Self-Aggregation and liquid crystalline behavior of new ester-functionalized quinuclidinolium surfactants

Langmuir

Volumn 30, Issue 30, 2014, Pages 9036-9044

  Bhadani, Avinash ^a   Endo, Takeshi ^a   Koura, Setsuko ^a   Sakai, Kenichi ^a   Abe, Masahiko ^a   Sakai, Hideki ^a  

^a TOKYO UNIVERSITY OF SCIENCE   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

ALCOHOLS; CATIONIC SURFACTANTS; CRYSTALLINE MATERIALS; ESTERIFICATION; ESTERS; HIGH ENERGY PHYSICS; NUCLEAR MAGNETIC RESONANCE SPECTROSCOPY;

CONDUCTIVITY MEASUREMENTS; FATTY ALCOHOLS; LIQUID CRYSTALLINE; PHYSICOCHEMICAL PROPERTY; SELF AGGREGATION; SMALL ANGLE X-RAY SCATTERING; SPECTROSCOPIC TECHNIQUE; SURFACE TENSIOMETRY;

AGGLOMERATION;

EID: 84905714879     PISSN: 07437463     EISSN: 15205827     Source Type: Journal    
DOI: 10.1021/la502098h     Document Type: Article

References (35)

1. Rubingh, D. N.; Holland, P. M. Cationic Surfactants: Physical Chemistry; Marcel Dekker: New York, 1991.
2. Richmond, J. M. Cationic Surfactants: Organic Chemistry; Marcel Dekker: New York, 1990.
3. Putlitz, B. Z.; Hentze, H.-P.; Landfester, K.; Antonietti, M. New cationic surfactants with sulfonium headgroups Langmuir 2000, 16, 3214
4. Garcia, M. T.; Ribosa, I.; Perez, L.; Manresa, A.; Comelles, F. Aggregation behavior and antimicrobial activity of ester-functionalized imidazolium- and pyridinium-based ionic liquids in aqueous solution Langmuir 2013, 29, 2536-2545
5. Rozycka-Roszak, B.; Misiak, P.; Wozniak, E.; M, A.; Dega-Szafran, Z. Calorimetric and molecular modeling studies of N -Alkoxycarbonylmethyl- N -Alkyl-piperidinium chlorides Colloids Surf., A 2008, 318, 301-306
6. Bhadani, A.; Singh, S.; Kamboj, R.; Chauhan, V. Synthesis and self aggregation properties of ester-functionalized heterocyclic pyrrolidinium surfactants Colloid Polym. Sci. 2012, 291, 2289-2297
7. Janiak, J.; Piculell, L.; Schillen, K.; Lundberg, D. Responsive release of polyanions from soluble aggregates formed with a hydrolyzable cationic surfactant and a nonionic surfactant Soft Matter 2013, 9, 4103
8. Santos, S. d.; Lundberg, D.; Piculell, L. Responsive and evolving mixtures of a hydrolyzing cationic surfactant and oppositely charged polyelectrolytes Soft Matter 2011, 7, 5540-5544
9. Bos, M.; Canesso, R. EPC-synthesis of (S)-3-hydroxy-3- mercaptomethylquinuclidine, a chiral building block for the synthesis of the muscarinic agonist AF 102B Heterocycles 1994, 38, 1889-1896
10. Ashwood, M. S.; Gibson, A.W.; Houghton, P. G.; Humphrey, G. R.; Roberts, D. C.; Wright, S. H. B. Synthesis of the selective muscarinic agonist (3 R)-3-(6-chloropyrazin-2-yl)-1-Azabicyclo[2.2.2]octane J. Chem. Soc., Perkin Trans. 1 1995, 6, 641-644
11. a and reactivity of quinuclidine-based catalysts in the Baylis-Hillman reaction: Discovery of quinuclidine as optimum catalyst leading to substantial enhancement of scope J. Org. Chem. 2003, 68, 692-700
12. Haldar, J.; Aswal, V. K.; Goyal, P. S.; Bhattacharya, S. Aggregation properties of novel cationic surfactants with multiple pyridinium headgroups. Small-Angle neutron scattering and conductivity studies J. Phys. Chem. B 2004, 108, 11406-11411
13. Blesic, M.; Lopes, A.; Melo, E.; Petrovski, Z.; Plechkova, N. V.; C. Lopes, J. N.; Seddon, K. R.; Rebelo, L. P. N. On the self-Aggregation and fluorescence quenching aptitude of surfactant ionic liquids J. Phys. Chem. B 2008, 112, 8645-8650
14. Dong, B.; Li, N.; Zheng, L.; Yu, L.; Inoue, T. Langmuir 2007, 23, 4178-4182
15. Santhiya, D.; Dias, R. S.; Shome, A.; Das, P. K.; Miguel, M. G.; Lindman, B.; Maiti, S. Role of linker groups between hydrophilic and hydrophobic moieties of cationic surfactants on oligonucleotide-surfactant interactions Langmuir 2009, 25, 13770-13775
16. Zhao, Y.; Yue, X.; Wang, X.; 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
17. Rane, J. P.; Harbottle, D.; Pauchard, P.; Couzis, A.; Banerjee, S. Adsorption kinetics of asphaltenes at the oil-water interface and nanoaggregation in the bulk Langmuir 2012, 28, 9986-9995
18. Brown, P.; Bushmelev, A.; Butts, C. P.; Cheng, J.; Eastoe, J.; Grillo, I.; Heenan, R. K.; Schmidt, A. M. Magnetic control over liquid surface properties with responsive surfactants Angew. Chem., Int. Ed. 2012, 51, 2414-2416
19. Shrestha, R. K.; Sakai, K.; Sakai, H.; Abe, M. Rheological properties of polyoxyethylene cholesteryl ether wormlike micelles in aqueous system J. Phys. Chem. B 2011, 115, 2937-2946
20. Sakai, K.; Umemoto, N.; Aburai, K.; Takamatsu, Y.; Endo, T.; Kitiyanan, B.; Matsumoto, M.; Sakai, H.; Abe, M. Physicochemical properties of oleic acid-based partially fluorinated gemini surfactants J. Oleo Sci. 2014, 63, 257-267
21. Mehta, S. K.; Bhasin, K. K.; Dham, S.; Singla, M. L. Micellar behavior of aqueous solutions of dodecyldimethylethylammonium bromide, dodecyltrimethylammonium chloride, and tetradecyltrimethylammonium chloride in the presence of α-, β-, HPβ-, and Î3-cyclodextrins J. Colloid Interface Sci. 2008, 321, 442-451
22. Galán, J. J.; González-Pérez, A.; Seijas, J. A.; Uriarte, E.; Rodríguez, J. R. Effect of counterion on thermodynamic micellar properties of tetradecylpyridinium in aqueous solutions Colloid Polym. Sci. 2005, 283, 458
23. El Seoud, O. A.; Pires, P. A. R.; Abdel-Moghny, T.; Bastos, E. L. Synthesis and micellar properties of surface-Active ionic liquids: 1-Alkyl-3-methylimidazolium chlorides J. Colloid Interface Sci. 2007, 313, 301
24. Varade, D.; Joshi, T.; Aswal, V. K.; Goyal, P. S.; Hassan, P. A.; Bahadur, P. Effect of salt on the micelles of cetyl pyridinium chloride Colloids Surf., A 2005, 259, 95
25. Vanyur, R.; Biczok, L.; Miskolczy, Z. Micelle formation of 1-Alkyl-3-methylimidazolium bromide ionic liquids in aqueous solution Colloids Surf., A 2007, 299, 256-261
26. Bhadani, A.; Singh, S. Novel gemini pyridinium surfactants: Synthesis and study of their surface activity, DNA binding, and cytotoxicity Langmuir 2009, 25, 11703-11712
27. Viscardi, G.; Quagliotto, P.; Barolo, C.; Savarino, P.; Barni, E.; Fisicaro, E. Synthesis and surface and antimicrobial properties of novel cationic surfactants J. Org. Chem. 2000, 65, 8197-8203
28. Hunt, P. A.; Kirchner, B.; Welton, T. Characterising the electronic structure of ionic liquids: An examination of the 1-butyl-3-methylimidazolium chloride ion pair Chem. - Eur. J. 2006, 12, 6762-6775
29. Thangamani, A.; Jayabharathi, J.; Manimekalai, A. Conformation of hindered piperidines: Spectroscopic evidence for contribution of boat conformations J. Chem. Sci. 2012, 122, 579-586
30. Tanford, C. Micelle shape and size J. Phys. Chem. 1972, 21, 3021
31. Yue, X.; Chen, X.; Wang, X.; Li, Z. Lyotropic liquid crystalline phases formed by phyosterol ethoxylates in room-temperature ionic liquids Colloids Surf., A 2011, 392, 227
32. Zhao, M.; Gao, Y.; Zheng, L. 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
33. Shi, L.; Zhao, M.; Zheng, L. Lyotropic liquid crystalline phases formed in ternary mixtures of N -Alkyl- N -methylpyrrolidinium bromide/1-decanol/water RSC Adv. 2012, 2, 11922-11929
34. 3 (M = B, Al or Ga), studied by gas-phase electron diffraction, X-ray diffraction, and quantum chemical calculations Dalton Trans. 2007, 17, 1687-1696
35. Prestegard, J. H.; Bougault, C. M.; Kishore, A. I. Residual dipolar couplings in structure determination of biomolecules Chem. Rev. 2004, 104, 3519-3540