Bolaamphiphiles bearing bipyridine as mesogenic core: Rational exploitation of molecular architectures for controlled self-assembly

Langmuir

Volumn 28, Issue 11, 2012, Pages 5023-5030

  Wu, Guanglu ^a   Verwilst, Peter ^b   Xu, Jun ^a   Xu, Huaping ^a   Wang, Ruji ^a   Smet, Mario ^b   Dehaen, Wim ^b   Faul, Charl F J ^c   Wang, Zhiqiang ^a   Zhang, Xi ^a  

^a TSINGHUA UNIVERSITY   (China)

^b UNIVERSITY OF LEUVEN   (Belgium)

^c UNIVERSITY OF BRISTOL   (United Kingdom)

Author keywords

[No Author keywords available]

Indexed keywords

ALKYL CHAIN; BIPYRIDINES; BOLAAMPHIPHILES; COLLOIDAL AGGREGATES; CONTROLLED SELF-ASSEMBLY; FIBROUS STRUCTURES; MESOGENIC CORES; MOLECULAR ARCHITECTURE; SELF-ASSEMBLE; STRUCTURAL DIFFERENCES;

CONDENSED MATTER PHYSICS; ELECTROCHEMISTRY;

CHAIN LENGTH;

EID: 84863379540     PISSN: 07437463     EISSN: 15205827     Source Type: Journal    
DOI: 10.1021/la300369w     Document Type: Article

References (52)

1. Ringsdorf, H.; Schlarb, B.; Venzmer., J. Molecular Architecture and Function of Polymeric Oriented Systems: Models for the Study of Organization, Surface Recognition, and Dynamics of Biomembranes Angew. Chem., Int. Ed. 1988, 27, 113
2. Whitesides, G. M.; Mathias, J. P.; Seto, C. T. Molecular Self-Assembly and Nanochemistry: A Chemical Strategy for the Synthesis of Nanostructures Science 1991, 254, 1312
3. Hartgerink, J. D.; Beniash, E.; Stupp, S. I. Self-Assembly and Mineralization of Peptide-Amphiphile Nanofibers Science 2001, 294, 1684
4. Faul, C. F. J.; Antonietti, M. Ionic Self-Assembly: Facile Synthesis of Supramolecular Materials Adv. Mater. 2003, 15, 673
5. Hill, J. P.; Jin, W. S.; Kosaka, A.; Fukushima, T.; Ichihara, H.; Shimomura, T.; Ito, K.; Hashizume, T.; Ishii, N.; Aida, T. Self-Assembled Hexa-peri-hexabenzocoronene Graphitic Nanotube Science 2004, 304, 1481
6. Shimizu, T.; Masuda, M.; Minamikawa, H. Supramolecular Nanotube Architectures Based on Amphiphilic Molecules Chem. Rev. 2005, 105, 1401
7. Lee, E.; Kim, J. K.; Lee, M. Reversible Scrolling of Two-Dimensional Sheets from the Self-Assembly of Laterally Grafted Amphiphilic Rods Angew. Chem., Int. Ed. 2009, 48, 3657
8. Yan, Y.; Lin, Y. Y.; Qiao, Y.; Huang, J. B. Construction and Application of Tunable One-dimensional Soft Supramolecular Assemblies Soft Matter 2011, 7, 6385
9. Kunitake, T.; Okahata, Y.; Shimomura, M.; Yasunami, S.; Takarabe, K. Formation of Stable Bilayer Assemblies in Water from Single-Chain Amphiphiles. Relationship Between the Amphiphile Structure and the Aggregate Morphology J. Am. Chem. Soc. 1981, 103, 5401
10. Duivenvoorde, F. L.; Feiters, M. C.; van der Gaast, S. J.; Engberts, J. B. F. N. Synthesis and Properties of Di-n-dodecyl α,ω-Alkyl Bisphosphate Surfactants Langmuir 1997, 13, 3737
11. Oda, R.; Huc, I.; Schmutz, M.; Candau, S. J.; MacKintosh, F. C. Tuning Bilayer Twist Using Chiral Counterions Nature 1999, 399, 566
12. Brizard, A.; Aimé, 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
13. Israelachvili, J. N. Intermolecular and Surface Forces; Academic Press: Boston, 1992.
14. Gulik, A.; Luzzati, V.; De Rosa, M.; Gambacorta, A. Structure and Polymorphism of Bipolar Isopranyl Ether Lipids from Archaebacteria J. Mol. Biol. 1985, 182, 131
15. Fuoss, R. M.; Edelson, D. Bolaform Electrolytes. I. Di-(β- trimethylammonium Ethyl) Succinate Dibromide and Related Compounds J. Am. Chem. Soc. 1951, 73, 269
16. Menger, F. M.; Wrenn, S. Interfacial and Micellar Properties of Bolaform Electrolytes J. Phys. Chem. 1974, 78, 1387
17. Yiv, S.; Kale, K. M.; Lang, J.; Zana, R. Chemical Relaxation and Equilibrium Studies of Association in Aqueous Solutions of Bolaform Detergents. 1. Dodecane-1,12-Bis(trimethylammonium Bromide) J. Phys. Chem. 1976, 80, 2651
18. Fuhrhop, J. H.; David, H. H.; Mathieu, J.; Liman, U.; Winter, H. J.; Boekema, E. Bolaamphiphiles and Monolayer Lipid Membranes Made from 1,6,19,24-Tetraoxa-3,21-Cyclohexatriacontadiene-2,5,20,23-Tetrone J. Am. Chem. Soc. 1986, 108, 1785
19. Fuhrhop, J. H.; Fritsch, D. Bolaamphiphiles Form Ultrathin, Porous and Unsymmetric Monolayer Lipid Membranes Acc. Chem. Res. 1986, 19, 130
20. Nagarajan, R. Self-Assembly of Bola Amphiphiles Chem. Eng. Commun. 1987, 55, 251
21. Fuhrhop, J. H.; Wang, T. Y. Bolaamphiphiles Chem. Rev. 2004, 104, 2901
22. Benvegnu, T.; Brard, M.; Plusquellec, D. Archaeabacteria Bipolar Lipid Analogues: Structure, Synthesis and Lyotropic Properties Curr. Opin. Colloid Interface Sci. 2004, 8, 469
23. Meister, A.; Blume, A. Self-Assembly of Bipolar Amphiphiles Curr. Opin. Colloid Interface Sci. 2007, 12, 138
24. Okahata, Y.; Kunitake, T. Formation of Stable Monolayer Membranes and Related Structures in Dilute Aqueous Solution from Two-Headed Ammonium Amphiphiles J. Am. Chem. Soc. 1979, 101, 5231
25. Wang, X. F.; Shen, Y. Z.; Pan, Y.; Liang, Y. Q. Bolaamphiphilic Single-Chain Bis-Schiff Base Derivatives: Aggregation and Thermal Behavior in Aqueous Solution Langmuir 2001, 17, 3162
26. Masuda, M.; Shimizu, T. Lipid Nanotubes and Microtubes: Experimental Evidence for Unsymmetrical Monolayer Membrane Formation from Unsymmetrical Bolaamphiphiles Langmuir 2004, 20, 5969
27. Song, B.; Wang, Z. Q.; Chen, S. L.; Zhang, X.; Fu, Y.; Smet, M.; Dehaen, W. The Introduction of π-π Stacking Moieties for Fabricating Stable Micellar Structure: Formation and Dynamics of Disklike Micelles Angew. Chem., Int. Ed. 2005, 44, 4731
28. Gao, P.; Liu, M. H. Compression Induced Helical Nanotubes in a Spreading Film of a Bolaamphiphile at the Air/Water Interface Langmuir 2006, 22, 6727
29. Prehm, M.; Liu, F.; Zeng, X. B.; Ungar, G.; Tschierske, C. 2D and 3D Ordered Columnar Liquid Crystal Phases by Bundles of Bolaamphiphiles with Swallow-Tail Side Chains J. Am. Chem. Soc. 2008, 130, 14922
30. Xiao, F. P.; Misdrahi, M. F.; Zhang, J.; Yin, P. C.; Hao, J.; Lv, C. L.; Xiao, Z. C.; Liu, T. B.; Wei, Y. G. Buildup of Amphiphilic Molecular Bola from Organic-Inorganic Hybrid Polyoxometalates and Their Vesicle-Like Supramolecular Assembly Chem.-Eur. J. 2011, 17, 12006
31. Köhler, K.; Förster, G.; Hauser, A.; Dobner, B.; Heiser, U. F.; Ziethe, F.; Richter, W.; Steiniger, F.; Drechsler, M. Stettin, H.; Blume, A. Self-Assembly in a Bipolar Phosphocholine-Water System: The Formation of Nanofibers and Hydrogels Angew. Chem., Int. Ed. 2004, 43, 245
32. Ray, S.; Das, A. K.; Banerjee, A. pH-Responsive, Bolaamphiphile-Based Smart Metallo-Hydrogels as Potential Dye-Adsorbing Agents, Water Purifier, and Vitamin B12 Carrier Chem. Mater. 2007, 19, 1633
33. Englert, J. M.; Röhrl, J.; Schmidt, C. D.; Graupner, R.; Hundhausen, M.; Hauke, F.; Hirsch, A. Soluble Graphene: Generation of Aqueous Graphene Solutions Aided by a Perylenebisimide-Based Bolaamphiphile Adv. Mater. 2009, 21, 4265
34. Shao, H.; Seifert, J.; Romano, N. C.; Gao, M.; Helmus, J. J.; Jaroniec, C. P.; Modarelli, D. A.; Parquette, J. R. Amphiphilic Self-Assembly of an n-Type Nanotube Angew. Chem., Int. Ed. 2010, 49, 7688
35. Wang, T. Y.; Jiang, J.; Liu, Y.; Li, Z. B.; Liu, M. H. Hierarchical Self-Assembly of Bolaamphiphiles with a Hybrid Spacer and l-Glutamic Acid Headgroup: pH- and Surface-Triggered Hydrogels, Vesicles, Nanofibers, and Nanotubes Langmuir 2010, 26, 18694
36. Voronin, M. A.; Gabdrakhmanov, D. R.; Semenov, V. E.; Valeeva, F. G.; Mikhailov, A. S.; Nizameev, I. R.; Kadirov, M. K.; Zakharova, L. Y.; Reznik, V. S.; Konovalov, A. I. Novel Bolaamphiphilic Pyrimidinophane as Building Block for Design of Nanosized Supramolecular Systems with Concentration-Dependent Structural Behavior ACS Appl. Mater. Interfaces 2011, 3, 402
37. Wang, C.; Yin, S. C.; Chen, S. L.; Xu, H. P.; Wang, Z. Q.; Zhang, X. Controlled Self-Assembly Manipulated by Charge-Transfer Interactions: From Tubes to Vesicles Angew. Chem., Int. Ed. 2008, 47, 9049
38. Liu, K.; Wang, C.; Li, Z. B.; Zhang, X. Superamphiphiles Based on Directional Charge-Transfer Interactions: From Supramolecular Engineering to Well-Defined Nanostructures Angew. Chem., Int. Ed. 2011, 50, 4952
39. Zhang, X.; Wang, C. Supramolecular amphiphiles Chem. Soc. Rev. 2011, 40, 94
40. Wang, C.; Wang, Z. Q.; Zhang, X. Superamphiphiles as Building Blocks for Supramolecular Engineering: Towards Functional Materials and Surfaces Small 2011, 7, 1379
41. Shimizu, T.; Masuda, M. Stereochemical Effect of Even-Odd Connecting Links on Supramolecular Assemblies Made of 1-Glucosamide Bolaamphiphiles J. Am. Chem. Soc. 1997, 119, 2812
42. Meister, A.; Bastrop, M.; Koschoreck, S.; Garamus, V. M.; Sinemus, T.; Hempel, G.; Drescher, S.; Dobner, B.; Richtering, W.; Huber, K.; Blume, A. Structure-Property Relationship in Stimulus-Responsive Bolaamphiphile Hydrogels Langmuir 2007, 23, 7715
43. Yan, Y.; Xiong, W.; Li, X. S.; Lu, T.; Huang, J. B.; Li, Z. C.; Fu, H. L. Molecular Packing Parameter in Bolaamphiphile Solutions: Adjustment of Aggregate Morphology by Modifying the Solution Conditions J. Phys. Chem. B 2007, 111, 2225
44. Song, B.; Liu, G. Q.; Xu, R.; Yin, S. C.; Wang, Z. Q.; Zhang, X. Interfacial Self-Organization of Bolaamphiphiles Bearing Mesogenic Groups: Relationships between the Molecular Structures and Their Self-Organized Morphologies Langmuir 2008, 24, 3734
45. Wang, M.; Qiu, D.; Zou, B.; Wu, T.; Zhang, X. Stabilizing Bolaform Amphiphile Interfacial Assemblies by Introducing Mesogenic Groups Chem.-Eur. J. 2003, 9, 1876
46. Gao, S.; Zou, B.; Chi, L. F.; Fuchs, H.; Sun, J. Q.; Zhang, X.; Shen, J. C. Nano-Size Stripes of Self-Assembled Bolaform Amphiphiles Chem. Commun. 2000, 1273
47. Zou, B.; Wang, M. F.; Qiu, D. L.; Zhang, X.; Chi, L. F.; Fuchs, H. Confined Supramolecular Nanostructures of Mesogen-Bearing Amphiphiles Chem. Commun. 2002, 1008
48. Yin, S. C.; Song, B.; Liu, G. Q.; Wang, Z. Q.; Zhang, X. Self-Organization of Polymerizable Bolaamphiphiles Bearing Diacetylene Mesogenic Group Langmuir 2007, 23, 5936
49. Job, P. Studies on the Formation of Complex Minerals in Solution and on Their Stability Ann. Chim. Ser. 1928, 9, 113
50. Conners, K. A. Binding Constants: The Measurement of Molecular Complex Stability; Wiley: New York, 1987.
51. Willett, R. D.; Pon, G.; Nagy, C. Crystal Chemistry of the 4,4′-Dimethyl-2,2′bipyridine/Copper Bromide System Inorg. Chem. 2001, 40, 4342
52. Martell, A. E.; Smith, R. M. Critical Stability Constants; Plenum Press: New York, 1974; Vol. 1, pp 204-211.