Chemical functionalization of graphene by carbene cycloaddition: A density functional theory study

Applied Surface Science

Volumn 311, Issue , 2014, Pages 377-383

  Zan, Wenyan ^a  

^a LANZHOU UNIVERSITY   (China)

Author keywords

Carbene groups; DFT; Functionalization; Graphene

Indexed keywords

BINDING ENERGY; CHLORINE COMPOUNDS; DENSITY FUNCTIONAL THEORY; ELECTRONIC PROPERTIES; ENERGY GAP; MOLECULES; NANORIBBONS; NITROGEN OXIDES; ORGANIC COMPOUNDS;

CARBENES; CHEMICAL FUNCTIONALIZATION; DENSITY FUNCTIONAL THEORY STUDIES; ENERGETIC AND ELECTRONIC PROPERTIES; FUNCTIONALIZATIONS; GRAPHENE NANO-RIBBON; MOLECULAR MECHANISM; THREE-MEMBERED RINGS;

GRAPHENE;

EID: 84903398415     PISSN: 01694332     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.apsusc.2014.05.071     Document Type: Article

References (40)

1. A.K. Geim, and K.S. Novoselov The rise of graphene Nat. Mater. 6 2007 183 191
2. A.K. Geim Graphene: status and prospects Science 324 2009 1530 1534
3. K.S. Novoselov, Z. Jiang, Y. Zhang, S. Morozov, H. Stormer, U. Zeitler, J. Maan, G. Boebinger, P. Kim, and A. Geim Room-temperature quantum Hall effect in graphene Science 315 2007 1379
4. C. Lee, X. Wei, J.W. Kysar, and J. Hone Measurement of the elastic properties and intrinsic strength of monolayer graphene Science 321 2008 385 388
5. J.S. Bunch, A.M. Van der Zande, S.S. Verbridge, I.W. Frank, D.M. Tanenbaum, J.M. Parpia, H.G. Craighead, and P.L. McEuen Electromechanical resonators from graphene sheets Science 315 2007 490 493
6. M.Y. Han, B. Özyilmaz, Y. Zhang, and P. Kim Energy band-gap engineering of graphene nanoribbons Phys. Rev. Lett. 98 2007 206805
7. W. Choi, I. Lahiri, R. Seelaboyina, and Y.S. Kang Synthesis of graphene and its applications: a review Crit. Rev. Solid State Mater. Sci. 35 2010 52 71
8. D. Abergel, V. Apalkov, J. Berashevich, K. Ziegler, and T. Chakraborty Properties of graphene: a theoretical perspective Adv. Phys. 59 2010 261 482
9. J. Chen, M.A. Hamon, H. Hu, Y. Chen, A.M. Rao, P.C. Eklund, and R.C. Haddon Solution properties of single-walled carbon nanotubes Science 282 1998 95 98
10. K. Kamaras, M. Itkis, H. Hu, B. Zhao, and R. Haddon Covalent bond formation to a carbon nanotube metal Science 301 2003 1501
11. M.-D. Su Theoretical study of addition reactions of heavy carbenes to carbon and boron nitride nanotubes J. Phys. Chem. B 109 2005 21647 21657
12. Y.-S. Lee, and N. Marzari Cycloadditions to control bond breaking in naphthalenes, fullerenes, and carbon nanotubes: a first-principles study J. Phys. Chem. C 112 2008 4480 4485
13. H.F. Bettinger Addition of carbenes to the sidewalls of single-walled carbon nanotubes Chem.-A Eur. J. 12 2006 4372 4379
14. F. Cao, W. Ren, X. Xu, Y.-m. Ji, and C. Zhao Boron nitride nanotubes functionalized by a series of carbenes Phys. Chem. Chem. Phys. 11 2009 6256 6262
15. J. Lu, S. Nagase, X. Zhang, Y. Maeda, T. Wakahara, T. Nakahodo, T. Tsuchiya, T. Akasaka, D. Yu, and Z. Gao Structural evolution of [2 + 1] cycloaddition derivatives of single-wall carbon nanotubes: from open structure to closed three-membered ring structure with increasing tube diameter J. Mol. Struct: Theochem 725 2005 255 257
16. T. Yumura, and M. Kertesz Cooperative behaviors in carbene additions through local modifications of nanotube surfaces Chem. Mater. 19 2007 1028 1034
17. H. Xu, and K.S. Suslick Sonochemical preparation of functionalized graphenes J. Am. Chem. Soc. 133 2011 9148 9151
18. L.-H. Liu, M.M. Lerner, and M. Yan Derivitization of pristine graphene with well-defined chemical functionalities Nano Lett. 10 2010 3754 3756
19. H. Ismaili, D. Geng, A.X. Sun, T.T. Kantzas, and M.S. Workentin Light-activated covalent formation of gold nanoparticle-graphene and gold nanoparticle-glass composites Langmuir 27 2011 13261 13268
20. C. KiangáChua, A. Ambrosi, and M. Pumera Introducing dichlorocarbene in graphene Chem. Commun. 48 2012 5376 5378
21. X. Zhong, J. Jin, S. Li, Z. Niu, W. Hu, R. Li, and J. Ma Aryne cycloaddition: highly efficient chemical modification of graphene Chem. Commun. 46 2010 7340 7342
22. J.P. Perdew, K. Burke, and M. Ernzerhof Generalized gradient approximation made simple Phys. Rev. Lett. 77 1996 3865 3868
23. B. Delley An all-electron numerical method for solving the local density functional for polyatomic molecules J. Chem. Phys. 92 1990 508
24. J. Dai, and J. Yuan Adsorption of molecular oxygen on doped graphene: atomic, electronic, and magnetic properties Phys. Rev. B 81 2010 165414
25. K. Suggs, D. Reuven, and X.-Q. Wang Electronic properties of cycloaddition-functionalized graphene J. Phys. Chem. C 115 2011 3313 3317
26. W.I. Choi, S.-H. Jhi, K. Kim, and Y.-H. Kim Divacancy-nitrogen-assisted transition metal dispersion and hydrogen adsorption in defective graphene: a first-principles study Phys. Rev. B 81 2010 085441
27. P.V. Medeiros, G.K. Gueorguiev, and S. Stafström Benzene, coronene, and circumcoronene adsorbed on gold, and a gold cluster adsorbed on graphene: structural and electronic properties Phys. Rev. B 85 2012 205423
28. H.J. Monkhorst, and J.D. Pack Special points for Brillouin-zone integrations Phys. Rev. B 13 1976 5188 5192
29. T.A. Halgren, and W.N. Lipscomb The synchronous-transit method for determining reaction pathways and locating molecular transition states Chem. Phys. Lett. 49 1977 225 232
30. N. Govind, M. Petersen, G. Fitzgerald, D. King-Smith, and J. Andzelm A generalized synchronous transit method for transition state location Comput. Mater. Sci. 28 2003 250 258
31. E. Song, Z. Wen, and Q. Jiang CO catalytic oxidation on copper-embedded graphene J. Phys. Chem. C 115 2011 3678 3683
32. Z. Ao, and F. Peeters Electric field: a catalyst for hydrogenation of graphene Appl. Phys. Lett. 96 2010 253106-253106-253103
33. Z. Ao, and F. Peeters Electric field activated hydrogen dissociative adsorption to nitrogen-doped graphene J. Phys. Chem. C 114 2010 14503 14509
34. S. Tang, and Z. Cao Adsorption and dissociation of ammonia on graphene oxides: a first-principles study J. Phys. Chem. C 116 2012 8778 8791
35. L. Xu, C.E. Doubleday, and K. Houk Dynamics of carbene cycloadditions J. Am. Chem. Soc. 133 2011 17848 17854
36. S. Lany, and A. Zunger Assessment of correction methods for the band-gap problem and for finite-size effects in supercell defect calculations: case studies for ZnO and GaAs Phys. Rev. B 78 2008 235104
37. Z. Wu, J. Neaton, and J.C. Grossman Charge separation via strain in silicon nanowires Nano Lett. 9 2009 2418 2422
38. W. Geng, H. Liu, and X. Yao Enhanced photocatalytic properties of titania - graphene nanocomposites: a density functional theory study Phys. Chem. Chem. Phys. 15 2013 6025 6033
39. W. Geng, X. Zhao, W. Zan, H. Liu, and X. Yao Effects of the electric field on the properties of ZnO - graphene composites: a density functional theory study Phys. Chem. Chem. Phys. 2014
40. K. Nakada, M. Fujita, G. Dresselhaus, and M.S. Dresselhaus Edge state in graphene ribbons: nanometer size effect and edge shape dependence Phys. Rev. B 54 1996 17954