Electrochemical oxidative formation of ordered monolayers of thiol molecules on Au(111) surface

Chemical Record

Volumn 9, Issue 3, 2009, Pages 199-209

  Uosaki, Kohei ^a  

^a HOKKAIDO UNIVERSITY   (Japan)

Author keywords

Au(111); surface x ray diffraction; Electrochemical formation; Self assembled monolayer; Thiol monolayer

Indexed keywords

GOLD; THIOL DERIVATIVE;

ARTICLE; CHEMISTRY; ELECTROCHEMISTRY; OXIDATION REDUCTION REACTION; SCANNING TUNNELING MICROSCOPY; SURFACE PROPERTY; X RAY DIFFRACTION;

ELECTROCHEMISTRY; GOLD; MICROSCOPY, SCANNING TUNNELING; OXIDATION-REDUCTION; SULFHYDRYL COMPOUNDS; SURFACE PROPERTIES; X-RAY DIFFRACTION;

EID: 67649406558     PISSN: 15278999     EISSN: 15280691     Source Type: Journal    
DOI: 10.1002/tcr.200900002     Document Type: Article

References (83)

1. Ulman, A. An Introduction to Ultrathin Organic Films: From Langmuir-Blodgett to Self-Assembly; Academic Press: San Diego, CA, 1991.
2. Porter, M. D.; Bright, T. B.; Aliara, D. L.; Chidsey, C. E. D. J. Am. Chem. Soc. 1987, 109, 3559.
3. Chidsey, C. E. D.; Bertozzi, C. R.; Putvinski, T. M.; Mujsce, A. M. J. Am. Chem. Sci. 1990, 112, 4301.
4. Uosaki, K.; Sato, Y.; Kita, H. Langmuir 1991, 7, 1510.
5. Laibinis, P. E.; Whitesides, G. M.; Allara, D. L.; Tao, Y.-T.; Parikin, A. N.; Nuzzo, R. G. J. Am. Chem. Soc. 1991, 113, 7152.
6. Dubois, L. H.; Nuzzo, R. G. Annu. Rev. Phys. Chem. 1992, 43, 437.
7. Fawcett, W. R.; Opallo, M. Angew. Chem.-Int. Edit. 1994, 33, 2131.
8. Finklea, H. O. Electroanalytical Chemistry; Marcel Dekker: New York, 1996; Vol. 19, p 109.
9. Ulman, A. Chem. Rev. 1996, 96, 1533.
10. Uosaki, K.; Kondo, T.; Zhang, X.-Q.; Yanagida, M. J. Am. Chem. Soc. 1997, 119, 8367.
11. Ulman, A. Thin Films: Self-Assembled Monolayers of Thiols; Academic Press: San Diego, 1998.
12. Kondo, T.; Uosaki, K. Encyclopedia of Electrochemistry, Volume 10: Modified Electrodes, 1.2.2; Wiley-VCH: Weinheim, 80-104, 2007.
13. Kondo T.; Uosaki K., J. Photochem. Photobio. C., 8, No. l, 1-17, 2007.
14. Kondo T., Uosaki K. In: Bottom-Up Nanofabrication: Supramolecules, Self-Assemblies, and Organized Films, Vol. 4, Chapt. 19; American Scientific Publishers: California, 2009.
15. Bryant, M. A.; Pemberton, J. E. J. Am. Chem. Soc. 1991, 113, 8284.
16. Sato, Y.; Frey, B. L.; Corn, R. M.; Uosaki, K. Bull. Chem. Soc. Jpn. 1994, 67, 21.
17. Bensebaa, F.; Voicu, R.; Huron, L.; Ellis, T. H.; Kruus, E. Langmuir 1997, 13, 5335.
18. Ye, S.; Haba, T.; Sato, Y.; Shimazu, K.; Uosaki, K. Phys. Chem. Chem. Phys. 1999, 1, 3653.
19. Roy, D.; Fendler, J. Adv. Mater. 2004, 16, 479.
20. Shimazu, K.; Yagi, I.; Sato, Y.; Uosaki, K. Langmuir 1992, 8, 1385.
21. Buttry, D. A.; Ward, M. D. Chem. Rev. 1992, 92, 1355.
22. Karpovich, D. S.; Blanchard, G. J. Langmuir 1994, 10, 3315.
23. Yamada, R.; Uosaki, K. Langmuir 1997, 13, 5218.
24. Poirier, G. E. Chem. Rev. 1997, 97, 1117.
25. Yamada, R.; Uosaki, K. Langmuir 1998, 14, 855.
26. Yamada, R.; Uosaki, K. Langmuir 2000, 16, 4413.
27. Schreiber, F. Prog. Surf. Sci. 2000, 65, 151.
28. Yang, G.; Liu, G.-Y. J. Phys. Chem. B 2003, 107, 8746.
29. Alves, C. A.; Smith, E. L.; Porter, M. D. J. Am. Chem. Soc. 1992, 114, 1222.
30. Xu, S.; Cruchon-Dupeyrat, S. J. N.; Garno, J. C.; Liu, G.-Y.; Jennings, G. K.; Yong, T.-H.; Laibinis, P. E. J. Chem. Phys. 1998, 108, 5002.
31. Noh, J.; Hara, M. Langmuir 2002, 18, 1953.
32. Kondo T., Uosaki K. Bottom-Up Nanofabrication: Supramolecules, Self-Assemblies, and Organized Films, Vol. 3, Chapt. 13; American Scientific Publishers: California, 2009.
33. Camillone, N., III; Chidsey, C. D. E.; Eisenberger, P.; Fenter, P.; Li, J.; Liang, K. S.; Liu, G.-Y.; Scoles, G. J. Chem. Phys. 1993, 99, 744.
34. Dannenberger, O.; Buck, M.; Grunze, M. J. Phys. Chem. B 1999, 103, 2202.
35. Petralli-Mallow, T. P.; Briggman, K. A.; Richter, L. J.; Stephenson, J. C.; Plant, A. L. Proc. SPIE-Int. Soc. Opt. Eng. 1999, 3858, 25.
36. Himmelhaus, M.; Eisert, F.; Buck, M.; Grunze, M. J. Phys. Chem. B 2000, 104, 576.
37. Boubour, E.; Lennox, R. B. J. Phys. Chem. B 2000, 104, 9004.
38. Protsailo, L.; Fawcett, W. R. Langmuir 2002, 18, 8933.
39. Edinger, K.; Gölzhäuser, A.; Demora, K.; Wöll, Ch.; Grunze, M. Langmuir 1993, 9, 4.
40. Schönenberger, C.; Sondag-Huethorst, J. A. M.; Jorritsma, J.; Fokkink, L. G. J. Langmuir 1994, 10, 611.
41. Sondag-Huethorst, J. A. M.; Schönenberger, C.; Fokkink, L. G. J. J. Phys. Chem. 1994, 98, 6826.
42. Schönenberger, C.; Jorritsma, J.; Sondag-Huethorst, J. A. M.; Fokkink, L. G. J. J. Phys. Chem. 1995, 99, 3259.
43. McDermott, C. A.; McDermott, M. T.; Green, J.-B.; Porter, M. D. J. Phys. Chem. 1995, 99, 13257.
44. Yamada, R.; Sakai, H.; Uosaki, K. Chem. Lett. 1999, 667.
45. Yamada, R.; Wano, H.; Uosaki, K. Langmuir 2000, 16, 5523.
46. Widrig, C. A.; Chung. C.; Porter, M. D. J. Electroanal. Chem. 1991, 310, 335
47. Yang, D.-F.; Wilde, C. P.; Morin, M. Langmuir 1996, 12, 6570.
48. Yang, D.-F.; Wilde, C. P.; Morin, M. Langmuir 1997, 13, 243.
49. Kondo, T.; Sumi, T.; Uosaki, K. J. Electroanal. Chem. 2002, 59, 538-539.
50. Weisshaar, D. E.; Lamp, B. D.; Porter, M. D. J. Am. Chem. Soc. 1992, 114, 5860.
51. Fruböse, C.; Doblhofer, K. J. Chem. Soc.-Faraday Trans. 1995, 91, 1949.
52. Ron, H.; Rubinstein, I. J. Am. Chem. Soc. 1998, 120, 13444.
53. Eu, S.; Paik, W. Chem. Lett. 1998, 405.
54. Ma, F.; Lennox, R. B. Langmuir 2000, 16, 6188.
55. Qu, D.; Morin, M. J. Electroanal. Chem. 2001, 517, 45.
56. Subramanian, R.; Lakshminarayanan, V. Electrochim. Acta 2000, 45, 4501.
57. Paik, W.; Eu, S.; Lee, K.; Chon, S.; Kim, M. Langmuir 2000, 16, 10198.
58. Chon, S.; Paik, W. Phys. Chem. Chem. Phys. 2001, 3, 3405.
59. Lee, M.-T.; Hsueh, C.-C.; Freund, M. S.; Ferguson, G. S. Langmuir 2003, 19, 5246.
60. Brett, C. M. A.; Kresak, S.; Hianik, T.; Brett, A. M. O. Electroanalysis 2003, 15, 557.
61. Doneux, TH.; Nichols, R. J.; Buess-Herman, CI.; J. Electroanal. Chem. 2008, 621, 267.
62. Wöll, Ch.; Chiang, S.; Wilson, R. J.; Lippel, P. H. Phys. Rev. B 1989, 39, 7988.
63. Barth, J. V.; Brune, H.; Ertl, G.; Behm, R. J. Phys. Rev. B 1990, 42, 9307.
64. Uosaki, K.; Yamada, R. J. Am. Chem. Soc., 1999, 121, 4090.
65. Yamada, R.; Uosaki, K. J. Phys. Chem. B, 2000, 104, 6021.
66. Takakusagi, S.; Kitamura, K.; Uosaki, K. J. Phys. Chem. C 2008, 112, 3073.
67. 68 from a gold wire was used as a substrate for electrochemical STM (EC-STM) measurements. In situ EC-STM measurements were carried out using a Pico SPM (Molecular Imaging) controlled by a Nanoscope E (Digital Instruments). STM tips were mechanically cut Pt/Ir (80:20) wire (ø = 0.3 mm, Tanaka Precious Metal) insulated with Apiezon wax. STM observations were carried out in a homemade PCTFE cell, which was placed in an Ar filled STM chamber, at room temperature with a bias of 300-850 mV and a tunneling current of 15 pA-5 nA in a constant-current mode. Potentials of the Au(111) electrode and the STM tip were independently controlled by a bipotentiostat (PicoSTAT, Molecular Imaging), and a Ag/AgCl (saturated NaCl) electrode and a Pt wire were used as reference and counter electrodes, respectively. An ethanol solution containing 20 mM KOH, which was deaerated by bubbling Ar for 30 min, was injected into the cell while the Au(111) electrode was held at -450 mV.
68. Clavilier, J.; Faure, R.; Guinet, G.; Durand, R. J. Electroanal. Chem. 1980, 107, 205.
69. Wano, H.; Uosaki, K. Langmuir 2005, 21, 4024-4033.
70. 71 was not expected.
71. 72,73 and the pH of 0.1 M KOH ethanol solution is ca. 13, the thiol molecules are expected to be fully ionized and to exist as thiolate ion.
72. Crampton, M. R. The Chemistry of the Thiol Group: Part 1; (Ed.: S. Patai), Wiley: New York, 1974.
73. Serjeant, E. P.; Dempsey, B. Ionisation Constants of Organic Compounds in Aqueous Solutions; IUPAC Chemical Data Series, No. 23; Pergamon Press: Oxford, 1983.
74. Sumi, T.; Wano, H.; Uosaki, K. J. Electroanal. Chem. 2003, 550,321.
75. Sumi, T.; Uosaki, K. J. Phys. Chem. B, 2004, 108, 6422.
76. Kawaguchi, T.; Yasuda, Y.; Shimazu, K.; Porter, M. D. Langmuir 2000, 16, 9830.
77. Bard, A. J.; Faulkner, L. R. Electrochemical Methods: Fundamentals and Applications; Wiley: New York, 1980.
78. Poirier, G. E.; Tarlov, M. J. J. Phys. Chem. 1995, 99, 10966.
79. Cavalleri, O.; Hirstein, A.; Kern, K. Surf. Sci. 1995, 340, L960.
80. Schweizer, M.; Hagenström, H.; Kolb, D. M. Surf. Sci. 2001, 490, L627.
81. Wano, H.; Uosaki, K. Langmuir 2001, 17, 8224.
82. Wang, J.; Davenport, A. J.; Isaacs, H. S.; Ocko, B. M. Science 1992, 255, 1416.
83. Uosaki, K.; Kondo, T.; Morita, J.; Takakusagi, S.; Sumi, T. submitted, 2009.