Fluorination of single-wall carbon nanotubes and subsequent derivatization reactions

Accounts of Chemical Research

Volumn 35, Issue 12, 2002, Pages 1087-1095

  Khabashesku, Valery N ^a   Billups, W Edward ^a   Margrave, John L ^a  

^a RICE UNIVERSITY   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

CARBON; FLUORINE;

ARTICLE; ATOMIC FORCE MICROSCOPY; CHEMICAL REACTION; DERIVATIZATION; FLUORINATION; MATERIAL STATE; MATERIALS; NANOPARTICLE; NANOTUBE; PYROLYSIS; STRUCTURE ANALYSIS; TRANSMISSION ELECTRON MICROSCOPY;

EID: 0036919937     PISSN: 00014842     EISSN: None     Source Type: Journal    
DOI: 10.1021/ar020146y     Document Type: Article

References (42)

1. Iijima, S. Helical microtubules of graphitic carbon. Nature 1991, 354, 56.
2. Dresselhaus, M. S.; Dresselhaus, G.; Eklund, P. C. Science of Fullerenes and Carbon Nanotubes; Academic Press: San Diego, 1996; Vol. 1.
3. Saito, R.; Dresselhaus, M. S.; Dresselhaus, G. Physical Properties of Carbon Nanotubes; Imperial College Press: London, 1998.
4. Odom, T. W.; Huang, J.-L.; Kim, P.; Lieber, C. M. Structure and Electronic Properties of Carbon Nanotubes. J. Phys. Chem. B 2000, 104, 2794-2809.
5. Rao, C. N. R.; Satishkumar, B. C.; Govindaraj, A.; Nath, M. Nanotubes. ChemPhysChem 2001, 2, 78-105.
6. Gong, X.; Liu, J.; Baskaran, S.; Voise, R. D.; Young, J. S. Surfactant-Assisted Processing of Carbon Nanotube/Polymer Composites. Chem. Mater. 2000, 12,1049-1052.
7. Gao, B.; Yue, G. Z.; Qiu, Q.; Cheng, Y.; Shimodu, H.; Fleming, L.; Zhou, O. Fabrication and electron field emission properties of carbon nanotube films by electrophoretic deposition. Adv. Mater. 2001, 13, 1770-1773.
8. Wong, S. S.; Harper, J. D.; Lansbury, P. T.; Lieber, C. M. Carbon Nanotube Tips: High-Resolution Probes for Imaging Biological Systems. J. Am. Chem. Soc. 1998, 120, 603-604.
9. Liu, C.; Fan, Y. Y.; Liu, M.; Cong, H. T.; Cheng, H. M.; Dresselhaus, M. S. Hydrogen Storage in Single-Walled Carbon Nanotubes at Room Temperature. Science 1999, 286, 1127-1129.
10. Chen, J.; Hamon, M. A.; Hu, H.; Chen, Y.; Rao, A. M.; Eklund, P. C.; Haddon, R. C. Solution Properties of Singled-Walled Carbon Nanotubes. Science 1998, 282, 95-98.
11. Hamon, M. A.; Chen, J.; Hu, H.; Chen, Y. S.; Itkis, M. E.; Rao, A. M.; Eklund, P. C.; Haddon, R. C. Dissolution of single-walled carbon nanotubes. Adv. Mater. 1999, 11, 834-840.
12. Riggs, J. E.; Guo, Z.; Carroll, D. L.; Sun, Y.-P. Strong luminescence of solubilized carbon nanotubes. J. Am. Chem. Soc. 2000, 122, 5879-5880.
13. Sun, Y.-P.; Huang, W.; Lin, Y.; Fu, K.; Kitaigorodsky, A.; Riddle, L. A.; Yu, Y. J.; Carroll, D. L. Soluble dendron-functionalized carbon nanotubes: preparartion, characterization, and properties. Chem. Mater. 2001, 13, 2864-2869.
14. Pekker, S.; Salvelat, J.-P.; Jakab, E.; Bonard, J.-M.; Forro, L. Hydrogenation of carbon nanotubes and graphite in liquid ammonia. J. Phys. Chem. B 2001, 105, 7938-7943.
15. Bahr, J. L.; Yang, J.; Kosynkin, D. V.; Bronikowski, M. J.; Smalley, R. E.; Tour, J. M. Functionalization of carbon nanotubes by electrochemical reduction of aryl diazonium salts: A bucky paper electrode. J. Am. Chem. Soc. 2001, 123, 6536-6542.
16. Bahr, J. L.; Tour, J. M. Highly functionalized carbon nanotubes using in situ generated diazonium compounds. Chem. Mater. 2001, 13, 3823-3824.
17. Holzinger, M.; Vostrowsky, O.; Hirsch, A.; Hennrich, F.; Kappes, M.; Weiss, R.; Jellen, F. Sidewall functionalization od carbon nanotubes. Angew. Chem. 2001, 40, 4002-4005.
18. Georgakilas, V.; Kordatos, K.; Prato, M.; Guldi, D. M.; Holzinger, M.; Hirsch, A. Organic functionalization of carbon nanotubes. J. Am. Chem. Soc. 2001, 124, 760-761.
19. Thess, A.; Lee, R.; Nikolaev, P.; Dai, H.; Petit, P.; Robert, J.; Xu, C.; Lee, Y. H.; Kim, S. G.; Rinzler, A. G.; Colbert, D. T.; Scusseria, G. E.; Tomanek, D.; Fischer, J. E.; Smalley, R. E. Crystalline ropes of metallic carbon nanotubes. Science 1996, 273, 483-487.
20. Rinzler, A. G.; Liu, J.; Dai, H.; Nikolaev, P.; Huffman, C. B.; Rodriguez-Macias, F. J.; Boul, P. J.; Liu, A. H.; Heymann, D.; Colbert, D. T.; Lee, R. S.; Fischer, J. E.; Rao, A. M.; Eklund, P. C.; Smalley, R. E. Large-scale purification of single-wall carbon nanotubes: Process, product, and characterization. Appl. Phys. A 1998, 67, 29-37.
21. Nikolaev, P.; Bronikowski, M. J.; Bradley, R. K.; Rohmund, F.; Colbert, D. T.; Smith, K. A.; Smalley, R. E. Gas-phase catalytic growth of single-walled carbon nanotubes from carbon monooxide. Chem. Phys. Lett. 1999, 313, 91-97.
22. Bronikowski, M. J.; Willis, P. A.; Colbert, D. T.; Smith, K. A.; Smalley, R. E. Gas-phase production of carbon single-walled nanotubes from carbon monooxide via the HiPco process: A parametric study. J. Vac. Sci. Technol. A 2001, 19, 1800-1805.
23. Lagow, R. J.; Badachape, R. B.; Wood, J. L.; Margrave, J. L. Some new synthetic approaches to graphite-fluorine chemistry. J. Chem. Soc., Dalton Trans. 1974, 12, 1268-1273.
24. (a) Mickelson, E. T.; Huffman, C. B.; Rinzler, A. G.; Smalley, R. E.; Hauge, R. H.; Margrave, J. L. Fluorination of Single-Wall Carbon Nanotubes. Chem. Phys. Lett. 1998, 296, 188-194.
25. (b) Mickelson, E. T. Novel Chemistry of Elemental Carbon: Graphite, Fullerenes and Nanotubes. Ph.D. Thesis, Rice University, Houston, TX, 1999.
26. Chiang, I. W. Science of Single-Wall Carbon Nanotubes: Purification, Characterization and Chemistry. Ph.D. Thesis, Rice University, Houston, TX, 2001.
27. Mickelson, E. T.; Chiang, I. W.; Zimmerman, J. L.; Boul, P. J.; Lozano, J.; Liu, J.; Smalley, R. E.; Hauge, R. H.; Margrave, J. L. Solvation of fluorinated single-wall carbon nanotubes in alcohol solvents. J. Phys. Chem. B 1999, 103, 4318-4322.
28. Dunitz, J. D.; Taylor, R. Organic fluorine hardly ever accepts hydrogen bonds. Chem. Eur. J. 1997, 3, 89-98.
29. Kelly, K. F.; Chiang, I. W.; Mickelson, E. T.; Hauge, R. H.; Margrave, J. L.; Wang, X.; Scusseria, G. E.; Radloff, C.; Halas, N. J. Insight into the mechanism of sidewall functionalization of single-walled nanotubes: An STM study. Chem. Phys. Lett. 1999, 313, 445-450.
30. Kudun, K. N.; Bettinger, H. F.; Scuseria, G. E. Fluorinated single-wall carbon nanotubes. Phys. Rev. B 2001, 63, 45413-45421.
31. Gu, Z.; Peng, H.; Hauge, R. H.; Smalley, R. E.; Margrave, J. L. Cutting single-wall carbon nanotubes through fluorination. NanoLett. 2002, 2, 1009-1013.
32. Chiang, I. W.; Brinson, B. E.; Huang, A. Y.; Willis, P. A.; Bronikowski, M. J.; Margrave, J. L.; Smalley, R. E.; Hauge, R. H. Purification and characterization of single-wall carbon nanotubes (SWNTs) obtained from the gas-phase decomposition of CO (HiPco Process). J. Phys. Chem. B 2001, 105, 8297-8301.
33. Taylor, R. Progress in Fullerene Fluorination. Russ. Chem. Bull. 1998, 47, 823-832.
34. Bettinger, H. F.; Kudin, K. N.; Scuseria, G. E. Thermochemistry of fluorinated single wall carbon nanotubes. J. Am. Chem. Soc. 2001, 123, 12849-12856.
35. Saini, R. K.; Chiang, I. W.; Peng, H.; Smalley, R. E.; Billups, W. E.; Hauge, R. H.; Margrave, J. L. Covalent Sidewall Functionalization of Single Wall Carbon Nanotubes. J. Am. Chem. Soc. 2002, in press.
36. Boul, P. J.; Liu, J.; Mickelson, E. T.; Huffman, C. B.; Ericson, L. M.; Chiang, I. W.; Smith, K. A.; Colbert, D. T.; Hauge, R. H.; Margrave, J. L.; Smalley, R. E. Reversible Sidewall Functionalization of Buckytubes. Chem. Phys. Lett. 1999, 310, 367-372.
37. Lobo, R.; Khabashesku, V. N.; Margrave, J. L. Unpublished results.
38. Stevens, J. L.; Huang, A. Y.; Chiang, I. W.; Khabashesku, V. N.; Margrave, J. L. Sidewall Aminoalkyl Functionalization of Single-Walled Carbon Nanotubes Using Fluoronanotube Precursors. Angew. Chem., Int. Ed. 2002, in press.
39. 70. Russ. Chem. Bull. 1996, 45, 2267-2278.
40. Peng, H.; Reverdy, P.; Khabashesku, V. N.; Margrave, J. L. Sidewall functionalization of single-wall carbon nanotubes with organic peroxides. Chem Commun. 2002, in press.
41. Peng, H.; Gu, Z.; Liu, Y.; Chiang, I. W.; Smalley, R. E.; Hauge, R. H.; Khabashesku, V. N.; Margrave, J. L. Oxidative Properties and Chemical Stability of Fluoronanotubes in Matrixes of Binary Inorganic Compounds. J. Nanosci. Nanotech. 2002, in press.
42. Peng, H.; Gu, Z.; Yang, J.; Zimmerman, J. L.; Willis, P. A.; Bronikowski, M. J.; Smalley, R. E.; Hauge, R. H.; Margrave, J. L. Fluorotubes as cathodes in lithium electrochemical cells. Nano-Lett. 2001, 1, 625-629.