Chemical Bonding of Partially Fluorinated Graphene

Journal of Physical Chemistry C

Volumn 118, Issue 45, 2014, Pages 26402-26408

  Zhou, Si ^a   Sherpa, Sonam D ^a   Hess, Dennis W ^a   Bongiorno, Angelo ^a  

^a GEORGIA INSTITUTE OF TECHNOLOGY   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

CARBON; DENSITY FUNCTIONAL THEORY; FLUORINE; FLUORINE COMPOUNDS; GRAPHENE;

CARBON FLUORIDES; CHEMICAL ADDITIVE; CHEMICAL BONDINGS; CHEMICALLY-MODIFIED GRAPHENE; HIGHLY STABLES; ORTHO POSITION; PARA POSITION; PARTIALLY FLUORINATED;

CHEMICAL BONDS;

EID: 84937231913     PISSN: 19327447     EISSN: 19327455     Source Type: Journal    
DOI: 10.1021/jp508965q     Document Type: Article

References (59)

1. Worsley, K. A.; Ramesh, P.; Mandal, S. K.; Niyogi, S.; Itkis, M. E.; Haddon, R. C. Soluble Graphene Derived from Graphite Fluoride Chem. Phys. Lett. 2007, 445, 51-56
2. Damien, D.; Sudeep, P. M.; Narayanan, T. N.; Anantharaman, M. R.; Ajayan, P. M.; Shaijumon, M. M. Fluorinated Graphene Based Electrodes for High Performance Primary Lithium Batteries RSC Adv. 2013, 3, 25702-25706
3. Kwon, S.; Ko, J. H.; Jeon, K. J.; Kim, Y. H.; Park, J. Y. Enhanced Nanoscale Friction on Fluorinated Graphene Nano Lett. 2012, 12, 6043-6048
4. Robinson, J. T.; Burgess, J. S.; Junkermeier, C. E.; Badescu, S. C.; Reinecke, T. L.; Perkins, F. K.; Zalalutdniov, M. K.; Baldwin, J. W.; Culbertson, J. C.; Sheehan, P. E. Properties of Fluorinated Graphene Films Nano Lett. 2010, 10, 3001-3005
5. Nair, R. R.; Sepioni, M.; Tsai, I. L.; Lehtinen, O.; Keinonen, J.; Krasheninnikov, A. V.; Thomson, T.; Geim, A. K.; Grigorieva, I. V. Spin-Half Paramagnetism in Graphene Induced by Point Defects Nat. Phys. 2012, 8, 199-202
6. Cheng, S. H.; Zou, K.; Okino, F.; Gutierrez, H. R.; Gupta, A.; Shen, N.; Eklund, P. C.; Sofo, J. O.; Zhu, J. Reversible Fluorination of Graphene: Evidence of a Two-Dimensional Wide Bandgap Semiconductor Phys. Rev. B 2010, 81, 205435
7. Withers, F.; Dubois, M.; Savchenko, A. K. Electron Properties of Fluorinated Single-Layer Graphene Transistors Phys. Rev. B 2010, 82, 073403
8. Zboril, R.; Karlicky, F.; Bourlinos, A. B.; Steriotis, T. A.; Stubos, A. K.; Georgakilas, V.; Safarova, K.; Jancik, D.; Trapalis, C.; Otyepka, M. Graphene Fluoride: A Stable Stoichiometric Graphene Derivative and Its Chemical Conversion to Graphene Small 2010, 6, 2885-2891
9. Lee, W. K.; Haydell, M.; Robinson, J. T.; Laracuente, A. R.; Cimpoiasu, E.; King, W. P.; Sheehan, P. E. Nanoscale Reduction of Graphene Fluoride Via Thermochemical Nanolithography ACS Nano 2013, 7, 6219-6224
10. Sherpa, S. D.; Levitin, G.; Hess, D. W. Effect of the Polarity of Carbon-Fluorine Bonds on the Work Function of Plasma-Fluorinated Epitaxial Graphene Appl. Phys. Lett. 2012, 101, 111602
11. Dikin, D. A.; Stankovich, S.; Zimney, E. J.; Piner, R. D.; Dommett, G. H. B.; Evmenenko, G.; Nguyen, S. T.; Ruoff, R. S. Preparation and Characterization of Graphene Oxide Paper Nature 2007, 448, 457-460
12. Jung, I.; Dikin, D. A.; Piner, R. D.; Ruoff, R. S. Tunable Electrical Conductivity of Individual Graphene Oxide Sheets Reduced at Low Temperatures Nano Lett. 2008, 8, 4283-4287
13. Yang, D.; Velamakanni, A.; Bozoklu, G.; Park, S.; Stoller, M.; Piner, R. D.; Stankovich, S.; Jung, I.; Field, D. A.; Ventrice, C. A. Chemical Analysis of Graphene Oxide Films after Heat and Chemical Treatments by X-Ray Photoelectron and Micro-Raman Spectroscopy Carbon 2009, 47, 145-152
14. Kim, S.; Zhou, S.; Hu, Y. K.; Acik, M.; Chabal, Y. J.; Berger, C.; de Heer, W.; Bongiorno, A.; Riedo, E. Room-Temperature Metastability of Multilayer Graphene Oxide Films Nat. Mater. 2012, 11, 544-549
15. Zhou, S.; Bongiorno, A. Origin of the Chemical and Kinetic Stability of Graphene Oxide. Sci. Rep-Uk 2013, 3.
16. Zhou, S.; Kim, S.; Bongiorno, A. Chemical Structure of Oxidized Multilayer Epitaxial Graphene: A Density Functional Theory Study J. Phys. Chem. C 2013, 117, 6267-6274
17. Zhou, S.; Bongiorno, A. Density Functional Theory Modeling of Multilayer Epitaxial Graphene Oxide. Acc. Chem. Res. 2014.
18. Zhou, S.; Kim, S.; Di Gennaro, E.; Hu, Y.; Gong, C.; Lu, X.; Berger, C.; de Heer, W.; Riedo, E.; Chabal, Y. J. Film Structure of Epitaxial Graphene Oxide on SiC: Insight on the Relationship between Interlayer Spacing, Water Content, and Intralayer Structure Adv. Mater. Interfaces 2014, 1, 1300106
19. Bekyarova, E.; Itkis, M. E.; Ramesh, P.; Berger, C.; Sprinkle, M.; de Heer, W. A.; Haddon, R. C. Chemical Modification of Epitaxial Graphene: Spontaneous Grafting of Aryl Groups J. Am. Chem. Soc. 2009, 131, 1336-1337
20. Sarkar, S.; Bekyarova, E.; Haddon, R. C. Chemistry at the Dirac Point: Diels-Alder Reactivity of Graphene Acc. Chem. Res. 2012, 45, 673-682
21. Stine, R.; Lee, W. K.; Whitener, K. E.; Robinson, J. T.; Sheehan, P. E. Chemical Stability of Graphene Fluoride Produced by Exposure to XeF2 Nano Lett. 2013, 13, 4311-4316
22. Withers, F.; Russo, S.; Dubois, M.; Craciun, M. F. Tuning the Electronic Transport Properties of Graphene through Functionalisation with Fluorine Nanoscale Res. Lett. 2011, 6, 526-537
23. Mallouk, T.; Bartlett, N. Reversible Intercalation of Graphite by Fluorine: A New Bifluoride, C12HF2, and Graphite Fluorides, Cxf (5 > x > 2) J. Chem. Soc., Chem. Commun. 1983, 103-105
24. Palchan, I.; Crespin, M.; Estradeszwarckopf, H.; Rousseau, B. Graphite Fluorides-an XPS Study of a New Type of C-F Bonding Chem. Phys. Lett. 1989, 157, 321-327
25. Divittorio, S. L.; Dresselhaus, M. S.; Dresselhaus, G. A Model for Disorder in Fluorine-Intercalated Graphite J. Mater. Res. 1993, 8, 1578-1585
26. Tressaud, A.; Moguet, F.; Flandrois, S.; Chambon, M.; Guimon, C.; Nanse, G.; Papirer, E.; Gupta, V.; Bahl, O. P. On the Nature of C-F Bonds in Various Fluorinated Carbon Materials: XPS and TEM Investigations J. Phys. Chem. Solids 1996, 57, 745-751
27. Nansé, G.; Papirer, E.; Fioux, P.; Moguet, F.; Tressaud, A. Fluorination of Carbon Blacks: An X-Ray Photoelectron Spectroscopy Study: I. A Literature Review of Xps Studies of Fluorinated Carbons. XPS Investigation of Some Reference Compounds Carbon 1997, 35, 175-194
28. 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
29. Khabashesku, V. N.; Billups, W. E.; Margrave, J. L. Fluorination of Single-Wall Carbon Nanotubes and Subsequent Derivatization Reactions Acc. Chem. Res. 2002, 35, 1087-1095
30. Pehrsson, P. E.; Zhao, W.; Baldwin, J. W.; Song, C. H.; Liu, J.; Kooi, S.; Zheng, B. Thermal Fluorination and Annealing of Single-Wall Carbon Nanotubes J. Phys. Chem. B 2003, 107, 5690-5695
31. Chamssedine, F.; Claves, D. Three Different Modes of Fluorine Chemisorption at the Surface of Single Wall Carbon Nanotubes Chem. Phys. Lett. 2007, 443, 102-106
32. Shulga, Y. M.; Tien, T. C.; Huang, C. C.; Lo, S. C.; Muradyan, V.; Polyakova, N. V.; Ling, Y. C.; Loutfy, R. O.; Moravsky, A. P. XPS Study of Fluorinated Carbon Multi-Walled Nanotubes J. Electron Spectrosc. Relat. Phenom. 2007, 160, 22-28
33. Panich, A. M. Nuclear Magnetic Resonance Study of Fluorine-Graphite Intercalation Compounds and Graphite Fluorides Synth. Met. 1999, 100, 169-185
34. Sato, Y.; Itoh, K.; Hagiwara, R.; Fukunaga, T.; Ito, Y. On the So-Called Semi-Ionic C-F Bond Character in Fluorine-GIC Carbon 2004, 42, 3243-3249
35. Delabarre, C.; Guerin, K.; Dubois, M.; Giraudet, J.; Fawal, Z.; Hamwi, A. Highly Fluorinated Graphite Prepared from Graphite Fluoride Formed Using BF3 Catalyst J. Fluor. Chem. 2005, 126, 1078-1087
36. Lee, Y. S. Syntheses and Properties of Fluorinated Carbon Materials J. Fluor. Chem. 2007, 128, 392-403
37. Vyalikh, A.; Bulusheva, L. G.; Chekhova, G. N.; Pinakov, D. V.; Okotrub, A. V.; Scheler, U. Fluorine Patterning in Room-Temperature Fluorinated Graphite Determined by Solid-State NMR and DFT J. Phys. Chem. C 2013, 117, 7940-7948
38. Sherpa, S. D.; Paniagua, S. A.; Levitin, G.; Marder, S. R.; Williams, M. D.; Hess, D. W. Photoelectron Spectroscopy Studies of Plasma-Fluorinated Epitaxial Graphene J. Vac. Sci. Technol. B 2012, 30, 03D102-107
39. Leenaerts, O.; Peelaers, H.; Hernandez-Nieves, A. D.; Partoens, B.; Peeters, F. M. First-Principles Investigation of Graphene Fluoride and Graphane Phys. Rev. B 2010, 82, 195436
40. Sahin, H.; Topsakal, M.; Ciraci, S. Structures of Fluorinated Graphene and Their Signatures Phys. Rev. B 2011, 83, 115432
41. Sivek, J.; Leenaerts, O.; Partoens, B.; Peeters, F. M. First-Principles Investigation of Bilayer Fluorographene J. Phys. Chem. C 2012, 116, 19240-19245
42. Wei, W.; Jacob, T. Electronic and Optical Properties of Fluorinated Graphene: A Many-Body Perturbation Theory Study Phys. Rev. B 2013, 87, 115431
43. Han, S. S.; Yu, T. H.; Merinov, B. V.; van Duin, A. C. T.; Yazami, R.; Goddard, W. A. Unraveling Structural Models of Graphite Fluorides by Density Functional Theory Calculations Chem. Mater. 2010, 22, 2142-2154
44. Bettinger, H. F.; Kudin, K. N.; Scuseria, G. E. Structural Models of Fluorine-Graphite Intercalation Compounds from Density Functional Theory J. Phys. Chem. A 2004, 108, 3016-3018
45. Karlicky, F.; Zboril, R.; Otyepka, M. Band Gaps and Structural Properties of Graphene Halides and Their Derivates: A Hybrid Functional Study with Localized Orbital Basis Sets J. Chem. Phys. 2012, 137, 034709
46. Shi, H. L.; Pan, H.; Zhang, Y. W.; Yakobson, B. I. Electronic and Magnetic Properties of Graphene/Fluorographene Superlattices J. Phys. Chem. C 2012, 116, 18278-18283
47. Dresselhaus, M. S.; Dresselhaus, G. Intercalation Compounds of Graphite Adv. Phys. 1981, 30, 139-326
48. Dresselhaus, M. S.; Dresselhaus, G. Intercalation Compounds of Graphite Adv. Phys. 2002, 51, 1-186
49. Panich, A. M. Nuclear Magnetic Resonance Study of Fluorine-Graphite Intercalation Compounds and Graphite Fluorides Synth. Met. 1999, 100, 169-185
50. Giannozzi, P.; Baroni, S.; Bonini, N.; Calandra, M.; Car, R.; Cavazzoni, C.; Ceresoli, D.; Chiarotti, G. L.; Cococcioni, M.; Dabo, I. Quantum Espresso: A Modular and Open-Source Software Project for Quantum Simulations of Materials J. Phys.: Condens. Mater. 2009, 21, 395502
51. Troullier, N.; Martins, J. L. Efficient Pseudopotentials for Plane-Wave Calculations Phys. Rev. B 1991, 43, 1993-2006
52. Perdew, J. P.; Burke, K.; Ernzerhof, M. Generalized Gradient Approximation Made Simple Phys. Rev. Lett. 1996, 77, 3865-3868
53. Grimme, S. Semiempirical GGA-Type Density Functional Constructed with a Long-Range Dispersion Correction J. Comput. Chem. 2006, 27, 1787-1799
54. Andersen, J. N.; Hennig, D.; Lundgren, E.; Methfessel, M.; Nyholm, R.; Scheffler, M. Surface Core-Level Shifts of Some 4d-Metal Single-Crystal Surfaces: Experiments and Ab Initio Calculations Phys. Rev. B 1994, 50, 17525-17533
55. Fuchs, M.; Scheffler, M. Ab Initio Pseudopotentials for Electronic Structure Calculations of Poly-Atomic Systems Using Density-Functional Theory Comput. Phys. Commun. 1999, 119, 67-98
56. Blondel, C.; Delsart, C.; Goldfarb, F. Electron Spectrometry at the ∼eV Level and the Electron Affinities of Si and F J. Phys. B: At. Mol. Opt. 2001, 34, 2757-2757
57. Panchal, V.; Pearce, R.; Yakimova, R.; Tzalenchuk, A.; Kazakova, O. Standardization of Surface Potential Measurements of Graphene Domains Sci. Rep. 2013, 3, 2597
58. Perdew, J. P.; Parr, R. G.; Levy, M.; Balduz, J. L. Density-Functional Theory for Fractional Particle Number-Derivative Discontinuities of the Energy Phys. Rev. Lett. 1982, 49, 1691-1694
59. Berger, C.; Song, Z.; Li, T.; Li, X.; Ogbazghi, A. Y.; Feng, R.; Dai, Z.; Marchenkov, A. N.; Conrad, E. H.; First, P. N. Ultrathin Epitaxial Graphite: 2d Electron Gas Properties and a Route toward Graphene-Based Nanoelectronics J. Phys. Chem. B 2004, 108, 19912-19916