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Original Articles

One‐step Synthesis of Water‐soluble Fullerenols Bearing Nitrogen‐containing Substituents

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Pages 440-456 | Published online: 22 Jul 2009

REFERENCES

  • Hirsh , A. 2002 . Angew. Chem. Int. Eng. , 41 : 1853 – 1859 . (a), (b) Nakashima, N. (2005) Int. J. Nanosci., 4: 119–137
  • Gharbi , N. , Pressac , M. , Hadchouel , M. , Szwarc , H. , Wilson , S. R. and Moussa , F. 2005 . Nano Lett. , 5 : 2578 – 2585 . (a), (b) Xiao, L., Takada, H., Maeda, K., Haramoto, M., and Miwa, N. (2005) Biomed. Pharmacother., 59: 351–358; (c) Bensasson, R.V., Brettreich, M., Frederiksen, J., Göttinger, H., Hirsch, A., Land, E.J., Leach, S., McGarvey, D.J., and Schönberger, H. (2000) Free Radical Biol. Med., 29: 26–33; (d) Wang, I.C., Tai, L.A., Lee, D.D., Kanakamma, P.P., Shen, C.K.‐F., Luh, T.‐Y., Cheng, C.H., and Hwang, K.C. (1999) J. Med. Chem., 42: 4614–4620; (e) Dugan, L.L., Turetsky, D.M., Du, C., Lobner, D., Wheeler, M., Almli, C.R., Shen, C.K.‐F., Luh, T.‐Y., Choi, D.W., and Lin, T.‐S. (1997) Proc. Natl. Acad. Sci. U.S.A., 94: 9434–9439; (f) Okuda, K., Mashino, T., and Hirobe, M. (1996) Bioorg. Med. Chem. Lett., 6: 539–542
  • Chiang , L. Y. , Lu , F.‐J. and Lin , J.‐T. 1995 . J. Chem. Soc., Chem. Commun. , : 1283 – 1284 . (a), (b) Dugan, L.L., Gabrielsen, J.K., Yu, S.P., Lin, T.‐S., and Choi, D.W. (1996) Nerobiol. Dis., 3: 129–135; (c) Sun, D., Zhu, Y., Liu, Z., Liu, G., Guo, X., Zhan, R., and Liu, S. (1997) Chin. Sci. Bull., 42: 748–752; (d) Lai, H.‐S., Chen, W.‐J., and Chiang, L.‐Y. (2000) World J. Surg., 24: 450–454; (e) Guldi, D.M. and Asmus, K.‐D. (1999) Radiat. Phys. Chem., 56: 449–456
  • Chiang , L. Y. , Wang , L.‐Y. , Swirczewski , J. W. , Soled , S. and Cameron , S. 1994 . J. Org. Chem. , 59 : 3960 – 3968 .
  • Wang , S. , He , P. , Zhang , J.‐M. , Jiang , H. and Zhu , S.‐Z. 2005 . Synth. Commun. , 35 : 1803 – 1807 .
  • Li , J. , Takeuchi , A. , Ozawa , M. , Li , X. , Saigo , K. and Kitazawa , K. 1993 . J. Chem. Soc., Chem. Commun. , : 1784 – 1785 .
  • Husebo , L. O. , Sitharaman , B. , Furukawa , K. , Kato , T. and Wilson , L. J. 2004 . J. Am. Chem. Soc. , 126 : 12055 – 12064 . (a), (b) Vileno, B., Marcoux, P.R., Lekka, M., Sienkiewicz, A., Fehér, T., and Forró, L. (2006) Adv. Funct. Mater., 16: 120–128
  • Kokubo , K. , Matsubayashi , K. , Tategaki , H. , Takada , H. and Oshima , T. 2008 . ACS Nano , 2 : 327 – 333 .
  • Hu , X. , Jiang , Z. , Jia , Z. , Huang , S. , Yang , X. , Li , Y. , Gan , L. , Zhang , S. and Zhu , D. 2007 . Chem. Eur. J. , 13 : 1129 – 1141 .
  • Anantharaj , V. , Bhonsle , J. , Canteenwala , T. and Chiang , L. Y. 1999 . J. Chem. Soc., Perkin Trans. 1 , : 31 – 36 . (a), (b) Anantharaj, V., Wang, L.Y., and Chiang, L.Y. (1999) Fullerene Sci. Tech., 7: 493–504; (c) Chiang, L.Y., Upasani, R.B., Swirczewski, J.W. (1992) J. Am. Chem. Soc., 114: 10154
  • The positive ion FAB mass spectrum of fullerenol 1 was clearly obtained, showing the distribution of 8–14 hydroxyl groups with the maximum average at 11 (m/z 907)
  • Chiang , L. Y. , Upasani , R. B. , Swirczewski , J. W. and Soled , S. 1993 . J. Am. Chem. Soc. , 115 : 5453 – 5457 .
  • She , Y.‐M. , Tu , Y.‐P. and Liu , S.‐Y. 1996 . Rapid Commun. Mass Spectrom. , 10 : 676 – 678 .
  • Although the number of hydroxyl groups of C60(OH)16 is rather low, the solubility is quite high as >200 mg/mL. According to the report of Wilson et al. 7, the synthesis of this fullerenol was carried out using sodium hydroxide, for example, C60(OH)24 and the above C60(OH)16, might result in some contamination of sodium salt. The extremely high water solubility of C60(OH)16 and our fullerenol 4 may due to a partial salt form of fullerenol, such as sodium and ammonium salt, respectively
  • Fukui , K. , Mori , N. , Takekuma , S. , Takekuma , H. , Yoshida , Z. , Sato , K. , Shiomi , D. , Kato , T. and Takui , T. 2001 . Synth. Met. , 121 : 1171 – 1172 .
  • Hirsch , A. , Li , Q. and Wudl , F. 1991 . Angew. Chem. Int. Eng. , 30 : 1309 – 1310 . (a), (b) Kampe, K.‐D., Egger, N., and Vogel, M. (1993) Angew. Chem. Int. Eng., 32: 1174–1176; (c) Isobe, H., Tanaka, T., Nakanishi, W., Lemiègre, L., and Nakamura, E. (2005) J. Org. Chem., 70: 4826–4832; (d) Lemiègre, L., Tanaka, T., Nanao, T., Isobe, H., and Nakamura, E. (2007) Chem. Lett., 36: 20–21
  • Indeed, such aminofullerene C60Hn(NH2)n has not been reported yet
  • Stry , J. J. , Coolbaugh , T. , Turos , E. and Garvey , J. F. 1992 . Although the reaction of C60On with ammonia has not been explored, the reaction of cationic C60 with ammonia has been reported. . J. Am. Chem. Soc. , 114 : 7914 – 7916 . (a), (b) Petrie, S. (2006) Int. J. Mass Spectromet., 255–256: 213–224
  • Emmons , W. D. 1957 . Oxidation of amino group to nitro group by hydrogen peroxide has been reported. . J. Am. Chem. Soc. , 79 : 5528 – 5530 . (a), (b) Kofman, T.P. and Paketina, E.A. (1997) Russ. J. Org. Chem., 33: 1125–1132
  • A mixture of oxidized fullerenes C60On was purchased from Frontier Carbon Corporation. The component ratio was determined by LCMS (mass spectra and peak area) as follows: C60, 22; C60O, 33; C60O2, 27; C60O3, 14; C60O4, 5%
  • Janaki , J. , Premila , M. , Gopalan , P. , Sastry , V. S. and Sundar , C. S. 2000 . Thermochimica Acta , 356 : 109 – 116 .

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