
31. Shinoda, K.; Hutchinson, E. Pseudo-phase separation model for thermodynamic calculations on micellar solutions. J. Phys. Chem. 66, 577-582 1962.
32. Kunieda, H.; Shinoda, K. Krafft points, critical micelle concentrations, surface tension, and solubilizing power of aqueous solutions of fluorinated surfactants. J. Phys. Chem. 80, 2468-2470 1976
33. Takahashi, Y.; Kondo, Y.; Schmidt, J.; Talmon, Y. Self- assembly of a fluorocarbon-hydrocarbon hybrid surfactant: Dependence of morphology on surfactant concentration and time. J. Phys. Chem. B 114, 13319-1332 2010.
34. Bard, A. J.; Faulkner, L. R. Electrochemical Methods. Wiley, USA. p. 13 1980.
35. Gallardo, B. S.; Hwa, M. J.; Abbott, N. L. In situ and reversible control of the surface activity of ferrocenyl surfactants in aqueous solutions. Langmuir 11, 4209-421 1995.
36. Gallardo, B. S.; Metcalfe, K. L.; Abbott, N. L. Ferrocenyl surfactants at the surface of water: principles for active control of interfacial properties. Langmuir 12, 4116-412 1996.
37. nd ed. Academic Press, USA 1992.
38. Saji, T.; Hoshino, K.; Aoyagui, S. Reversible formation and disruption of micelles by control of the redox state of the surfactant tail group. J. Chem. Soc. Commun. 865-86 1985
39. Nishimura, S.; Scales, P. J.; Biggs, S. R.; Healy, T. W. AFM studies of amine surfactant hemimicelle structures at the mica-water interface. Colloid Surf. A 103, 289-29 1995.
40. Nishimura, S.; Scales, P. J.; Biggs, S. R.; Healy, T. W. An electrokinetic study of the adsorption of dodecyl ammonium amine surfactants at the muscovite mica-water interface. Langmuir 16, 690-69 2000
41. Kataoka, K.; Harada, A.; Nagasaki, Y. Block copolymer micelles for drug delivery: design, characterization and biological significance. Adv. Drug Deliv. Rev. 47, 113-13 2001.
42. Rapoport, N. Physical stimuli-responsive polymeric micelles for anti-cancer drug delivery. Prog. Polym. Sci. 32, 962-99 2007
43. Ganta, S.; Devalapally, H.; Shahiwala, A.; Amiji, M. A Review of stimuli-responsive nanocarriers for drug and gene delivery. J. Control. Release 126, 187-204 2008.
44. Abbott, N. L.; Jewell, C. M.; Hays, M. E.; Kondo, Y.; Lynn, D. M. Ferrocene-containing cationic lipids: influence of redox state on cell transfection. J. Am. Chem. Soc. 127, 11576-1157 2005.