Influence of anions and alkyl chain lengths of N -Alkyl- n -(R)-12-hydroxyoctadecyl ammonium salts on their hydrogels and organogels

Langmuir

Volumn 29, Issue 21, 2013, Pages 6476-6484

  Mallia, V Ajay ^a   Seo, Hyae In ^a   Weiss, Richard G ^a  

^a GEORGETOWN UNIVERSITY   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

ALKYL CHAIN LENGTHS; CONCENTRATION RANGES; CONDUCTIVITY MEASUREMENTS; CRITICAL AGGREGATION CONCENTRATION; LAMELLAR PACKING; MOLECULAR PACKINGS; SOLID-SOLID PHASE TRANSITIONS; X-RAY DIFFRACTOGRAMS;

CHLORINE COMPOUNDS; GELATION; NEGATIVE IONS; SALTS; SOLS;

HYDROGELS;

ANION; GEL; INORGANIC SALT; QUATERNARY AMMONIUM DERIVATIVE;

CHEMICAL STRUCTURE; CHEMISTRY; GEL; PARTICLE SIZE; SURFACE PROPERTY;

ANIONS; GELS; MOLECULAR STRUCTURE; PARTICLE SIZE; QUATERNARY AMMONIUM COMPOUNDS; SALTS; SURFACE PROPERTIES;

EID: 84878306221     PISSN: 07437463     EISSN: 15205827     Source Type: Journal    
DOI: 10.1021/la400748q     Document Type: Article

References (57)

1. Shinkai, S.; Murata, K. Cholesterol-based functional tectons as versatile building-blocks for liquid crystals, organic gels and monolayers J. Mater. Chem. 1998, 8, 485-495
2. van Esch, J. H.; Feringa, B. L. New functional materials based on self-assembling organogels: from serendipity towards design Angew. Chem., Int. Ed. 2000, 39, 2263-2266
3. Sangeetha, N. M.; Maitra, U. Supramolecular gels: functions and uses Chem. Soc. Rev. 2005, 34, 821-836
4. Weiss, R. G.; Terech, P., Eds.; Molecular Gels: Materials with Self-Assembled Fibrillar Networks; Springer: Dordrecht, The Netherlands, 2006.
5. Teresh, P.; Weiss, R. G. Low-molecular mass gelators of organic liquids and the properties of their gels Chem. Rev. 1997, 97, 3133-3159
6. George, M.; Weiss, R. G. Molecular organogels. soft matter comprised of low-molecular-mass organic gelators and organic liquids Acc. Chem. Res. 2006, 39, 489-497
7. van Esch, J. H.; Schoonbeek, F.; Loos, M. D.; Veen, E. M.; Kellog, R. M.; Feringa, B. L. In Supramolecular Science: Where It Is and Where It Is Going; Ungar, R.; Dalcanale, E., Eds.; Kluwer Academic Publishers: Dordrecht, The Netherlands, 1999; pp 233-259.
8. Shankar, R.; Ghosh, T. K.; Spontak, R. J. Dielectric elastomers as next generation polymeric actuators Soft Matter 2007, 3, 1116-1129
9. Edwards, W.; Lagadec, C. A.; Smith, D. K. Solvent-gelator interactions-using empirical solvent parameters to better understand the self-assembly of gel-phase materials Soft Matter 2011, 7, 110-117
10. Steed, J. W. Anion-tuned supramolecular gels: a natural evolution from urea supramolecular chemistry Chem. Soc. Rev. 2010, 39, 3686-3699
11. Muro-Small, M. L.; Chen, J.; McNeil, A. J. Dissolution parameters reveal role of structure and solvent in molecular gelation Langmuir 2011, 27, 13248-13253
12. Dawn, A.; Shiraki, T.; Haraguchi, H.; Tamaru, S.; Shinkai, S. What kind of "soft materials" can we design from molecular gels? Chem.-Asian J. 2011, 6, 266-282
13. Fages, F.; Vögtle, F.; Žinić, M. Systematic design of amide- and urea-type gelators with tailored properties Top. Curr. Chem. 2005, 256, 77-131
14. Cai, M.; Liang, Y.; Zhou, F.; Liu, W. Functional ionic gels formed by supramolecular assembly of a novel low molecular weight anticorrosive/ antioxidative gelator J. Mater. Chem. 2011, 21, 13399-13405
15. George, M.; Weiss, R. G. In Molecular Gels: Materials with Self-Assembled Fibrillar Networks; Weiss, R. G.; Terech, P., Eds.; Springer: Dordrecht, The Netherlands, 2006; Chapter 14.
16. Mallia, V. A.; George, M.; Blair, D. L.; Weiss, R. G. Robust organogels from nitrogen-containing derivatives of (R)-12-hydroxystearic acid as gelators: comparisons with gels from stearic acid derivatives Langmuir 2009, 25, 8615-8625
17. Mallia, V. A.; Terech, P.; Weiss, R. G. Correlations of properties and structures at different length scales of hydro- and organo-gels based on N-alkyl-(R)-12-hydroxyoctadecylammonium chlorides J. Phys. Chem. B 2011, 115, 12401-12414
18. We have been unable to find other examples of the use of conductivity to locate CGCs, although there is ample precedent for the use of this technique to determine critical micellar concentrations. See, for example, Frindi, M.; Michels, B.; Levy, H.; Zana, R. Alkanediyl-α,ω- bis(dimethylalkylammonium bromide) surfactants. 4. Ultrasonic absorption studies of amphiphile exchange between micelles and bulk phase in aqueous micellar solution Langmuir 1994, 10, 1140-1145
19. Takahashi, A.; Sakai, M.; Kato, T. Melting temperature of thermally reversible gel. VI. Effect of branching on the sol-gel transition of polyethylene gels Polym. J. 1980, 12, 335-341
20. Alexander, L. E. X-ray Diffraction Method in Polymer Science; John Wiley & Sons: New York, 1969; pp 102-104.
21. Desiraju, G. R. Crystal Engineering: The Design of Organic Solids; Elsevier: New York, 1989.
22. Liu, X.-Y.; Sawant, P. D. Formation kinetics of fractal nanofiber networks in organogels Appl. Phys. Lett. 2001, 79, 3518-3520
23. Ungar, G. Structure of rotator phases in n-alkanes J. Phys. Chem. 1983, 87, 689-695
24. Tsau, J.; Gilson, D. F. R. Polymorphism in n-alkylammonium halides. A differential scanning calorimetric study J. Phys. Chem. 1968, 72, 4082-4085
25. Ichikawa, T.; Yoshio, M.; Hamasaki, A.; Taguchi, S.; Liu, F.; Zeng, X.; Ungar, G.; Ohno, H.; Kato, T. Induction of thermotropic bicontinuous cubic phases in liquid-crystalline ammonium and phosphonium salts J. Am. Chem. Soc. 2012, 134, 2634-2643
26. Abdallah, D. J.; Robertson, A.; Hsu, H.-F.; Weiss, R. G. Smectic liquid-crystalline phases of group VA (especially phosphonium) salts with three equivalent long n -alkyl chains. How do layered assemblies form in liquid-crystalline and crystalline phases? J. Am. Chem. Soc. 2000, 122, 3053-3062
27. Ma, K.; Somashekhar, B. S.; Nagana Gowda, G. A.; Khetrapal, C. L.; Weiss, R. G. Induced amphotropic and thermotropic ionic liquid crystallinity in phosphonium halides. "Lubrication" by hydroxy groups Langmuir 2008, 24, 2746-2758
28. Using Chem 3 D Ultra 8 software (Cambridge Soft Corporation, USA) and adding the van der Waals radii of the terminal atoms according to Bondi, A. van der Waals volumes and radii J. Phys. Chem. 1964, 68, 441-451
29. Using JADE software from Materials Data Inc., Release 5.0.35 (SPS), Livermore, CA.
30. Iwasaki, A.; Fujii, A.; Watanabe, T.; Ebata, T.; Mikami, N. Infrared spectroscopy of hydrogen-bonded phenol-amine clusters in supersonic jets J. Phys. Chem. 1996, 100, 16053-16057
31. Ratcliffe, C. I. Phase behaviour and dynamics in ethylammonium halide salts Can. J. Chem. 2004, 82, 1517-1525
32. Migliorati, V.; Ballirano, P.; Gontrani, L.; Triolo, A.; Caminiti, R. Thermal and structural properties of ethylammonium chloride and its mixture with water J. Phys. Chem. B 2011, 115, 4887-4899
33. Mukkamala, R.; Weiss, R. G. Physical gelation of organic fluids by anthraquinone-steroid-based molecules. Structural features influencing the properties of gels Langmuir 1996, 12, 1474-1482
34. Lu, L.; Cocker, T. M.; Bachman, R. E.; Weiss, R. G. Gelation of organic liquids by some 5-α-cholestan-3-β-yl N-(2-aryl)carbamates and 3-β-cholesteryl 4-(2-anthrylamino)butanoates. How important are H-bonding interactions in the gel and neat assemblies of aza aromatic-linker-steroid gelators? Langmuir 2000, 16, 20-34
35. Wang, T.; Li, Y.; Liu, M. Gelation and self-assembly of glutamate bolaamphiphiles with hybrid linkers: effect of the aromatic ring and alkyl spacers Soft Matter 2009, 5, 1066-1073
36. Lide, D. R. Handbook of Organic Solvents; CRC Press: London, 1995; pp 561-565.
37. Lin, Y.; Kachar, B.; Weiss, R. G. Liquid-crystalline solvents as mechanistic probes. Part 37. Novel family of gelators of organic fluids and the structure of their gels J. Am. Chem. Soc. 1989, 111, 5542-5551
38. Furman, I.; Weiss, R. G. Factors influencing the formation of thermally reversible gels comprised of cholesteryl 4-(2-anthryloxy)butanoate in hexadecane, 1-octanol, or their mixtures Langmuir 1993, 9, 2084-2088
39. Davey, R. J.; Garside, J. From Molecules to Crystallizers; Oxford University Press: New York, 2000; Chapter 2 and references cited therein.
40. Douglas, J. F. Theoretical issues relating to thermally reversible gelation by supermolecular fiber formation Langmuir 2010, 25, 8386-8391
41. Rogers, M. A.; Alejandro, G. Solvent-modulated nucleation and crystallization kinetics of 12-hydroxystearic acid: a nonisothermal approach Langmuir 2009, 25, 8556-8566
42. Wang, R.-Y.; Liu, X.-Y. Kinetic studies of spherulitic crystallization in the gelation process of low molecular-mass organic gelator Int. J. Nanosci. 2006, 5, 645-649
43. Wang, R. Y.; Liu, X.-Y.; Xiong, J. Y.; Li, J. L. Real-time observation of fiber network formation in molecular organogel: supersaturation-dependent microstructure and its related rheological property J. Phys. Chem. B 2006, 110, 7275-7280
44. Huang, X.; Terech, P.; Raghavan, S. R.; Weiss, R. G. Kinetics of 5α-cholestan-3-β-yl N -(2-naphthyl)carbamate/ n -alkane organogel formation and its influence on the fibrillar networks J. Am. Chem. Soc. 2005, 127, 4336-4344
45. Huang, X.; Terech, P.; Raghavan, S. R.; Weiss, R. G. Distinct kinetic pathways generate organogel networks with contrasting fractality and thixotropic properties J. Am. Chem. Soc. 2006, 128, 15341-15352
46. Li, J.-L.; Liu, X.-Y. Microengineering of soft functional materials by controlling the fiber network formation J. Phys. Chem. B 2009, 113, 15467-15472
47. George, M.; Tan, G.; John, V. T.; Weiss, R. G. Urea and thiourea derivatives as low molecular-mass organogelators Chem.-Eur. J. 2005, 11, 3243-3255
48. Liu, X.-Y.; Sawant, P. D. Formation kinetics of fractal nanofiber networks in organogels Appl. Phys. Lett. 2001, 79, 3518-3520
49. Patterson, A. L. The Scherrer formula for I-ray particle size determination Phys. Rev. 1939, 56, 978-982
50. Mallia, V. A.; Butler, P. D.; Sarkar, B.; Holman, K. T.; Weiss, R. G. Reversible phase transitions within self-assembled fibrillar networks of (R)-18-(n -alkylamino)octadecan-7-ols in their carbon tetrachloride gels J. Am. Chem. Soc. 2011, 133, 15045-15054
51. Murata, K.; Aoki, M.; Suzuki, T.; Harada, T.; Kawabata, H.; Komori, T.; Ohseto, F.; Ueda, K.; Shinkai, S. Cholesterol-based functional tectons as versatile building-blocks for liquid crystals, organic gels and monolayers J. Am. Chem. Soc. 1994, 116, 6664-6676
52. Bag, B. G.; Dinda, S. K.; Dey, P. P.; Mallia, V. A.; Weiss, R. G. Self-assembly of esters of arjunolic acid into fibrous networks and the properties of their organogels Langmuir 2009, 25, 8663-8671
53. Paul, C. B.; Ismail, K. Micellization of sodium dodecyl sulfate in sodium acetate-acetic acid buffer. A conductivity study Bull. Chem. Soc. Jpn. 1993, 66, 703-708
54. Zhang, Y.; Cremer, P. S. Interactions between macromolecules and ions: the Hofmeister series Curr. Opin. Chem. Biol. 2006, 10, 658-666
55. Baldwin, R. L. How Hofmeister ion interactions affect protein stability Biophys. J. 1996, 71, 2056-2063
56. He, X.; Zhu, B.-Y.; Huang, J.; Zhao, G.-X. A study on organized assemblies in the aqueous systems of alkylammonium chlorides J. Colloid Interface Sci. 1999, 220, 338-346
57. Roy, S.; Javid, N.; Frederix, P. W. J. M.; Lamprou, D. A.; Urquhart, A. J.; Hunt, N. T.; Halling, P. J.; Ulijn, R. V. Dramatic specific-ion effect in supramolecular hydrogels Chem.-Eur. J. 2012, 18, 11723-11731