Abstract
The UV-Vis spectra, HRTEM and AFM images of cationic fullerene derivative 1 with ammonium head group directly connected to C60 skeleton in tetrahydrofuran (THF)-water (H2O) binary mixtures and in pure H2O were investigated. It was found that the UV-Vis spectra of ammonium 1 in the THF-H2O mixtures with THF% ⩾ 20% were nearly overlapped, while those with THF% < 20% showed broadened and red-shifted peaks, indicating the formation of aggregates. Corresponding to the UV-Vis spectral changes, the solvatochromism of ammonium 1 in THF-H2O mixtures was observed. Ammonium 1 in binary THF-H2O mixtures existing as the monomer state could aggregate upon prolonged standing. Higher temperature and lower concentration speeded up the aggregation process.
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Da Ros, T., Prato, M., Medicinal chemistry with fullerene and fullerene derivatives, Chem. Commun., 1999: 663–669.
Bosi, S., Da Ros, T., Spalluto, G. et al., Fullerene derivatives: an attractive tool for biological applications, Eur. J. Med. Chem., 2003, 38: 913–923.
Nakamura, E., Isobe, H., Functionalized fullerenes in water, The first 10 years of their chemistry, biology, and nanoscience, Acc. Chem. Res., 2003, 36: 807–815.
Cassel, A. M., Asplund, C. L., Tour, J. M., Self-assembling supramolecular nanostructures from a C60 derivative: Nanoroad and Vesicles, Angew. Chem. Int. Ed., 1999, 38: 2403–2405.
Sano, M., Oishi, K., Ishi-i, T. et al., Vesicle formation and its fractal distribution by bola-amphiphilic [60]fullerene, Langmuir, 2000, 16: 3773–3776.
Sawamura, M., Toganoh, M., Kuninobu, Y. et al., Pentaorgano[60]fullerene R5C60-, A water soluble hydrocarbon anion, Chem. Lett., 2000: 1098–1099.
Zhou, S., Burger, C., Chu, B. et al., Spherical bilayer vesicles of fullerene-based surfactants in water: a laser light scattering study, Science, 2001, 291: 1944–1947.
Murakami, H., Shirakusa, M., Sagara, T. et al., Synthesis, aggregate structure and electrochemical properties of a water-soluble fullerene-bearing ammonium amphiphile, Chem. Lett., 1999: 815 –816.
Shi, Z., **, J., Li, Y. et al., C60 based nanoparticles: self-assembly of a novel fullerene derivative, New. J. Chem., 2001, 25: 670–672.
Shi, Z., Li, Y., Wang, S. et al., Formation and properties of the nanoparticles based on salt-derivatived C 60, Solid State Commun., 2001, 120: 269–272.
Nakashima, N., Ishii, T., Shirakusa, M. et al., Molecular bilayer-based superstructures of a fullerene-carrying ammonium amphiphile: structure and electrochemistry, Chem. Eur. J., 2001, 7: 1766–1772.
Oishi, K., Ishi-I, T., Sano, M. et al., Unexpected discovery of novel organic gel system comprised of [60]fullerene-containing amphiphiles, Chem. Lett., 1999: 1089–1090.
Guldi, D. M., Hungerbuhler, H., Asmus, K. D., Unusual redox behavior of a water-soluble malonic acid derivative of C 60 evidence for possible cluster formation, J. Phys. Chem., 1995, 99: 13487–13493.
Guldi, D. M., Hungerbühler, H., Asmus, K. -D., Radiolytic reduction of a water-soluble fullerene cluster, J. Phys. Chem. A, 1997, 101: 1783–1786.
Brettreich, M., Hirsch, A., A highly water-soluble dentro[60]fullerene, Tetrahedron Lett., 1998, 39: 2731–2734.
Lamparth, I., Hirsch, A., Water-soluble malonic acid derivative of C60 with a defined three-dimensional structure, J. Chem. Soc., Chem. Commun., 1994: 1727–1728.
Chiang, Y. L., Bhonsle, J. B., Wang, L. et al., Efficient one-flask synthesis of water-soluble [60]fullerenols, Tetrahedron, 1996, 52: 4963–4972.
Okuda, K., Hirota, T., Hirobe, M. et al., Synthesis of various water-soluble C 60 derivatives and their superoxide-quenching activity, Fullerene Sci. Techn., 2000, 8: 89–104.
Kampe, K. -D., Egger, N., Vogel, M., Diamino and tetraamino derivatives of buckminsterfullerene C 60, Angew. Chem., Int. Ed. Engl., 1993, 32: 1174–1176.
Angelini, G., De Maria, P., Fontana, A. et al., Study of the aggregation properties of a novel amphiphilic C 60 fullerene derivative, Langmuir, 2001, 17: 6404–6407.
Guldi, D. M., Capped fullerenes: stabilization of water-soluble fullerene monomers as studied by flash photolysis and pulse radiolysis, J. Phys. Chem. A, 1997, 101: 3895–3900.
Janot, J. -M., Bienvenüe, E., Seta, P. et al., [60]Fullerene and three [60]fullerene derivatives in membrane model environments, J. Chem. Soc., Perkin 2, 2000: 301–306.
Wang, G. W., Hao, E. H., Jiao, L. J. et al., Investigation of solvato-chromism and aggregation behavior of C60(C4H10N+)I- in binary solvent mixtures, Chinese Sci. Bull., 2003, 48(18): 1938–1942.
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Wang, G., Zhao, G. & Yan, L. Investigation on the aggregation properties of cationic [60]fullerene derivative. Chin.Sci.Bull. 49, 1441–1445 (2004). https://doi.org/10.1360/04wb0044
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DOI: https://doi.org/10.1360/04wb0044