Influence of the hydroxyl position in racemic hydroxyoctadecanoic acids on the crystallization kinetics and activation energies of gels and dispersions in mineral oil

Crystal Growth and Design

Volumn 12, Issue 11, 2012, Pages 5497-5504

  Rogers, Michael A ^a   Abraham, Shibu ^b   Bodondics, Ferenc ^c   Weiss, Richard G ^b  

^a RUTGERS UNIVERSITY   (United States)

^b GEORGETOWN UNIVERSITY   (United States)

^c CANADIAN LIGHT SOURCE INC   (Canada)

Author keywords

[No Author keywords available]

Indexed keywords

CARBOXYLIC ACID DIMERS; CRITICAL NUCLEI; CRITICAL SIZE; CRYSTAL PACKINGS; HYDROXYL GROUPS; INTERFACIAL FREE ENERGY; LIQUID COMPONENTS; MOLECULAR GELS; POLAR GROUPS; SUPRAMOLECULAR STRUCTURE;

CARBOXYLIC ACIDS; CRYSTALLIZATION KINETICS; DIMERS; GELS; ISOMERS; LIQUIDS; MINERAL OILS; SOLS;

ACTIVATION ENERGY;

EID: 84868674845     PISSN: 15287483     EISSN: 15287505     Source Type: Journal    
DOI: 10.1021/cg301071x     Document Type: Article

References (48)

1. Mallia, V. A. 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
2. Weiss, R. G.; Terech, P. Introduction. In Molecular Gels: Materials with Self-Assebled Fibrillar Networks; Weiss, R. G.; Terech, P., Eds.; Springer: Dordrecht, The Netherlands, 2006; pp 1-13.
3. 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
4. Fahrländer, M. Linear and Nonlinear Rheological Properties of Self-Assembling Tectons in Polypropylene Matrices Macromolecules 2003, 36, 3749-3757
5. Isare, B. The Weak Help the Strong: Low-Molar-Mass Organogelators Harden Bitumen Langmuir 2009, 25, 8400-8403
6. 2 Solar Cells: Effective Charge Transport in Mesoporous Space Filled with Gel Electrolytes Containing Iodide and Iodine J. Phys. Chem. B 2001, 105, 12809-12815
7. Sugiyasu, K.; Fujita, N.; Shinkai, S. Visible-Light-Harvesting Organogel Composed of Cholesterol-Based Perylene Derivatives Angew. Chem., Int. Ed. 2004, 43, 1229-1233
8. Friggeri, A.; Feringa, B. L.; van Esch, J. Entrapment and release of quinoline derivatives using a hydrogel of a low molecular weight gelator J. Controlled Release 2004, 97, 241-248
9. Wu, Y. Solvent effects on structure, photoresponse and speed of gelation of a dicholesterol-linked azobenzene organogel Soft Matter 2011, 7, 9177-9183
10. Suzuki, M. Effects of hydrogen bonding and van der Waals interactions on organogelation using designed low-molecular-weight gelators and gel formation at room temperature Langmuir 2003, 19 (21) 8622-8624
11. Rogers, M. A.; Marangoni, A. G. Solvent-Modulated Nucleation and Crystallization Kinetics of 12-Hydroxystearic Acid: A Nonisothermal Approach Langmuir 2009, 25 (15) 8556-8566
12. Raynal, M.; Bouteiller, L. Organogel Formation Rationalized by Hansen Solubility Parameters Chem. Commun. 2011, 47, 8271-8273
13. Gao, J.; Wu, S.; Rogers, M. A. Harnessing Hansen Solubility Parameters to Predict Organogel Formation J. Mater. Chem. 2012, 22, 12651-12658
14. Hardy, J. G.; Hirst, A. R.; Smith, D. K. Exploring molecular recognition pathways in one- and two-component gels formed by dendritic lysine-based gelators Soft Matter 2012, 8, 3399-3406
15. 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
16. Zhu, G.; Dordick, J. S. Solvent Effect on Organogel Formation by Low Molecular Weight Molecules 2006, 18 (Chemistry of Materials) 5988-5995
17. Kuwahara, T. Crystal structure of DL-12-hydroxystearic acid Chem. Lett. 1996, 25, 435-436
18. Lam, R. A molecular insight into the nature of crystallographic mismatches in self-assembled fibrillar networks under non-isothermal crystallization conditions Soft Matter 2010, 6 (2) 404-408
19. Li, J. L. Arichitecture of a Biocompatible Supramolecular Material by Supersaturation-Driven Fabrication of its Network J. Phys. Chem. B 2005, 109, 24231-24235
20. Rogers, M. A. Multicomponent Hollow Tubules Formeed Using Phytosterol and γ-Oryzanol-Based Compounds: An Understanding of Their Molecular Embrace J. Phys. Chem. A 2010, 114, 8278-8295
21. Moffat, J. R.; Smith, D. K. Controlled Self-Sorting in the Assembly of Multi-Gelator Gels Chem. Commun. 2009, 3, 316-318
22. Brotin, T.; Devergne, J. P.; Fages, F. Photostationary Fluorescence Emission and Time Resoved Spectroscopy of Symmetrically Disubstituted Anthracenes on teh meso and Side Rings: The Unusual Behavior of the 1,4 Derivative Photochem. Photobiol. 1992, 55, 349-358
23. Terech, P.; Furman, I.; Weiss, R. G. Structures of Organogels Based Upon Cholesteryl 4-(2-Anthryloxy)Butanoate, A Highly Efficient Luminescing Gelator-Neutron and X-Ray Small-Angle Scattering Investigations J. Phys. Chem. 1995, 99 (23) 9558-9566
24. Toro-Vazquez, J. F. Relationship Between Molecular Structure and Thermo-mechanical Properties of Candelilla Wax and Amides Derived from (R)-12-Hydroxystearic Acid as Gelators of Safflower Oil Food Biophys. 2010, 5 (3) 193-202
25. van Esch, J.; Feringa, B. L. New functional materials based on self-assembling organogels: From serendipity towards design Angew. Chem., Int. Ed. 2000, 39, 2263-2266
26. Grahame, D. A. S. Influence of Chirality on the Modes of Self-Assembly of 12-Hydroxystearic Acid in Molecular Gels of Mineral Oil Soft Matter 2011, 7, 7359-7365
27. Tachibana, T.; Kambara, H. Sense of twist in fibrous aggregates from 12-hydroxystearic acid and its alkali metal soaps J. Colloid Interface Sci. 1968, 28 (1) 173-178
28. Tachibana, T.; Mori, T.; Hori, K. Chiral Mesophases of 12-Hydroxyoctadecanoic Acid in Jelly and in the Solid State. I. A New Type of Lyotropic Mesophase in Jelly with Organic Solvents Bull. Chem. Soc. Jpn. 1980, 53, 1714-1719
29. Terech, P. Kinetics of Aggregation in a Steroid Derivative/Cyclohexane Gelifying System J. Colloid Interface Sci. 1985, 107 (1) 244-255
30. Rogers, M. A.; Marangoni, A. G. Non-Isothermal Nucleation and Crystallization of 12-Hydroxystearic Acid in Vegetable Oils Cryst. Growth Des. 2008, 8 (12) 4596-4601
31. Lam, R. S. H.; Rogers, M. A. Experimental Validation of the Modified Avrami Model for Non-Isothermal Crystallization Conditions CrystEngComm 2010, 13, 866-875
32. Li, J. L. Nanoengineering of a Biocompatible Organogel by Thermal Processing J. Phys. Chem. B 2009, 113 (15) 5011-5015
33. Rogers, M. A.; Wright, A. J.; Marangoni, A. G. Engineering the oil binding capacity and crystallinity of self-assembled fibrillar networks of 12-hydroxystearic acid in edible oils Soft Matter 2008, 4 (7) 1483-1490
34. Rogers, M. A.; Wright, A. J.; Marangoni, A. G. Nanostructuring fiber morphology and solvent inclusions in 12-hydroxystearic acid/canola oil organogels Curr. Opin. Colloid Interface Sci. 2009, 14 (3) 223-223
35. Rogers, M. A.; Wright, A. J.; Marangoni, A. G. Nanostructuring fiber morphology and solvent inclusions in 12-hydroxystearic acid/canola oil organogels Curr. Opin. Colloid Interface Sci. 2009, 14 (1) 33-42
36. Wang, R. Y. Architecture of Fiber Network: From Understanding to Engineering of Molecular Gels J. Phys. Chem. B 2006, 10, 25797-25802
37. Menger, F. M. Chain-Substituted Lipids in Monomolecular Films. Effect of Polar Substituents on Molecular Packing Langmuir 1989, 5, 833-838
38. Mallia, V. A. Robust Organogels from Nitrogen-Containing Derivatives of (R)-12-Hydroxystearic Acid as Gelators: Comparisons with Gels from Stearic Acid Derivatives Langmuir 2009, 25 (15) 8615-8625
39. Fameau, A. L. 12-Hydroxystearic acid lipid tubes under various experimental conditions J. Colloid Interface Sci. 2010, 341 (1) 38-47
40. Huang, X.; Weiss, R. G. Molecular organogels of the sodium salt of (R)-12-hydroxystearic acid and their templated syntheses of inorganic oxides Tetrahedron 2007, 63 (31) 7375-7385
41. Sakurai, T. A Comparative Study on Chiral and Racemic 12-Hydroxyoctadecanoic Acids in the Slutions and Aggregation States: Does the Racemic Form Really Form a Gel? Bull. Chem. Soc. Jpn. 2010, 83 (2) 145-149
42. Terech, P. Organogels and Areogels of Racemic and Chiral 12-Hydroxyoctadecanoic Acid Langmuir 1994, 10 (10) 3406-3418
43. Wright, A. J.; Marangoni, A. G. Time, temperature, and concentration dependence of ricinelaidic acid-canola oil organogelation J. Am. Oil Chem. Soc. 2007, 84 (1) 3-9
44. Abraham, S. Influence of Positional Isomers on the Macroscale and Nanoscale Architectures of Aggregates of Racemic Hydroxyoctadecanoic Acids in Their Molecular Gel, Dispersion, and Solid States Langmuir 2012, 28, 4955-4964
45. Avrami, M. Kinetics of Phase Change. I. General Theory J. Chem. Phys. 1939, 7 (12) 1103-1112
46. Avrami, M. Kinetics of Phase Change. II. Transformation-Time Relations for Random Distribution of Nuclei J. Chem. Phys. 1940, 8 (22) 212-226
47. Avrami, M. Kinetics of Phase Change. III. Granulation, Phase Change, and Microstructure J. Chem. Phys. 1941, 9 (2) 177-184
48. Marangoni, A. G. Crystallization Kinetics. In Fat Crystal Networks; Marangoni, A. G., Ed.; Marcel Dekker: New York, 2005; pp 21-82.