Isomerization reactions on single adsorbed molecules

Accounts of Chemical Research

Volumn 42, Issue 2, 2009, Pages 213-223

  Morgenstern, Karina ^a  

^a LEIBNIZ UNIVERSITY HANNOVER   (Germany)

Author keywords

[No Author keywords available]

Indexed keywords

AZO COMPOUND; AZOBENZENE; BENZENE DERIVATIVE; RETINAL; SULFONIC ACID DERIVATIVE;

ADSORPTION; ARTICLE; CHEMICAL STRUCTURE; CHEMISTRY; HUMAN; ISOMERISM; SCANNING TUNNELING MICROSCOPY;

ADSORPTION; AZO COMPOUNDS; BENZENE DERIVATIVES; HUMANS; ISOMERISM; MICROSCOPY, SCANNING TUNNELING; MODELS, MOLECULAR; MOLECULAR STRUCTURE; RETINALDEHYDE; SULFONIC ACIDS;

EID: 61749087657     PISSN: 00014842     EISSN: None     Source Type: Journal    
DOI: 10.1021/ar800021q     Document Type: Article

References (43)

1. Gimzewski, J. K.; Joachim, C. Nanoscale Science of Single Molecules Using Local Probes. Science 1999, 283, 1683-1688.
2. Donhauser, Z. J.; Mantooth, B. A.; Kelly, K. F.; Bumm, L. A.; Monnell, J. D.; Stapleton, J. J., Jr.; Rawlett, A. M.; Allara, D. L.; Tour, J. M.; Weiss, P. S. Conductance Switching in Single Molecules through Conformational Changes. Science 2001, 292, 2303-2307.
3. Heinrich, A. J.; Lutz, C. P.; Gupta, J. A.; Eigler, D. M. Molecule Cascades. Science 2002, 295, 1381-1387.
4. Joachim, C.; Gimzewski, J. K.; Aviram, A. Electronics Using Hybrid-Molecular and Mono-Molecular Devices. Nature 2000, 408, 541-548.
5. Aviram, A.; Ratner, M. A. Molecular Rectifiers. Chem. Phys. Lett. 1974, 29, 277-283.
6. Molecular Switches; Feringa, B. L. Ed.; Wiley-VCH: Weinheim, Germany, 2001.
7. Simic-Milosevic, V.; Mehlhorn, M.; Rieder, K.-H.; Meyer, J.; Morgenstern, K. Electron Induced ortho-meta Isomerization of Single Molecules. Phys. Rev. Lett. 2007, 98, 116102.
8. Simic-Milosevic, V.; Meyer, J.; Morgenstern, K. Electron Induced Isomerization of Dichlorobenzene on Cu(111) and Ag(111). Phys. Chem. Chem. Phys. 2008, 70, 1916-1920.
9. Henzl, J.; Mehlhorn, M.; Gawronski, H.; Rieder, K.-H.; Morgenstern, K. Reversible cis-trans Isomerization of a Single Azobenzene Molecule. Angew. Chem., Int. Ed. 2006, 45, 603-606.
10. Henzl, J.; Bredow, Th.; Morgenstern, K. Irreversible Isomerization of the Azobenzene Derivate Methyl Orange on Au(111). Chem. Phys. Lett. 2007, 435, 278-282.
11. Henzl, J.; Mehlhorn, M.; Morgenstern, K. Amino-Nitro-Azobenzene Dimers as a Prototype for a Molecular-Level Machine. Nanotechnology 2007, 18, 495502.
12. Ho, W. Single-Molecule Chemistry. J. Chem. Phys. 2002, 117, 11033-11061.
13. Komeda, T.; Kim, Y.; Kawai, M.; Persson, B. N. J.; Ueba, H. Lateral Hopping of Molecules Induced by Excitation of Internal Vibration Mode. Science 2002, 295, 2055-2058.
14. Morgenstern, K.; Rieder, K. H. Formation of the Cyclic Ice Hexamer via Excitation of Vibrational Molecular Modes by the Scanning Tunneling Microscope. J. Chem. Phys. 2002, 116, 5746-5752.
15. Pascual, J. I.; Lorente, N.; Song, Z.; Conrad, H.; Rust, H.-P. Selectivity in Vibrationally Mediated Single-Molecule Chemistry. Nature 2003, 423, 525-528.
16. Gawronski, H.; Morgenstern, K.; Rieder, K.-H. Electronic Excitations of Ice Monomers on Au(111) by Scanning Tunneling Microscopy. Eur. Phys. J. D 2005, 35, 349-353.
17. Stipe, B. C.; Rezaei, M. A.; Ho, W.; Gao, S.; Persson, M.; Lundqvist, B. I. Single-Molecule Dissociation by Tunneling Electrons. Phys. Rev. Lett. 1997, 78, 4410-4413.
18. Hla, S.-W.; Bartels, L.; Meyer, G.; Rieder, K. H. Inducing all Steps of a Chemical Reaction with the Scanning Tunneling Microscope Tip: Towards Single Molecule Engineering. Phys. Rev. Lett. 2000, 85, 2777-2780.
19. Morgenstern, K.; Rieder, K. H. Dissociation of Water Molecules with the Scanning Tunneling Microscope. Chem. Phys. Lett. 2002, i358, 250-256.
20. Kim, Y.; Komeda, T.; Kawai, M. Single-Molecule Reaction and Characterization by Vibrational Excitation. Phys. Rev. Lett. 2002, 89, 126104.
21. 60 Molecule. Phys. Rev. Lett. 1995, 74, 2102-2105.
22. Moresco, F.; Meyer, G.; Rieder, K.-H.; Tang, H.; Gourdon, A.; Joachim, C. Conformational Changes of Single Molecules Induced by Scanning Tunneling Microscopy Manipulation: A Route to Molecular Switching. Phys. Rev. Lett. 2001, 86, 672-675.
23. Qiu, X. H.; Nazin, G. V.; Ho, W. Mechanisms of Reversible Conformational Transitions in a Single Molecule. Phys. Rev. Lett. 2004, 93, 196806.
24. Choi, B. Y.; Kahng, S. J.; Kim, S.; Kim, H.; Kim, H. W.; Song, Y. J.; Ihm, J.; Kuk, Y. Conformational Molecular Switch of the Azobenzene Molecule: A Scanning Tunneling Microscopy Study. Phys. Rev. Lett. 2006, 96, 156106.
25. Alemani, M.; Peters, M. V.; Hecht, S.; Rieder, K.-H.; Moresco, F.; Grill, L. Electric Field-Induced Isomerization of Azobenzene by STM. J. Am. Chem. Soc. 2006, 128, 14446-14447.
26. Comstock, M. J.; Levy, N.; Kirakosian, A.; Cho, J.; Lauterwasser, F.; Harvey, J. H.; Strubbe, D. A.; Frechet, J. M. J.; Trauner, D.; Louie, S. G.; Crommie, M. F. Reversible Photomechanical Switching of Individual Engineered Molecules at a Metallic Surface. Phys. Rev. Lett. 2007, 99, 038301.
27. Hagen, S.; Leyssner, F.; Nandi, D.; Wolf, M.; Tegeder, P. Reversible Switching of Tetra-Tert-Butyl-Azobenzene on a Au(111) Surface Induced by Light and Thermal Activation. Chem. Phys. Lett. 2007, 444, 85-90.
28. Ovari, L.; Wolf, M.; Tegeder, P. Reversible Changes in the Vibrafional Structure Induced by Light and Thermal Activation. J. Phys. Chem. C 2007, 111, 15370-15374.
29. Henningsen, N.; Franke, K. J.; Torrente, I. F.; Schulze, G.; Priewisch, B.; Ruck-Braun, K.; Dokic, J.; Klamroth, T.; Saalfrank, P.; Pascual, J. I. Indusing the Rotation of a Single Phenyl Ring with Tunneling Electrons. J. Phys. Chem. C 2007, 111, 14843-14848.
30. lancu, V.; Hla, S.-W. Realization of a Four-Step Molecular Switch in Scanning Tunneling Microscope Manipulation of Single Chlorophyll-a Molecules. Proc. Natl. Acad. Sci. U.S.A. 2006, 103, 13718-13721.
31. Liljeroth, P.; Repp, J.; Meyer, G. Current-Induced Hydrogen Tautomerization and Conductance Switching of Naphthalocyanin Molecules. Science 2007, 317, 1203-1206.
32. Mehlhorn, M.; Gawronski, H.; Nedelmann, L.; Grujic, A.; Morgenstern, K. An Instrument to Investigate Femtochemistry on Metal Surfaces in Real Space. Rev. Sci. Instrum. 2007, 78, 033905.
33. Gawronski, H.; Henzl, J.; Simic-Milosevic, V.; Morgenstern, K. Using a Chemical Concept for Reactivity for the Interpretation of STM Images of Physisorbed Molecules. Appl. Surf. Sci. 2007, 253, 9047-9053.
34. Nieminen, J.; Niemi, E.; Simic-Milosevic, V.; Morgenstern, K. STM Images and Tunneling Channels of Substituted Benzene Molecules. Phys. Rev. 2005, B72, 195421.
35. With courtesy of Young Kuk and Jisoon Ihm, Seoul National University, Korea, private communication.
36. Ikeda, T.; Tsutsumi, 0. Optical Switching and Image Storage by Means of Azobenzene Liquid-Crystal Films. Science 1995, 268, 1873-1875.
37. Tamai, N.; Miyasaka, H. Ultrafast Dynamics of Photochromic Systems. Chem. Rev. 2000, 100, 1875-1890.
38. Salam, G. P.; Persson, M.; Palmer, R. E. Possibility of Coherent Multiple Excitation in Atom Transfer with a Scanning Tunneling Microscope. Phys. Rev. B 1994, 49, 10655-10662.
39. Ueba, H.; Persson, B. N. J. Theoretical State-of-the Art in Adsorbate Motions and Reactions Induced by Inelastic Tunneling Current with STM. Surf. Sci. 2004, 566, 1-12.
40. Weigelt, S.; Busse, C.; Petersen, L.; Rauls, E.; Hammer, B.; Gotthelf, K. V.; Besenbacher, F.; Linderoth, T. R. Chiral Switching by Spontaneous Conformational Change in Adsorbed Organic Molecules. Nat. Mater. 2006, 5, 112-117.
41. Cattaneo, P.; Persico, M. An ab-initio Study of the Photochemistry of Azobenzene. Phys. Chem. Chem. Phys. 1999, 1, 4739-4743.
42. Rao, B. V.; Kwon, K.-Y.; Liu, A.; Bartels, L. Measurement of a Linear Free Energy Relationship One Molecule at a Time. Proc. Natl. Acad. Sci. U.S.A. 2004, 101, 17920-17923.
43. Gawronski, H.; Carrasco, J.; Michaelides, A.; Morgenstern, K. Manipulation and control of hydrogen bond dynamics in adsorbed ice nanoclusters. Phys. Rev. Lett. 2008, 101, 136102.