Surface structure, adsorption, and thermal desorption behaviors of methaneselenolate monolayers on Au(111) from dimethyl diselenides

Journal of Physical Chemistry C

Volumn 118, Issue 16, 2014, Pages 8322-8330

  Lee, Sang Yun ^a,b   Ito, Eisuke ^b   Kang, Hungu ^a   Hara, Masahiko ^b,c   Lee, Haiwon ^a   Noh, Jaegeun ^a  

^a Hanyang University   (South Korea)

^b RIKEN   (Japan)

^c TOKYO INSTITUTE OF TECHNOLOGY   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

ADSORPTION; DEPOSITION; DIMERS; MOLECULES; PHOTOELECTRONS; SCANNING TUNNELING MICROSCOPY; SELENIUM; SELENIUM COMPOUNDS; SELF ASSEMBLED MONOLAYERS; SULFUR; SURFACE STRUCTURE; VAPORS; X RAY PHOTOELECTRON SPECTROSCOPY;

ADSORPTION AFFINITY; ADSORPTION STATE; AU(111) SURFACES; DESORPTION BEHAVIOR; DESORPTION PEAKS; DIMETHYL DISULFIDES; DISORDERED PHASE; VAPOR PHASE DEPOSITION;

THERMAL DESORPTION;

EID: 84899514603     PISSN: 19327447     EISSN: 19327455     Source Type: Journal    
DOI: 10.1021/jp409531w     Document Type: Article

References (73)

1. Lee, W.; Kim, E. R.; Lee, H. Chemical Approach to High-Resolution Patterning on Self-Assembled Monolayers Using Atomic Force Microscope Lithography Langmuir 2002, 18, 8375-8380
2. Park, J.; Lee, H. Effect of Surface Functional Groups on Nanostructure Fabrication Using AFM Lithography Mater. Sci. Eng., C 2004, 24, 311-314
3. Nakamura, F.; Ito, E.; Hayashi, T.; Hara, M. Fabrication of COOH-Terminated Self-Assembled Monolayers for DNA Sensors Colloids Surf., A 2006, 284, 495-498
4. Hamoudi, H.; Guo, Z. A.; Prato, M.; Dablemont, C.; Zheng, W. Q.; Bourguignon, B.; Canepa, M.; Esaulov, V. A. On the Self Assembly of Short Chain Alkanedithiols Phys. Chem. Chem. Phys. 2008, 10, 6836-6841
5. 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
6. Noh, J.; Hara, M. Final Phase of Alkanethiol Self-Assembled Monolayers on Au(111) Langmuir 2002, 18, 1953-1956
7. Noh, J.; Kato, H. S.; Kawai, M.; Hara, M. Surface and Adsorption Structures of Dialkyl Sulfide Self-Assembled Monolayers on Au(111) J. Phys. Chem. B 2002, 106, 13268-13272
8. Ulman, A. Formation and Structure of Self-Assembled Monolayers Chem. Rev. 1996, 96, 1533-1554
9. Liu, G. Y.; Xu, S.; Qian, Y. L. Nanofabrication of Self-Assembled Monolayers Using Scanning Probe Lithography Acc. Chem. Res. 2000, 33, 457-466
10. Gorman, C. B.; He, Y. F.; Carroll, R. L. The Influence of Headgroup on the Structure of Self-Assembled Monolayers as Viewed by Scanning Tunneling Microscopy Langmuir 2001, 17, 5324-5328
11. Ito, E.; Konno, K.; Noh, J.; Kanai, K.; Ouchi, Y.; Seki, K.; Hara, M. Chain Length Dependence of Adsorption Structure of COOH-Terminated Alkanethiol Sams on Au(111) Appl. Surf. Sci. 2005, 244, 584-587
12. Konno, K.; Ito, E.; Noh, J.; Hara, M. Surface Structures and Adsorption States of Self-Assembled Monolayers Formed by Various COOH-Terminated Alkanethiols on Au(111) Jpn. J. Appl. Phys. 2006, 45, 405-408
13. Lee, S. Y.; Noh, J.; Ito, E.; Lee, H.; Hara, M. Solvent Effect on Formation of Cysteamine Self-Assembled Monolayers on Au(111) Jpn. J. Appl. Phys. 2003, 42, 236-241
14. 3-Terminated Alkanethiol Sams on Au(111) Langmuir 2005, 21, 933-936
15. Tamada, K.; Nagasawa, J.; Nakanishi, F.; Abe, K.; Hara, M.; Knoll, W.; Ishida, T.; Fukushima, H.; Miyashita, S.; Usui, T.; Koini, T.; Lee, T. R. Structure of SAMs Generated from Functionalized Thiols on Gold Thin Solid Films 1998, 327, 150-155
16. Tsukamoto, K.; Kubo, T.; Nozoye, H. Structure of Mercaptoalcohol Self-Assembled Monolayers on Au(111) Appl. Surf. Sci. 2005, 244, 578-583
17. Wang, H.; Chen, S. F.; Li, L. Y.; Jiang, S. Y. Improved Method for the Preparation of Carboxylic Acid and Amine Terminated Self-Assembled Monolayers of Alkanethiolates Langmuir 2005, 21, 2633-2636
18. Poirier, G. E. Characterization of Organosulfur Molecular Monolayers on Au(111) Using Scanning Tunneling Microscopy Chem. Rev. 1997, 97, 1117-1127
19. Azzam, W.; Bashir, A.; Shekhah, O. Thermal Study and Structural Characterization of Self-Assembled Monolayers Generated from Diadamantane Disulfide on Au(1 1 1) Appl. Surf. Sci. 2011, 257, 3739-3747
20. Jia, J. J.; Mukherjee, S.; Hamoudi, H.; Nannarone, S.; Pasquali, L.; Esaulov, V. A. Lying-Down to Standing-Up Transitions in Self Assembly of Butanedithiol Mono Layers on Gold and Substitutional Assembly by Octanethiols J. Phys. Chem. C 2013, 117, 4625-4631
21. Cai, L. T.; Yao, Y. X.; Yang, J. P.; Price, D. W.; Tour, J. M. Chemical and Potential-Assisted Assembly of Thiolacetyl-Terminated Oligo(Phenylene Ethynylene)S on Gold Surfaces Chem. Mater. 2002, 14, 2905-2909
22. Lukkari, J.; Meretoja, M.; Kartio, I.; Laajalehto, K.; Rajamaki, M.; Lindstrom, M.; Kankare, J. Organic Thiosulfates (Bunte Salts): Novel Surface-Active Sulfur Compounds for the Preparation of Self-Assembled Monolayers on Gold Langmuir 1999, 15, 3529-3537
23. Tour, J. M.; Jones, L.; Pearson, D. L.; Lamba, J. J. S.; Burgin, T. P.; Whitesides, G. M.; Allara, D. L.; Parikh, A. N.; Atre, S. V. Self-Assembled Monolayers and Multilayers of Conjugated Thiols, α,ω-Dithiols, and Thioacetyl-Containing Adsorbates. Understanding Attachments between Potential Molecular Wires and Gold Surfaces J. Am. Chem. Soc. 1995, 117, 9529-9534
24. Lusk, A. T.; Jennings, G. K. Characterization of Self-Assembled Monolayers Formed from Sodium S-Alkyl Thiosulfates on Copper Langmuir 2001, 17, 7830-7836
25. Lau, K. H. A.; Huang, C.; Yakovlev, N.; Chen, Z. K.; O'Shea, S. J. Direct Adsorption and Monolayer Self-Assembly of Acetyl-Protected Dithiols Langmuir 2006, 22, 2968-2971
26. Lee, S. Y.; Choi, Y.; Ito, E.; Hara, M.; Lee, H.; Noh, J. Growth, Solvent Effects, and Thermal Desorption Behavior of Octylthiocyanate Self-Assembled Monolayers on Au(111) Phys. Chem. Chem. Phys. 2013, 15, 3609-3617
27. Choi, Y.; Jeong, Y.; Chung, H.; Ito, E.; Hara, M.; Noh, J. Formation of Ordered Self-Assembled Monolayers by Adsorption of Octylthiocyanates on Au(111) Langmuir 2008, 24, 91-96
28. Ciszek, J. W.; Stewart, M. P.; Tour, J. M. Spontaneous Assembly of Organic Thiocyanates on Gold Sufaces. Alternative Precursors for Gold Thiolate Assemblies J. Am. Chem. Soc. 2004, 126, 13172-13173
29. Ciszek, J. W.; Tour, J. M. Mechanistic Implications of the Assembly of Organic Thiocyanates on Precious Metals Chem. Mater. 2005, 17, 5684-5690
30. Dreesen, L.; Volcke, C.; Sartenaer, Y.; Peremans, A.; Thiry, P. A.; Humbert, C.; Grugier, J.; Marchand-Brynaert, J. Comparative Study of Decyl Thiocyanate and Decanethiol Self-Assembled Monolayers on Gold Substrates Surf. Sci. 2006, 600, 4052-4057
31. Shen, C.; Buck, M.; Wilton-Ely, J. D. E. T.; Weidner, T.; Zharnikov, M. On the Importance of Purity for the Formation of Self-Assembled Monolayers from Thiocyanates Langmuir 2008, 24, 6609-6615
32. CRC Handbook of Chemistry and Physics, 92 nd ed.; CRC Press: Boca Raton, FL, 2012.
33. Bandyopadhyay, K.; Vijayamohanan, K.; Venkataramanan, M.; Pradeep, T. Self-Assembled Monolayers of Small Aromatic Disulfide and Diselenide Molecules on Polycrystalline Gold Films: A Comparative Study of the Geometrical Constraint Using Temperature-Dependent Surface-Enhanced Raman Spectroscopy, X-Ray Photoelectron Spectroscopy, and Electrochemistry Langmuir 1999, 15, 5314-5322
34. Choi, J.; Kang, H.; Ito, E.; Hara, M.; Noh, J. Phase Transition of Octaneselenolate Self-Assembled Monolayers on Au(111) Studied by Scanning Tunneling Microscopy Bull. Korean Chem. Soc. 2011, 32, 2623-2627
35. Choi, J.; Lee, Y. J.; Kang, H.; Han, J. W.; Noh, J. Self-Assembled Monolayers of Dioctyl Diselenides on Au(111) Bull. Korean Chem. Soc. 2008, 29, 1229-1232
36. de la Llave, E.; Scherlis, D. A. Selenium-Based Self-Assembled Monolayers: The Nature of Adsorbate-Surface Interactions Langmuir 2010, 26, 173-178
37. Dishner, M. H.; Hemminger, J. C.; Feher, F. J. Scanning Tunneling Microscopy Characterization of Organoselenium Monolayers on Au(III) Langmuir 1997, 13, 4788-4790
38. Han, S. W.; Lee, S. J.; Kim, K. Self-Assembled Monolayers of Aromatic Thiol and Selenol on Silver: Comparative Study of Adsorptivity and Stability Langmuir 2001, 17, 6981-6987
39. Huang, F. K.; Horton, R. C.; Myles, D. C.; Garrell, R. L. Selenolates as Alternatives to Thiolates for Self-Assembled Monolayers: A SERS Study Langmuir 1998, 14, 4802-4808
40. Kafer, D.; Bashir, A.; Witte, G. Interplay of Anchoring and Ordering in Aromatic Self-Assembled Monolayers J. Phys. Chem. C 2007, 111, 10546-10551
41. Samant, M. G.; Brown, C. A.; Gordon, J. G. Formation of an Ordered Self-Assembled Monolayer of Docosaneselenol on Gold(111). Structure by Surface X-Ray-Diffraction Langmuir 1992, 8, 1615-1618
42. Sato, Y.; Mizutani, F. Formation and Characterization of Aromatic Selenol and Thiol Monolayers on Gold: In-Situ IR Studies and Electrochemical Measurements Phys. Chem. Chem. Phys. 2004, 6, 1328-1331
43. Shaporenko, A.; Ulman, A.; Terfort, A.; Zharnikov, A. Self-Assembled Monolayers of Alkaneselenolates on (111) Gold and Silver J. Phys. Chem. B 2005, 109, 3898-3906
44. Szelagowska-Kunstman, K.; Cyganik, P.; Schupbach, B.; Terfort, A. Relative Stability of Thiol and Selenol Based SAMs on Au(111)-Exchange Experiments Phys. Chem. Chem. Phys. 2010, 12, 4400-4406
45. Weidner, T.; Shaporenko, A.; Ballav, N.; Ulman, A.; Zhamikov, M. Modification of Alkaneselenolate Monolayers by Low-Energy Electrons J. Phys. Chem. C 2008, 112, 1191-1198
46. Yee, C. K.; Ulman, A.; Ruiz, J. D.; Parikh, A.; White, H.; Rafailovich, M. Alkyl Selenide- and Alkyl Thiolate-Functionalized Gold Nanoparticles: Chain Packing and Bond Nature Langmuir 2003, 19, 9450-9458
47. Romashov, L. V.; Ananikov, V. P. Self-Assembled Selenium Monolayers: From Nanotechnology to Material Science and Adaptive Catalysis Chem.-Eur. J. 2013, 19, 17640-17660
48. Jia, J. J.; Bendounan, A.; Kotresh, H. M. N.; Chaouchi, K.; Sirotti, F.; Sampath, S.; Esaulov, V. A. Selenium Adsorption on Au(111) and Ag(111) Surfaces: Adsorbed Selenium and Selenide Films J. Phys. Chem. C 2013, 117, 9835-9842
49. Azzam, W. A Novel Method for Elimination of the Gold-Islands Formed in the Self-Assembled Monolayers of Benzeneselenol on Au(111) Surface Appl. Surf. Sci. 2010, 256, 2299-2303
50. Nakano, K.; Sato, T.; Tazaki, M.; Takagi, M. Self-Assembled Monolayer Formation from Decaneselenol on Polycrystalline Gold as Characterized by Electrochemical Measurements, Quartz-Crystal Microbalance, XPS, and IR Spectroscopy Langmuir 2000, 16, 2225-2229
51. Subramanian, S.; Sampath, S. Enhanced Stability of Short- and Long-Chain Diselenide Self-Assembled Monolayers on Gold Probed by Electrochemistry, Spectroscopy, and Microscopy J. Colloid Interface Sci. 2007, 312, 413-424
52. Bain, C. D.; Troughton, E. B.; Tao, Y. T.; Evall, J.; Whitesides, G. M.; Nuzzo, R. G. Formation of Monolayer Films by the Spontaneous Assembly of Organic Thiols from Solution onto Gold J. Am. Chem. Soc. 1989, 111, 321-335
53. Dishner, M. H.; Hemminger, J. C.; Feher, F. J. Direct Observation of Substrate Influence on Chemisorption of Methanethiol Adsorbed from the Gas Phase onto the Reconstructed Au(111) Surface Langmuir 1997, 13, 2318-2322
54. Jung, C.; Dannenberger, O.; Xu, Y.; Buck, M.; Grunze, M. Self-Assembled Monolayers from Organosulfur Compounds: A Comparison between Sulfides, Disulfides, and Thiols Langmuir 1998, 14, 1103-1107
55. Noh, J.; Jang, S.; Lee, D.; Shin, S.; Ko, Y. J.; Ito, E.; Joo, S. W. Abnormal Adsorption Behavior of Dimethyl Disulfide on Gold Surfaces Curr. Appl. Phys. 2007, 7, 605-610
56. Cometto, F. P.; Macagno, V. A.; Paredes-Olivera, P.; Patrito, E. M.; Ascolani, H.; Zampieri, G. Decomposition of Methylthiolate Monolayers on Au(111) Prepared from Dimethyl Disulfide in Solution Phase J. Phys. Chem. C 2010, 114, 10183-10194
57. Hayashi, T.; Morikawa, Y.; Nozoye, H. Adsorption State of Dimethyl Disulfide on Au(111): Evidence for Adsorption as Thiolate at the Bridge Site J. Chem. Phys. 2001, 114, 7615-7621
58. Noh, J.; Hara, M. Nanoscopic Evidence for Dissociative Adsorption of Asymmetric Disulfide Self-Assembled Monolayers on Au(111) Langmuir 2000, 16, 2045-2048
59. Noh, J.; Murase, T.; Nakajima, K.; Lee, H.; Hara, M. Nanoscopic Investigation of the Self-Assembly Processes of Dialkyl Disulfides and Dialkyl Sulfides on Au(111) J. Phys. Chem. B 2000, 104, 7411-7416
60. Yang, G. H.; Liu, G. Y. New Insights for Self-Assembled Monolayers of Organothiols on Au(111) Revealed by Scanning Tunneling Microscopy J. Phys. Chem. B 2003, 107, 8746-8759
61. Monnell, J. D.; Stapleton, J. J.; Jackiw, J. J.; Dunbar, T.; Reinerth, W. A.; Dirk, S. M.; Tour, J. M.; Allara, D. L.; Weiss, P. S. Ordered Local Domain Structures of Decaneselenolate and Dodecaneselenolate Monolayers on Au{111} J. Phys. Chem. B 2004, 108, 9834-9841
62. Ishida, T.; Choi, N.; Mizutani, W.; Tokumoto, H.; Kojima, I.; Azehara, H.; Hokari, H.; Akiba, U.; Fujihira, M. High-Resolution X-Ray Photoelectron Spectra of Organosulfur Monolayers on Au(111): S(2p) Spectral Dependence on Molecular Species Langmuir 1999, 15, 6799-6806
63. Kang, H.; Shin, D. G.; Han, J. W.; Ito, E.; Hara, M.; Noh, J. Unique Ordered Domains of Biphenylthiol Self-Assembled Monolayers on Au(111) J. Nanosci. Nanotechnol. 2012, 12, 557-562
64. Chesneau, F.; Zhao, J. L.; Shen, C.; Buck, M.; Zharnikov, M. Adsorption of Long-Chain Alkanethiols on Au(111): A Look from the Substrate by High Resolution X-Ray Photoelectron Spectroscopy J. Phys. Chem. C 2010, 114, 7112-7119
65. Castner, D. G.; Hinds, K.; Grainger, D. W. X-Ray Photoelectron Spectroscopy Sulfur 2p Study of Organic Thiol and Disulfide Binding Interactions with Gold Surfaces Langmuir 1996, 12, 5083-5086
66. Fonder, G.; Delhalle, J.; Mekhalif, Z. Exchange versus Intercalation of n -Dodecanethiol Monolayers on Copper in the Presence of n -Dodecaneselenol and vice versa Appl. Surf. Sci. 2010, 256, 2968-2973
67. Kondoh, H.; Nakai, I.; Nambu, A.; Ohta, T.; Nakamura, T.; Kimura, R.; Matsumoto, M. Dissociative and Non-dissociative Adsorption of Selenophene on Au(111) Depending on the Preparation Method Chem. Phys. Lett. 2001, 350, 466-472
68. Hayashi, T.; Wakamatsu, K.; Ito, E.; Hara, M. Effect of Steric Hindrance on Desorption Processes of Alkanethiols on Au(111) J. Phys. Chem. C 2009, 113, 18795-18799
69. Ito, E.; Ito, H.; Kang, H.; Hayashi, T.; Hara, M.; Noh, J. Influence of Surface Morphology and Substrate on Thermal Stability and Desorption Behavior of Octanethiol Self-Assembled Monolayers: Cu, Ag, and Au J. Phys. Chem. C 2012, 116, 17586-17593
70. Kondoh, H.; Kodama, C.; Sumida, H.; Nozoye, H. Molecular Processes of Adsorption and Desorption of Alkanethiol Monolayers on Au(111) J. Chem. Phys. 1999, 111, 1175-1184
71. Lavrich, D. J.; Wetterer, S. M.; Bernasek, S. L.; Scoles, G. Physisorption and Chemisorption of Alkanethiols and Alkyl Sulfides on Au(111) J. Phys. Chem. B 1998, 102, 3456-3465
72. Nuzzo, R. G.; Zegarski, B. R.; Dubois, L. H. Fundamental-Studies of the Chemisorption of Organosulfur Compounds on Gold(111). Implications for Molecular Self-Assembly on Gold Surfaces J. Am. Chem. Soc. 1987, 109, 733-740
73. Stettner, J.; Winkler, A. Characterization of Alkanethiol Self-Assembled Monolayers on Gold by Thermal Desorption Spectroscopy Langmuir 2010, 26, 9659-9665