The interface energetics of self-assembled monolayers on metals

Accounts of Chemical Research

Volumn 41, Issue 6, 2008, Pages 721-729

  Heimel, Georg ^a,b   Romaner, Lorenz ^a,c   Zojer, Egbert ^a,c   Bredas, Jean Luc ^a  

^a GEORGIA INSTITUTE OF TECHNOLOGY   (United States)

^b Massachusetts Institute of Technology Cambridge   (United States)

^c GRAZ UNIVERSITY OF TECHNOLOGY   (Austria)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 45749136864     PISSN: 00014842     EISSN: None     Source Type: Journal    
DOI: 10.1021/ar700284q     Document Type: Review

References (41)

1. Ulman, A. Formation and Structure of Self-Assembled Monolayers. Chem. Rev. 1996, 96, 1533-1554.
2. Love, J. C.; Estroff, L. A.; Kriebel, J. K.; Nuzzo, R. G.; Whitesides, G. M. Self-Assembled Monolayers of Thiolates on Metals as a Form of Nanotechnology. Chem. Rev. 2005, 105, 1103-1169.
3. Jennings, G. K.; Laibinis, P. E. Self-Assembled Monolayers of Alkanethiols on Copper Provide Corrosion Resistance in Aqueous Environments. Colloids Surf., A 1996, 116, 105-114.
4. Genzer, J.; Efimenko, K. Creating Long-Lived Superhydrophobic Polymer Surfaces Through Mechanically Assembled Monolayers. Science 2000, 290, 2130-2133.
5. Gooding, J. J.; Mearns, F.; Yang, W. R.; Liu, J. Q. Self-Assembled Monolayers into the 21(st) Century: Recent Advances and Applications. Electroanalysis 2003, 15, 81-96.
6. Campbell, I. H.; Rubin, S.; Zawodzinski, T. A.; Kress, J. D.; Martin, R. L.; Smith, D. L.; Barashkov, N. N.; Ferraris, J. P. Controlling Schottky Energy Barriers in Organic Electronic Devices Using Self-Assembled Monolayers. Phys. Rev. B 1996, 54, 14321-14324.
7. Ganzorig, C.; Kwak, K. J.; Yagi, K.; Fujihira, M. Fine Tuning Work Function of Indium Tin Oxide by Surface Molecular Design: Enhanced Hole Injection in Organic Electroluminescent Devices. Appl. Phys. Lett. 2001, 79, 272-274.
8. de Boer, B.; Hadipour, A.; Mandoc, M. M.; van Woudenbergh, T.; Blom, P. W. M. Tuning of Metal Work Functions with Self-Assembled Monolayers. Adv. Mater. 2005, 17, 621-625.
9. Bock, C.; Pham, D. V.; Kunze, U.; Kater, D.; Witte, G.; Woll, C. Improved Morphology and Charge Carrier Injection in Pentacene Field-Effect Transistors with Thiol-Treated Electrodes. J. Appl. Phys. 2006, 100, 114517.
10. 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.
11. Kahn, A.; Koch, N.; Gao, W. Y. Electronic Structure and Electrical Properties of Interfaces between Metals and π-Conjugated Molecular Films. J. Polym. Sci., Part B 2003, 41, 2529-2548.
12. Bumm, L. A.; Arnold, J. J.; Cygan, M. T.; Dunbar, T. D.; Burgin, T. P.; Jones, L.; Allara, D. L.; Tour, J. M.; Weiss, P. S. Are Single Molecular Wires Conducting? Science 1996, 271, 1705-1707.
13. Chen, J.; Reed, M. A.; Rawlett, A. M.; Tour, J. M. Large On-Off Ratios and Negative Differential Resistance in a Molecular Electronic Device. Science 1999, 286, 1550-1552.
14. Park, J.; Pasupathy, A. N.; Goldsmith, J. I.; Chang, C.; Yaish, Y.; Petta, J. R.; Rinkoski, M.; Sethna, J. P.; Abruna, H. D.; McEuen, P. L.; Ralph, D. C. Coulomb Blockade and the Kondo Effect in Single-Atom Transistors. Nature 2002, 417, 722-725.
15. Akkerman, H. B.; Blom, P. W. M.; de Leeuw, D. M.; de Boer, B. Towards Molecular Electronics with Large-Area Molecular Junctions. Nature 2006, 441, 69-72.
16. Vondrak, T.; Wang, H.; Winget, P.; Cramer, C. J.; Zhu, X. Y. Interfacial Electronic Structure in Thiolate Self-Assembled Monolayers: Implication for Molecular Electronics. J. Am. Chem. Soc. 2000, 122, 4700-4707.
17. Xue, Y. Q.; Datta, S.; Ratner, M. A. Charge Transfer and "Band Lineup" in Molecular Electronic Devices: A Chemical and Numerical Interpretation. J. Chem. Phys. 2001, 115, 4292-4299.
18. Vásquez, H.; Flores, F.; Oszwaldowski, R.; Ortega, J.; Pérez, R.; Kahn, A. Barrier Formation at Metal-Organic Interfaces: Dipole Formation and the Charge Neutrality Level. Appl. Surf. Sci. 2004, 234, 107-112.
19. Heimel, G.; Romaner, L.; Bredas, J. L.; Zojer, E. Interface Energetics and Level Alignment at Covalent Metal-Molecule Junctions: π-Conjugated Thiols on Gold. Phys. Rev. Lett. 2006, 96, 196806.
20. Heimel, G.; Romaner, L.; Bredas, J. L.; Zojer, E. Organic/Metal Interfaces-in Self-Assembled Monolayers of Conjugated Thiols: A First-Principles Benchmark Study. Surf. Sci. 2006, 600, 4548-4562.
21. Heimel, G.; Romaner, L.; Zojer, E.; Bredas, J. L. Toward Control of the Metal-Organic Interfacial Electronic Structure in Molecular Electronics: A First-Principles Study on Self-Assembled Monolayers of π-Conjugated Molecules on Noble Metals. Nano Lett. 2007, 7, 932-940.
22. Tao, Y. T.; Wu, C. C.; Eu, J. Y.; Lin, W. L.; Wu, K. C.; Chen, C. H. Structure Evolution of Aromatic-Derivatized Thiol Monolayers on Evaporated Gold. Langmuir 1997, 13, 4018-4023.
23. Leung, T. Y. B.; Schwartz, P.; Scoles, G.; Schreiber, F.; Ulman, A. Structure and Growth of 4-Methyl-4′-mercaptobiphenyl Monolayers on Au(111): A Surface Diffraction Study. Surf. Sci. 2000, 458, 34-52.
24. Azzam, W.; Fuxen, C.; Birkner, A.; Rong, H. T.; Buck, M.; Wöll, C. Coexistence of Different Structural Phases in Thioaromatic Monolayers on Au(111). Langmuir 2003, 19, 4958-4968.
25. Frey, S.; Stadler, V.; Heister, K.; Eck, W.; Zharnikov, M.; Grunze, M.; Zeysing, B.; Terfort, A. Structure of Thioaromatic Self-Assembled Monolayers on Gold and Silver. Langmuir 2001, 17, 2408-2415.
26. Kang, J. F.; Ulman, A.; Liao, S.; Jordan, R.; Yang, G. H.; Liu, G. Y. Self-Assembled Rigid Monolayers of 4 ′-Substituted-4-Mercaptobiphenyls on Gold and Silver Surfaces. Langmuir 2001, 17, 95-106.
27. Shaporenko, A.; Heister, K.; Ulman, A.; Grunze, M.; Zharnikov, M. The Effect of Halogen Substitution in Self-Assembled Monolayers of 4-Mercaptobiphenyls on Noble Metal Substrates. J. Phys. Chem. B 2005, 109, 4096-4103.
28. Natan, A.; Kronik, L.; Haick, H.; Tung, R. T. Electrostatic Properties of Ideal and Non-ideal Polar Organic Monolayers: Implications for Electronic Devices. Adv. Mater. 2007, 19, 4103-4117.
29. Deutsch, D.; Natan, A.; Shapira, Y.; Kronik, L. Electrostatic Properties of Adsorbed Polar Molecules: Opposite Behavior of a Single Molecule and a Molecular Monolayer. J. Am. Chem. Soc. 2007, 129, 2989-2997.
30. Meyers, F.; Bredas, J. L. On the Nature of the Ground State in Push-Pull Conjugated Molecules with Large Quadratic Optical Nonlinearities: From Paranitroaniline to P-Nitro-p′-aminodiphenyl-hexatriyne. Nonlinear Opt. 1991, 1, 119-123.
31. Romaner, L.; Heimel, G.; Zojer, E. Electronic Structure of Thiol-Bonded Self-Assembled Monolayers: Impact of Coverage. Phys. Rev. B 2008, 77, 045113.
32. Topping, J. On the Mutual Potential Energy of a Plane Network of Doublets. Proc. R. Soc. London, Ser. A 1927, 114, 67-72.
33. Maschhoff, B. L.; Cowin, J. P. Corrected Electrostatic Model for Dipoles Adsorbed on a Metal-Surface. J. Chem. Phys. 1994, 101, 8138-8151.
34. Iwamoto, M.; Mizutani, Y.; Sugimura, A. Calculation of the Dielectric Constant of Monolayer Films on a Material Surface. Phys. Rev. B 1996, 54, 8186-8190.
35. Cornil, D.; Olivier, Y.; Geskin, V.; Cornil, J. Depolarization Effects in Self-Assembled Monolayers: A Quantum-Chemical Insight. Adv. Funct. Mater. 2007, 17, 1143-1148.
36. j in Density-Functional Theory. Phys. Rev. B 1978, 18, 7165-7168.
37. Lang, N. D.; Kohn, W. Theory of Metal Surfaces: Work Function. Phys. Rev. B 1971, 3, 1215-1223.
38. Lang, N. D. Interaction between Closed-Shell Systems and Metal-Surfaces. Phys. Rev. Lett. 1981, 46, 842-845.
39. Chen, Y. C.; Cunningham, J. E.; Flynn, C. P. Dependence of Rare-Gas-Adsorbate Dipole-Moment on Substrate Work Function. Phys. Rev. B 1984, 30, 7317-7319.
40. Witte, G.; Lukas, S.; Bagus, P. S.; Wöll, C. Vacuum Level Alignment at Organic/Metal Junctions: "Cushion" Effect and the Interface Dipole. Appl. Phys. Lett. 2005, 87, 263502.
41. Koch, N.; Elschner, A.; Schwartz, J.; Kahn, A. Organic Molecular Films on Gold versus Conducting Polymer: Influence of Injection Barrier Height and Morphology on Current-Voltage Characteristics. Appl. Phys. Lett. 2003, 82, 2281-2283 .