Functionalization of carbon nanotubes by free radicals

Organic Letters

Volumn 5, Issue 9, 2003, Pages 1471-1473

  Ying, Yunming ^a   Saini, Rajesh K ^a   Liang, Feng ^a   Sadana, Anil K ^a   Billups, W E ^a  

^a RICE UNIVERSITY   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

ALKYL GROUP; ARGON; BENZOYL PEROXIDE; CARBON; FERROUS GLUCONATE; FREE RADICAL; IODINE DERIVATIVE; ORGANIC SOLVENT; REAGENT; SULFOXIDE;

ARTICLE; ASSAY; ATMOSPHERE; CHEMICAL STRUCTURE; DECOMPOSITION; DERIVATIZATION; HEATING; SOLUBILITY; SYNTHESIS; THERMOGRAVIMETRY;

EID: 0141519285     PISSN: 15237060     EISSN: None     Source Type: Journal    
DOI: 10.1021/ol0342453     Document Type: Article

References (24)

1. For recent reviews: (a) Hirsch, A. Angew. Chem., Int. Ed. 2002, 1853-1859. (b) Bahr, J. L.; Tour, J. M. J. Mater. Chem. 2002, 1952-1958. (c) Special issue on carbon nanotubes. Acc. Chem. Res. 2002, 35 (12).
2. For recent reviews: (a) Hirsch, A. Angew. Chem., Int. Ed. 2002, 1853-1859. (b) Bahr, J. L.; Tour, J. M. J. Mater. Chem. 2002, 1952-1958. (c) Special issue on carbon nanotubes. Acc. Chem. Res. 2002, 35 (12).
3. For recent reviews: (a) Hirsch, A. Angew. Chem., Int. Ed. 2002, 1853-1859. (b) Bahr, J. L.; Tour, J. M. J. Mater. Chem. 2002, 1952-1958. (c) Special issue on carbon nanotubes. Acc. Chem. Res. 2002, 35 (12).
4. Mickelson, E. T.; Huffman, C. B.; Rinzler, A. G.; Smalley, R. E.; Hauge, R. H.; Margrave, J. L. Chem. Phys. Lett. 1998, 296, 188-194.
5. 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. Chem. Phys. Lett. 1999, 310, 367-372.
6. Mickelson, E. T.; Chiang, I. W.; Zimmerman, J. L.; Boul, P. J.; Lazano, J.; Liu, J.; Smalley, R. E.; Hauge, R. H.; Margrave, J. L. J. Phys. Chem. B 1999, 103, 4318-4322.
7. Georgakilas, V.; Kordatos, K.; Prato, M.; Guldi, D. M.; Holzinger, M.; Hirsch, A. J. Am. Chem. Soc. 2002, 124, 760-761.
8. Chen, Y.; Haddon, R. C.; Fang, S.; Rao, A. M.; Eklund, P. C.; Lee, W. H. ; Dickey, E. C.; Grulke, E. A.; Pendergrass, J. C.; Chavan, A.; Haley, B. E.; Smalley, R. E. J. Mater. Res. 1998, 13, 2423-2431.
9. Chen, J.; Hamon, M. A.; Hu, H.; Chen, Y.; Rao, A. M.; Ecklund, P. C.; Haddon, R. C. Science 1998, 282, 95-98.
10. Holzinger, M.; Vostrowsky, O.; Hirsch, A.; Hennrich, F.; Kappes, M.; Weiss, R.; Jellen, F. Angew. Chem., Int. Ed. 2001, 40, 4002-4005.
11. Bahr, J. L.; Yang, J. P.; Kosynkin, D. V.; Bronikowski, M. J.; Smalley, R. E.; Tour, J. M. J. Am. Chem. Soc. 2001, 123, 6536-6542.
12. Bahr, J. L.; Tour, J. M. Chem. Mater. 2001, 13, 3823-3824.
13. Sun, Y.; Wilson, S. R.; Schuster, D. I. J. Am. Chem. Soc. 2001, 123, 5348-5349.
14. Kooi, S. E.; Schlecht, U.; Burghard, M.; Kern, K. Angew. Chem., Int. Ed. 2002, 41, 1353-1355.
15. Tagmatarchis, N.; Georgakilas, V.; Prato, M.; Shinohara, H. Chem. Commun. 2002, 2010-2011.
16. Pekker, S.; Salvetat, J.-P.; Jakab, E.; Bonard, J.-M.; Forro, L. J. Phys. Chem. B 2001, 105, 7938-7943.
17. (a) Liu, J.; Rinzler, A. G.; Dai, H.; Hafner, J. H.; Bradley, R. K.; Boul, P. J.; Lu, A.; Iverson, T.; Shelimov, K.; Huffman, C. B.; Rodriguez-Macias, F.; Shon, Y.; Lee, T. R.; Colbert, D. T.; Smalley, R. E. Science 1998, 280, 1253-1256.
18. (b) Hamon, M. A.; Chen, J.; Hu, H.; Chen, Y.; Itkis, M. E.; Rao, A. M.; Eklund, P. C.; Haddon, R. C. Adv. Mater. 1999, 11, 834-840.
19. (a) Chiu, P. W.; Duesberg, G. S.; Dettlaff-Weglikowska, U.; Roth, S. Appl. Phys. Lett. 2002, 3811-3813.
20. (b) Huang, W.; Lin, Y.; Taylor, S.; Gaillard, J.; Rao, A. M.; Sun, Y. Nano Lett. 2002, 2, 231-234 and references therein.
21. Chiang, I. W.; Brinson, B. E.; Huang, A. Y.; Willis, P. A.; Bronikowski, M. J.; Margrave, J. L.; Smalley, R. E.; Hauge, R. H. J. Phys. Chem. B 2001, 105, 8297-8301.
22. General Procedure. SWNTs (20 mg, 1.6 mmol of carbon) were suspended in benzene (30 mL) and sonicated for 30 min in a bath sonicator (Cole Parmer). The alkyl iodide (4.0 mmol) and benzoyl peroxide (403 mg, 1.6 mmol) were then added to this suspension. The contents were heated under argon at 75°C for 24 h with stirring. The contents of the flask were diluted with 100 mL of benzene, filtered over a PTFE (0.2 μM) membrane, and washed exhaustively with benzene. The material was then suspended in benzene, sonicated for 20 min, and filtered. This procedure was repeated twice with benzene and once each with acetone and methanol. The bucky-paper was then dried in vacuo at 80°C for 12 h.
23. Peng, H.; Reverdy, P.; Khabashesku, V. N.; Margrave, J. L. Chem. Commun. 2003, 362-363.
24. Fontana, F.; Minisci, F.; Vismara, E. Tetrahedron Lett. 1988, 29, 1975-1978.