Bulletin of the Korean Chemical Society

Korean Chemical Society (대한화학회)
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Formation and Structure of Self-Assembled Monolayers of Octylthioacetates on Au(111) in Catalytic Tetrabutylammonium Cyanide Solution

  • Published : 2009.02.20
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Abstract

The formation and structure of self-assembled monolayers (SAMs) by the adsorption of acetyl-protected octylthioacetate (OTA) on Au(111) in a catalytic tetrabutylammonium cyanide (TBACN) solution were examined by means of scanning tunneling microscopy (STM), X-ray photoelectron spectroscopy (XPS), and cyclic voltammetry (CV). Molecular-scale STM imaging revealed that OTA molecules on Au(111) in a pure solvent form disordered SAMs, whereas they form well-ordered SAMs showing a c(4 × 2) structure in a catalytic TBACN solution. XPS and CV measurements also revealed that OTA SAMs on Au(111) formed in a TBACN solution have a stronger chemisorbed peak in the S 2p region at 162 eV and a higher blocking effect compared to OTA SAMs formed in a pure solvent. In this study, we clearly demonstrate that TBACN can be used as an effective deprotecting reagent for obtaining well-ordered SAMs of thioacetyl-protected molecules on gold.

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References

  1. Love, J. C.; Estroff, L. A.; Kriebel, J. K.; Nuzo, R. G.; Whitesides, G. M. Chem. Rev. 2005, 105, 1103. https://doi.org/10.1021/cr0300789
  2. Krämer, S.; Fuierer, R. R.; Gorman, C. B. Chem. Rev. 2003, 103, 4367. https://doi.org/10.1021/cr020704m
  3. Schreiber, F. J. Phys.: Condens. Matter 2004, 16, R881. https://doi.org/10.1088/0953-8984/16/28/R01
  4. Yokota, Y.; Fukui, K.-i.; Enoki, T.; Hara, M. J. Am. Chem. Soc. 2007, 129, 6571. https://doi.org/10.1021/ja070632m
  5. Crook, R. M.; Ricco, A. J. Acc. Chem. Res. 1998, 31, 219. https://doi.org/10.1021/ar970246h
  6. Flood, A. H.; Stoddart, J. F.; Steuerman, D. W.; Heath, J. R. Science 2004, 306, 2055. https://doi.org/10.1126/science.1106195
  7. Choi, Y.; Jeong, Y.; Chung, H.; Ito, E.; Hara, M.; Noh, J. Langmuir 2008, 24, 91. https://doi.org/10.1021/la701302g
  8. Noh, J.; Jeong, Y.; Ito, E.; Hara, M. J. Phys. Chem. C 2007, 111, 2691. https://doi.org/10.1021/jp067093c
  9. Poirier, G. E. Chem. Rev. 1997, 97, 1117. https://doi.org/10.1021/cr960074m
  10. Kwon, S.; Choi, J.; Lee, H.; Noh, J. Colloids and Surfaces A:Physicochem. Eng. Aspects 2008, 313-314, 324. https://doi.org/10.1016/j.colsurfa.2007.04.131
  11. Noh, J.; Kato, H. S.; Kawai, M.; Hara, M. J. Phys. Chem. B 2006, 110, 2793. https://doi.org/10.1021/jp055538b
  12. Noh, J.; Hara, M. Langmuir 2001, 17, 7280. https://doi.org/10.1021/la0100441
  13. Noh, J.; Hara, M. Langmuir 2002, 18, 1953. https://doi.org/10.1021/la010803f
  14. Cai, L.; Yao, Y.; Yang, J.; Price, D. W.; Tour, J. M. Chem. Mater. 2002, 14, 2905. https://doi.org/10.1021/cm011509b
  15. Holmes, B. T.; Snow, A. W. Tetrahedron 2005, 61, 12339. https://doi.org/10.1016/j.tet.2005.09.092
  16. Tour, J. M.; Jones II, L.; Pearson, D. L.; Lamba, J. J. S.; Burgin, T. P.; Whitesides, G. M.; Allara, D. L.; Parikh, A. N.; Atre, S. V. J. Am. Chem. Soc. 1995, 117, 9529. https://doi.org/10.1021/ja00142a021
  17. Jeong, Y.; Lee, C.; Ito, E.; Hara, M.; Noh, J. Jpn. J. Appl. Phys. 2006, 45, 5906. https://doi.org/10.1143/JJAP.45.5906
  18. Jeong, Y.; Han, J. W.; Kim, N.; Lee, Y.; Lee, C.; Hara, M.; Noh, J. Bull. Korean Chem. Soc. 2007, 28, 2445. https://doi.org/10.5012/bkcs.2007.28.12.2445
  19. Jeong, Y.; Kwon, S.; Kang, Y.; Lee, C.; Ito, E.; Hara, M.; Noh, J. Ultramicroscopy 2007, 107, 1000. https://doi.org/10.1016/j.ultramic.2007.02.038
  20. Jeong, Y.; Chung, H.; Noh, J. Colloids and Surfaces A: Physicochem. Eng. Aspects 2008, 313-314, 608. https://doi.org/10.1016/j.colsurfa.2007.04.132
  21. Jeong, Y.; Han, J. W.; Lee, C.; Noh, J. Bull. Korean Chem. Soc. 2008, 29, 1105. https://doi.org/10.5012/bkcs.2008.29.6.1105
  22. Stapleton, J. J.; Harder, P.; Daniel, T. A.; Reinard, M. D.; Yao, Y.;Price, D. W.; Tour, J. M.; Allara, D. L. Langmuir 2003, 19, 8245. https://doi.org/10.1021/la035172z
  23. Chen, L.; Yang, J.; Yao, Y.; Price, D. W. Jr.; Dirk, S. M.; Tour, J. M. Langmuir 2004, 20, 1335. https://doi.org/10.1021/la036254q
  24. Poirier, G. E.; Tarlov, M. J. Langmuir 1994, 10, 2853. https://doi.org/10.1021/la00021a001
  25. Delamarhe, E.; Michel, B.; Gerber, C.; Anselmetti, D.; Güntherodt, H.-J.; Wolf, H.; Ringsdorf, H. Langmuir 1994, 10, 2869. https://doi.org/10.1021/la00021a006
  26. Ishida, T.; Hara, H.; Kojima, I.; Tsuneda, S.; Nishida, N.; Sasabe, H.; Knoll, W. Langmuir 1998, 14, 2092. https://doi.org/10.1021/la971104z
  27. Castner, D. G.; Hinds, K.; Grainger, D. W. Langmuir 1996, 12, 5038

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