Solvent-induced polymorphic nanoscale transitions for 12- hydroxyoctadecanoic acid molecular gels

Crystal Growth and Design

Volumn 13, Issue 3, 2013, Pages 1360-1366

  Wu, Songwei ^a,b   Gao, Jie ^a,b   Emge, Thomas J ^a,b   Rogers, Michael A ^a,b  

^a RUTGERS UNIVERSITY   (United States)

^b RUTGERS UNIVERSITY   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

CRYSTALLINE NETWORKS; FIBRILLAR NETWORKS; INTERDIGITATIONS; MOLECULAR GELS; MULTILAMELLAR; NANO SCALE; POLYMORPHIC FORMS; SELF-ASSEMBLED;

CYANIDES; KETONES; ORGANIC SOLVENTS;

GELS;

EID: 84876904565     PISSN: 15287483     EISSN: 15287505     Source Type: Journal    
DOI: 10.1021/cg400124e     Document Type: Article

References (41)

1. Kuwahara, T.; et al. Crystal structure of DL-12-hydroxystearic acid. Chem. Lett. 1996, 25, 435-436.
2. Lam, R.; et al. A molecular insight into the nature of crystallographic mismatches in self-assembled fibrillar networks under non-isothermal crystallization conditions. Soft Matter 2010, 6.
3. Li, J. L.; et al. Architecture of a Biocompatible Supramolecular Material by Supersaturation-Driven Fabrication of its Network. J. Phys. Chem. B 2005, 109, 24231-24235.
4. Rogers, M. A.; et al. Multicomponent Hollow Tubules Formed Using Phytosterol and γ-Oryzanol-Based Compounds: An Understanding of Their Molecular Embrace. J. Phys. Chem. 2010, 114, 8278-8295.
5. Moffat, J. R.; Smith, D. K. Controlled Self-Sorting in the Assembly of 'Multi-Gelator' Gels. Chem. Commun. 2009, 3, 316-318.
6. Brotin, T.; Devergne, J. P.; Fages, F. Photostationary Fluorescence Emission and Time Resoved Spectroscopy of Symmetrically Disubstituted Anthracenes on the Meso and Side Rings: The Unusual Behavior of the 1,4 Derivative. Photochem. Photobiol. 1992, 55, 349-358.
7. Terech, P.; Furman, I.; Weiss, R. G. Structures of Organogels Based Upon Cholesteryl 4-Anthryloxy)Butanoate, A Highly Efficient Luminescing Gelator-Neutron and X-Ray Small-Angle Scattering Investigations. J. Phys. Chem. 1995, 99 3), 9558-9566.
8. Toro-Vazquez, J. F.; et al. 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 Biophysics 2010, 5) , 193-202.
9. Mallia, V. A.; et al. 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.
10. Weiss, R. G., Terech, P. Introduction. In Molecular Gels: Materials with Self-Assembled Fibrillar Networks; Weiss, R. G., Terech, P., Eds.; Springer: Dordrecht, The Netherlands, 2006; p 1-13.
11. 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.
12. Zhu, G.; Dordick, J. S. Solvent Effect on Organogel Formation by Low Molecular Weight Molecules. Chem. Mater. 2006, 18, 5988-5995.
13. Gao, J.; Wu, S.; Rogers, M. A. Harnessing Hansen Solubility Parameters to Predict Organogel Formation. J. Mater. Chem. 2012, 22, 12651-12658.
14. Suzuki, M.; et al. 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.
15. 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.
16. Raynal, M.; Bouteiller, L. Organogel Formation Rationalized by Hansen Solubility Parameters. Chem. Commun. 2011, 47, 8271-8273.
17. 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.
18. 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.
19. Wang, R. Y.; et al. Architecture of Fiber Network: From Understanding to Engineering of Molecular Gels. J. Phys. Chem. B 2006, 10, 25797-25802.
20. Li, J. L.; et al. Nanoengineering of a Biocompatible Organogel by Thermal Processing. J. Phys. Chem. B 2009, 113 5), 5011-5015.
21. Liu, X. Y.; Sawant, P. D. Determination of the Fractal Characteristic of Nanofiber-Network Formation in Supramolecular Materials. ChemPhysChem 2002, 4, 374-377.
22. Huang, X.; et al. Distinct Kinetic Pathways Generate Organogel Networks with Contrasting Fractality and Thixotopic Properties. J. Am. Chem. Soc. 2006, 128, 15341-15352.
23. Terech, P. Kinetics of Aggregation in a Steroid Derivative/Cyclohexane Gelifying System. J. Colloid Interface Sci. 1985, 107) , 244-255.
24. Rogers, M. A.; Marangoni, A. G. Non-Isothermal Nucleation and Crystallization of 12-Hydroxystearic Acid in Vegetable Oils. Cryst. Growth Des. 2008, 8 2), 4596-4601.
25. Lam, R. S. H.; Rogers, M. A. Experimental Validation of the Modified Avrami Model for Non-Isothermal Crystallization Conditions. Cryst. Eng. Commun. 2010, 13, 866-875.
26. 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.
27. 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, 223-223.
28. 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, 33-42.
29. Menger, F. M.; et al. Chain-Substituted Lipids in Monomolecular Films. Effect of Polar Substituents on Molecular Packing. Langmuir 1989, 5, 833-838.
30. Mallia, V. A.; et al. Robust Organogels from Nitrogen-Containing Derivatives of (R)-12-Hydroxystearic Acid as Gelators: Comparisons with Gels from Stearic Acid Derivatives. Langmuir 2009, 25 5), 8615-8625.
31. Fameau, A. L.; et al. 12-Hydroxystearic acid lipid tubes under various experimental conditions. J. Colloid Interface Sci. 2010, 341) , 38-47.
32. Grahame, D. A. S.; et al. 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.
33. 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 1), 7375-7385.
34. Sakurai, T.; et al. 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) , 145-149.
35. Terech, P.; et al. Organogels and Areogels of Racemic and Chiral 12-Hydroxyoctadecanoic Acid. Langmuir 1994, 10 (10), 3406-3418.
36. Wright, A. J.; Marangoni, A. G. Time, temperature, and concentration dependence of ricinelaidic acid-canola oil organogelation. J. Am. Oil Chem. Soc. 2007, 84, 3-9.
37. Hansen, C. M. Hansen Solubility Parameters, 2nd ed.; CRC Press: Boca Raton, FL, 2007.
38. Marangoni, A. G. Crystallography, in Fat Crystal Networks; Marangoni, A. G., Ed.; Marcel Dekker: New York, 2005; p 1-20.
39. Sato, H.; Ueno, S. Polymorphism in Fats and Oils, in Bailey's Industrial Oil and Fat Products; Shahidi, F., Ed.; John Wiley & Sons, Inc: New York, 2005; p 77-120.
40. Lin-Vien, D., et al., The Handbook of Infrared and Raman Characteristic Frequencies of Organic Molecules; London: Academic Press, 1991.
41. Rogers, M. A.; Pedersen, T.; Quaroni, L. Hydrogen-Bonding Density of Supramolecular Self-Assembled Fibrillar Networks Probed Using Synchrotron Infrared Spectromicroscopy. Cryst. Growth Des. 2009, 9) , 3621-3625.