Advanced molecular self-assemblies facilitated by simple molecules

Langmuir

Volumn 30, Issue 48, 2014, Pages 14375-14384

  Wu, Zheng ^a   Yan, Yun ^a   Huang, Jianbin ^a  

^a PEKING UNIVERSITY   (China)

Author keywords

[No Author keywords available]

Indexed keywords

MOLECULES; SELF ASSEMBLY;

ADVANCED MATERIALS; AMPHIPHILIC SYSTEMS; CHEMICAL EQUATIONS; EXTERNAL STIMULUS; FUNCTIONAL MOLECULES; HIERARCHICAL STRUCTURES; MOLECULAR SELF-ASSEMBLIES; SUPRAMOLECULAR ARCHITECTURES;

SYNTHESIS (CHEMICAL);

EID: 84915758135     PISSN: 07437463     EISSN: 15205827     Source Type: Journal    
DOI: 10.1021/la501361f     Document Type: Article

References (70)

1. van de Manakker, F.; van der Pot, M.; Vermonden, T.; van Nostrum, C. F.; Hennink, W. E. Self-assembling Hydrogels Based on Beta-cyclodextrin/cholesterol Inclusion Complexes. Macromolecules 2008, 41, 1766-1773.
2. Wang, Y.; Ma, N.; Wang, Z.; Zhang, X. Photocontrolled Reversible Supramolecular Assemblies of an Azobenzene-containing Surfactant with Alpha-cyclodextrin. Angew. Chem., Int. Ed. 2007, 46, 2823-2826.
3. Alarcon, C. D. H.; Pennadam, S.; Alexander, C. Stimuli Responsive Polymers for Biomedical Applications. Chem. Soc. Rev. 2005, 34, 276-285.
4. Whitesides, G. M.; Grzybowski, B. Self-assembly at All Scales. Science 2002, 295, 2418-2421.
5. Ku, T.-H.; Chien, M.-P.; Thompson, M. P.; Sinkovits, R. S.; Olson, N. H.; Baker, T. S.; Gianneschi, N. C. Controlling and Switching the Morphology of Micellar Nanoparticles with Enzymes. J. Am. Chem. Soc. 2011, 133, 8392-8395.
6. Lehn, J. M. Toward Complex Matter: Supramolecular Chemistry and Self-organization. Proc. Natl. Acad. Sci. U.S.A. 2002, 99, 4763-4768.
7. Nayak, S.; Lyon, L. A. Soft Nanotechnology with Soft Nanoparticles. Angew. Chem., Int. Ed. 2005, 44, 7686-7708.
8. Svenson, S. Controlling Surfactant Self-assembly. Curr. Opin. Colloid Interface Sci. 2004, 9, 201-212.
9. Wu, L.; Lal, J.; Simon, K. A.; Burton, E. A.; Luk, Y.-Y. Nonamphiphilic Assembly in Water: Polymorphic Nature, Thread Structure, and Thermodynamic Incompatibility. J. Am. Chem. Soc. 2009, 131, 7430-7443.
10. Guo, J.; Zhuang, J. M.; Wang, F.; Raghupathi, K. R.; Thayumanavan, S. Protein And Enzyme Gated Supramolecular Disassembly. J. Am. Chem. Soc. 2014, 136, 2220-2223.
11. Guo, D. S.; Wang, K.; Wang, Y. X.; Liu, Y. Cholinesterase-Responsive Supramolecular Vesicle. J. Am. Chem. Soc. 2012, 134, 10244-10250.
12. Ahn, S.-K.; Kasi, R. M.; Kim, S.-C.; Sharma, N.; Zhou, Y. Stimuli-responsive Polymer Gels. Soft Matter 2008, 4, 1151-1157.
13. Morimoto, N.; Ogino, N.; Narita, T.; Kitamura, S.; Akiyoshi, K. Enzyme-responsive Molecular Assembly System with Amylose-primer Surfactants. J. Am. Chem. Soc. 2007, 129, 458-459.
14. Mart, R. J.; Osborne, R. D.; Stevens, M. M.; Ulijn, R. V. Peptide-based Stimuli-Responsive Biomaterials. Soft Matter 2006, 2, 822-835.
15. Medina, J. C.; Gay, I.; Chen, Z. H.; Echegoyen, L.; Gokel, G. W. Redox-switched Molecular Aggregates - The 1st Example of Vesicle Formation From Hydrophobic Ferrocene Derivatives. J. Am. Chem. Soc. 1991, 113, 365-366.
16. Reeves, P. J.; Hwa, J.; Khorana, H. G. Structure and Function in Rhodopsin: Kinetic Studies of Retinal Binding to Purified Opsin Mutants in Defined Phospholipid-detergent Mixtures Serve as Probes of the Retinal Binding Pocket. Proc. Natl. Acad. Sci. U.S.A. 1999, 96, 1927-1931.
17. Winnik, F. M.; Whitten, D. G.; Urban, M. W. Stimuli-responsive Materials: Polymers, Colloids, and Multicomponent Systems. Langmuir 2007, 23, 1-2.
18. Tung, S. H.; Huang, Y. E.; Raghavan, S. R. A New Reverse Wormlike Micellar System: Mixtures of Bile Salt and Lecithin in Organic Liquids. J. Am. Chem. Soc. 2006, 128, 5751-5756.
19. Jiang, L.; Wang, K.; Ke, F.; Liang, D.; Huang, J. Endowing Catanionic Surfactant Vesicles With Dual Responsive Abilities via a Noncovalent Strategy: Introduction of a Responser, Sodium Cholate. Soft Matter 2009, 5, 599.
20. Sakai, H.; Matsumura, A.; Yokoyama, S.; Saji, T.; Abe, M. Photochemical Switching of Vesicle Formation Using an Azobenzene-modified Surfactant. J. Phys. Chem. B 1999, 103, 10737-10740.
21. Song, X. D.; Perlstein, J.; Whitten, D. G. Supramolecular Aggregates of Azobenzene Phospholipids and Related Compounds in Bilayer Assemblies and Other Microheterogeneous Media: Structure, Properties, and Photoreactivity. J. Am. Chem. Soc. 1997, 119, 9144-9159.
22. Dugave, C.; Demange, L. cis-trans Isomerization of Organic Molecules and Biomolecules: Implications and Applications. Chem. Rev. 2003, 103, 2475-2532.
23. Ferri, V.; Elbing, M.; Pace, G.; Dickey, M. D.; Zharnikov, M.; Samori, P.; Mayor, M.; Rampi, M. A. Light-powered Electrical Switch Based on Cargo-lifting Azobenzene Monolayers. Angew. Chem., Int. Ed. 2008, 47, 3407-3409.
24. Hayashita, T.; Kurosawa, T.; Miyata, T.; Tanaka, K.; Igawa, M. Effect of Structural Variation Within Cationic Azo-surfactant Upon Photoresponsive Function in Aqueous-solution. Colloid Polym. Sci. 1994, 272, 1611-1619.
25. Ikeda, T.; Tsutsumi, O. Optical Switching and Image Storage by Means of Azobenzene Liquid-crystal Films. Science 1995, 268, 1873-1875.
26. Kumar, G. S.; Neckers, D. C. Photochemistry of Azobenzene-containing Polymers. Chem. Rev. 1989, 89, 1915-1925.
27. Shimizu, T.; Masuda, M.; Minamikawa, H. Supramolecular Nanotube Architectures Based on Amphiphilic Molecules. Chem. Rev. 2005, 105, 1401-1443.
28. Eastoe, J.; Zou, A.; Espidel, Y.; Glatter, O.; Grillo, I. Photo-labile Lamellar Phases. Soft Matter 2008, 4, 1215-1218.
29. Lin, Y.; Cheng, X.; Qiao, Y.; Yu, C.; Li, Z.; Yan, Y.; Huang, J. Creation of Photo-modulated Multi-state and Multi-scale Molecular Assemblies via Binary-state Molecular Switch. Soft Matter 2010, 6, 902-908.
30. Eastoe, J.; Hatzopoulos, M. H.; Dowding, P. J. Action of Hydrotropes and Alkyl-hydrotropes. Soft Matter 2011, 7, 5917-5925.
31. Hodgdon, T. K.; Kaler, E. W. Hydrotropic Solutions. Curr. Opin. Colloid Interface Sci. 2007, 12, 121-128.
32. Abdel-Rahem, R. The Influence of Hydrophobic Counterions on Micellar Growth of Ionic Surfactants. Adv. Colloid Interface Sci. 2008, 141, 24-36.
33. Israelachvili, J. N.; Mitchell, D. J.; Ninham, B. W. Theory of Self-assembly of Hydrocarbon Amphiphiles into Micelles and Bilayers. J. Chem. Soc., Faraday Trans. 2 1976, 72, 1525-1568.
34. Hoffmann, H.; Ulbricht, W. Vesicle Phases of Surfactants and Their Behaviour in Shear Flow. Tenside Surfact. Deterg. 1998, 35, 421-438.
35. Schonfelder, E.; Hoffmann, H. From Vesicle to Micelles. Ber. Bunsen-Ges. Phys. Chem. Chem. Phys. 1994, 98, 842-852.
36. English, R. J.; Raghavan, S. R.; Jenkins, R. D.; Khan, S. A. Associative Polymers Bearing n-alkyl Hydrophobes: Rheological Evidence for Microgel-like Behavior. J. Rheol. 1999, 43, 1175-1194.
37. Lin, Y.; Han, X.; Huang, J.; Fu, H.; Yu, C. A Facile Route to Design pH-responsive Viscoelastic Wormlike Micelles: Smart Use of Hydrotropes. J. Colloid Interface Sci. 2009, 330, 449-455.
38. Dorrego, A. B.; Garcia-Rio, L.; Herves, P.; Leis, J. R.; Mejuto, J. C.; Perez-Juste, J. Micellization Versus Cyclodextrin-surfactant Complexation. Angew. Chem., Int. Ed. 2000, 39, 2945-2948.
39. Mao, M.; Huang, J. B.; Zhu, B. Y.; Ye, J. P. The Transition from Vesicles to Micelles Induced by Octane in Aqueous Surfactant Two-phase Systems. J. Phys. Chem. B 2002, 106, 219-225.
40. Renoncourt, A.; Vlachy, N.; Bauduin, P.; Drechsler, M.; Touraud, D.; Verbavatz, J. M.; Dubois, M.; Kunz, W.; Ninham, B. W. Specific Alkali Cation Effects in the Transition From Micelles to Vesicles Through Salt Addition. Langmuir 2007, 23, 2376-2381.
41. Lin, Y.; Qiao, Y.; Cheng, X.; Yan, Y.; Li, Z.; Huang, J. Hydrotropic Salt Promotes Anionic Surfactant Self-assembly into Vesicles and Ultralong Fibers. J. Colloid Interface Sci. 2012, 369, 238-244.
42. Akiyoshi, K.; Sasaki, Y.; Kuroda, K.; Sunamoto, J. Controlled Association of Hydrophobized Polysaccharide by Cyclodextrin. Chem. Lett. 1998, 93-94.
43. Akiyoshi, K.; Ueminami, A.; Kurumada, S.; Nomura, Y. Self-association of Cholesteryl-bearing Poly(L-lysine) in Water and Control of Its Secondary Structure by Host-guest Interaction with Cyclodextrin. Macromolecules 2000, 33, 6752-6756.
44. De Lisi, R.; Lazzara, G.; Milioto, S.; Muratore, N. Characterization of the Cyclodextrin-surfactant Interactions by Volume and Enthalpy. J. Phys. Chem. B 2003, 107, 13150-13157.
45. Saenger, W. R.; Jacob, J.; Gessler, K.; Steiner, T.; Hoffmann, D.; Sanbe, H.; Koizumi, K.; Smith, S. M.; Takaha, T. Structures of the Common Cyclodextrins and Their Larger Analogues - Beyond the doughnut. Chem. Rev. 1998, 98, 1787-1802.
46. van de Manakker, F.; Kroon-Batenburg, L. M. J.; Vermonden, T.; van Nostrum, C. F.; Hennink, W. E. Supramolecular Hydrogels Formed by Beta-cyclodextrin Self-association and Host-guest Inclusion Complexes. Soft Matter 2010, 6, 187-194.
47. Carlstedt, J.; Gonzalez-Perez, A.; Alatorre-Meda, M.; Dias, R. S.; Lindman, B. Release of DNA From Surfactant Complexes Induced by 2-hydroxypropyl-beta-cyclodextrin. Int. J. Biol. Macromol. 2010, 46, 153-158.
48. Jiang, L. X.; Yan, Y.; Huang, J. B.; Yu, C. F.; Jin, C. W.; Deng, M. L.; Wang, Y. L. Selectivity and Stoichiometry Boosting of beta-Cyclodextrin in Cationic/Anionic Surfactant Systems: When Host- Guest Equilibrium Meets Biased Aggregation Equilibrium. J. Phys. Chem. B 2010, 114, 2165-2174.
49. Jiang, L. X.; Deng, M. L.; Wang, Y. L.; Liang, D. H.; Yan, Y.; Huang, J. B. Special Effect of beta-Cyclodextrin on the Aggregation Behavior of Mixed Cationic/Anionic Surfactant Systems. J. Phys. Chem. B 2009, 113, 7498-7504.
50. Signorell, G. A.; Kaufmann, T. C.; Kukulski, W.; Engel, A.; Remigy, H. W. Controlled 2D Crystallization of Membrane Proteins Using Methyl-beta-cyclodextrin. J. Struct. Biol. 2007, 157, 321-328.
51. DeGrip, W. J.; VanOostrum, J.; Bovee-Geurts, P. H. M. Selective Detergent-extraction From Mixed Detergent/lipid/protein Micelles, Using Cyclodextrin Inclusion Compounds: a Novel Generic Approach for the Preparation of Proteoliposomes. Biochem. J. 1998, 330, 667-674.
52. Amir, R. J.; Zhong, S.; Pochan, D. J.; Hawker, C. J. Enzymatically Triggered Self-Assembly of Block Copolymers. J. Am. Chem. Soc. 2009, 131, 13949-13951.
53. Azagarsamy, M. A.; Sokkalingam, P.; Thayumanavan, S. Enzyme-Triggered Disassembly of Dendrimer-Based Amphiphilic Nanocontainers. J. Am. Chem. Soc. 2009, 131, 14184-14185.
54. Park, C.; Kim, H.; Kim, S.; Kim, C. Enzyme Responsive Nanocontainers with Cyclodextrin Gatekeepers and Synergistic Effects in Release of Guests. J. Am. Chem. Soc. 2009, 131, 16614-16615.
55. Ulijn, R. V. Enzyme-responsive Materials: a New Class of Smart Biomaterials. J. Mater. Chem. 2006, 16, 2217-2225.
56. Wang, C.; Chen, Q.; Wang, Z.; Zhang, X. An Enzyme-Responsive Polymeric Superamphiphile. Angew. Chem., Int. Ed. 2010, 49, 8612-8615.
57. Jiang, L.; Yan, Y.; Drechsler, M.; Huang, J. Enzyme-triggered Model Self-assembly in Surfactant- cyclodextrin Systems. Chem. Commun. 2012, 48, 7347-7349.
58. Zhao, L.; Cheng, X.; Ding, Y.; Yan, Y.; Huang, J. A Surfactant-assisted Unimolecular Platform For Multicolor Emissions. Soft Matter 2012, 8, 10472-10478.
59. Jiang, L.; Peng, Y.; Yan, Y.; Deng, M.; Wang, Y.; Huang, J. Annular Ring" Microtubes Formed by SDS@2β-CD Complexes in Aqueous Solution. Soft Matter 2010, 6, 1731-1736.
60. Jiang, L.; Peng, Y.; Yan, Y.; Huang, J. Aqueous Self-assembly of SDS@2β-CD Complexes: Lamellae and Vesicles. Soft Matter 2011, 7, 1726-1731.
61. Yan, Y.; Jiang, L.; Huang, J. Unveil the Potential Function of CD in Surfactant Systems. Phys. Chem. Chem. Phys. 2011, 13, 9074-9082.
62. Zhou, C.; Cheng, X.; Yan, Y.; Wang, J.; Huang, J. Reversible Transition between SDS@ 2β-CD Microtubes and Vesicles Triggered by Temperature. Langmuir 2014, 30, 3381-3386.
63. Zhou, C.; Cheng, X.; Zhao, Q.; Yan, Y.; Wang, J.; Huang, J. Self-Assembly of Nonionic Surfactant Tween 20@2β-CD Inclusion Complexes in Dilute Solution. Langmuir 2013, 29, 13175-13182.
64. Jiang, L. X.; Wang, K.; Ke, F. Y.; Liang, D. H.; Huang, J. B. Endowing Catanionic Surfactant Vesicles with Dual Responsive Abilities via a Noncovalent Strategy: Introduction of a Responser, Sodium cholate. Soft Matter 2009, 5, 599-606.
65. Lin, S. C.; Blankschtein, D. Role of the Bile Salt Surfactant Sodium Cholate in Enhancing the Aqueous Dispersion Stability of Single-Walled Carbon Nanotubes: A Molecular Dynamics Simulation Study. J. Phys. Chem. B 2010, 114, 15616-15625.
66. Meyuhas, D.; Bor, A.; Pinchuk, I.; Kaplun, A.; Talmon, Y.; Kozlov, M. M.; Lichtenberg, D. Effect of Ionic Strength on the Self-assembly in Mixtures of Phosphatidylcholine and Sodium Cholate. J. Colloid Interface Sci. 1997, 188, 351-362.
67. Qiao, Y.; Lin, Y. Y.; Wang, Y. J.; Yang, Z. Y.; Liu, J.; Zhou, J.; Yan, Y.; Huang, J. B. Metal-Driven Hierarchical Self-Assembled One-Dimensional Nanohelices. Nano Lett. 2009, 9, 4500-4504.
68. Qiao, Y.; Lin, Y.; Zhang, S.; Huang, J. Lanthanide-Containing Photoluminescent Materials: From Hybrid Hydrogel to Inorganic Nanotubes. Chem. - Eur. J. 2011, 17, 5180-5187.
69. Qiao, Y.; Lin, Y. Y.; Yang, Z. Y.; Chen, H. F.; Zhang, S. F.; Yan, Y.; Huang, J. B. Unique Temperature-Dependent Supramolecular Self-Assembly: From Hierarchical 1D Nanostructures to Super Hydrogel. J. Phys. Chem. B 2010, 114, 11725-11730.
70. Qiao, Y.; Wang, Y.; Yang, Z.; Lin, Y.; Huang, J. Self-Templating of Metal-Driven Supramolecular Self-Assembly: A General Approach toward 1D Inorganic Nanotubes. Chem. Mater. 2011, 23, 1182-1187.