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Self-Assembled Structures of Benzoic Acid on Au(111) Surface

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Abstract

Electrochemical scanning tunneling microscopy combined with cyclic voltammetry were employed to explore the self-assembly of benzoic acid (BA) on a Au(111) substrate surface in a 0.1-M HClO4 solution. At the negatively charged surface, BA molecules form two highly ordered physisorbed adlayers with their phenyl rings parallel to the substrate surface. High-resolution scanning tunneling microscopy images reveal the packing arrangement and internal molecular structures. The striped pattern and zigzag structure of the BA adlayers are composed of parallel rows of dimers, in which two BA molecules are bound through a pair of O–H···O hydrogen bonds. Increasing the electrode potential further to positive charge densities of Au(111) leads to the desorption of the physisorbed hydrogen-bonded networks and the formation of a chemisorbed adlayer. BA molecules change their orientation from planar to upright fashion, which is accompanied by the deprotonation of the carboxyl group. Furthermore, potential-induced formation and dissolution of BA adlayers were also investigated. Structural transitions between the various types of ordered adlayers occur according to a nucleation and growth mechanism.

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References

  1. J.V. Barth, G. Costantini, and K. Kern, Nature 437, 671 (2005).

    Article  Google Scholar 

  2. L. Kampschulte, Ph.D. Thesis, Ludwig-Maximilians-Universität München, 2006.

  3. J.A.A.W. Elemans, S. Lei, and S. De Feyter, Angew. Chem. Int. Ed. Engl. 48, 7298 (2009).

    Article  Google Scholar 

  4. T. Balandina, K. Tahara, N. Sändig, M.O. Blunt, J. Adisoejoso, S. Lei, F. Zerbertto, Y. Tobe, and S. De Feyter, ACS Nano 6, 8381 (2012).

    Article  Google Scholar 

  5. S. De Feyter and F.C. De Schryver, Chem. Soc. Rev. 32, 139 (2003).

    Article  Google Scholar 

  6. H. Noda, L. Wan, and M. Osawa, Phys. Chem. Chem. Phys. 3, 3336 (2001).

    Article  Google Scholar 

  7. S. Clair, A.P. Seitsonen, H. Brune, K. Kern, and J.V. Barth, J. Phys. Chem. B 108, 14585 (2004).

    Article  Google Scholar 

  8. M. Lackinger and W.M. Heckl, Langmuir 25, 11307 (2009).

    Article  Google Scholar 

  9. F. De Marchi, D. Cui, J. Lipton-Duffin, C. Santato, J.M. MacLeod, and F. Rosei, J. Chem. Phys. 142, 101923 (2015).

    Article  Google Scholar 

  10. G.A. Sim, J.M. Robertson, and T.H. Goodwin, Acta Crystallogr. 8, 157 (1955).

    Article  Google Scholar 

  11. P. Waszczuk, P. Zelenay, and J. Sobkowski, Eletrochim. Acta 40, 1717 (1995).

    Article  Google Scholar 

  12. T.-H. Vu and T. Wandlowski, J. Electroanal. Chem. 776, 40 (2016).

    Article  Google Scholar 

  13. M.H. Hözle, Th. Wandlowski, and D.M. Kolb, J. Electroanal. Chem. 394, 271 (1995).

    Article  Google Scholar 

  14. D.M. Kolb, Prog. Surf. Sci. 51, 109 (1996).

    Article  Google Scholar 

  15. Y. Ikezawa, R. Sekiguchi, and T. Kitazume, Electrochim. Acta 46, 731 (2000).

    Article  Google Scholar 

  16. F. Montilla and E. Morallo, Langmuir 19, 10241 (2003).

    Article  Google Scholar 

  17. S. Chiang, Chem. Rev. 97, 1083 (1997).

    Article  Google Scholar 

  18. P. Sautet, Chem. Rev. 97, 1097 (1997).

    Article  Google Scholar 

  19. G. Su, H. Zhang, L. Wan, C. Bai, and T. Wandlowski, J. Phys. Chem. B 108, 1931 (2004).

    Article  Google Scholar 

  20. Z. Li, B. Han, and L.J. Wan, Langmuir 21, 6915 (2005).

    Article  Google Scholar 

  21. Z. Li and T. Wandlowski, J. Phys. Chem. C 113, 7821 (2009).

    Article  Google Scholar 

  22. N.T.M. Hai, M. Van Der Auweraer, K. Mu, and S. De Feyter, J. Phys. Chem. C 113, 11567 (2009).

    Article  Google Scholar 

  23. P. Dai, T. Chen, D. Wang, and L. Wan, J. Phys. Chem. C 116, 6208 (2012).

    Article  Google Scholar 

  24. B. Han, Z. Li, and T. Wandlowski, Anal. Bioanal. Chem. 388, 121 (2007).

    Article  Google Scholar 

  25. H. Li, S.G. Roscoe, and J. Lipkowski, J. Electroanal. Chem. 478, 67 (1999).

    Article  Google Scholar 

  26. C. Rabot, S. Clair, Y. Kim, and M. Kawai, Jpn. J. Appl. Phys. 46, 5572 (2007).

    Article  Google Scholar 

  27. Q. Chen, C.C. Perry, B.G. Frederick, P.W. Murray, S. Haq, and N.V. Richardson, Surf. Sci. 446, 63 (2000).

    Article  Google Scholar 

  28. G. Roelofsen, S.C. Group, and R. Utrecht, Acta Cryst. B32, 3328 (1972).

    Google Scholar 

  29. Th. Dretschkow, D. Lampner, and Th. Wandlowski, J. Electroanal. Chem. 458, 121 (1998).

    Article  Google Scholar 

  30. B.G. Federick, Q. Chen, F.M. Leibsle, M.B. Lee, K.J. Kitching, and N.V. Richardson, Surf. Sci. 394, 1 (1997).

    Article  Google Scholar 

  31. J. Gao, Y. Hu, S. Li, Y. Zhang, and X. Chen, Spectrochim. Acta A. 104, 41 (2013).

    Article  Google Scholar 

  32. P. Meakin, J.L. Cardy, E. Loh, and D.J. Scalapino, J. Chem. Phys. 86, 2380 (1987).

    Article  Google Scholar 

  33. J. Hotlos, O.M. Magnussen, and R.J. Behm, Surf. Sci. 335, 129 (1995).

    Article  Google Scholar 

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Acknowledgement

The authors acknowledge the financial support of the Hanoi University of Science and Technology under Grant No. T2016-PC-134.

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Correspondence to Thu-Hien Vu.

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Thomas Wandlowski: ISE member.

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Vu, TH., Wandlowski, T. Self-Assembled Structures of Benzoic Acid on Au(111) Surface. J. Electron. Mater. 46, 3463–3471 (2017). https://doi.org/10.1007/s11664-017-5358-3

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