Preparation of Fullerene Oxides by Fullerenes[$C_{60},C_{70}$] with Several Oxidants under Ultrasonic Condition

초음파 조건에서 산화제를 이용한 풀러렌 산화물의 제조

  • Published : 2003.06.30

Abstract

Synthesis of fullerene oxides by fullerenes [$C_{60},\;C_{70}$] and several oxidants such as benzoylperoxide, trichloroisocyanuric acid, methyltrioxorhenium(VII), iodosobenzene, phosphorous pentoxide take place under ultrasonic condition at room temperature. The MALDI-TOF MS,UV-visible spectra and HPLC analysis confirmed that the products of fullerenes oxidation are [$C_{60}(O)_n$], ($n=1{\sim}3$ or n=1) and [$C_{70}(O)_n$], ($n=1{\sim}2$ or n=1). As compared with the reactivity of epoxidation of fullerenes [$C_{60},\;C_{70}$], the reaction rate of $C_{70}$ was lower than that of $C_{60}$ under same reaction condition.

풀러렌[$C_{60},\;C_{70}$]을 benzoylperoxide, trichloroisocyanuric acid, methyltrioxorhenium(VII), iodosobenzene 그리고 phosphorous pentoxide 등의 산화제를 사용하여 상온, 초음파 조건에서 풀러렌 산화물을 제조하였다. MALDI-TOF MS, UV-VIS 그리고 HPLC를 사용하여 분석한 결과 생성된 풀러렌 산화물은 [$C_{60}(O)_n$], ($n=1{\sim}3$ 또는 n=1)과 [$C_{70}(O)_n$], ($n=1{\sim}2$ 또는 n=1)임을 알 수 있었다. 한편, 동일한 실험 조건에서 $C_{60}$ 반응속도는 $C_{70}$ 보다 높았다.

Keywords

References

  1. For reviews on fullerene preparation and chemistry see:RE.Smalley, 'Self-Assembly of the Fullerenes' Ace. Chem. Res., 25 (1992), Special Issue on Buckminsterfullerenes Published by The American Chemical Society;. G. S. Hammond, V. J. Kuck, 'Fullerenes: Synthesis, Properities and Chemistry of Large Carbon Clusters', G. S. Hammond, V. J. Kuck, Eds., ACS Symposium Series481;American Chemical Society: Washington, CD, 1992. R. Taylor, D. R. M. Walton, 'The Chemistry of Fullerenes' Nature., 363, 685 (1993)㈴㤀ㄵ㌲ⴲ㐱㘀ㄵ㌲ⴲ㤸砀ㄵ㌲ⴶ㤳㐀ㄵ㌳ⴴ㈸㜀ㄵ㌳ⴴ㐰㘀ㄵ㌴ⴶ〸 ㄵ㌷ⴲ㤹㔀ㄵ㌸ⴳ㔹㠀ㄵ㌸ⴳ㘴㐀ㄵ㌸ⴴ㌵㜀ㄵ㌹ⴶ㤲㐀ㄵ㐰ⴸㄴ ㄵ㐱ⴰ〴㠀ㄵ㐱ⴵ㜲㐀ㄵ㐳ⴱ㠶砀ㄵ㐵ⴴ㔰㤀ㄵ㐶ⴱ㜱㠀ㄵ㐷ⴷㄸ㔀ㄵ㐸ⴲ㘳㐀ㄵ㔰ⴲ㌵堀ㄵ㔱ⴶ㜰㤀ㄵ㔲ⴸ㘱㠀ㄵ㔶ⴹ㔱㤀ㄵ㔸ⴲ㈰㔀ㄵ㔸ⴴ㈵㤀ㄵ㔸ⴹ㌳㄀ㄵ㘹ⴸ〴㄀ㄵ㜲ⴹ㌷ ㄵ㜳ⴱ㐷㈀ㄵ㜳ⴲ㤳㈀ㄵ㜳ⴵ〳㘀ㄵ㜳ⴵ〶
  2. J. M. Wood, B. Kahr, S. H. Hake II., 'Oxygen and Methylene Adducts of $C_{60}$ and $C_{70}$ J. Am. Chem. Soc., 113, 5907 (1991)
  3. K. M. Creegan, W. K. Robbins, J. M. Millar., 'Chromatographic Separations of Fullerene: discovery and characterization' J. Am. Chem. Soc., 114, 1103 (1992)
  4. W. A. Kalsbeck and H. H. Thorp, 'Electrochemical Reduction of Fullerenes in the Presence of $O_2$ and $H_2O$: Polyoxygen Adducts and Fragmentation of the $C_{60}$ Framework' J. Electroanal. Chem., 314, 363 (1991)
  5. Y. Elemes, S. K. Silverman, C. Sheu., 'Reaction of $C_{60}$ with Dimethyldioxirane Formation of an Epoxide and a 1,3-Dioxolane Derivative' Angew. Chem. Int. Ed. Engl., 31, 351 (1992)
  6. D. Heymann and L. P. F. Chibante, 'Photot-ransformations of $C_{60}$, $C_{70}$, $C_{60}O$, and $C_{60}O_2$ Chem. Phys. Lett., 207, 339 (1993)
  7. F. Diederich, R. Ettl, Y. Rubin., 'The Higher Fullerenes: Isolation and Characterization of $C_{76}$, $C_{84}$, $C_{90}$, $C_{94}$ an Oxide of $D_{SH}-C_{70}$' Science., 252, 548 (1991)
  8. J. B. Howard, A. L. Lafleur, Y. Makarovsky., 'Fullerenes Synthesis in Combustion' Carbon., 30, 1183 (1992)
  9. D. Heymann and L. P. F. Chibante, 'Reaction of $C_{60}$ and $C_{70}$ with Ozone at Different Temperatures' Reel. Trav. Chim. Pays-Bas., 112, 531 (1993)
  10. P. J. Fagan, J. C. Calabrese, B. Malone, 'Metal Complexes of Buckminster-fullerene($C_{60}$)' Ace. Chem. Res., 25, 134 (1992)
  11. A Van Cleempoel, R. Gijbels, H. Van den Heuvel and M. Claeys, 'Analysis of $C_{60}$ and $C_{70}$ Oxides by HPLC and Low-and High-Energy Collision-Induced Dissocatiori Tandem Mass Spectrometry' Proceedings of the Electrochemical Society., 14, 783 (1997)
  12. W. B. Ko and K. N. Back, 'The Oxidation of Fullerenes ($C_{60}$, $C_{70}$) with Various Oxidants under Ultrasonication' Phys. Solid State., 44, 424 (2002) https://doi.org/10.1134/1.1462660
  13. W. B. Ko and K. N. Baek, 'The Oxidation of Fullerene [$C_{70}$] with Various Oxidants by Ultra-sonication' Ultrasonics., 39(10), 729 (2002) https://doi.org/10.1016/S0041-624X(02)00377-3
  14. F. Cataldo and D. Heymann, 'Effects of Intense Ultrasound Treatment of $C_{60}$ Solutions' Fullerene Sci.Technol., 7, 725 (1999)
  15. K. S. Suslick, 'Ultrasound, Its Chemical, Physical and Biological Effects', ed. By K. S. Suslick, VCH publishers, Weinheim, 1989
  16. R. Katoh, E.Yanase, H. Yokoi, et al., 'Possible New Route for the Production of $C_{60}$ by Ultrasound' Ultrason. Sonochem 5(1) 37 (1998)
  17. J.M. Millar, K. M. Creegan, J. L. Robbins., 'Synthesis and Characterization of $C_{60}O$, the First Fullerene Epoxide' Synth. Met., 59, 317 (1993)