Solvent-induced molecular gel formation at room temperature and the preparation of related gel-emulsions

Science China Chemistry

Volumn 56, Issue 7, 2013, Pages 982-991

  Jing, Ping ^a   Yan, Junlin ^a   Cai, Xiuqin ^a   Liu, Jing ^a   Hu, Baolong ^a   Fang, Yu ^a  

^a SHAANXI NORMAL UNIVERSITY   (China)

Author keywords

cholesterol; gel emulsion; low molecular mass gelators (LMMGs); super gelation

Indexed keywords

CHOLESTERYL DERIVATIVES; GEL-EMULSION; GELATION CONCENTRATIONS; GELATORS; H NMR SPECTROSCOPY; LAYERED STRUCTURES; SUPER-GELATION; THIXOTROPIC PROPERTIES;

ACETONE; CHOLESTEROL; EMULSIFICATION; GELATION; HYDROGEN BONDS; PETROLEUM REFINING;

SOLVENTS;

EID: 84880252383     PISSN: 16747291     EISSN: None     Source Type: Journal    
DOI: 10.1007/s11426-013-4869-x     Document Type: Conference Paper

References (37)

1. Xiao K, Luo J, Fowler WL, Li Y, Lee JS, Xing L, Cheng RH, Wang L, Lam KS. A self-assembling nanoparticle for paclitaxel delivery in ovarian cancer. Biomaterials, 2009, 30: 6006-6016
2. Steed JW. Supramolecular gel chemistry: Developments over the last decade. Chem Commun, 2011, 47: 1379-1383
3. Bellomo A, Daniellou R, Plusquellec D. Aqueous solutions of facial amphiphilic carbohydrates as sustainable media for organocatalyzed direct aldol reactions. Green Chem, 2012, 14: 281-284
4. Minakuchi N, Hoe K, Yamaki D, Ten-no S, Nakashima K, Goto M, Mizuhata M, Maruyama T. Versatile supramolecular gelators that can harden water, organic solvents and ionic liquids. Langmuir, 2012, 28: 9259-9266
5. Sánchez-Ferrer A, Adamcik J, Mezzenga R. Edible supramolecular chiral nanostructures by self-assembly of an amphiphilic phytosterol conjugate. Soft Matter, 2012, 8: 149-155
6. Wang TY, Li YG, Liu MH. Gelation and self-assembly of glutamate bolaamphiphiles with hybrid linkers: Effect of the aromatic ring and alkyl spacers. Soft Matter, 2009, 5: 1066-1073
7. Estroff LA, Hamilton AD. Water gelation by small organic molecules. Chem Rev, 2004, 104: 1201-1218
8. Iwai H, Fukasawa J, Suzuki T. A liquid crystal application in skin care cosmetics. Int J Cosmet Sci, 1998, 20: 87-102
9. Vinogradov SV, Bronich TK, Kabanov AV. Nanosized cationic hydrogels for drug delivery: Preparation, properties and interactions with cells. Adv Drug Deliv Rev, 2002, 54: 135-147
10. Huang QD, Zhong GX, Zhang Y, Ren J, Fu Y, Zhang J, Zhu W, Yu XQ. Cyclen-based cationic lipids for highly efficient gene delivery towards tumor cells. PLoS ONE, 2011, 6: e23134
11. Jadhav SR, Vemula PK, Kumar R, Raghavan SR, John G. Sugar-derived phase-selective molecular gelators as model solidifiers for oil spills. Angew Chem Int Ed, 2010, 122: 7861-7864
12. Jung JH, Kobayashi H, Masuda M, Shimizu T, Shinkai S. Helical ribbon aggregate composed of a crown-appended cholesterol derivative which acts as an amphiphilic gelator of organic solvents and as a template for chiral silica transcription. J Am Chem Soc, 2001, 123: 8785-8789
13. Wallimann P, Marti T, Fürer A, Diederich F. Steroids in molecular recognition. Chem Rev, 1997, 97: 1567-1608
14. Jyothish K, Hariharan M, Ramaiah D. Chiral supramolecular assemblies of a squaraine dye in solution and thin films: Concentration-, temperature-, and solvent-induced chirality inversion. Chem Eur J, 2007,13: 5944-5951
15. Lu L, Weiss RG. Cholestanyl substituted quaternary ammonium salts as gelators of organic liquids. Langmuir, 1995,11: 3630-3632
16. Liu KQ, He PL, Fang Y. Progress in the studies of low-molecular mass gelators with unusual properties. Sci China Chem, 2010, 54: 575-586
17. Amaike M, Kobayashi H, Shinkai S. New organogelators bearing both sugar and cholesterol units: An approach toward molecular design of universal gelators. Bull Chem Soc Jpn, 2000, 73: 2553-2558
18. Gao D, Xue M, Peng JX, Liu J, Yan N, He PL, Fang Y. Preparation and gelling properties of sugar-contained low-molecular-mass gelators: Combination of cholesterol and linear glucose. Tetrahedron, 2010, 66: 2961-2968
19. Yan JL, Liu J, Jing P, Xu CK, Wu JM, Gao D, Fang Y. Cholesterol-based low-molecular mass gelators towards smart ionogels. Soft Matter, 2012, 8: 11697-11703
20. -1]. Chem Lett, 2000, 29: 1148-1149
21. Lissant KJ. The geometry of high-internal-phase ratio emulsions. J Colloid Interface Sci, 1966, 22: 462-468
22. Rocca S, Stébé MJ. Mixed concentrated water/oil emulsions (fluorinated/hydrogenated): Formulation, properties, and structural studies. J Phys Chem B, 2000, 104: 10490-10497
23. Chen YH, Ballard N, Gayet F, Bon SAF. High internal phase emulsion gels (HIPE-gels) from polymer dispersions reinforced with quadruple hydrogen bond functionality. Chem Commun, 2012, 48: 1117-1119
24. Marquardt D, Sucker H. Oil-in-water-emulsion gels: Determination and mathematical treatment of flow properties. Eur J Pharm Biopharm, 1998, 46: 115-124
25. Kunieda H, Fukui Y, Uchiyama H, Solans C. Spontaneous formation of highly concentrated water-in-oil emulsions (gel-emulsions). Langmuir, 1996, 12, 2136-2140
26. Kirilov P, Gauffre F, Franceschi-Messant S, Perez E, Rico-Lattes I. Rheological characterization of a new type of colloidal dispersion based on nanoparticles of gelled oil. J Phys Chem B, 2009, 113: 11101-11108
27. Trappe V, Weitz DA. Scaling of the viscoelasticity of weakly attractive particles. Phys Rev Lett, 2000, 85: 449-452
28. Yang MC, Scriven LE, Macosko CW. Some rheological measurements on magnetic iron oxide suspensions in silicone oil. J Rheol, 1986, 30: 1015-1029
29. Yamada N, Imai T, Koyama E. Lyotropic aggregate of tripeptide derivatives within organic solvents: Relationship between interpeptide hydrogen bonding and packing arrangements of components. Langmuir, 2001, 17: 961-963
30. Jung JH, John G, Masuda M, Yoshida K, Shinkai S, Shimizu T. Self-assembly of a sugar-based gelator in water: Its remarkable diversity in gelation ability and aggregate structure. Langmuir, 2001, 17: 7229-7232
31. Wang C, Zhang D, Xiang J, Zhu D. New organogels based on an anthracene derivative with one urea group and its photodimer: Fluorescence enhancement after gelation. Langmuir, 2007, 23: 9195-9200
32. Bieser AM, Tiller JC. Structure and properties of an exceptional low molecular weight hydrogelator. J Phys Chem B, 2007, 111: 13180-13187
33. Ostuni E, Kamaras P, Weiss RG. Novel X-ray method for in situ determination of gelator strand structure: Polymorphism of cholesteryl anthraquinone-2-carboxylate. Angew Chem Int Ed, 1996, 35: 1324-1326
34. Shimizu T, Masuda M. Stereochemical effect of even-odd connecting links on supramolecular assemblies made of 1-glucosamide bolaamphiphiles. J Am Chem Soc, 1997, 119: 2812-2818
35. Imae T, Hayashi N, Matsumoto T, Tada T, Furusaka M. Structures of fibrous supramolecular assemblies constructed by amino acid surfactants: Investigation by AFM, SANS, and SAXS. J Colloid Interface Sci, 2000, 225: 285-290
36. Luo XZ, Li C, Liang YQ. Self-assembled organogels formed by monoalkyl derivatives of oxamide. Chem Commun, 2000, 2091-2092
37. Zubarev ER, Pralle MU, Sone ED, Stupp SI. Scaffolding of polymers by supramolecular nanoribbons. Adv Mater, 2002, 14: 198-203