Structure and energy level alignment of tetramethyl benzenediamine on Au(111)

Journal of Physical Chemistry C

Volumn 115, Issue 25, 2011, Pages 12625-12630

  Kamenetska, M ^a   Dell'angela, M ^b,c,e   Widawsky, J R ^a   Kladnik, G ^b,d   Verdini, A ^b   Cossaro, A ^b   Cvetko, D ^b,d   Morgante, A ^b,e   Venkataraman, L ^a  

^a Columbia University ^*  (United States)

^b LABORATORIO TASC   (Italy)

^c UNIVERSITY OF HAMBURG   (Germany)

^d UNIVERSITY OF LJUBLJANA   (Slovenia)

^e UNIVERSITY OF TRIESTE   (Italy)

Author keywords

[No Author keywords available]

Indexed keywords

ADSORPTION ENERGIES; AU(1 1 1 ); BOUND MOLECULES; CHARGE DONATION; ENERGY LEVEL ALIGNMENT; FLAT SURFACES; HELIUM ATOM SCATTERING; LONE PAIR; NITROGEN BONDS; SCANNING TUNNELING MICROSCOPY (STM); STEP EDGE; TETRAMETHYL; X-RAY PHOTOEMISSIONS;

ADSORPTION; ALIGNMENT; HELIUM; MOLECULAR ORBITALS; MOLECULES;

SCANNING TUNNELING MICROSCOPY;

EID: 79959527112     PISSN: 19327447     EISSN: 19327455     Source Type: Journal    
DOI: 10.1021/jp202555d     Document Type: Article

References (32)

1. Aviram, A.; Ratner, M. A. Molecular Rectifiers Chem. Phys. Lett. 1974, 29, 277-283
2. Mishchenko, A.; Vonlanthen, D.; Meded, V.; Burkle, M.; Li, C.; Pobelov, I. V.; Bagrets, A.; Viljas, J. K.; Pauly, F.; Evers, F. Influence of Conformation on Conductance of Biphenyl-Dithiol Single-Molecule Contacts Nano Lett. 2010, 10, 156-163
3. Kiguchi, M.; Miura, S.; Takahashi, T.; Hara, K.; Sawamura, M.; Murakoshi, K. Conductance of Single 1,4-Benzenediamine Molecule Bridging between Au and Pt Electrodes J. Phys. Chem. C 2008, 112, 13349-13352
4. Venkataraman, L.; Klare, J. E.; Tam, I. W.; Nuckolls, C.; Hybertsen, M. S.; Steigerwald, M. L. Single-Molecule Circuits with Well-Defined Molecular Conductance Nano Lett. 2006, 6, 458-462
5. Xu, B. Q.; Tao, N. J. J. Measurement of Single-Molecule Resistance by Repeated Formation of Molecular Junctions Science 2003, 301, 1221-1223
6. Wu, S. M.; Gonzalez, M. T.; Huber, R.; Grunder, S.; Mayor, M.; Schonenberger, C.; Calame, M. Molecular Junctions Based on Aromatic Coupling Nat. Nano. 2008, 3, 569-574
7. Hybertsen, M. S.; Venkataraman, L.; Klare, J. E.; Whalley, A. C.; Steigerwald, M. L.; Nuckolls, C. Amine-Linked Single-Molecule Circuits: Systematic Trends across Molecular Families J. Phys.:Cond. Mat. 2008, 20, 374115
8. Hoft, R. C.; Ford, M. J.; McDonagh, A. M.; Cortie, M. B. Adsorption of Amine Compounds on the Au(111) Surface: A Density Functional Study J. Phys. Chem. C 2007, 111, 13886-13891 (Pubitemid 47522635)
9. Frei, M.; Aradhya, S. V.; Koentopp, M.; Hybertsen, M. S.; Venkataraman, L. Mechanics and Chemistry: Single Molecule Bond Rupture Forces Correlate with Molecular Backbone Structure Nano Lett. 2011, 11, 1518-1523
10. Li, Z.; Kosov, D. S. Nature of Well-Defined Conductance of Amine Anchored Molecular Junctions Phys. Rev. B 2007, 76, 035415
11. Kamenetska, M.; Koentopp, M.; Whalley, A.; Park, Y. S.; Steigerwald, M.; Nuckolls, C.; Hybertsen, M.; Venkataraman, L. Formation and Evolution of Single-Molecule Junctions Phys. Rev. Lett. 2009, 102, 126803
12. Park, Y. S.; Whalley, A. C.; Kamenetska, M.; Steigerwald, M. L.; Hybertsen, M. S.; Nuckolls, C.; Venkataraman, L. Contact Chemistry and Single-Molecule Conductance: A Comparison of Phosphines, Methyl Sulfides, and Amines J. Am. Chem. Soc. 2007, 129, 15768-15769
13. Bagrets, A.; Arnold, A.; Evers, F. Conduction Properties of Bipyridinium-Functionalized Molecular Wires J. Am. Chem. Soc. 2008, 130, 9013-9018 (Pubitemid 352000839)
14. Wang, W. H.; Shi, X. Q.; Lin, C. S.; Zhang, R. Q.; Minot, C.; Van Hove, M. A.; Hong, Y. N.; Tang, B. Z.; Lin, N. Manipulating Localized Molecular Orbitals by Single-Atom Contacts Phys. Rev. Lett. 2010, 105, 126801
15. Dell'Angela, M.; Kladnik, G.; Cossaro, A.; Verdini, A.; Kamenetska, M.; Tamblyn, I.; Quek, S. Y.; Neaton, J. B.; Cvetko, D.; Morgante, A. Relating Energy Level Alignment and Amine-Linked Single Molecule Junction Conductance Nano Lett. 2010, 10, 2470-2474
16. Martin, C. A.; Ding, D.; van der Zant, H. S. J.; van Ruitenbeek, J. M. Lithographic Mechanical Break Junctions for Single-Molecule Measurements in Vacuum: Possibilities and Limitations New J. Phys. 2008, 10, 065008
17. Sobczyk, L.; Prager, M.; Sawka-Dobrowolska, W.; Bator, G.; Pawlukojc, A.; Grech, E.; van Eijck, L.; Ivanov, A.; Rols, S.; Wuttke, J. The Structure of Diaminodurene and the Dynamics of the Methyl Groups J. Chem. Phys. 2009, 130, 164519
18. Venkataraman, L.; Park, Y. S.; Whalley, A. C.; Nuckolls, C.; Hybertsen, M. S.; Steigerwald, M. L. Electronics and Chemistry: Varying Single Molecule Junction Conductance Using Chemical Substituents Nano Lett. 2007, 7, 502-506 (Pubitemid 46383622)
19. Barth, J. V.; Brune, H.; Ertl, G.; Behm, R. J. Scanning Tunneling Microscopy Observations on the Reconstructed Au(111) Surface-Atomic-Structure, Long-Range Superstructure, Rotational Domains, and Surface-Defects Phys. Rev. B 1990, 42, 9307-9318
20. Harten, U.; Lahee, A. M.; Toennies, J. P.; Woll, C. Observation of a Soliton Reconstruction of Au(111) by High-Resolution Helium-Atom Diffraction Phys. Rev. Lett. 1985, 54, 2619-2622
21. Woll, C.; Chiang, S.; Wilson, R. J.; Lippel, P. H. Determination of Atom Positions at Stacking-Fault Dislocations on Au(111) by Scanning Tunneling Microscopy Phys. Rev. B 1989, 39, 7988-7991
22. Silly, F.; Shaw, A. Q.; Castell, M. R.; Briggs, G. A. D.; Mura, M.; Martsinovich, N.; Kantorovich, L. Melamine Structures on the Au(111) Surface J. Phys. Chem. C 2008, 112, 11476-11480
23. Redhead, P. A. Thermal Desorption of Gases Vacuum 1962, 12, 203-211
24. Fichthorn, K. A.; Miron, R. A. Thermal Desorption of Large Molecules from Solid Surfaces Phys. Rev. Lett. 2002, 89, 196103
25. Bilic, A.; Reimers, J. R.; Hush, N. S.; Hafner, J. Adsorption of Ammonia on the Gold(111) Surface J. Chem. Phys. 2002, 116, 8981-8987
26. Dion, M.; Rydberg, H.; Schroder, E.; Langreth, D. C.; Lundqvist, B. I. Van Der Waals Density Functional for General Geometries Phys. Rev. Lett. 2004, 92, 246401
27. Hufner, S.; Schmidt, S.; Reinert, F. Photoelectron Spectroscopy-an Overviewadvanced Materials Nucl. Instrum. Meth. A 2005, 547, 8-23
28. Bjorneholm, O.; Tillborg, H.; Nilsson, A.; Martensson, N.; Agren, H.; Liegener, C. M. Vibrationally and Orientationally Selective Probing of Intramolecular Potentials in Physisorbed Molecules Phys. Rev. Lett. 1994, 73, 2551-2554 (Pubitemid 24977877)
29. Ohta, T.; Fujikawa, T.; Kuroda, H. Core-Electron Spectra of Monosubstituted Benzenes Obtained by Gas-Phase X-Ray Photoelectron-Spectroscopy B. Chem. Soc. Jpn. 1975, 48, 2017-2024
30. Ishii, H.; Sugiyama, K.; Ito, E.; Seki, K. Energy Level Alignment and Interfacial Electronic Structures at Organic Metal and Organic Organic Interfaces Adv. Mater. 1999, 11, 605-625 (Pubitemid 129675481)
31. Stroscio, J. A.; Kaiser, W. J. Scanning Tunneling Microscopy; Academic Press, San Diego, CA, 1993.
32. Smoluchowski, R. Anisotropy of the Electronic Work Function of Metals Phys. Rev. 1941, 60, 661