Scanning tunneling and atomic force microscopy evidence for covalent and noncovalent interactions between aryl films and highly ordered pyrolytic graphite

Journal of Physical Chemistry C

Volumn 118, Issue 11, 2014, Pages 5820-5826

  Ma, Haifeng ^a   Lee, Lita ^a   Brooksby, Paula A ^a   Brown, Simon A ^a   Fraser, Sara J ^a,b   Gordon, Keith C ^a,b   Leroux, Yann R ^c   Hapiot, Philippe ^c   Downard, Alison J ^a  

^a UNIVERSITY OF CANTERBURY   (New Zealand)

^b UNIVERSITY OF OTAGO   (New Zealand)

^c CNRS   (France)

Author keywords

[No Author keywords available]

Indexed keywords

ATOMIC-LEVEL RESOLUTION; COVALENT ATTACHMENT; GRAPHITE SURFACES; HIGHLY ORDERED PYROLYTIC GRAPHITES; NON-COVALENT INTERACTION; NONCONTACT ATOMIC FORCE MICROSCOPY; SCANNING TUNNELING AND ATOMIC FORCE MICROSCOPY; ULTRAHIGH VACUUM SCANNING TUNNELING MICROSCOPIES;

ATOMIC FORCE MICROSCOPY; ELECTROLYTIC REDUCTION; GRAPHITE; IONS; SCANNING TUNNELING MICROSCOPY;

PYROLYSIS;

EID: 84897854330     PISSN: 19327447     EISSN: 19327455     Source Type: Journal    
DOI: 10.1021/jp411826s     Document Type: Article

References (38)

1. McCreery, R. L. Advanced Carbon Electrode Materials for Molecular Electrochemistry Chem. Rev. 2008, 108, 2646-2687
2. Bélanger, D.; Pinson, J. Electrografting: A Powerful Method for Surface Modification Chem. Soc. Rev. 2011, 40, 3995-4048
3. Delamar, M.; Hitmi, R.; Pinson, J.; Saveant, J. M. Covalent Modification of Carbon Surfaces by Grafting of Functionalized Aryl Radicals Produced from Electrochemical Reduction of Diazonium Salts J. Am. Chem. Soc. 1992, 114, 5883-5884
4. Doppelt, P.; Hallais, G.; Pinson, J.; Podvorica, F.; Verneyre, S. Surface Modification of Conducting Substrates. Existence of Azo Bonds in the Structure of Organic Layers Obtained from Diazonium Salts Chem. Mater. 2007, 19, 4570-4575
5. Allongue, P.; Delamar, M.; Desbat, B.; Fagebaume, O.; Hitmi, R.; Pinson, J.; Saveant, J.-M. Covalent Modification of Carbon Surfaces by Aryl Radicals Generated from the Electrochemical Reduction of Diazonium Salts J. Am. Chem. Soc. 1997, 119, 201-207
6. Kariuki, J. K.; McDermott, M. T. Nucleation and Growth of Functionalized Aryl Films on Graphite Electrodes Langmuir 1999, 15, 6534-6540
7. Holm, A. H.; Moller, R.; Vase, K. H.; Dong, M. D.; Norrman, K.; Besenbacher, F.; Pedersen, S. U.; Daasbjerg, K. Nucleophilic and Electrophilic Displacements on Covalently Modified Carbon: Introducing 4,4′-Bipyridinium on Grafted Glassy Carbon Electrodes New J. Chem. 2005, 29, 659-666
8. Liu, S. Q.; Tang, Z. Y.; Shi, Z.; Niu, L.; Wang, E. K.; Dong, S. J. Electrochemical Preparation and Characterization of Silicotungstic Heteropolyanion Monolayer Electrostatically Linked Aminophenyl on Carbon Electrode Surface Langmuir 1999, 15, 7268-7275
9. Tanaka, M.; Sawaguchi, T.; Sato, Y.; Yoshioka, K.; Niwa, O. Surface Modification of GC and HOPG with Diazonium, Amine, Azide, and Olefin Derivatives Langmuir 2011, 27, 170-178
10. 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
11. Farmer, D. B.; Golizadeh-Mojarad, R.; Perebeinos, V.; Lin, Y. M.; Tulevski, G. S.; Tsang, J. C.; Avouris, P. Chemical Doping and Electron-Hole Conduction Asymmetry in Graphene Devices Nano Lett. 2009, 9, 388-392
12. 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. 2008, 130, 16201-16206
13. Georgakilas, V.; Otyepka, M.; Bourlinos, A. B.; Chandra, V.; Kim, N.; Kemp, K. C.; Hobza, P.; Zboril, R.; Kim, K. S. Functionalization of Graphene: Covalent and Non-Covalent Approaches, Derivatives and Applications Chem. Rev. 2012, 112, 6156-6214
14. Paulus, G. L. C.; Wang, Q. H.; Strano, M. S. Covalent Electron Transfer Chemistry of Graphene with Diazonium Salts Acc. Chem. Res. 2012, 46, 160-170
15. Koehler, F. M.; Jacobsen, A.; Ensslin, K.; Stampfer, C.; Stark, W. J. Selective Chemical Modification of Graphene Surfaces: Distinction between Single- and Bilayer Graphene Small 2010, 6, 1125-1130
16. de Andres, P. L.; Verges, J. A. First-Principles Calculation of the Effect of Stress on the Chemical Activity of Graphene Appl. Phys. Lett. 2008, 93, 171915
17. Liu, Y. C.; McCreery, R. L. Reactions of Organic Monolayers on Carbon Surfaces Observed with Unenhanced Raman-Spectroscopy J. Am. Chem. Soc. 1995, 117, 11254-11259
18. Dunker, M. F. W.; Starkey, E. B.; Jenkins, G. L. The Preparation of Some Organic Mercurials from Diazonium Borofluorides J. Am. Chem. Soc. 1936, 58, 2308-2309
19. Anderson, S. Phenylene Ethynylene Pentamers for Organic Electroluminescence Chem.-Eur. J. 2001, 7, 4706-4714
20. Brooksby, P. A.; Downard, A. J. Electrochemical and Atomic Force Microscopy Study of Carbon Surface Modification Via Diazonium Reduction in Aqueous and Acetonitrile Solutions Langmuir 2004, 20, 5038-5045
21. Lee, L.; Brooksby, P. A.; Leroux, Y. R.; Hapiot, P.; Downard, A. J. Mixed Monolayer Organic Films via Sequential Electrografting from Aryldiazonium Ion and Arylhydrazine Solutions Langmuir 2013, 29, 3133-3139
22. Yu, S. S. C.; Tan, E. S. Q.; Jane, R. T.; Downard, A. J. An Electrochemical and XPS Study of Reduction of Nitrophenyl Films Covalently Grafted to Planar Carbon Surfaces Langmuir 2007, 23, 11074-11082
23. Adenier, A.; Cabet-Deliry, E.; Chausse, A.; Griveau, S.; Mercier, F.; Pinson, J.; Vautrin-Ul, C. Grafting of Nitrophenyl Groups on Carbon and Metallic Surfaces without Electrochemical Induction Chem. Mater. 2005, 17, 491-501
24. Leroux, Y. R.; Fei, H.; Noel, J.-M.; Roux, C.; Hapiot, P. Efficient Covalent Modification of a Carbon Surface: Use of a Silyl Protecting Group to Form an Active Monolayer J. Am. Chem. Soc. 2010, 132, 14039-14041
25. Jiang, D. E.; Sumpter, B. G.; Dai, S. How Do Aryl Groups Attach to a Graphene Sheet? J. Phys. Chem. B 2006, 110, 23628-23632
26. Chang, H. P.; Bard, A. J. Observation and Characterization by Scanning Tunneling Microscopy of Structuress Generated by Cleaving Highly Oriented Pyrolytic Graphite Langmuir 1991, 7, 1143-1153
27. 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. 2010, 10, 398-405
28. Wang, Q. H.; Jin, Z.; Kim, K. K.; Hilmer, A. J.; Paulus, G. L. C.; Shih, C.-J.; Ham, M.-H.; Sanchez-Yamagishi, J. D.; Watanabe, K.; Taniguchi, T. Understanding and Controlling the Substrate Effect on Graphene Electron-Transfer Chemistry via Reactivity Imprint Lithography Nat. Chem. 2012, 4, 724-732
29. Niyogi, S.; Bekyarova, E.; Itkis, M. E.; Zhang, H.; Shepperd, K.; Hicks, J.; Sprinkle, M.; Berger, C.; Lau, C. N.; deHeer, W. A. Spectroscopy of Covalently Functionalized Graphene Nano Lett. 2010, 10, 4061-4066
30. Zeb, G.; Gaskell, P.; Le, X. T.; Xiao, X. C.; Szkopek, T.; Cerruti, M. Decoration of Graphitic Surfaces with Sn Nanoparticles through Surface Functionalization Using Diazonium Chemistry Langmuir 2012, 28, 13042-13050
31. Ray, K.; McCreery, R. L. Spatially Resolved Raman Spectroscopy of Carbon Electrode Surfaces: Observations of Structural and Chemical Heterogeneity Anal. Chem. 1997, 69, 4680-4687
32. Dong, X. C.; Fu, D. L.; Fang, W. J.; Shi, Y. M.; Chen, P.; Li, L. J. Doping Single-Layer Graphene with Aromatic Molecules Small 2009, 5, 1422-1426
33. Singh, A. K.; Iqbal, M. W.; Singh, V. K.; Iqbal, M. Z.; Lee, J. H.; Chun, S. H.; Shin, K.; Eom, J. Molecular N-Doping of Chemical Vapor Deposition Grown Graphene J. Mater. Chem. 2012, 22, 15168-15174
34. Hossain, M. Z.; Walsh, M. A.; Hersam, M. C. Scanning Tunneling Microscopy, Spectroscopy, and Nanolithography of Epitaxial Graphene Chemically Modified with Aryl Moieties J. Am. Chem. Soc. 2010, 132, 15399-15403
35. Gross, A. J.; Downard, A. J. Regeneration of Pyrolyzed Photoresist Film by Heat Treatment Anal. Chem. 2011, 83, 2397-2402
36. Torbensen, K.; Iruthayaraj, J.; Ceccato, M.; Kongsfelt, M.; Breitenbach, T.; Pedersen, S. U.; Daasbjerg, K. Conducting and Ordered Carbon Films Obtained by Pyrolysis of Covalently Attached Polyphenylene and Polyanthracene Layers on Silicon Substrates J. Mater. Chem. 2012, 22, 18172-18180
37. Toupin, M.; Bélanger, D. Thermal Stability Study of Aryl Modified Carbon Black by in Situ Generated Diazonium Salt J. Phys. Chem. C 2007, 111, 5394-5401
38. Matveev, V. G. Kinetics of Radical Reactions Involved in the Gas-Phase Thermal Decomposition of Nitrobenzene Russ. J. Phys. Chem. B 2010, 4, 719-725