Diarylethene molecules on a Ag(111) surface: Stability and electron-induced switching

Journal of Physical Chemistry C

Volumn 119, Issue 9, 2015, Pages 4874-4883

  Wirth, J ^a   Hatter, N ^b   Drost, R ^b   Umbach, T R ^b   Barja, S ^b,c   Zastrow, M ^d   Ruck Braun K ^d   Pascual, J I ^e,f   Saalfrank, P ^a   Franke, K J ^b  

^a UNIVERSITY OF POTSDAM   (Germany)

^b FREIE UNIVERSITÄT BERLIN   (Germany)

^c UNIVERSIDAD AUTÓNOMA DE MADRID   (Spain)

^d TECHNISCHE UNIVERSITÄT BERLIN   (Germany)

^e CIC NANOGUNE   (Spain)

^f BASQUE FOUNDATION FOR SCIENCE   (Spain)

Author keywords

[No Author keywords available]

Indexed keywords

ELECTRIC FIELDS; REACTION INTERMEDIATES; SCANNING TUNNELING MICROSCOPY; SILVER METALLOGRAPHY;

AG(111) SURFACE; CONTROLLED MANIPULATIONS; CYCLIZATION PRODUCTS; DIARYLETHENE DERIVATIVES; ELECTROSTATIC MODELING; INTERMEDIATE STATE; MOLECULAR SWITCHES; SWITCHING PROCESS;

DENSITY FUNCTIONAL THEORY;

EID: 84924167158     PISSN: 19327447     EISSN: 19327455     Source Type: Journal    
DOI: 10.1021/jp5122036     Document Type: Article

References (67)

1. Feringa, B. L. The Art of Building Small: From Molecular Switches to Molecular Motors J. Org. Chem. 2007, 72, 6635-6652
2. Irie, M. Diarylethenes for Memories and Switches Chem. Rev. 2000, 100, 1685-1716
3. Feringa, B. Molecular Switches; Wiley-VCH: Weinheim, Germany, 2001.
4. van der Molen, S. J.; Liljeroth, P. Charge Transport Through Molecular Switches J. Phys.: Condens. Matter 2010, 22, 133001
5. Tegeder, P. Optically and Thermally Induced Molecular Switching Processes at Metal Surfaces J. Phys.: Condens. Matter 2012, 24, 394001
6. 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
7. Comstock, M. J.; Levy, N.; Kirakosian, A.; Cho, J.; Lauterwasser, F.; Harvey, J. H.; Strubbe, D. A.; Frechet, J. M.; 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
8. Comstock, M. J.; Levy, N.; Cho, J.; Berbil-Bautista, L.; Crommie, M. F.; Poulsen, D. A.; Frechet, J. M. J. Measuring Reversible Photomechanical Switching Rates for a Molecule at a Surface Appl. Phys. Lett. 2008, 92, 123107
9. Pechenezhskiy, I. V.; Cho, J.; Nguyen, G. D.; Berbil-Bautista, L.; Giles, B. L.; Frechet, J. M. J.; Crommie, M. F. Self-Assembly and Photomechanical Switching of an Azobenzene Derivative on GaAs(110): Scanning Tunneling Microscopy Study J. Phys. Chem. C 2012, 116, 1052-1055
10. Schulze, G.; Koch, M.; Franke, K.; Pascual, J. I. Induction of a Photostationary Ring-Opening-Ring-Closing State of Spiropyran Monolayers on the Semimetallic Bi(110) Surface Phys. Rev. Lett. 2012, 109, 026102
11. Piantek, M.; Schulze, G.; Koch, M.; Franke, K.; Leyssner, F.; Krüger, A.; Navío, C.; Miguel, J.; Bernien, M.; Wolf, M.; Kuch, W.; egeder, P.; Pascual, J. I. Reversing the Thermal Stability of a Molecular Switch on a Gold Surface: Ring-Opening Reaction of Nitrospiropyran J. Am. Chem. Soc. 2009, 131, 12729-12735
12. Mielke, J.; Leyssner, F.; Koch, M.; Meyer, S.; Luo, Y.; Selvanathan, S.; Haag, R.; Tegeder, P.; Grill, L. Imine Derivatives on Au(111): Evidence for "Inverted" Thermal Isomerization ACS Nano 2011, 5, 2090-2097
13. Shimizu, T. K.; Jung, J.; Imada, H.; Kim, Y. Adsorption-Induced Stability Reversal of Photochromic Diarylethene on Metal Surface ChemComm 2013, 49, 8710
14. Henzl, J.; Bredow, T.; Morgenstern, K. Irreversible Isomerization of the Azobenzene Derivate Methyl Orange on Au(111) Chem. Phys. Lett. 2007, 435, 278-282
15. Schmidt, T. M.; Horn, K.; Dil, J. H.; Kampen, T. U. Conformational Isomers of Stilbene on Si(100) Surf. Sci. 2007, 601, 1775-1780
16. Henningsen, N.; Rurali, R.; Franke, K. J.; Fernandez-Torrente, I.; Pascual, J. I. Trans to Cis Isomerization of an Azobenzene Derivative on a Cu(100) Surface Appl. Phys. A: Mater. Sci. Process. 2008, 93, 241-246
17. Piantek, M.; Miguel, J.; Krüger, A.; Navío, C.; Bernien, M.; Ball, D. K.; Hermann, K.; Kuch, W. Temperature, Surface, and Coverage-Induced Conformational Changes of Azobenzene Derivatives on Cu(001) J. Phys. Chem. C 2009, 113, 20307-20315
18. Bronner, C.; Schulze, M.; Hagen, S.; Tegeder, P. The Influence of the Electronic Structure of Adsorbate-Substrate Complexes on Photoisomerization Ability New J. Phys. 2012, 14, 043023
19. Bronner, C.; Priewisch, B.; Rück-Braun, K.; Tegeder, P. Photoisomerization of an Azobenzene on the Bi(111) Surface J. Phys. Chem. C 2013, 117, 27031-27038
20. Tian, H.; Yang, S. Recent Progresses on Diarylethene Based Photochromic Switches Chem. Soc. Rev. 2004, 33, 85-97
21. Irie, M.; Mohri, M. Thermally Irreversible Photochromic Systems. Reversible Photocyclization of Diarylethene Derivatives J. Org. Chem. 1988, 53, 803-808
22. Woodward, R. B.; Hoffmann, R. The Conservation of Orbital Symmetry Angew. Chem., Int. Ed. 1969, 8, 781-853
23. Kudernac, T.; van der Molen, S. J.; van Wees, B. J.; Feringa, B. L. Uni- and Bi-Directional Light-Induced Switching of Diarylethenes on Gold Nanoparticles Chem. Commun. 2006, 34, 3597-3599
24. Katsonis, N.; Kudernac, T.; Walko, M.; van der Molen, S. J.; van Wees, B. J.; Feringa, B. L. Reversible Conductance Switching of Single Diarylethenes on a Gold Surface Adv. Mater. 2006, 18, 1397-1400
25. Arramel; Pijper, T. C.; Kudernac, T.; Katsonis, N.; van der Maas, M.; Feringa, B. L.; van Wees, B. J. Reversible Light Induced Conductance Switching of Asymmetric Diarylethenes on Gold: Surface and Electronic Studies Nanoscale 2013, 5, 9277
26. Dulic, D.; van der Molen, S. J.; Kudernac, T.; Jonkman, H. T.; de Jong, J. J. D.; Bowden, T. N.; van Esch, J.; Feringa, B. L.; van Wees, B. One-Way Optoelectronic Switching of Photochromic Molecules on Gold Phys. Rev. Lett. 2003, 91, 207402
27. Tam, E. S.; Parks, J. J.; Shum, W. W.; Zhong, Y. W.; Santiago-Berrios, M. B.; Zheng, X.; Yang, W. T.; Chan, G. K. L.; Abruna, H. D.; Ralph, D. C. Single-Molecule Conductance of Pyridine-Terminated Dithienylethene Switch Molecules ACS Nano 2011, 5, 5115-5123
28. Kim, Y.; Hellmuth, Y.; Sysoiev, T. J.; Pauly, D.; Pietsch, F.; Wolf, T.; Erbe, J.; Huhn, A.; Groth, T.; Steiner, U.; Scheer, U. E.; Charge Transport, E. Characteristics of Diarylethene Photoswitching Single-Molecule Junctions Nano Lett. 2012, 12, 3736
29. Briechle, B. M.; Y, Y. Kim; Ehrenreich, P.; Erbe, A.; Sysoiev, D.; Huhn, T.; Groth, U.; Steiner, U. E.; Scheer, E. Current-Voltage Characteristics of Single-Molecule Diarylethene Junctions Measured with Adjustable Gold Electrodes in Solution Beilstein J. Nanotechnol. 2012, 3, 798
30. Coudret, C.; Guirado, G.; Estrampes, N.; Coratger, R. Adsorption of a Single Molecule of a Diarylethene Photochromic Dye on Cu(111) Phys. Chem. Chem. Phys. 2011, 13, 20946-20953
31. Mercurio, G.; McNellis, E. R.; Martin, I.; Hagen, S.; Leyssner, F.; Soubatch, S.; Meyer, J.; Wolf, M.; Tegeder, P.; Tautz, F. S.; Reuter, K. Structure and Energetics of Azobenzene on Ag(111): Benchmarking Semiempirical Dispersion Correction Approaches Phys. Rev. Lett. 2010, 104, 036102
32. McNellis, E. R.; Meyer, J.; Reuter, K. Azobenzene at Coinage Metal Surfaces: Role of Dispersive van der Waals Interactions Phys. Rev. B 2009, 80, 205414
33. Perdew, J. P. Density Functional Theory and the Band Gap Problem Int. J. Quantum Chem. 1985, 28, 497-523
34. 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
35. Morin, M.; Levinos, N. J.; Harris, A. L. Vibrational Energy Transfer of CO/Cu(100): Nonadiabatic Vibration/Electron Coupling J. Chem. Phys. 1992, 96, 3950-3956
36. Menzel, D.; Gomer, R. Desorption from Metal Surfaces by Low-Energy Electrons J. Chem. Phys. 1964, 41, 3311-3328
37. Redhead, P. A. Interaction of Slow Electrons with Chemisorbed Oxygen Can. J. Phys. 1964, 42, 886-905
38. Antoniewicz, P. R. Model for Electron- and Photon-Stimulated Desorption Phys. Rev. B 1980, 21, 3811-3815
39. Gilat, S. L.; Kawai, S. H.; Lehn, J.-M. Light-Triggered Molecular Devices: Photochemical Switching Of optical and Electrochemical Properties in Molecular Wire Type Diarylethene Species Chem.-Eur. J. 1995, 1, 275-284
40. Zastrow, M.; Thyagarajan, S.; Ahmed, S. A.; Haase, P.; Seedorff, S.; Gelman, D.; Wachtveitl, J.; Galoppini, E.; Rück-Braun, K. Efficient Preparation of Photoswitchable Dithienylethene-Linker-Conjugates by Palladium-Catalyzed Coupling Reactions of Terminal Alkynes with Thienyl Chlorides and Other Aryl Halides Chem.-Asian J. 2010, 5, 1202-1212
41. Kohn, W.; Sham, L. J. Self-Consistent Equations Including Exchange and Correlation Effects Phys. Rev. 1965, 140, A1133-A1138
42. Blöchl, P. E. Projector Augmented-Wave Method Phys. Rev. B 1994, 50, 17953-17979
43. Kresse, G.; Joubert, D. From Ultrasoft Pseudopotentials to the Projector Augmented-Wave Method Phys. Rev. B 1999, 59, 1758-1775
44. Kresse, G.; Hafner, J. Ab Initio Molecular Dynamics for Liquid Metals Phys. Rev. B 1993, 47, 558-561
45. Kresse, G.; Hafner, J. Ab Initio Molecular Dynamics for Open-Shell Transition Metals Phys. Rev. B 1993, 48, 13115-13118
46. Kresse, G.; Hafner, J. Ab Initio Molecular-Dynamics Simulation of the Liquid-Metal-Amorphous-Semiconductor Transition in Germanium Phys. Rev. B 1994, 49, 14251-14269
47. Perdew, J. P.; Chevary, J. A.; Vosko, S. H.; Jackson, K. A.; Pederson, M. R.; Singh, D. J.; Fiolhais, C. Atoms, Molecules, Solids, and Surfaces: Applications of the Generalized Gradient Approximation for Exchange and Correlation Phys. Rev. B 1992, 46, 6671-6687
48. Monkhorst, H. J.; Pack, J. D. Special Points for Brillouin-Zone Integrations Phys. Rev. B 1976, 13, 5188-5192
49. Grimme, S. Semiempirical GGA-Type Density Functional Constructed with a Long-Range Dispersion Correction J. Comput. Chem. 2006, 27, 1787-1799
50. Grimme, S.; Antony, J.; Ehrlich, S.; Krieg, H. A Consistent and Accurate Ab Initio Parametrization of Density Functional Dispersion Correction (DFT-D) for the 94 Elements H-Pu J. Chem. Phys. 2010, 132, 154104
51. Grimme, S.; Ehrlich, S.; Goerigk, L. Effect of the Damping Function in Dispersion Corrected Density Functional Theory J. Comput. Chem. 2011, 32, 1456-1465
52. Liu, L.; Bassett, W. A. Compression of Ag and Phase Transformation of NaCl J. Appl. Phys. 1973, 44, 1475-1479
53. Dunning, T. H. Gaussian Basis Sets for Use in Correlated Molecular Calculations. I. The Atoms Boron through Neon and Hydrogen J. Chem. Phys. 1989, 90, 1007-1023
54. Kendall, R. A.; Dunning, T. H., Jr.; Harrison, R. J. Electron Affinities of the First-Row Atoms Rrevisited. Systematic Basis Sets and Wave Functions J. Chem. Phys. 1992, 96, 6796-6806
55. Woon, D. E.; Dunning, T. H., Jr. Gaussian Basis Sets for Use in Correlated Molecular Calculations. III. The Atoms Aluminum through Argon J. Chem. Phys. 1993, 98, 1358-1371
56. Frisch, M. J.; Trucks, G. W.; Schlegel, H. B.; Scuseria, G. E.; Robb, M. A.; Cheeseman, J. R.; Scalmani, G.; Barone, V.; Mennucci, B.; Petersson, G. A.;., Gaussian 09, revision A.02; Gaussian, Inc.: Wallingford, CT, 2009.
57. Piccini, G. M.; Sauer, J. Quantum Chemical Free Energies: Structure Optimization and Vibrational Frequencies in Normal Modes J. Chem. Theory Comput. 2013, 9, 5038-5045
58. Mills, G.; Jónsson, H.; Schenter, G. K. Reversible Work Transition State Theory: Application to Dissociative Adsorption of Hydrogen Surf. Sci. 1995, 324, 305-337
59. Jónsson, H.; Mills, G.; Jacobsen, K. W. Nudged Elastic Band Method for Finding Minimum Energy Paths of Transitions. In Classical and Quantum Dynamics in Condensed Phase Simulations; Berne, B. J.; Ciccotti, G.; Coker, D. F., Eds.; World Scientific: Singapore, 1995.
60. Henkelman, G.; Jónsson, H. Improved Tangent Estimate in the Nudged Elastic Band Method for Finding Minimum Energy Paths and Saddle Points J. Chem. Phys. 2000, 113, 9978-9985
61. Henkelman, G.; Uberuaga, B. P.; Jónsson, H. A Climbing Image Nudged Elastic Band Method for Finding Saddle Points and Minimum Energy Paths J. Chem. Phys. 2000, 113, 9901-9904
62. Eyring, H. The Activated Complex and the Absolute Rate of Chemical Reactions Chem. Rev. 1937, 17, 65-77
63. Saalfrank, P. Quantum Dynamics of Laser- and Field-Induced Desorption of Molecules from Metal Surfaces Int. J. Quantum Chem. 2000, 80, 210-219
64. Füchsel, G.; Klamroth, T.; Dokić, J.; Saalfrank, P. On the Electronic Structure of Neutral and Ionic Azobenzenes and Their Possible Role as Surface Mounted Molecular Switches J. Phys. Chem. B 2006, 110, 16337-16345
65. Tang, W.; Sanville, E.; Henkelman, G. A Grid-Based Bader Analysis Algorithm without Lattice Bias J. Phys.: Condens. Matter 2009, 21, 084204
66. Sanville, E.; Kenny, S. D.; Smith, R.; Henkelman, G. Improved Grid-Based Algorithm for Bader Charge Allocation J. Comput. Chem. 2007, 28, 899-908
67. Henkelman, G.; Arnaldsson, A.; Jónsson, H. A Fast and Robust Algorithm for Bader Decomposition of Charge Density Comput. Mater. Sci. 2006, 36, 354-360