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

Volumn 28, Issue 11, 2012, Pages 4955-4964

  Abraham, Shibu ^a   Lan, Yaqi ^b   Lam, Ricky S H ^c   Grahame, Douglas A S ^c   Kim, Jennifer Jae Hee ^c   Weiss, Richard G ^a   Rogers, Michael A ^b  

^a GEORGETOWN UNIVERSITY   (United States)

^b RUTGERS UNIVERSITY   (United States)

^c UNIVERSITY OF SASKATCHEWAN   (Canada)

Author keywords

[No Author keywords available]

Indexed keywords

CYCLIC DIMERS; H-BONDS; HYDROXYL GROUPS; HYDROXYSTEARIC ACIDS; MACRO SCALE; MOLECULAR DIMERS; MOLECULAR GELS; NANOSCALE ARCHITECTURES; POSITIONAL ISOMERS; SELF-ASSEMBLE; XRD;

HYDROGEN BONDS; ISOMERS; LANGMUIR BLODGETT FILMS;

DIMERS;

STEARIC ACID DERIVATIVE;

ARTICLE; CHEMISTRY; INFRARED SPECTROSCOPY; NUCLEAR MAGNETIC RESONANCE SPECTROSCOPY; STEREOISOMERISM; X RAY DIFFRACTION;

MAGNETIC RESONANCE SPECTROSCOPY; SPECTROSCOPY, FOURIER TRANSFORM INFRARED; STEARATES; STEREOISOMERISM; X-RAY DIFFRACTION;

EID: 84863338387     PISSN: 07437463     EISSN: 15205827     Source Type: Journal    
DOI: 10.1021/la204412t     Document Type: Article

References (33)

1. Terech, P.; Weiss, R. G. Low Molecular Mass Gelators of Organic Liquids and the Properties of Their Gels Chem. Rev. 1997, 3133-3159 (Pubitemid 127667409)
2. Abdallah, A. J.; Weiss, R. G. Organogels and low molecular mass organic gelators Adv. Mater. (Weinheim, Ger.) 2000, 12, 1237-1247
3. 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.
4. Terech, P.; Rodriguez, V.; Barnes, J. D.; McKenna, G. B. Organogels and Areogels of Racemic and Chiral 12-Hydroxyoctadecanoic Acid Langmuir 1994, 10 (10) 3406-3418
5. 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 (15) 8615-8625
6. Suzuki, M.; Nakajima, Y.; Yumoto, M.; Kimura, M.; Shirai, H.; Hanabusa, K. 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
7. Grahame, D. A. S.; Olauson, C.; Lam, R. S. H.; Pedersen, T.; Borondics, F.; Abraham, S.; Weiss, R. G.; Rogers, M. A. 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
8. 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
9. 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. 1980, 53, 1714-1719
10. Li, J. L.; Lui, X. Y. Architecture of Supramolecular Soft Functional Materials: From Understanding to Micro-/Nanoscale Engineering Adv. Funct. Mater. 2010, 20, 3196-3216
11. Wang, R. Y.; Liu, X. Y.; Narayanan, J.; Xiong, J. X.; Li, J. L. Architecture of Fiber Network: From Understanding to Engineering of Molecular Gels J. Phys. Chem. B 2006, 10, 25797-25802 (Pubitemid 46133292)
12. Terech, P. Kinetics of Aggregation in a Steroid Derivative/Cyclohexane Gelifying System J. Colloid Interface Sci. 1985, 107 (1) 244-255 (Pubitemid 15587421)
13. 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
14. Lam, R.; Quaroni, L.; Pederson, T.; Rogers, M. A. 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
15. Lam, R. S. H.; Rogers, M. A. Experimental Validation of the Modified Avrami Model for Non-Isothermal Crystallization Conditions CrystEngComm 2010, 13, 866-875
16. Li, J. L.; Liu, X. Y.; Wang, R. Y.; Xiong, J. Y. Arichitecture of a Biocompatible Supramolecular Material by Supersaturation-Driven Fabrication of its Network J. Phys. Chem. B 2005, 109, 24231-24235
17. Li, J. L.; Wang, R. Y.; Liu, X. Y.; Pan, H. H. Nanoengineering of a Biocompatible Organogel by Thermal Processing J. Phys. Chem. B 2009, 113 (15) 5011-5015
18. 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 (Pubitemid 351875605)
19. Rogers, M. A.; Wright, A. J.; Marangoni, A. G. Corrigendum to " Nanostructuring fiber morphology and solvent inclusions in 12-hydroxystearic acid/canola oil organogels " [Current Opinion in Colloid & Interface Science 14(1) (2009) 33-42]. Curr. Opin. Colloid Interface Sci. 2009, 14, (3), 223.
20. 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
21. Menger, F. M.; Richardson, S. D.; Wood, M. G.; Sherrod, M. J. Chain-Substituted Lipids in Monomolecular Films. Effect of Polar Substituents on Molecular Packing Langmuir 1989, 5, 833-838
22. 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
23. Fameau, A. L.; Houinsou-Houssou, B.; Novales, B.; Navailles, L.; Nallet, F.; Douliez, J. P. 12-Hydroxystearic acid lipid tubes under various experimental conditions J. Colloid Interface Sci. 2010, 341 (1) 38-47
24. 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 (Pubitemid 46950896)
25. Sakurai, T.; Masuda, Y.; Sato, H.; Yamagishi, A.; Kawaji, H.; Atake, T.; Hori, K. A Comparative Study on Chiral and Racemic 12-Hydroxyoctadecanoic Acids in the Solutions and Aggregation States: Does the Racemic Form Really Form a Gel? Bull. Chem. Soc. 2010, 83 (2) 145-149
26. 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 (Pubitemid 46931886)
27. Mallia, V. A.; Terech, P.; Weiss, R. G. Correlations of Properties and Structures at Different Length Scales of Hydro- and Organogels Based on N -Alkyl-(R)-12-Hydroxyoctadecylammonium Chlorides J. Phys. Chem. B 2011, 115, 12401-12414
28. Menger, F. M.; Richardson, S. D.; Wood, M. G.; Sherrod, M. J. Langmuir 1989, 5, 833
29. Kuwahara, T.; Nagase, H.; Endo, T.; Ueda, H.; Nakagaki, M. Crystal structure of DL-12-hydroxystearic acid Chem. Lett. 1996, 25, 435-436
30. Terech, P.; Pasquier, D.; Bordas, V.; Rossat, C. Rheological properties and structural correlations in molecular gels Langmuir 2000, 16, 4485-4494
31. Tamura, T.; Ichikawa, M. Effect of lecithin on organogel formation of 12-hydroxystearic acid J. Am. Oil Chem. Soc. 1997, 74 (5) 491-495 (Pubitemid 127553525)
32. Marangoni, A. G. Crystallography. In Fat Crystal Networks; Marangoni, A. G., Ed.; Marcel Dekker: New York, 2005; pp 1-20.
33. Lin-Vien, D.; Colthup, N. B.; Fateley, W. G.; Grasselli, J. G. The Handbook of Infrared and Raman Characteristic Frequencies of Organic Molecules; Academic Press: London, UK, 1991.