Synthesis of Fullerene Oxide by Fullerene ($C_{70}$) and Various Amino N-Oxides under Ultrasonic Irradiation

초음파 조건에서 여러가지 아민 N-옥시드와 풀러렌($C_{70}$)를 이용한 풀러렌 산화물의 합성

  • Ko, Weon-Bae (Department of Chemistry, Sahmyook University) ;
  • Han, Ji-Yeon (Department of Chemistry, Sahmyook University) ;
  • Lim, Young-A (Department of Chemistry, Sahmyook University) ;
  • Shin, Won-Jic (Department of Chemistry, Sahmyook University) ;
  • Yu, Gu-Yong (Department of Chemistry, Sahmyook University)
  • Published : 2004.06.30


Fullerene oxides were synthesized by fullerene ($C_{70}$) and several amine N-oxides such as 3-picoline N-oxide, pyridine N-oxide hydrate, quinoline N-oxide, and isoquinoline N-oxide under ultrasonic condition at $25{\sim}43^{\circ}C$. The reactivity of fullerene ($C_{70}$) with various amine N-oxides undo, ultrasonic irradiation showed the same in all of the proceeding experiments; 3-picoline N-oxide : pyridine N-oxide hydrate : quinoline N-oxide : isoquinoline N-oxide. The MALDI-TOF MS, UV-vis spectrophotometer and HPLC analysis confirmed that the products of fullerene oxidation are [$C_{70}(O)n$] (n=1).


  1. H.W Kroto, J.R Heath, S.C O’Brien, R.F Curl, and R.E Smalley, '$C_{60}$-Buckminsterfuller ene', Natur, 318, 162 (1985)
  2. W Kratschmer, L.C Lamb, K Fostiropoulos, and D.R Huffman, 'Solid $C_{60}$ - A New Form of Carbon' Nature, 347, 354 (1990)
  3. B.C Wang, H.W Wang, H.C Tso, T.L Chen, and Y.M Chou, 'Theoretical studies of $C_{70}(OH)_n$ (n=14, 16, 18 and 20) Fullerenols', J. Mol. Struct. (Theochem), 581, 177 (2002)
  4. M.S AI-Jafari, M.P Barrow, R. Taylor, and T. Drewello, 'laser-Induced Gas-phase synthesis of Dimeric $C_{70}$ Oxides', Int. J.Mass Spectrom, 184, L1 (1999)
  5. K.M Creegan, J.L Robbins, W.K Robbins, J.M Millar, R.D Sherwood, P.J Tindall, D.M. Cox, A.B. Smith, J.P McCau-Iey, D.R Jones, and R.T Gallagher, 'Chromatographic Separation of Fullerene:discovery and characterization', J. Am. Chem. Soc, 114, 1103 (1992)
  6. D Heymann, and L.P.F Chibante, 'Reaction of $C_{60}$ and $C_{70}$ with ozone at different temperature', Rec. Trav. Chim, 112, 531 (1993)
  7. D Heymann, and L.P.F Chibante, 'Reaction of $C_{70},\;C_{76},\;C_{78}\;and\;C_{84}$ with ozone at $25^\circ$C', Rec. Trav. Chim, 112, 639 (1993)
  8. R Malhotra, S Kumar, and A. Satyam, 'Ozonolysis of [60] Fullerene', J. Chem. Soc., Chem.Commun, 11, 1339 (1994)
  9. J. P Deng, C.Y Mou, and C.C Han, 'Oxidation of fullenenes by Ozone', Fullerene Sci. Technol, 5, 1033 (1997)
  10. A.L Balch, D.A Costa, B.C Noll, and M.M Olmstead, 'Oxidation of Buckminsterfullenr ene with m-chloroperoxy benzoic acid.Characterizationof a Cs isomer of the Diepoxide $C_{60}O_2$', J. Am. Chem. Soc, 117, 8926 (1995)
  11. V.D Blank, B.A Kulnitskiy, and O.P.M Zhigalina, 'Dimerisation and polymerisation of $C_{70}$ after thermobaric theatment', Carbon, 38, 2051 (2000)
  12. W. B Ko, and K.N Baek, 'The Oxidantion of Fullerenes ($C_{60},\;C_{70}$) with Various Oxidants under Ultrasonication,' Phys. Solid State, 44, 424 (2002)
  13. J.A Nisha, N Premila, V Sridharan, C.S Sundar, and T.S Radhakrishnan, 'UV-irradiation studies on $C_{70}$ clusters in mixed solvents', Carbon, 36, 637 (1998)
  14. S.G Penn, D.A Costa, A.L Balch, and C.B Lebrilla, 'Analysis of $C_{60}$ oxides and $C_{120}O_n$ (n = 1, 2, 3) using matrix assisted laser desorptionionization Fourier fransform mass spectrometry', Int. J. Mass Spectrom. Ion processes, 169, 371 (1997)
  15. W.B Ko, and K.N Baek, 'The oxidation of fullerene[$C_{70}$] with various oxidants by ultrasonication', Ultrasonics, 39(10), 729 (2002)
  16. R Balick, '$TiCl_4$/Nal-A Novel, Efficient Reagent for Mild Reduction of the N-O bond in Amine N-oxides and Nitrones', Chem. Ber, 647 (1990)
  17. R Balick, L Kaczmarkek, and M Malinnowski, 'Selective Reduction of The N-O Bond in Heteroaromatic N-oxides by $TiCl_4\;/SnCl_2$', Synth.. Commun, 19, 897 (1989)
  18. R Malhotra, S Kumar, and A. Satyam, 'Ozonolysis of [60] Fullerene', J. Chem. Soc., Chem.Commun, 11, 1339 (1994)
  19. R Balick, L Kaczmarkek, and M Malinnowski, 'Selective Reduction of The N-O Bond in Heteroaromatic N-oxides by $TiCl_4$ /$SnCl_2$', Synth.. Commun, 19, 897 (1989)
  20. M Malinoswaki,. 'Titanium(0) Reagents;1.A Facile Deoxygenation of unfunctionalized Aromatic Noxides' Synthesis, 732 (1987)
  21. B.W Yoo., J.W Choi, D.Y Kim, S.K Hwang, K.I Choi, and J.H Kim, 'Mild and Efficient Deoxygenation of Amine N-Oxides with Bis(cyclopentadienyl) titanium(IV) Dichloride-Indium system', Bull. Kor.Chem. Soc, 23(6), 797 (2002)
  22. P Ilankumaran, and S Chandrasekaran,'Chemoselective Deoxygenation of Nitrones and N-oxides with Tetrathiomolybdate', Tetrahedron. Lett, 36(27), 4881 (1995)
  23. R Balicki, 'Efficient Deoxygenation of Heteroaromatic N-Oxides with Ammonium Formate as a a Catalytic Hydrogen Transfer Agent', Synthesis, 645 (1989)
  24. J. L Zhang, Y.L Liu, and C.M Che, 'Chiral ruthenium porphyrin encapsulated in ordered mesoporous Molecular sieves (MCM-41 and MCM-48) as catalysts for Asymmetric Alkene Epoxidation and Cyclopropanation', Chem. Commun, 2906 (2002)