Covalent bulk functionalization of graphene
10.1038/nchem.1010
Crossref journal-article
Springer Science and Business Media LLC
Nature Chemistry (297)
Bibliography

Englert, J. M., Dotzer, C., Yang, G., Schmid, M., Papp, C., Gottfried, J. M., Steinrück, H.-P., Spiecker, E., Hauke, F., & Hirsch, A. (2011). Covalent bulk functionalization of graphene. Nature Chemistry, 3(4), 279–286.

Authors 10
  1. Jan M. Englert (first)
  2. Christoph Dotzer (additional)
  3. Guang Yang (additional)
  4. Martin Schmid (additional)
  5. Christian Papp (additional)
  6. J. Michael Gottfried (additional)
  7. Hans-Peter Steinrück (additional)
  8. Erdmann Spiecker (additional)
  9. Frank Hauke (additional)
  10. Andreas Hirsch (additional)
References 53 Referenced 609
  1. Novoselov, K. et al. Electric field effect in atomically thin carbon films. Science 306, 666–669 (2004). (10.1126/science.1102896) / Science by K Novoselov (2004)
  2. Allen, M., Tung, V. & Kaner, R. Honeycomb carbon: a review of graphene. Chem. Rev. 110, 132–145 (2010). (10.1021/cr900070d) / Chem. Rev. by M Allen (2010)
  3. Park, S. & Ruoff, R. S. Chemical methods for the production of graphenes. Nature Nanotech. 4, 217–224 (2009). (10.1038/nnano.2009.58) / Nature Nanotech. by S Park (2009)
  4. Bae, S. et al. Roll-to-roll production of 30-inch graphene films for transparent electrodes. Nature Nanotech. 5, 574–578 (2010). (10.1038/nnano.2010.132) / Nature Nanotech. by S Bae (2010)
  5. Emtsev, K. V. et al. Towards wafer-size graphene layers by atmospheric pressure graphitization of silicon carbide. Nature Mater. 8, 203 (2009). (10.1038/nmat2382) / Nature Mater. by KV Emtsev (2009)
  6. Englert, J. M. et al. Soluble graphene: generation of aqueous graphene solutions aided by a perylenebisimide-based bolaamphiphile. Adv. Mater. 21, 4265–4269 (2009). (10.1002/adma.200901578) / Adv. Mater. by JM Englert (2009)
  7. Hernandez, Y. et al. High-yield production of graphene by liquid-phase exfoliation of graphite. Nature Nanotech. 3, 563–568 (2008). (10.1038/nnano.2008.215) / Nature Nanotech. by Y Hernandez (2008)
  8. Staudenmaier, L. Verfahren zur Darstellung der Graphitsäure. Ber. Deutsch. Chem. Ges. 32, 1394–1399 (1899). (10.1002/cber.18990320208) / Ber. Deutsch. Chem. Ges. by L Staudenmaier (1899)
  9. Hummers, W. S. & Offeman, R. E. Preparation of graphitic oxide. J. Am. Chem. Soc. 80, 1339 (1958). (10.1021/ja01539a017) / J. Am. Chem. Soc. by WS Hummers (1958)
  10. Lotya, M. et al. Liquid phase production of graphene by exfoliation of graphite in surfactant/water solutions. J. Am. Chem. Soc. 131, 3611–3620 (2009). (10.1021/ja807449u) / J. Am. Chem. Soc. by M Lotya (2009)
  11. Liu, H. et al. Photochemical reactivity of graphene. J. Am. Chem. Soc. 131, 17099–17101 (2009). (10.1021/ja9043906) / J. Am. Chem. Soc. by H Liu (2009)
  12. Bekyarova, E. et al. Chemical modification of epitaxial graphene: spontaneous grafting of aryl groups. J. Am. Chem. Soc. 131, 1336–1337 (2009). (10.1021/ja8057327) / J. Am. Chem. Soc. by E Bekyarova (2009)
  13. Lomeda, J. R., Doyle, C. D., Kosynkin, D. V., Hwang, W-F. & Tour, J. M. Diazonium functionalization of surfactant-wrapped chemically converted graphene sheets. J. Am. Chem. Soc. 130, 16201–16206 (2008). (10.1021/ja806499w) / J. Am. Chem. Soc. by JR Lomeda (2008)
  14. Pan, Q., Wang, H. & Jiang, Y. Covalent modification of natural graphite with lithium benzoate multilayers via diazonium chemistry and their application in lithium ion batteries. Electrochem. Commun. 9, 754–760 (2007). (10.1016/j.elecom.2006.11.013) / Electrochem. Commun. by Q Pan (2007)
  15. Sharma, R., Baik, J. H., Perera, C. J. & Strano, M. S. Anomalously large reactivity of single graphene layers and edges toward electron transfer chemistries. Nano Lett. 10, 398 (2010). (10.1021/nl902741x) / Nano Lett. by R Sharma (2010)
  16. Sun, Z., Kohama, S-i., Zhang, Z., Lomeda, J. R. & Tour, J. M. Soluble graphene through edge-selective functionalization. Nano Res. 3, 117 (2010). (10.1007/s12274-010-1016-2) / Nano Res. by Z Sun (2010)
  17. Zhu, Y., Higginbotham, A. L. & Tour, J. M. Covalent functionalization of surfactant-wrapped graphene nanoribbons. Chem. Mater. 21, 5284–5291 (2009). (10.1021/cm902939n) / Chem. Mater. by Y Zhu (2009)
  18. Kudin, K. N. et al. Raman spectra of graphite oxide and functionalized graphene sheets. Nano Lett. 8, 36–41 (2008). (10.1021/nl071822y) / Nano Lett. by KN Kudin (2008)
  19. Syrgiannis, Z. et al. Reductive retrofunctionalization of single-walled carbon nanotubes. Angew. Chem. Int. Ed. 49, 3322–3325 (2010). (10.1002/anie.200906819) / Angew. Chem. Int. Ed. by Z Syrgiannis (2010)
  20. Liang, F. et al. A convenient route to functionalized carbon nanotubes. Nano Lett. 4, 1257–1260 (2004). (10.1021/nl049428c) / Nano Lett. by F Liang (2004)
  21. Billups, W. E., Liang, F., Chattopadhyay, J. & Beach, J. M. Uses of single wall carbon nanotube salts in organic syntheses. ECS Trans. 2, 65–76 (2007). (10.1149/1.2408953) / ECS Trans. by WE Billups (2007)
  22. Wunderlich, D., Hauke, F. & Hirsch, A. Preferred functionalization of metallic and small-diameter single walled carbon nanotubes via reductive alkylation. J. Mater. Chem. 18, 1493–1497 (2008). (10.1039/b716732f) / J. Mater. Chem. by D Wunderlich (2008)
  23. Haddon, R. C. π-electrons in three dimensions. Acc. Chem. Res. 21, 243–249 (1988). (10.1021/ar00150a005) / Acc. Chem. Res. by RC Haddon (1988)
  24. Haddon, R. C. C60: sphere or polyhedron? J. Am. Chem. Soc. 119, 1797–1798 (1997). (10.1021/ja9637659) / J. Am. Chem. Soc. by RC Haddon (1997)
  25. Chen, Z., Thiel, W. & Hirsch, A. Reactivity of the convex and concave surfaces of single-walled carbon nanotubes (SWCNTs) towards addition reactions: dependence on the carbon-atom pyramidalization. ChemPhysChem 4, 93–97 (2003). (10.1002/cphc.200390015) / ChemPhysChem by Z Chen (2003)
  26. Stephenson, J. J., Sadana, A. K., Higginbotham, A. L. & Tour, J. M. Highly functionalized and soluble multiwalled carbon nanotubes by reductive alkylation and arylation: the Billups reaction. Chem. Mater. 18, 4658–4661 (2006). (10.1021/cm060832h) / Chem. Mater. by JJ Stephenson (2006)
  27. Strano, M. S. et al. Electronic structure control of single-walled carbon nanotube functionalization. Science 301, 1519–1522 (2003). (10.1126/science.1087691) / Science by MS Strano (2003)
  28. Sinitskii, A. et al. Kinetics of diazonium functionalization of chemically converted graphene nanoribbons. ACS Nano 4, 1949–1954 (2010). (10.1021/nn901899j) / ACS Nano by A Sinitskii (2010)
  29. Sharma, R., Nair, N. & Strano, M. S. Structure–reactivity relationships for graphene nanoribbons. J. Phys. Chem. C 113, 14771–14777 (2009). (10.1021/jp904814h) / J. Phys. Chem. C by R Sharma (2009)
  30. Usrey, M. L., Lippmann, E. S. & Strano, M. S. Evidence for a two-step mechanism in electronically selective single-walled carbon nanotube reactions. J. Am. Chem. Soc. 127, 16129–16135 (2005). (10.1021/ja0537530) / J. Am. Chem. Soc. by ML Usrey (2005)
  31. Fantini, C., Pimenta, M. A. & Strano, M. S. Two-phonon combination Raman modes in covalently functionalized single-wall carbon nanotubes. J. Phys. Chem. C 112, 13150–13155 (2008). (10.1021/jp803855z) / J. Phys. Chem. C by C Fantini (2008)
  32. Rüdorff, W. Einlagerungsverbindungen mit Alkali- und Erdalkalimetallen. Angew. Chem. 71, 487–491 (1959). (10.1002/ange.19590711504) / Angew. Chem. by W Rüdorff (1959)
  33. Rüdorff, W. & Schulze, E. Über Alkaligraphitverbindungen. Z. Anorg. Allg. Chem. 277, 156–171 (1954). (10.1002/zaac.19542770307) / Z. Anorg. Allg. Chem. by W Rüdorff (1954)
  34. Ginderow, D. Preparation of insertion compounds in graphite from liquid reagents. Ann. Chim. 6, 5–16 (1971). / Ann. Chim. by D Ginderow (1971)
  35. Vallés, C. et al. Solutions of negatively charged graphene sheets and ribbons. J. Am. Chem. Soc. 130, 15802–15804 (2008). (10.1021/ja808001a) / J. Am. Chem. Soc. by C Vallés (2008)
  36. Allongue, P. et al. Covalent modification of carbon surfaces by aryl radicals generated from the electrochemical reduction of diazonium salts. J. Am. Chem. Soc. 119, 201–207 (1997). (10.1021/ja963354s) / J. Am. Chem. Soc. by P Allongue (1997)
  37. Viculis, L. M., Mack, J. J. & Kaner, R. B. A chemical route to carbon nanoscrolls. Science 299, 1361 (2003). (10.1126/science.1078842) / Science by LM Viculis (2003)
  38. Schniepp, H. C. et al. Functionalized single graphene sheets derived from splitting graphite oxide. J. Phys. Chem. B 110, 8535–8539 (2006). (10.1021/jp060936f) / J. Phys. Chem. B by HC Schniepp (2006)
  39. Erickson, K. et al. Determination of the local chemical structure of graphene oxide and reduced graphene oxide. Adv. Mater. 22, 4467–4472 (2010). (10.1002/adma.201000732) / Adv. Mater. by K Erickson (2010)
  40. Ferrari, A. et al. Raman spectrum of graphene and graphene layers. Phys. Rev. Lett. 97, 187401 (2006). (10.1103/PhysRevLett.97.187401) / Phys. Rev. Lett. by A Ferrari (2006)
  41. Abergel, D. S. L., Russell, A. & Fal'ko, V. I. Visibility of graphene flakes on a dielectric substrate. Appl. Phys. Lett. 91, 063125 (2007). (10.1063/1.2768625) / Appl. Phys. Lett. by DSL Abergel (2007)
  42. Blake, P. et al. Making graphene visible. Appl. Phys. Lett. 91, 063124 (2007). (10.1063/1.2768624) / Appl. Phys. Lett. by P Blake (2007)
  43. Solin, S. A. Raman and IR studies of intercalated graphite. Physica 99B, 443–453 (1980). / Physica by SA Solin (1980)
  44. Berciaud, S., Ryu, S., Brus, L. E. & Heinz, T. F. Probing the intrinsic properties of exfoliated graphene: Raman spectroscopy of free-standing monolayers. Nano Lett. 9, 346–352 (2009). (10.1021/nl8031444) / Nano Lett. by S Berciaud (2009)
  45. Nemanich, R. J., Glass, J. T., Lucovsky, G. & Shroder, R. E. Raman scattering characterization of carbon bonding in diamond and diamondlike thin films. J. Vac. Sci. Technol. A 6, 1783–1787 (1988). (10.1116/1.575297) / J. Vac. Sci. Technol. A by RJ Nemanich (1988)
  46. Ferrari, A. C. & Robertson, J. Origin of the 1150 cm−1 Raman mode in nanocrystalline diamond. Phys. Rev. B 63, 121405 (2001). (10.1103/PhysRevB.63.121405) / Phys. Rev. B by AC Ferrari (2001)
  47. Graf, D. et al. Spatially resolved Raman spectroscopy of single- and few-layer graphene. Nano Lett. 7, 238–242 (2007). (10.1021/nl061702a) / Nano Lett. by D Graf (2007)
  48. Basko, D. M. Effect of inelastic collisions on multiphonon Raman scattering in graphene. Phys. Rev. B 76, 081405 (2007). (10.1103/PhysRevB.76.081405) / Phys. Rev. B by DM Basko (2007)
  49. Jung, N. et al. Charge transfer chemical doping of few layer graphenes: charge distribution and band gap formation. Nano Lett. 9, 4133–4137 (2009). (10.1021/nl902362q) / Nano Lett. by N Jung (2009)
  50. Lindberg, B. J. et al. Molecular spectroscopy by means of ESCA. II. Sulfur compounds. Correlation of electron binding energy with structure. Phys. Scripta 1, 286 (1970). (10.1088/0031-8949/1/5-6/020) / Phys. Scripta by BJ Lindberg (1970)
  51. Ruangchuay, L., Schwank, J. & Sirivat, A. Surface degradation of α-naphthalene sulfonate-doped polypyrrole during XPS characterization. Appl. Surf. Sci. 199, 128 (2002). (10.1016/S0169-4332(02)00564-0) / Appl. Surf. Sci. by L Ruangchuay (2002)
  52. Tour, J. M. et al. Self-assembled monolayers and multilayers of conjugated thiols, α,w-dithiols, and thioacetyl-containing adsorbates. Understanding attachments between potential molecular wires and gold surfaces. J. Am. Chem. Soc. 117, 9529 (1995). (10.1021/ja00142a021) / J. Am. Chem. Soc. by JM Tour (1995)
  53. Buchner, F. et al. Coordination of iron atoms by tetraphenylporphyrin monolayers and multilayers on Ag(111) and formation of iron-tetraphenylporphyrin. J. Phys. Chem. C 112, 15458 (2008). (10.1021/jp8052955) / J. Phys. Chem. C by F Buchner (2008)
Dates
Type When
Created 14 years, 5 months ago (March 18, 2011, 9:51 a.m.)
Deposited 2 years, 3 months ago (May 18, 2023, 3:53 p.m.)
Indexed 1 day, 11 hours ago (Aug. 24, 2025, 6:48 p.m.)
Issued 14 years, 5 months ago (March 20, 2011)
Published 14 years, 5 months ago (March 20, 2011)
Published Online 14 years, 5 months ago (March 20, 2011)
Published Print 14 years, 4 months ago (April 1, 2011)
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@article{Englert_2011, title={Covalent bulk functionalization of graphene}, volume={3}, ISSN={1755-4349}, url={http://dx.doi.org/10.1038/nchem.1010}, DOI={10.1038/nchem.1010}, number={4}, journal={Nature Chemistry}, publisher={Springer Science and Business Media LLC}, author={Englert, Jan M. and Dotzer, Christoph and Yang, Guang and Schmid, Martin and Papp, Christian and Gottfried, J. Michael and Steinrück, Hans-Peter and Spiecker, Erdmann and Hauke, Frank and Hirsch, Andreas}, year={2011}, month=mar, pages={279–286} }