Tuning the gelation ability of racemic mixture by melamine: Enhanced mechanical rigidity and tunable nanoscale chirality

Langmuir

Volumn 30, Issue 35, 2014, Pages 10772-10778

  Shen, Zhaocun ^a   Wang, Tianyu ^a   Liu, Minghua ^a  

^a INSTITUTE OF GEOLOGY AND GEOPHYSICS   (China)

Author keywords

[No Author keywords available]

Indexed keywords

AMINO ACIDS; CHIRALITY; ENANTIOMERS; GELATION; HYDROGELS; MOLAR RATIO; NANOTECHNOLOGY; RIGIDITY; SUPRAMOLECULAR CHEMISTRY;

BOLAAMPHIPHILES; GELATION PROPERTIES; MECHANICAL RIGIDITY; MOLECULAR BUILDING BLOCKS; MOLECULAR CHIRALITY; RACEMIC MIXTURES; SUPRAMOLECULAR ASSEMBLIES; SUPRAMOLECULAR GELS;

STEREOCHEMISTRY;

EID: 84930677340     PISSN: 07437463     EISSN: 15205827     Source Type: Journal    
DOI: 10.1021/la502799j     Document Type: Article

References (60)

1. Smith, M. M.; Edwards, W.; Smith, D. K. Self-Organisation Effects in Dynamic Nanoscale Gels Self-Assembled from Simple Mixtures of Commercially Available Molecular-Scale Components. Chem. Sci. 2013, 4, 671-676.
2. Buerkle, L. E.; Rowan, S. J. Supramolecular Gels Formed from Multi-Component Low Molecular Weight Species. Chem. Soc. Rev. 2012, 41, 6089-6102.
3. Huang, B. Q.; Hirst, A. R.; Smith, D. K.; Castelletto, V.; Hamley, I. W. A Direct Comparison of One- and Two-Component Dendritic Self-Assembled Materials: Elucidating Molecular Recognition Pathways. J. Am. Chem. Soc. 2005, 127, 7130-7139.
4. Kumar, D. K.; Steed, J. W. Supramolecular Gel Phase Crystallization: Orthogonal Self-Assembly under Non-Equilibrium Conditions. Chem. Soc. Rev. 2014, 43, 2080-2088.
5. Piepenbrock, M. O. M.; Lloyd, G. O.; Clarke, N.; Steed, J. W. Metal- and Anion-Binding Supramolecular Gels. Chem. Rev. 2010, 110, 1960-2004.
6. Yan, X.; Xu, D.; Chi, X.; Chen, J.; Dong, S.; Ding, X.; Yu, Y.; Huang, F. A Multiresponsive, Shape-Persistent, and Elastic Supramolecular Polymer Network Gel Constructed by Orthogonal Self-Assembly. Adv. Mater. 2012, 24, 362-369.
7. Afrasiabi, R.; Kraatz, H. B. Small-Peptide-Based Organogel Kit: Towards the Development of Multicomponent Self-Sorting Organogels. Chem.-Eur. J. 2013, 19, 15862-15871.
8. Hirst, A. R.; Smith, D. K. Two-Component Gel-Phase Materials-Highly Tunable Self-Assembling Systems. Chem.-Eur. J. 2005, 11, 5496-5508.
9. Bairi, P.; Roy, B.; Nandi, A. K. A Light Harvesting Bi-Component Hydrogel with a Riboflavin Acceptor. Chem. Commun. 2012, 48, 10850-10852.
10. Yan, X.; Cook, T. R.; Pollock, J. B.; Wei, P.; Zhang, Y.; Yu, Y.; Huang, F.; Stang, P. J. Responsive Supramolecular Polymer Metallogel Constructed by Orthogonal Coordination-Driven Self-Assembly and Host/Guest Interactions. J. Am. Chem. Soc. 2014, 136, 4460-4463.
11. Zhang, M.; Xu, D.; Yan, X.; Chen, J.; Dong, S.; Zheng, B.; Huang, F. Self-Healing Supramolecular Gels Formed by Crown Ether Based Host-Guest Interactions. Angew. Chem., Int. Ed. 2012, 51, 7011-7015.
12. Shu, T.; Wu, J.; Lu, M.; Chen, L.; Yi, T.; Li, F.; Huang, C. Tunable Red-Green-Blue Fluorescent Organogels on the Basis of Intermolecular Energy Transfer. J. Mater. Chem. 2008, 18, 886-893.
13. Adhikari, B.; Nanda, J.; Banerjee, A. Multicomponent Hydrogels from Enantiomeric Amino Acid Derivatives: Helical nanofibers, Handedness and Self-Sorting. Soft Matter 2011, 7, 8913-8922.
14. Imaz, I.; Rubio-Martínez, M.; Saletra, W. J.; Amabilino, D. B.; Maspoch, D. Amino Acid Based Metal-Organic Nanofibers. J. Am. Chem. Soc. 2009, 131, 18222-18223.
15. Shen, J. S.; Cai, Q. G.; Jiang, Y. B.; Zhang, H. W. Anion-Triggered Melamine Based Self-Assembly and Hydrogel. Chem. Commun. 2010, 46, 6786-6788.
16. Bairi, P.; Roy, B.; Nandi, A. K. pH and Anion Sensitive Silver(I) Coordinated Melamine Hydrogel with Dye Absorbing Properties: Metastability at Low Melamine Concentration. J. Mater. Chem. 2011, 21, 11747-11749.
17. Hirst, A. R.; Miravet, J. E.; Escuder, B.; Noirez, L.; Castelletto, V.; Hamley, I. W.; Smith, D. K. Self-Assembly of Two-Component Gels: Stoichiometric Control and Component Selection. Chem.-Eur. J. 2009, 15, 372-379.
18. Suzuki, M.; Yumoto, M.; Shirai, H.; Hanabusa, K. Supramolecular Gels Formed by Amphiphilic Low-Molecular-Weight Gelators of N-alpha,N-epsilon-Diacyl-L-lysine Derivatives. Chem.-Eur. J. 2008, 14, 2133-2144.
19. Smith, D. K. Lost in Translation? Chirality Effects in the Self-Assembly of Nanostructured Gel-Phase Materials. Chem. Soc. Rev. 2009, 38, 684-694.
20. Jadhav, S. R.; Vemula, P. K.; Kumar, R.; Raghavan, S. R.; John, G. Sugar-Derived Phase-Selective Molecular Gelators as Model Solidifiers for Oil Spills. Angew. Chem., Int. Ed. 2010, 49, 7695-7698.
21. Xue, P. C.; Lu, R.; Yang, X. C.; Zhao, L.; Xu, D. F.; Liu, Y.; Zhang, H.; Nomoto, H.; Takafuji, M.; Ihara, H. Self-Assembly of a Chiral Lipid Gelator Controlled by Solvent and Speed of Gelation. Chem.-Eur. J. 2009, 15, 9824-9835.
22. Ikeda, M.; Tanida, T.; Yoshii, T.; Kurotani, K.; Onogi, S.; Urayama, K.; Hamachi, I. Installing Logic-Gate Responses to a Variety of Biological Substances in Supramolecular Hydrogel-Enzyme Hybrids. Nat. Chem. 2014, 6, 511-518.
23. 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.
24. Zhou, J.; Du, X.; Gao, Y.; Shi, J.; Xu, B. Aromatic-Aromatic Interactions Enhance Interfiber Contacts for Enzymatic Formation of a Spontaneously Aligned Supramolecular Hydrogel. J. Am. Chem. Soc. 2014, 136, 2970-2973.
25. Gao, J.; Wang, H. M.; Wang, L.; Wang, J. Y.; Kong, D. L.; Yang, Z. M. Enzyme Promotes the Hydrogelation from a Hydrophobic Small Molecule. J. Am. Chem. Soc. 2009, 131, 11286-11287.
26. Tu, T.; Fang, W.; Bao, X.; Li, X.; Dötz, K. H. Visual Chiral Recognition through Enantioselective Metallogel Collapsing: Synthesis, Characterization, and Application of Platinum-Steroid Low-Molecular-Mass Gelators. Angew. Chem., Int. Ed. 2011, 50, 6601-6605.
27. Raeburn, J.; Zamith Cardoso, A.; Adams, D. J. The Importance of the Self-Assembly Process to Control Mechanical Properties of Low Molecular Weight Hydrogels. Chem. Soc. Rev. 2013, 42, 5143-5156.
28. Yang, Z.; Liang, G.; Xu, B. Enzymatic Hydrogelation of Small Molecules. Acc. Chem. Res. 2008, 41, 315-326.
29. Dong, S.; Zheng, B.; Xu, D.; Yan, X.; Zhang, M.; Huang, F. A Crown Ether Appended Super Gelator with Multiple Stimulus Responsiveness. Adv. Mater. 2012, 24, 3191-3195.
30. Dong, S.; Luo, Y.; Yan, X.; Zheng, B.; Ding, X.; Yu, Y.; Ma, Z.; Zhao, Q.; Huang, F. A Dual-Responsive Supramolecular Polymer Gel Formed by Crown Ether Based Molecular Recognition. Angew. Chem., Int. Ed. 2011, 50, 1905-1909.
31. Lee, H. Y.; Nam, S. R.; Hong, J.-I. Microtubule Formation Using Two-Component Gel System. J. Am. Chem. Soc. 2007, 129, 1040-1041.
32. Meazza, L.; Foster, J. A.; Fucke, K.; Metrangolo, P.; Resnati, G.; Steed, J. W. Halogen-Bonding-Triggered Supramolecular Gel Formation. Nat. Chem. 2013, 5, 42-47.
33. Sobczuk, A. A.; Tamaru, S.; Shinkai, S. New Strategy for Controlling the Oligothiophene Aggregation Mode Utilizing the Gelto-Sol Phase Transition Induced by Crown-Alkali Metal Interactions. Chem. Commun. 2011, 47, 3093-3095.
34. Wang, Y.; Li, W.; Wu, L. Organic-Inorganic Hybrid Supramolecular Gels of Surfactant-Encapsulated Polyoxometalates. Langmuir 2009, 25, 13194-13200.
35. Bredikhin, A. A.; Bredikhina, Z. A.; Akhatova, F. S.; Gubaidullin, A. T. p-Tolyl Glycerol Ether: Is It Possible to Find More Simple Molecular Organogelator with Pronounced Chirality Driven Properties? Chem. Commun. 2010, 46, 3523-3525.
36. Koga, T.; Matsuoka, M.; Higashi, N. Structural Control of Self-Assembled Nanofibers by Artificial β-Sheet Peptides Composed of Dor L-Isomer. J. Am. Chem. Soc. 2005, 127, 17596-17597.
37. Luo, X.; Liu, B.; Liang, Y. Self-Assembled Organogels Formed by Mono-Chain L-Alanine Derivatives. Chem. Commun. 2001, 1556-1557.
38. Boettcher, C.; Schade, B.; Fuhrhop, J. H. Comparative Cryo-Electron Microscopy of Noncovalent N-Dodecanoyl-(D- and L-)Serine Assemblies in Vitreous Toluene and Water. Langmuir 2001, 17, 873-877.
39. Oda, R.; Huc, I.; Candau, S. J. Gemini Surfactants as New, Low Molecular Weight Gelators of Organic Solvents and Water. Angew. Chem., Int. Ed. 1998, 37, 2689-2691.
40. Fuhrhop, J. H.; Boettcher, C. Stereochemistry and Curvature Effects in Supramolecular Organization and Separation Processes of Micellar N-Alkylaldonamide Mixtures. J. Am. Chem. Soc. 1990, 112, 1768-1776.
41. Nakashima, N.; Asakuma, S.; Kunitake, T. Optical Microscopic Study of Helical Superstructures of Chiral Bilayer Membranes. J. Am. Chem. Soc. 1985, 107, 509-510.
42. Amemiya, R.; Mizutani, M.; Yamaguchi, M. Two-Component Gel Formation by Pseudoenantiomeric Ethynylhelicene Oligomers. Angew. Chem., Int. Ed. 2010, 49, 1995-1999.
43. Lin, J.; Guo, Z.; Plas, J.; Amabilino, D. B.; De Feyter, S.; Schenning, A. P. H. J. Homochiral and Heterochiral Assembly Preferences at Different Length Scales - Conglomerates and Racemates in the Same Assemblies. Chem. Commun. 2013, 49, 9320-9322.
44. Nagy, K. J.; Giano, M. C.; Jin, A.; Pochan, D. J.; Schneider, J. P. Enhanced Mechanical Rigidity of Hydrogels Formed from Enantiomeric Peptide Assemblies. J. Am. Chem. Soc. 2011, 133, 14975-14977.
45. Brizard, A.; Aime, C.; Labrot, T.; Huc, I.; Berthier, D.; Artzner, F.; Desbat, B.; Oda, R. Counterion, Temperature, and Time Modulation of Nanometric Chiral Ribbons from Gemini-Tartrate Amphiphiles. J. Am. Chem. Soc. 2007, 129, 3754-3762.
46. Oda, R.; Huc, I.; Schmutz, M.; Candau, S. J.; MacKintosh, F. C. Tuning Bilayer Twist Using Chiral Counterions. Nature 1999, 399, 566-569.
47. Zhu, X. F.; Li, Y. G.; Duan, P. F.; Liu, M. H. Self-Assembled Ultralong Chiral Nanotubes and Tuning of Their Chirality Through the Mixing of Enantiomeric Components. Chem.-Eur. J. 2010, 16, 8034-8040.
48. Jang, D.; Lee, H. Y.; Park, M.; Nam, S. R.; Hong, J.-I. Nano- and Microstructure Fabrication by Using a Three-Component System. Chem.-Eur. J. 2010, 16, 4836-4842.
49. He, Y.; Bian, Z.; Kang, C.; Gao, L. Self-Discriminating and Hierarchical Assembly of Racemic Binaphthyl-Bisbipyridines and Silver Ions: From Metallocycles to Gel Nanofibers. Chem. Commun. 2011, 47, 1589-1591.
50. Shen, Z. C.; Wang, T. Y.; Liu, M. H. H-Bond and π-π Stacking Directed Self-Assembly of Two-Component Supramolecular Nanotubes: Tuning Length, Diameter and Wall Thickness. Chem. Commun. 2014, 50, 2096-2099.
51. Saha, A.; Manna, S.; Nandi, A. K. Hierarchical Tuning of 1-D Macro Morphology by Changing the Composition of a Binary Hydrogel and Its Influence on the Photoluminescence Property. Chem. Commun. 2008, 3732-3734.
52. Zhang, X.-L.; Ye, B.-H.; Chen, X.-M. Infinite Water Chains Trapped in an Organic Framework Constructed from Melamine with 1,5-Naphthalenedisulfonic Acid via Hydrogen Bonds. Cryst. Growth Des. 2005, 5, 1609-1616.
53. Neumann, V.; Gericke, A.; Huehnerfuss, H. Comparison of Enantiomeric and Racemic Monolayers of 2-Hydroxyhexadecanoic Acid by External Infrared Reflection-Absorption Spectroscopy. Langmuir 1995, 11, 2206-2212.
54. Masuda, M.; Vill, V.; Shimizu, T. Conformational and Thermal Phase Behavior of Oligomethylene Chains Constrained by Carbohydrate Hydrogen-Bond Networks. J. Am. Chem. Soc. 2000, 122, 12327-12333.
55. Doan, V.; Köppe, R.; Kasai, P. H. Dimerization of Carboxylic Acids and Salts: An IR Study in Perfluoropolyether Media. J. Am. Chem. Soc. 1997, 119, 9810-9815.
56. Sukul, P. K.; Asthana, D.; Mukhopadhyay, P.; Summa, D.; Muccioli, L.; Zannoni, C.; Beljonne, D.; Rowan, A. E.; Malik, S. Assemblies of Perylene Diimide Derivatives with Melamine into Luminescent Hydrogels. Chem. Commun. 2011, 47, 11858-11860.
57. Roy, B.; Bairi, P.; Saha, A.; Nandi, A. K. Variation of Physical and Mechanical Properties in the Bicomponent Hydrogels of Melamine with Positional Isomers of Hydroxybenzoic Acid. Soft Matter 2011, 7, 8067-8076.
58. Bairi, P.; Roy, B.; Chakraborty, P.; Nandi, A. K. Co-assembled White-Light-Emitting Hydrogel of Melamine. ACS Appl. Mater. Interfaces 2013, 5, 5478-5485.
59. 4 and Anionic AzoNa. Chem.-Eur. J. 2013, 19, 8253-8260.
60. Cheng, G.; Castelletto, V.; Moulton, C. M.; Newby, G. E.; Hamley, I. W. Hydrogelation and Self-Assembly of Fmoc-Tripeptides: Unexpected Influence of Sequence on Self-Assembled Fibril Structure, and Hydrogel Modulus and Anisotropy. Langmuir 2010, 26, 4990-4998.