Claisen rearrangement of graphite oxide: A route to covalently functionalized graphenes

Angewandte Chemie - International Edition

Volumn 50, Issue 38, 2011, Pages 8848-8852

  Collins, William R ^a   Lewandowski, Wiktor ^a   Schmois, Ezequiel ^a   Walish, Joseph ^a   Swager, Timothy M ^a  

^a MASSACHUSETTS INSTITUTE OF TECHNOLOGY   (United States)

Author keywords

Claisen rearrangement; electrostatic stabilization; graphene; surface functionalization; water solubility

Indexed keywords

ALLYLIC ALCOHOL; AQUEOUS ENVIRONMENT; BASAL PLANES; CLAISEN REARRANGEMENT; DIMETHYL ACETAL; ELECTROSTATIC STABILIZATION; FUNCTIONALIZED; GRAPHENE SHEETS; GRAPHITE OXIDE; N ,N-DIMETHYLACETAMIDE; ON THE GO; SIGMATROPIC REARRANGEMENTS; SURFACE FUNCTIONALIZATION; WATER SOLUBILITY;

CARBOXYLIC ACIDS; GRAPHITE;

GRAPHENE;

EID: 80052564952     PISSN: 14337851     EISSN: 15213773     Source Type: Journal    
DOI: 10.1002/anie.201101371     Document Type: Article

References (57)

1. J. C. Love, L. A. Estroff, J. K. Kriebel, R. G. Nuzzo, G. M. Whitesides, Chem. Rev. 2005, 105, 1103-1169
2. G. Decher, Science 1997, 277, 1232-1237.
3. For fullerenes, see, S. Campidelli, A. Mateo-Alonso, M. Prato, in Fullerenes, Principles and Applications (Eds:, F. Langa, J. Nierengarten,), RSC, Cambridge, 2007, pp. 191-211; for carbon nanotubes, see
4. F. Hauke, A. Hirsch, in Carbon Nanotubes and Related Structures: Synthesis Characterization, Functionalization, and Applications (Eds.:, D. M. Guldi, N. Martin,), Wiley-VCH, Weinheim, 2010, pp. 135-179; for grapheme, see
5. M. J. Allen, V. C. Tung, R. B. Kaner, Chem. Rev. 2010, 110, 132-145.
6. C. Nguyen, T. Yamada, P. Sarrazin, J. Li, J. Li, E. V. Barrera, M. L. Shofner, E. L. Corral, M. Meyyappan, in Carbon Nanotubes, Science and Applications (Ed.:, M. Meyyappan,), CRC Press, Boca Raton, 2005, pp. 171-352
7. H. G. Chae, J. Liu, S. Kumar, C. A. Dyke, J. Tour, in Carbon Nanotubes: Properties and Applications (Ed. , M. J. OConnell,), CRC Press, Boca Raton, 2006, pp. 213-295.
8. K. P. Loh, Q. Bao, P. K. Ang, J. Yang, J. Mater. Chem. 2010, 20, 2277-2289
9. O. C. Compton, S. T. Nguyen, Small 2010, 6, 711-723
10. D. W. Boukhvalov, M. I. Katsnelson, J. Phys. Condens. Matter 2009, 34, 1-12
11. S. Park, R. S. Ruoff, Nat. Nanotechnol. 2009, 4, 217-224
12. G. Cravotto, P. Cintas, Chem. Eur. J. 2010, 16, 5246-5259
13. C. N. Rao, A. K. Sood, K. S. Subrahmanyam, A. Govindaraj, Angew. Chem. 2009, 121, 7890-7916
14. Angew. Chem. Int. Ed. 2009, 48, 7752-7777.
15. X. Zhong, J. Jin, S. Li, Z. Niu, W. Hu, R. Li, J. Ma, Chem. Commun. 2010, 46, 7340-7342
16. T. A. Strom, E. P. Dillon, C. E. Hamilton, A. R. Barron, Chem. Commun. 2010, 46, 4097-4099
17. V. Georgakilas, A. B. Bourlinos, R. Zboril, T. A. Steriotis, P. Dallas, A. K. Stubos, C. Trapalis, Chem. Commun. 2010, 46, 1766-1768
18. M. Quintana, K. Spyrou, M. Grzelczak, W. R. Browne, P. Rudolf, M. Prato, ACS Nano 2010, 4, 3527-3533
19. J. R. Lomeda, C. D. Doyle, D. V. Kosynkin, W. Hwang, J. M. Tour, J. Am. Chem. Soc. 2008, 130, 16201-16206.
20. E. Bekyarova, M. E. Itkis, P. Ramesh, C. Berger, M. Sprinkle, W. A. de Heer, R. C. Haddon, J. Am. Chem. Soc. 2009, 131, 1336-1337
21. H. Liu, S. Ryu, Z. Chen, M. L. Steigerwald, C. Nuckolls, L. E. Brus, J. Am. Chem. Soc. 2009, 131, 17099-17101
22. L. H. Liu, M. M. Lerner, M. Yan, Nano Lett. 2010, 10, 3754-3756
23. S. Ryu, M. Y. Han, J. Maultzsch, T. F. Heinz, P. Kim, M. L. Steigerwald, L. E. Brus, Nano Lett. 2008, 8, 4597-4602
24. D. C. Elias, R. R. Nair, T. M. Mohiuddin, S. V. Morozov, M. P. Halsall, A. C. Ferrari, D. W. Boukhvalov, M. I. Katsnelson, A. K. Geim, K. S. Novoselov, Science 2009, 323, 610-613
25. S. B. Bon, L. Valentini, R. Verdejo, J. L. Fierro, L. Peponi, M. Lopez-Manchado, J. M. Kenny, Chem. Mater. 2009, 21, 3433-3438.
26. A. Hirsch, O. Vostrowsky, in Functional Molecular Nanostructures (Ed.:, D. A. Schluter,), Springer, Berlin, 2005, pp. 193-237
27. Z. F. Chen, W. Thiel, A. Hirsch, ChemPhysChem 2003, 4, 93-97
28. M. A. Hamon, M. E. Itkis, S. Niyogi, T. Alvaraez, C. Kuper, M. Menon, R. C. Haddon, J. Am. Chem. Soc. 2001, 123, 11292-11293
29. R. C. Haddon, J. Am. Chem. Soc. 1990, 112, 3385-3389
30. R. C. Haddon, Science 1993, 261, 1545-1550.
31. D. Dreyer, S. Park, C. Bielawski, R. S. Ruoff, Chem. Soc. Rev. 2010, 39, 228-240
32. W. Gao, L. B. Alemany, L. Ci, P. M. Ajayan, Nat. Chem. 2009, 1, 403-408
33. D. W. Boukhvalov, M. L. Katsnelson, J. Am. Chem. Soc. 2008, 130, 10697-10701
34. K. N. Kudin, B. Ozbas, H. C. Schniepp, R. K. Prudhomme, I. A. Aksay, R. Car, Nano. Lett. 2008, 8, 36-41.
35. S. N. Gradl, D. Trauner, in The Claisen Rearrangment: Methods and Applications (Eds.:, M. Hiersemann, U. Nubbermeyer,), Wiley-VCH, Weinheim, 2007, pp. 367-394
36. A. M. Martin Castro, Chem. Rev. 2004, 104, 2939-3002
37. A. E. Wick, D. Felix, K. Steen; A. Eschenmoser, Helv. Chim. Acta 1964, 47, 2425-2427
38. A. Eschenmoser, Helv. Chim. Acta 1964, 47, 2425-2427.
39. A large excess of DMDA is utilized to compensate for the monolayer of water found within the intersheet gallery of graphite oxide (see:, N. V. Medhekar, A. Ramasubramaniam, R. S. Ruoff, V. B. Shenoy, ACS Nano 2010, 4, 2300-2306).
40. D. Li, M. B. Muller, S. Gilje, R. B. Kaner, G. G. Wallace, Nat. Nanotechnol. 2008, 3, 101-105.
41. S. Stankovich, R. Piner, S. T. Nguyen, R. Ruoff, Carbon 2006, 44, 3342-3347
42. Y. Si, E. T. Samulski, Nano. Lett. 2008, 8, 1679-1682
43. S. Park, K. S. Lee, G. Bozoklu, W. Cai, S. T. Nguyen, R. S. Ruoff, ACS Nano 2008, 2, 572-578.
44. S. Stankovich, D. A. Dikin, O. C. Compton, G. H. Dommett, R. S. Ruoff, S. T. Nguyen, Chem. Mater. 2010, 22, 4153-4157.
45. A. Lerf, H. Y. He, M. Forster, J. Klinowski, J. Phys. Chem. B 1998, 102, 4477-4482
46. S. Stankovich, D. A. Dikin, P. D. Piner, K. A. Kohlhaas, A. Kleinhammes, Y. Jia, Y. Wu, S. T. Nguyen, R. S. Ruoff, Carbon 2007, 45, 1558-1566.
47. Alkylamides covalently bound to the edges of graphene eliminate at 300 °C. For the TGA, see, S. Niyogi, E. Bekyarova, M. E. Itkis, J. L. McWilliams, M. A. Hamon, R. C. Haddon, J. Am. Chem. Soc. 2006, 128, 7720-7721.
48. R. J. Jansen, H. Bekkum, Carbon 1995, 33, 1021-1027.
49. Irreversible incorporation of nitrogen by-products into graphene through high-temperature decomposition of N-methylpyrrolidine (NMP) has been shown by:, S. Dubin, S. Gilje, K. Wang, V. C. Tung, K. Cha, A. S. Hall, J. Farrar, R. Varshneya, Y. Yang, R. B. Kaner, ACS Nano 2010, 4, 3845-3852.
50. S. Park, J. An, R. P. Piner, S. Jin, X. Li, A. Velamakanne, R. S. Ruoff, Nano. Lett. 2009, 9, 1593-1597
51. H. Chen, M. B. Muller, K. J. Gilmore, C. G. Wallace, D. Li, Adv. Mater. 2008, 20, 3557-3561
52. S. Park, J. An, R. D. Piner, I. Jung, D. Yang, A. Velamakanni, S. T. Nguyen, R. S. Ruoff, Chem. Mater. 2008, 20, 6592-6594.
53. I. W. Hamley, in Introduction to Soft Matter: Polymers, Colloids, Amphiphiles and Liquid Crystals, 2nd ed., Wiley, New York, 2007, p. 340
54. J. N. Israelachvili, in Intermolecular and Surface Forces, 2 nd ed.; Academic Press, San Diego, 1992, p. 450.
55. F. Li, Y. Bao, Q. Zhang, D. Han, L. Niu, Langmuir 2010, 26, 12314-12320
56. M. Lotya, Y. Hernandez, P. J. King, R. J. Smith, V. Nicolosi, L. S. Karlsson, F. M. Blighe, S. De, Z. Wang, I. T. McGovern, G. S. Duesberg, J. N. Coleman, J. Am. Chem. Soc. 2009, 131, 3611-3620
57. Y. Xu, H. Bai, G. Lu, G. Shi, J. Am. Chem. Soc. 2008, 130, 5856-5857.