Large-scale patterning of zwitterionic molecules on a Si(111)-7 × 7 surface

ACS Nano

Volumn 5, Issue 1, 2011, Pages 424-428

  Garah, Mohamed El ^a   Makoudi, Younes ^a   Duverger, Éric ^a   Palmino, Frank ^a   Rochefort, Alain ^b   Chérioux, Frédéric ^a  

^a UNIVERSITÉ DE FRANCHE COMTÉ   (France)

^b ÉCOLE POLYTECHNIQUE DE MONTRÉAL   (Canada)

Author keywords

Density functional theory calculations; Scanning tunneling microscopy; Self assembly; Semiconductors; Zwitterion

Indexed keywords

DENSITY FUNCTIONAL THEORY CALCULATIONS; HIGH RESOLUTION SCANNING TUNNELING MICROSCOPY; MOLECULAR GEOMETRIES; NANO STRUCTURATION; NEW SOLUTIONS; PERFECT MATCHES; SCALE PATTERN; SI (1 1 1); SURFACE TOPOLOGY; ZWITTER IONIC MOLECULE; ZWITTERION;

ADSORPTION; DENSITY FUNCTIONAL THEORY; MOLECULES;

SCANNING TUNNELING MICROSCOPY;

EID: 79959918723     PISSN: 19360851     EISSN: 1936086X     Source Type: Journal    
DOI: 10.1021/nn102398g     Document Type: Article

References (38)

1. MacDiarmid, A. G. Synthetic metals: A Novel Role for Organic Polymers (Nobel lecture). Angew. Chem., Int. Ed. 2001, 40, 2581-2590. (Pubitemid 32691690)
2. Heeger, A. J. Semiconducting and Metallic Polymers: The Fourth Generation of Polymeric Materials (Nobel lecture). Angew. Chem., Int. Ed. 2001, 40, 2591-2611. (Pubitemid 32691691)
3. Joachim, C.; Gimzewski, J. K.; Aviram, A. Electronics Using Hybrid-Molecular and Mono-Molecular Devices. Nature 2000, 408, 541-548.
4. Ratner, M. Molecular Electronics - Charged With Manipulation. Nature 2005, 435, 575-577.
5. Rochefort, A.; Martel, R.; Avouris, Ph. Electrical Switching in Pi-Resonant 1D Intermolecular Channels. Nano Lett. 2002, 2, 877-880. (Pubitemid 135708193)
6. Piva, P. G.; DiLabio, G. A.; Pitters, J. L.; Zikovski, J.; Rezeq, M.; Dogel, S.; Hofer, W. A.; Wolkow, R. A. Field Regulation of Single-Molecule Conductivity by a Charged Surface Atom. Nature 2005, 435, 658-661. (Pubitemid 40834249)
7. Barth, J. V.; Constantini, G.; Kern, K. Engineering Atomic and Molecular Nanostructures at Surfaces. Nature 2005, 437, 671-679. (Pubitemid 41486530)
8. Theobald, J. A.; Oxtoby, N. S.; Philipps, N. A.; Champness, N. R.; Beton, P. H. Controlling Molecular Deposition and Layer Structure with Supramolecular Surface Assemblies. Nature 2003, 424, 1029-1031. (Pubitemid 37064298)
9. Percec, V.; Glodde, M.; Bera, T. K.; Miura, Y.; Shiyanovskaya, I.; Singer, K. D.; Balagurusamy, V. S. K.; Heiney, P. A.; Schnell, I.; Rapp, A. Self-Organization of Supramolecular Helical Dendrimers into Complex Electronic Materials. Nature 2002, 419, 384-387.
10. Grill, L.; Dyer, M.; Lafferentz, L.; Perssson, M.; Peters, M. V.; Hecht, S. Nano-Architectures by Covalent Assembly of Molecular Building Blocks. Nat. Nanotechnol. 2007, 2, 687-691. (Pubitemid 350071067)
11. Lu, P. H.; Polanyi, J. C.; Rogers, D. Photoinduced Localized Atomic Reaction (LAR) of 1,2- and 1,4-Dichlorobenzene with Si(111)-7 × 7. J. Chem. Phys. 2000, 112, 11005-11010.
12. McNab, I. R.; Polanyi, J. C. Patterned Atomic Reaction at Surfaces. Chem. Rev. 2006, 106, 4321-4354. (Pubitemid 44782241)
13. Hossain, M. Z.; Kato, H. S.; Kawai, M. Self-Directed Chain Reaction by Small Ketones with the Dangling Bond Site on the Si(100)-2 × 1-H Surface: Acetophenone, a Unique Example. J. Am. Chem. Soc. 2008, 130, 11518-11523.
14. Lopinski, G. P.; Wayner, D. D. M.; Wolkow, R. A. Self-Directed Growth of Molecular Nanostructures on Silicon. Nature 2000, 406, 48-51. (Pubitemid 30460204)
15. Hamers, R. J.; Coulter, S. K.; Ellison, M. D.; Hovis, J. S.; Padowitz, D. F.; Schartz, M. P.; Greenlief, C. M.; Russel, J. N. Cycloaddition Chemistry of Organic Molecules with Semiconductor Surfaces. Acc. Chem. Res. 2000, 33, 617-624.
16. Hurley, P. T.; Nemanick, E. J.; Brunschwig, B. S.; Lewis, N. S. Covalent Attachement of Acetylene and Methylacetylene Functionality to Si(111) Surfaces: Scaffolds for Organic Surface Functionalization While Retaining Si-C Passivation of Si(111) Surface Sites. J. Am. Chem. Soc. 2006, 128, 9990-9991. (Pubitemid 44201065)
17. Harikumar, K. R.; Polanyi, J. C.; Sloan, P. A.; Ayissi, S.; Hofer, W. A. Electronic Switching of Single Silicon Atoms by Molecular Field Effects. J. Am. Chem. Soc. 2006, 128, 16791-16797. (Pubitemid 46032754)
18. Harikumar, K. R.; Lim, T. B.; McNab, I. R.; Polanyi, J. C.; Zotti, L.; Ayissi, S.; Hofer, W. A. Dipole-Directed Assembly of Lines of 1,5-Dichloropentane on Silicon Substrates by Displacement of Surface Charge. Nat. Nanotechnol. 2008, 3, 222-228. (Pubitemid 351499401)
19. Lu, X. K.; Polanyi, J. C.; Yang, J. A Reversible Molecular Switch Based on Pattern-Change in Chlorobenzene and Toluene on a Si(111)×7×7 Surface. Nano Lett. 2006, 6, 809-814.
20. Makoudi, Y.; Arab, M.; Palmino, F.; Duverger, E.; Cherioux, F. Complete Supramolecular Self-Assembled Adlayer on a Silicon Surface at Room Temperature. J. Am. Chem. Soc. 2008, 130, 6670-6671. (Pubitemid 351748379)
21. Price, W. D.; Jockusch, R. A.; Williams, E. R. Is Arginine a Zwitterion in the Gas Phase. J. Am. Chem. Soc. 1997, 119, 11988-11989.
22. Chapo, C. J.; Paul, J. B.; Provencal, R. A.; Roth, K.; Saykally, R. J. Is Arginine Zwitterionic or Neutral in the Gas Phase? Results from IR Cavity Ringdown Spectroscopy. J. Am. Chem. Soc. 1998, 120, 12956-12957. (Pubitemid 29013848)
23. Nazmutdinov, R. R.; Zhang, J.; Zinkicheva, T. T.; Manyurov, I. R.; Ulstrup, J. Adsorption and in situ Scanning Tunneling Microscopy of Cysteine on Au(111): Structure, Energy, and Tunneling Contrasts. Langmuir 2006, 22, 7556-7567. (Pubitemid 44373426)
24. Makoudi, Y.; Arab, M.; Palmino, F.; Duverger, E.; Picaud, F.; Ramseyer, Ch.; Cherioux, F. A Stable Room-Temperature Molecular Assembly of Zwitterionic Organic Dipoles Guided by a Si(111)×7×7 Template Effect. Angew. Chem., Int. Ed. 2007, 46, 9287-9290. (Pubitemid 350292160)
25. Makoudi, Y.; El Garah, M.; Palmino, F.; Duverger, E.; Arab, M.; Cherioux, F. Adsorption of an Organic Zwiterrion on a Si(111)×7×7 Surface at Room Temperature. Surf. Sci. 2008, 602, 2719-2723.
26. Kresse, G.; Furthmuller, J. Efficient Iterative Schemes for ab initio Total-Energy Calculations Using a Plane-Waves Basis Set. Phys. Rev. B: Condens. Matter Mater. Phys. 1996, 54, 11169-11186.
27. Blochl, P. E. Projected Augmented-Wave Method. Phys. Rev. B: Condens. Matter Mater. Phys. 1994, 50, 17953-17979.
28. Kresse, G.; Hafner, J. Ab initio Molecular-Dynamics for Open-Shell Transition-Metals. Phys. Rev. B: Condens. Matter Mater. Phys. 1993, 47, 558-561.
29. Vasco, E. Mechanisms of Preferential Adsorption on the Si(111)×7×7 Surface. Surf. Sci. 2005, 575, 247-249.
30. Janta-Polczynski, B.; Cerdá, J. I.;Éthier-Majcher, G.; Piyakis, K.; Rochefort, A. Parallel Scanning Tunneling Microscopy Imaging of Low Dimensional Nanostructures. J. Appl. Phys. 2008, 104, 023702.
31. Takayanagi, K.; Tanishiro, Y.; Takahashi, S.; Takahashi, M. Structural Analysis of Si(111)×7×7 Reconstructed Surface by Transmission Electron Diffraction. Surf. Sci. 1985, 164, 367-392.
32. Perdew, J. P.; Burke, K.; Ernzerhof, M. Generalized Gradient Approximation Made Simple. Phys. Rev. Lett. 1996, 77, 3865-3368.
33. Monkhorst, H. J.; Pack, J.-D. Special Points for Brillouin-Zone Integrations. Phys. Rev. B: Solid State 1976, 13, 5188-5192.
34. Csaszar, P.; Pulay, P. Predicted Vibrational Frequencies and Assignment of the Spectra of Uracil and its N, NDideutero Derivative by Quantum Chemical Methods. J. Mol. Struct. 1984, 114, 31-34.
35. Eckert, F.; Pulay, P.; Werner, H.-J. Ab initio Geometry Optimization for Large Molecules. J. Comput. Chem. 1997, 18, 1473-1483. (Pubitemid 127637345)
36. Bedwani, S.; Guibault, F.; Rochefort, A. Nanoscale Adaptive Meshing for Rapid STM Imaging. J. Comput. Phys. 2008, 227, 6720-6726.
37. Büttiker, M.; Imry, Y.; Landauer, R.; Pinhas, S. Generalized Many-Channel Conductance Formula with Application to Small Rings. Phys. Rev. B: Condens. Matter Mater. Phys. 1985, 31, 6207-6215.
38. Cerdá, J. I.; Van Hove, M. A.; Sautet, P.; Salmeron, M. Efficient Method for the Simulation of STM Images. I. Generalized Green-function formalism. Phys. Rev. B: Condens. Matter Mater. Phys. 1997, 56, 15885-15899.