Supramolecular Chemistry of Fullerene-Containing Micelles and Gels

Supramolecular Chemistry of Fullerenes and Carbon Nanotubes

Volumn , Issue , 2012, Pages 159-172

  Li, Hongguang ^a   Santhosh Babu, Sukumaran ^a,b   Nakanishi, Takashi ^b  

^a MAX PLANCK INSTITUTE OF COLLOIDS AND INTERFACES   (Germany)

^b NATIONAL INSTITUTE FOR MATERIALS SCIENCE   (Japan)

Author keywords

interaction; Aggregation behavior; C60 derivatives; Hydrophilic part; Hydrophobic part; Organogelation; Supramolecular assemblies

Indexed keywords

EID: 84886109117     PISSN: None     EISSN: None     Source Type: Book    
DOI: 10.1002/9783527650125.ch7     Document Type: Chapter

References (51)

1. Nakamura, E. and Isobe, H. (2003) Functionalized fullerenes in water. The first 10 years of their chemistry, biology, and nanoscience. Acc. Chem. Res., 36, 807-815.
2. Friedman, S.H., DeCamp, D.L., Sijbesma, R.P., Srdanov, G., Wudl, F., and Kenyon, G.L. (1993) Inhibition of the HIV-1 protease by fullerene derivatives: model building studies and experimental verification. J. Am. Chem. Soc., 115, 6506-6509.
3. Tokuyama, H., Yamago, S., Nakamura, E., Shiraki, T., and Sugiura, Y. (1993) Photoinduced biochemical activity of fullerene carboxylic acid. J. Am. Chem. Soc., 115, 7918-7919.
4. Ros, T.D. and Prato, M. (1999) Medicinal chemistry with fullerenes and fullerene derivatives. Chem. Commun., 663-669.
5. 60 fullerene derivatives. Acc. Chem. Res., 33, 695-703.
6. Israelachvili, J. (1991) Intermolecular and Surface Forces, Academic Press, London.
7. 5 and poly (ethylene oxide) investigated by dynamic light scattering and fluorescence methods. Macromolecules, 29, 6837-6846.
8. Panmai, S., Prud'homme, R.K., Peiffer, D.G., Jockusch, S., and Turro, N.J. (2002) Interactions between hydrophobically modified polymers and surfactants: a fluorescence study. Langmuir, 18, 3860-3864.
9. 60 in model biological systems: a visible-UV absorption study of solventdependent parameters and solute aggregation. J. Phys. Chem., 98, 3492-3500.
10. 60 in aqueous micellar solution. Chem. Commun., 173-175.
11. Yamakoshi, Y.N., Yagami, T., Fukuhara, K., Sueyoshi, S., and Miyata, N. (1994) Solubilization of fullerenes into water with polyvinylpyrrolidone applicable to biological tests. Chem. Commun., 517-518.
12. 60-micellar solutions. Chem. Phys. Lett., 245, 571-577.
13. 60 fullerene with cholesteryl group-bearing pullulan in aqueous medium. Chem. Lett., 64-65.
14. 60 solubilized. J. Phys. Chem. B, 111, 7719-7724.
15. 60 into artificial lipid membranes. J. Am. Chem. Soc., 115, 3386-3387.
16. 60 in water. J. Phys. Chem. B, 110, 68-74.
17. Ikeda, A., Sato, T., Kitamura, K., Nishiguchi, K., Sasaki, Y., Kikuchi, J., Ogawa, T., Yogo, K., and Takeya, T. (2005) Efficient photocleavage of DNA utilising water-soluble lipid membraneincorporated [60]fullerenes prepared using a [60]fullerene exchange method. Org. Biomol. Chem., 3, 2907-2909.
18. Ikeda, A., Doi, Y., Hashizume, M., Kikuchi, J., and Konish, T. (2007) An extremely effective DNA photocleavage utilizing functionalized liposomes with a fullerene-enriched lipid bilayer. J. Am. Chem. Soc., 129, 4140-4141.
19. Jenekhe, S.A. and Chen, X.L. (1998) Self-assembled aggregates of rod-coil block copolymers and their solubilization and encapsulation of fullerenes. Science, 279, 1903-1907.
20. Guldi, D.M., Zerbetto, F., Georgakilas, V., and Prato, M. (2005) Ordering fullerene materials at nanometer dimensions. Acc. Chem. Res., 38, 38-43.
21. 60- azobenzene derivative. Langmuir, 15, 2224-2226.
22. Sano, M., Oishi, K., Ishi-i, T., and Shinkai, S. (2000) Vesicle formation and its fractal distribution by bolaamphiphilic [60]fullerene. Langmuir, 16, 3773-3776.
23. Brettreich, M. and Hirsch, A. (1998) A highly water-soluble dendro[60] fullerene.Tetrahedron Lett., 39, 2731-2734.
24. Quaranta, A., McGarvey, D.J., Land, E.J., Brettreich, M., Burghardt, S., Schönberger, H., Hirsch, A., Gharbi, N., Moussa, F., Leach, S., Göttingere, H., and Bensasson, R.V. (2003) Photophysical properties of a dendritic methano[60] fullerene octadeca acid and its tert-butyl ester: evidence for aggregation of the acid form in water. Phys. Chem. Chem. Phys., 5, 843-848.
25. 60. Angew. Chem. Int. Ed., 39, 1845-1848.
26. 60. Chem. Commun., 602-603.
27. Zhou, S., Burger, C., Chu, B., Sawamura, M., Nagahama, N., Toganoh, M., Hackler, U.E., Isobe, H., and Nakamura, E. (2001) Spherical bilayer vesicles of fullerene-based surfactants in water: a laser light scattering study. Science, 291, 1944-1947.
28. 5K. J. Colloid Interface Sci., 275, 632-641.
29. 60 derivative: nanorods and vesicles. Angew. Chem. Int. Ed., 38, 2403-2405.
30. 8. Angew. Chem. Int. Ed., 49, 5293-5295.
31. 60-end-capped poly(ethylene oxide)s. Langmuir, 19, 4798-4803.
32. 60 conjugate vesicles in aqueous solution. Langmuir, 21, 3267-3272.
33. Oishi, K., Ishi-i, T., Sano, M., and Shinkai, S. (1999) Unexpected discovery of a novel organic gel system comprised of [60]fullerene containing amphiphiles. Chem. Lett., 28, 1089-1090.
34. Ishi-i, T., Ono, Y., and Shinkai, S. (2000) Chirally-ordered fullerene assemblies found in organic gel systems of cholesterol-appended [60]fullerenes. Chem. Lett., 808-809.
35. Tsunashima, R., Noro, S.-i., Akutagawa, T., Nakamura, T., Kawakami, H., and Toma, K. (2008) Fullerene nanowires: self-assembled structures of a low-molecular-weight organogelator fabricated by the Langmuir-Blodgett method. Chem. Eur. J., 14, 8169-8176.
36. Watanabe, N., Jintoku, H., Sagawa, T., Takafuji, M., Sawada, T., and Ihara, H. (2009) Self-assembling fullerene derivatives for energy transfer in molecular gel system. J. Phys. Conf. Ser., 159, 012016.
37. Ishi-i, T., Jung, J.H., and Shinkai, S. (2000) Intermolecular porphyrin-fullerene interaction can reinforce the organogel structure of a porphyrin-appended cholesterol derivative. J. Mater. Chem., 10, 2238-2240.
38. 2)n spacer on the organogel stability. Langmuir, 17, 5825-5833.
39. Shirakawa, M., Fujita, N., and Shinkai, S. (2003) [60]Fullerene-motivated organogel formation in a porphyrin derivative bearing programmed hydrogen-bonding sites. J. Am. Chem. Soc., 125, 9902-9903.
40. Shirakawa, M., Fujita, N., Shimakoshi, H., Hisaeda, Y., and Shinkai, S. (2006) Molecular programming of organogelators which can accept [60] fullerene by encapsulation. Tetrahedron, 62, 2016-2024.
41. Xue, P., Lu, R., Zhao, L., Xu, D., Zhang, X., Li, K., Song, Z., Yang, X., Takafuji, M., and Ihara, H. (2010) Hybrid self-assembly of a π gelator and fullerene derivative with photoinduced electron transfer for photocurrent generation. Langmuir, 26, 6669-6675.
42. Yang, X., Zhang, G., Zhang, D., and Zhu, D. (2010) A new ex-TTF-based organogelator: formation of organogels and tuning with fullerene. Langmuir, 26, 11720-11725.
43. Huang, W.Y., Huang, P.T., Han, Y.K., Lee, C.C., Hsieh, T.L., and Chang, M.Y. (2008) Aggregation and gelation effects on the performance of poly(3-hexylthiophene)/fullerene solar cells. Macromolecules, 41, 7485-7489.
44. Koppe, M., Brabec, C.J., Heiml, S., Schausberger, A., Duffy, W., Heeney, M., and McCulloch, I. (2009) Influence of molecular weight distribution on the gelation of P3HT and its impact on the photovoltaic performance. Macromolecules, 42, 4661-4666.
45. Inokuma, Y., Arai, T., and Fujita, M. (2010) Networked molecular cages as crystalline sponges for fullerenes and other guests. Nature Chem., 2, 780-783.
46. Nakanishi, T. (2010) Supramolecular soft and hard materials based on self-assembly algorithms of alkyl-conjugated fullerenes. Chem. Commun., 3425-3436.
47. Babu, S.S., Möhwald, H., and Nakanishi, T. (2010) Recent progress in morphology control of supramolecular fullerene assemblies and its applications. Chem. Soc. Rev., 39, 4021-4035.
48. Nakanishi, T., Schmitt, W., Michinobu, T., Kurth, D.G., and Ariga, K. (2005) Hierarchical supramolecular fullerene architectures with controlled dimensionality. Chem. Commun., 5982-5984.
49. Nakanishi, T., Michinobu, T., Yoshida, K., Shirahata, N., Ariga, K., Möhwald, H., and Kurth, D.G. (2008) Nanocarbon superhydrophobic surfaces created from fullerene-based hierarchical supramolecular assemblies. Adv. Mater., 20, 443-446.
50. Shen, Y., Wang, J., Kuhlmann, U., Hildebrandt, P., Ariga, K., Möhwald, H., Kurth, D.G., and Nakanishi, T. (2009) Supramolecular templates for nanoflake-metal surfaces. Chem. Eur. J., 15, 2763-2767.
51. Shen, Y., Skirtach, A.G., Seki, T., Yagai, S., Li, H., Möhwald, H., and Nakanishi, T. (2010) Assembly of fullerene-carbon nanotubes: temperature indicator for photothermal conversion. J. Am. Chem. Soc., 132, 8566-8568.