Synthesis of alkyl sulfonated fullerenes without catalyst: Improved water solubility by the sulfonate groups

Journal of Nanoscience and Nanotechnology

Volumn 11, Issue 11, 2011, Pages 10093-10101

  Chen, Muqing ^a   Geng, Zhi ^a   Yang, Shangfeng ^a  

^a UNIVERSITY OF SCIENCE AND TECHNOLOGY OF CHINA   (China)

Author keywords

Aggregation; Derivatization; Fullerenes; Sulfonation; Water Solubility

Indexed keywords

1H NMR SPECTROSCOPY; AQUEOUS PHASE; AVERAGE MOLECULAR; DERIVATIZATIONS; FTIR; FULLERENOLS; NEUTRAL AQUEOUS SOLUTION; STABLE RADICALS; SULFONATE GROUPS; WATER SOLUBILITIES; WATER SOLUBILITY; XPS SPECTROSCOPY;

AGGLOMERATION; CATALYSTS; DYNAMIC LIGHT SCATTERING; FOURIER TRANSFORM INFRARED SPECTROSCOPY; FULLERENES; FUNCTIONAL GROUPS; NUCLEAR MAGNETIC RESONANCE SPECTROSCOPY; SODIUM; SULFONATION;

SOLUBILITY;

EID: 84863125086     PISSN: 15334880     EISSN: None     Source Type: Journal    
DOI: 10.1166/jnn.2011.5003     Document Type: Article

References (54)

1. For reviews, see (a) E. Nakamura and H. Isobe, Acc. Chem. Res. 36, 807 (2003)
2. (b) A. Hirsch and M. Brettreich, Fullerenes: Chemistry and Reactions, Wiley-VCH, Weinheim (2005)
3. (c) S. F. Yang and L. Dunsch, Endohedral Fullerenes Nanomaterials: Inorganic and Bioinorganic Perspectives, edited by C. M. Lukehart and R. A. Scott, John Wiley & Sons, Ltd., Chichester, United Kingdom (2008), pp. 189-214
4. (d)L. Yan, F. Zhao, S. J. Li, Z. B. Hu, and Y. L. Zhao, Nanoscale 3, 362 (2011).
5. X. Qiao, C. Huang, Y. B. Ying, X. L. Yang, Y. Liu, and Q. Tian, J. Photochem. Photobiol., B: Biology 98, 193 (2010).
6. J. J. Yin, F. Lao, P. P. Fu, W. G. Wamer, Y. L. Zhao, P. C. Wang, Y. Qiu, B. Y. Sun, G. M. Xing, J. Q. Dong, X. J. Liang, and C. Y. Chen, Biomaterials 30, 611 (2009).
7. M. Horie, A. Fukuhara, Y. Saito, Y. Yoshida, H. Sato, H. Ohi, M. Obata, Y. Mikata, S. Yano, and E. Niki, Bioorg. Med. Chem. Lett. 19, 5902 (2009).
8. Z. Markovic and V. Trajkovic, Biomaterials 29, 3561 (2008).
9. G. L. Marcorin, T. D. Ros, S. Castellano, G. Stefancich, I. Bonin, S. Miertus, and M. Prato, Organic. Letters 2, 3955 (2000).
10. M. Ibrahima, N. A. Salehc, A. J. Hameedd, W. M. Elshemeyc, and A. A. Elsayedc, Spectrochimica Acta Part A 75, 702 (2010).
11. R. Maeda-Mamiya, E. Noiri, H. Isobe, W. Nakanishi, K.Okamoto, K. Doi, T. Sugaya, T. Izumi, T. Homma, and E. Nakamura, Proceedings of the National Academy of Sciences of the United States of America 107, 5339 (2010).
12. T. Y. Zakharian, A. Seryshev, B. Sitharaman, B. E. Gilbert, V. Knight, and L. J. Wilson, J. Am. Chem. Soc. 127, 12508 (2005).
13. L. Y. Huang, M. Terakawa, T. Zhiyentayev, Y. Y. Huang, Y. Sawayama, A. Jahnke, G. P. Tegos, T. Wharton, and M. R. Hamblin, Nanomedicine: Nanotechnology, Biology, and Medicine 6, 442 (2010).
14. X. Q. Cai, H. Q. Jia, Z. B. Liu, B. Hou, C. Luo, Z. H. Feng, W. X. Li, and J. K. Liu, J. Neurosci. Res. 86, 3622 (2008).
15. R. Injac, M. Perse, M. Cerne, N. Potocnik, N. Radic, B. Govedarica, A. Djordjevic, A. Cerar, and B. Strukelj, Biomaterials 30, 1184 (2009).
16. S. Trajković, S. Dobrić, V. Jacević, V. Dragojević-Simić, Z. Milovanović, and A. Dordević, Colloids Surf., B: Biointerfaces 58, 39 (2007).
17. Z. Q. Ji, H. F. Sun, H. F. Wang, Q. Y. Xie, Y. F. Liu, and Z. Wang, J. Nanopart. Res. 8, 53 (2006).
18. G. Zhang, Y. Liu, D. H. Liang, L. B. Gan, and Y. L. Li, Angew. Chem. Int. Ed. 49, 5293 (2010).
19. R. D. Bolskar, A. F. Benedetto, L. O. Husebo, R. E. Price, E. F. Jackson, S. Wallace, L. J. Wilson, and J. M. Alford, J. Am. Chem. Soc. 125, 5471 (2003).
20. I. Larnparth and A. Hirsch, J. Chem. Soc., Chem. Commun. 14, 1727 (1994).
21. S. S. Ali, J. I. Hardt, and L. L. Dugan, Nanomedicine: Nanotechnology, Biology, and Medicine 4, 283 (2008).
22. L. L. Dugan, D. M. Turetsky, C. Du, D. Lobner, M. Wheeler, C. R. Almli, C. K. F. Shen, T. Y. Luh, D. W. Choi, and T. S. Lin, Proceedings of the National Academy of Sciences of the United States of America 94, 9434 (1997).
23. Y. Chi, T. Canteenwala, L. Y. Chiang, B. Wilson, and K. Pritaker, Synthetic Metals 153, 37 (2005).
24. U. S. Jeng, T. L. Lin, T. S. Chang, H. Y. Lee, C. H. Hsu, T. Canteenwala, and L. Y. Chiang, Progress in Collid. Polymer Science 118, 232 (2001).
25. Y. Chi, J. B. Bhonsle, T. Canteenwala, J. P. Huang, J. Shiea, B. J. Chen, and L. Chiang, Chem. Lett. 27, 465 (1998).
26. S. S. Huang, S. K. Tsai, C. L. Chih, L. Y. Chiang, H. M. Hsieh, C. Teng, M. Ming, and C. Tsai, Free Radical Biol. Med. 30, 643 (2001).
27. H. H. Chen, C. Yu, T. H. Ueng, S. D. Chen, B. J. Chen, K. J. Huang, and L. Chiang, Toxicologic Pathology 26, 143 (1998).
28. U. S. Jeng, T. L. Lin, C. S. Tsao, and C. H. Lee, J. Phys. Chem. B 103, 1059 (1999).
29. C. Y. Shu, L. H. Gan, C. R. Wang, X. L. Pei, and H. B. Han, Carbon 44, 496 (2006).
30. Z. Hu, W. Guan, W. Wang, L. Huang, H. Xing, and Z. Zhu, Cell Biology International 31, 798 (2007).
31. H. Kato, A. Yashiro, A. Mizuno, Y. Nishida, K. Kobayashi, and H. Shinohara, Bioorg. Med. Chem. Lett. 11, 2935 (2001).
32. M. Horie, A. Fukuhara, Y. Saito, Y. Yoshida, H. Sato, H. Ohi, M. Obata, Y. Mikata, S. Yano, and E. Niki, Bioorg. Med. Chem. Lett. 19, 5902 (2009).
33. R. F. Enes, A. C. Tomé, J. A. S. Cavaleiro, A. El-Agamey, D. J. McGarvey, Tetrahedron 61, 11873 (2005).
34. P. P. Fatouros, F. D. Corwin, Z. J. Chen, W. C. Broaddus, J. L.Tatum, B. Kettenmann, Z. X. Ge, H. W. Gibson, J. L. Russ, A. P. Leonard, J. C. Duchamp, and H. C. Dorn, Radiology 240, 756 (2006).
35. Y. Tabata, Y. Murakami, and Y. Ikada, Fullerenes, Nanotubes and Carbon Nanostructures 5, 989 (1997).
36. Y. Tabata, Y. Murakami, and Y. Ikada, Japanese of Journal of Cancer Research 88, 1108 (1997).
37. X. F. Zhang, C. Y. Shu, L. Xie, C. R. Wang, Y. Z. Zhang, J. F. Xiang, L. Li, and Y. L. Tang, J. Phys. Chem. C 111, 14327 (2007).
38. C. Y. Shu, C. R. Wang, J. F. Zhang, H. W. Gibson, H. C. Dorn, F. D. Corwin, P. P. T. Fatouros, and J. S. Dennis, Chem. Mater. 20, 2106 (2008).
39. F. Y. Cheng, X. L. Yang, C. H. Fan, and H. S. Zhu, Tetrahedron 57, 7331 (2001).
40. K. Kokubo, K. Matsubayashi, H. Tategaki, H. Takada, and T. Oshima, ACS Nano 2, 327 (2008).
41. R. Injac, M. Perse, N. Obermajer, V. Djordjevic-Milic, M. Prijatelj, A. Djordjevic, A. Cerar, and B. Strukelj, Biomaterials 29, 3451 (2008).
42. R. Injac, M. Perse, M. Cerne, N. Potocnik, N. Radic, B. Govedarica, A. Djordjevic, A. Cerar, and B. Strukelj, Biomaterials 30, 1184 (2009).
43. M. Mikawa, H. Kato, M. Okumura, M. Narazaki, Y. Kanazawa, N. Miwa, and H. Shinohara, Bioconjugate Chem. 12, 510 (2001).
44. F. Beuerle, P. Witte, U. Hartnagel, R. Lebovitz, C. Parng, and A. Hirsch, Journal of Experimental Nanoscience 2, 147 (2007).
45. L. Y. Chiang, L. Y. Wang, and J. W. Swirczewsk, J. Org. Chem. 59, 3960 (1994).
46. S. F. Yang, C. Chen, A. A. Popov, W. F. Zhang, F. P. Liu, and L. Dunsch, Chem. Commun. 6391 (2009).
47. J. Li, A. Takeuchi, M. Ozawa, X. H. Li, K. Saigo, and K. Kitazawa, J. Chem. Soc., Chem. Commun. 23, 1784 (1993).
48. P. Chaudhuri, A. Paraskar, S. Soni, R. A. Mashelkar, and S. Sengupta, ACS Nano 3, 2505 (2009).
49. R. Singh and T. Goswami, J. Organomet. Chem. 693, 2021 (2008).
50. L. Y. Chiang, R. B. Upasani, J. W. Swirczewski, and S. Soled, J. Am. Chem. Soc. 115, 563 (1993).
51. G. M. Xing, J. Zhang, Y. L. Zhao, J. Tang, B. Zhang, X. F. Gao, H. Yuan, L. Qu, W. B. Cao, Z. F. Chai, K. Ibrahim, and R. Su, J. Phys. Chem. B 108, 11473 (2004).
52. N. Moncoffre, G. Hollinger, H. Jaffrezic, G. Marest, and J. Tousset, Nucl. Instrum. Methods Phys. Res. B7, 177 (1985).
53. Z. Q. Ji, H. F. Sun, H. F. Wang, Q. Y. Xie, Y. F. Liu, and Z. Wang, J. Nanopart. Res. 8, 53 (2006).
54. L. O. Husebo, B. Sitharaman, K. Furukawa, T. Kato, and L. J. Wilson, J. Am. Chem. Soc. 126, 12055 (2004).