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Self-assembly of Organic Molecules at Metal Surfaces

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Springer Handbook of Surface Science

Part of the book series: Springer Handbooks ((SHB))

Abstract

Adsorption and self-assembly of organic molecules at surfaces is a key issue in nanoscience and nanotechnology for the many possible uses of hybrid organic–inorganic interfaces. Depending on the nature of the molecules, applications are foreseen in the fields of molecular electronics, sensoristics, pharmacology, biocompatibility, hygiene and biofouling. As a consequence, there has been a large effort in the last few years to determine the structure of the layers and to unravel the mechanisms at the basis of the self-assembly process.

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References

  1. A.E. Nel, L. Mädler, D. Velegol, T. Xia, E.M.V. Hoek, P. Somasundaran, F. Klaessig, V. Castranova, M. Thompson: Understanding biophysicochemical interactions at the nano–bio interface, Nat. Mater. 8, 543–557 (2009)

    ADS  Google Scholar 

  2. Y. Pennec, W. Auwärter, A. Schiffrin, A. Weber-Bargioni, A. Riemann, J.V. Barth: Supramolecular gratings for tuneable confinement of electrons on metal surfaces, Nat. Nanotechnol. 2, 99–103 (2007)

    ADS  Google Scholar 

  3. J.C. Love, L.A. Estroff, J.K. Kriebel, R.G. Nuzzo, G.M. Whitesides: Self-assembled monolayers of thiolates on metals as a form of nanotechnology, Chem. Rev. 105, 1103–1170 (2005)

    Google Scholar 

  4. C. Joachim, J.K. Gimzewski, A. Aviram: Electronics using hybrid-molecular and mono-molecular devices, Nature 408, 541–548 (2000)

    ADS  Google Scholar 

  5. Z. Xu, Y. Fu, W. Han, D. Wei, H. Jiao, H. Gao: Recent developments in focused ion beam and its application in nanotechnology, Curr. Nanosci. 12, 696–711 (2016)

    ADS  Google Scholar 

  6. F.C. Simeone, C. Albonetti, M. Cavallini: Progress in micro- and nanopatterning via electrochemical lithography, J. Phys. Chem. C 113, 18987–18994 (2009)

    Google Scholar 

  7. H.-D. Yu, M.D. Regulacio, E. Ye, M.-Y. Han: Chemical routes to top-down nanofabrication, Chem. Soc. Rev. 42, 6006–6018 (2013)

    Google Scholar 

  8. K. Ariga, H. Ito, J.P. Hill, H. Tsukube: Molecular recognition: From solution science to nano/materials technology, Chem. Soc. Rev. 41, 5800–5835 (2012)

    Google Scholar 

  9. K. Kanazawa, A. Taninaka, H. Huang, M. Nishimura, S. Yoshida, O. Takeuchi, H. Shigekawa: Scanning tunneling microscopy/spectroscopy on self-assembly of a glycine/Cu(111) nanocavity array, Chem. Commun. 47, 11312–11314 (2011)

    Google Scholar 

  10. S. Haq, F. Hanke, M.S. Dyer, M. Persson, P. Iavicoli, D.B. Amabilino, R. Raval: Clean coupling of unfunctionalized porphyrins at surfaces to give highly oriented organometallic oligomers, J. Am. Chem. Soc. 133, 12031–12039 (2011)

    Google Scholar 

  11. M. Smerieri, I. Píš, L. Ferrighi, S. Nappini, A. Lusuan, C. Di Valentin, L. Vaghi, A. Papagni, M. Cattelan, S. Agnoli, E. Magnano, F. Bondino, L. Savio: Synthesis of graphene nanoribbons with a defined mixed edge-site sequence by surface assisted polymerization of (1,6)-dibromopyrene on Ag(110), Nanoscale 8, 17843–17853 (2016)

    Google Scholar 

  12. F. Rosei, M. Schunack, Y. Naitoh, P. Jiang, A. Gourdon, E. Laegsgaard, I. Stensgaard, C. Joachim, F. Besenbacher: Properties of large organic molecules on metal surfaces, Prog. Surf. Sci. 71, 95–146 (2003)

    ADS  Google Scholar 

  13. J. Cai, P. Ruffieux, R. Jaafar, M. Bieri, T. Braun, S. Blankenburg, M. Muoth, A.P. Seitsonen, M. Saleh, X. Feng, K. Müllen, R. Fasel: Atomically precise bottom-up fabrication of graphene nanoribbons, Nature 466, 470–473 (2010)

    ADS  Google Scholar 

  14. A. Klug: From macromolecules to biological assemblies (Nobel Lecture), Angew. Chem. Int. Ed. 22, 565–582 (1983)

    Google Scholar 

  15. J.V. Barth: Molecular architectonic on metal surfaces, Annu. Rev. Phys. Chem. 58, 375–407 (2007)

    ADS  Google Scholar 

  16. H. Cölfen, S. Mann: Higher-order organization by mesoscale self-assembly and transformation of hybrid nanostructures, Angew. Chem. Int. Ed. 42, 2350–2365 (2003)

    Google Scholar 

  17. S.M. Barlow, R. Raval: Complex organic molecules at metal surfaces: Bonding, organisation and chirality, Surf. Sci. Rep. 50, 201–341 (2003)

    ADS  Google Scholar 

  18. D. Costa, C.M. Pradier, F. Tielens, L. Savio: Adsorption and self-assembly of bio-organic molecules at model surfaces: A route towards increased complexity, Surf. Sci. Rep. 70, 449–453 (2015)

    ADS  Google Scholar 

  19. T. Kawai, H. Tanaka, T. Nakagawa: Low dimensional self-organization of DNA-base molecules on Cu(111) surfaces, Surf. Sci. 386, 124–136 (1997)

    ADS  Google Scholar 

  20. M. Furukawa, H. Tanaka, T. Kawai: The role of dimer formation in the self-assemblies of DNA base molecules on Cu(111) surfaces: A scanning tunneling microscope study, J. Chem. Phys. 115, 3419–3423 (2001)

    ADS  Google Scholar 

  21. Q. Chen, N.V. Richardson: Enantiomeric interactions between nucleic acid bases and amino acids on solid surfaces, Nat. Mater. 2, 324–328 (2003)

    ADS  Google Scholar 

  22. J.V. Barth, J. Weckesser, N. Lin, A. Dmitriev, K. Kern: Supramolecular architectures and nanostructures at metal surfaces, Appl. Phys. A 76, 645–652 (2003)

    ADS  Google Scholar 

  23. S. De Feyter, F.C. De Schryver: Two-dimensional supramolecular self-assembly probed by scanning tunneling microscopy, Chem. Soc. Rev. 32, 139–150 (2003)

    Google Scholar 

  24. D. Costa, P.A. Garrain, M. Baaden: Understanding small biomolecule-biomaterial interactions: A review of fundamental theoretical and experimental approaches for biomolecule interactions with inorganic surfaces, J. Biomed. Mater. Res. A 101, 1210–1222 (2013)

    Google Scholar 

  25. A. Ulman: Formation and structure of self-assembled monolayers, Chem. Rev. 96, 1533–1554 (1996)

    Google Scholar 

  26. L. Grill, M. Dyer, L. Lafferentz, M. Persson, M.V. Peters, S. Hecht: Nano-architectures by covalent assembly of molecular building blocks, Nat. Nanotechnol. 2, 687–691 (2007)

    ADS  Google Scholar 

  27. S. Nappini, I. Píš, G. Carraro, E. Celasco, M. Smerieri, L. Savio, E. Magnano, F. Bondino: On-surface synthesis of different boron–nitrogen–carbon heterostructures from dimethylamine borane, Carbon 120, 185–193 (2017)

    Google Scholar 

  28. I. Tranca, M. Smerieri, L. Savio, L. Vattuone, D. Costa, F. Tielens: Unraveling the self-assembly of the (S)-glutamic acid ‘‘flower'' structure on Ag(100), Langmuir 29, 7876–7884 (2013)

    Google Scholar 

  29. S. Blankenburg, W.G. Schmidt: Glutamic acid adsorbed on Ag(110): Direct and indirect molecular interactions, J. Phys. Condens. Matter 21, 185001 (2009)

    ADS  Google Scholar 

  30. J. Klimeš, D.R. Bowler, A. Michaelides: Van der Waals density functionals applied to solids, Phys. Rev. B 83, 195131 (2011)

    ADS  Google Scholar 

  31. M. Dion, H. Rydberg, E. Schröder, D.C. Langreth, B.I. Lundqvist: Van der Waals density functional for general geometries, Phys. Rev. Lett. 92, 246401 (2004)

    ADS  Google Scholar 

  32. T. Steiner: The hydrogen bond in the solid state, Angew. Chem. Int. Ed. 41, 48–76 (2002)

    Google Scholar 

  33. C.F.J. Faul, M. Antonietti: Ionic self-assembly: Facile synthesis of supramolecular materials, Adv. Mater. 15, 673–683 (2003)

    Google Scholar 

  34. L. Dong, W. Wang, T. Lin, K. Diller, J.V. Barth, J. Liu, B.Z. Tang, F. Klappenberger, N. Lin: Two-dimensional hierarchical supramolecular assembly of a silole derivative and surface-assisted chemical transformations, J. Phys. Chem. C 119, 3857–3863 (2015)

    Google Scholar 

  35. S.M. Barlow, S. Louafi, D. Le Roux, J. Williams, C. Muryn, S. Haq, R. Raval: Supramolecular assembly of strongly chemisorbed size-and shape-defined chiral clusters: S- and R-alanine on Cu(110), Langmuir 20, 7171–7176 (2004)

    Google Scholar 

  36. M. Smerieri, L. Vattuone, T. Kravchuk, D. Costa, L. Savio: (S)-Glutamic acid on Ag(100): Self-assembly in the nonzwitterionic form, Langmuir 27, 2393–2404 (2011)

    Google Scholar 

  37. A. Kühnle: Self-assembly of organic molecules at metal surfaces, Curr. Opin. Colloid Interface Sci. 14, 157–168 (2009)

    Google Scholar 

  38. A. Nilsson, L.G.M. Pettersson: Chemical bonding on surfaces probed by x-ray emission spectroscopy and density functional theory, Surf. Sci. Rep. 55, 49–167 (2004)

    ADS  Google Scholar 

  39. S.M. Barlow, S. Louafi, D. Le Roux, J. Williams, C. Muryn, S. Haq, R. Raval: Polymorphism in supramolecular chiral structures of R- and S-alanine on Cu(1 1 0), Surf. Sci. 590, 243–263 (2005)

    ADS  Google Scholar 

  40. X. Zhao, R.G. Zhao, W.S. Yang: Self-assembly of L-tryptophan on the Cu(001) surface, Langmuir 18, 433–438 (2002)

    Google Scholar 

  41. A. Gerlach, F. Schreiber, S. Sellner, H. Dosch, I.A. Vartanyants, B.C.C. Cowie, T.-L. Lee, J. Zegenhagen: Adsorption-induced distortion of F16CuPc on Cu(111) and Ag(111): An x-ray standing wave study, Phys. Rev. B 71, 205425 (2005)

    ADS  Google Scholar 

  42. T. Yokoyama, S. Yokoyama, T. Kamikado, S. Mashiko: Nonplanar adsorption and orientational ordering of porphyrin molecules on Au(111), J. Chem. Phys. 115, 3814–3818 (2001)

    ADS  Google Scholar 

  43. R. Raval: Chiral expression from molecular assemblies at metal surfaces: Insights from surface science techniques, Chem. Soc. Rev. 38, 707–721 (2009)

    Google Scholar 

  44. X. Zhao: Fabricating homochiral facets on Cu(001) with L-lysine, J. Am. Chem. Soc. 122, 12584–12585 (2000)

    Google Scholar 

  45. S. Linden, D. Zhong, A. Timmer, N. Aghdassi, J.H. Franke, H. Zhang, X. Feng, K. Müllen, H. Fuchs, L. Chi, H. Zacharias: Electronic structure of spatially aligned graphene nanoribbons on Au(788), Phys. Rev. Lett. 108, 216801 (2012)

    ADS  Google Scholar 

  46. R. Otero, Y. Naitoh, F. Rosei, P. Jiang, P. Thostrup, A. Gourdon, E. Lægsgaard, I. Stensgaard, C. Joachim, F. Besenbacher: One-dimensional assembly and selective orientation of Lander molecules on an O–Cu template, Angew. Chem. Int. Ed. 43, 2092–2095 (2004)

    Google Scholar 

  47. J.A. Miwa, S. Weigelt, H. Gersen, F. Besenbacher, F. Rosei, T.R. Linderoth: Azobenzene on Cu(110): Adsorption site-dependent diffusion, J. Am. Chem. Soc. 128, 3164–3165 (2006)

    Google Scholar 

  48. L.J. Lauhon, W. Ho: Single molecule thermal rotation and diffusion: Acetylene on Cu(001), J. Chem. Phys. 111, 5633–5636 (1999)

    ADS  Google Scholar 

  49. D.M. Eigler, E.K. Schweizer: Positioning single atoms with a scanning tunnelling microscope, Nature 344, 524–526 (1990)

    ADS  Google Scholar 

  50. J.R. Hahn, W. Ho: Oxidation of a single carbon monoxide molecule manipulated and induced with a scanning tunneling microscope, Phys. Rev. Lett. 87, 166102 (2001)

    ADS  Google Scholar 

  51. S.-W. Hla, L. Bartels, G. Meyer, K.-H. Rieder: Inducing all steps of a chemical reaction with the scanning tunneling microscope tip: Towards single molecule engineering, Phys. Rev. Lett. 85, 2777–2780 (2000)

    ADS  Google Scholar 

  52. W. Ho: Single-molecule chemistry, J. Chem. Phys. 117, 11033–11061 (2002)

    ADS  Google Scholar 

  53. R. Mas-Ballesté, C. Gómez-Navarro, J. Gómez-Herrero, F. Zamora: 2D materials: To graphene and beyond, Nanoscale 3, 20–30 (2011)

    ADS  Google Scholar 

  54. M. Batzill: The surface science of graphene: Metal interfaces, CVD synthesis, nanoribbons, chemical modifications, and defects, Surf. Sci. Rep. 67, 83–115 (2012)

    ADS  Google Scholar 

  55. J.W. Colson, W.R. Dichtel: Rationally synthesized two-dimensional polymers, Nat. Chem. 5, 453–465 (2013)

    Google Scholar 

  56. L. Lafferentz, V. Eberhardt, C. Dri, C. Africh, G. Comelli, F. Esch, S. Hecht, L. Grill: Controlling on-surface polymerization by hierarchical and substrate-directed growth, Nat. Chem. 4, 215–220 (2012)

    Google Scholar 

  57. A. Basagni, F. Sedona, C.A. Pignedoli, M. Cattelan, L. Nicolas, M. Casarin, M. Sambi: Molecules–oligomers–nanowires–graphene nanoribbons: A bottom-up stepwise on-surface covalent synthesis preserving long-range order, J. Am. Chem. Soc. 137, 1802–1808 (2015)

    Google Scholar 

  58. D. Heim, D. Écija, K. Seufert, W. Auwärter, C. Aurisicchio, C. Fabbro, D. Bonifazi, J.V. Barth: Self-assembly of flexible one-dimensional coordination polymers on metal surfaces, J. Am. Chem. Soc. 132, 6783–6790 (2010)

    Google Scholar 

  59. J.V. Barth, J. Weckesser, G. Trimarchi, M. Vladimirova, A. De Vita, C. Cai, H. Brune, P. Günter, K. Kern: Stereochemical effects in supramolecular self-assembly at surfaces: 1-D versus 2-D enantiomorphic ordering for PVBA and PEBA on Ag(111), J. Am. Chem. Soc. 124, 7991–8000 (2002)

    Google Scholar 

  60. Q. Fan, J.M. Gottfried, J. Zhu: Surface-catalyzed C–C covalent coupling strategies toward the synthesis of low-dimensional carbon-based nanostructures, Acc. Chem. Res. 48, 2484–2494 (2015)

    Google Scholar 

  61. I. Píš, L. Ferrighi, T.H. Nguyen, S. Nappini, L. Vaghi, A. Basagni, E. Magnano, A. Papagni, F. Sedona, C. Di Valentin, S. Agnoli, F. Bondino: Surface-confined polymerization of halogenated polyacenes: The case of dibromotetracene on Ag(110), J. Phys. Chem. C 120, 4909–4918 (2016)

    Google Scholar 

  62. F. Ullmann, J. Bielecki: Ueber Synthesen in der Biphenylreihe, Ber. Dtsch. Chem. Ges. 34, 2174–2185 (1901)

    Google Scholar 

  63. M. Di Giovannantonio, M. El Garah, J. Lipton-Duffin, V. Meunier, L. Cardenas, Y.F. Revurat, A. Cossaro, A. Verdini, D.F. Perepichka, F. Rosei, G. Contini: Insight into organometallic intermediate and its evolution to covalent bonding in surface-confined Ullmann polymerization, ACS Nano 7, 8190–8198 (2013)

    Google Scholar 

  64. W. Wang, X. Shi, S. Wang, M.A. Van Hove, N. Lin: Single-molecule resolution of an organometallic intermediate in a surface-supported Ullmann coupling reaction, J. Am. Chem. Soc. 133, 13264–13267 (2011)

    Google Scholar 

  65. Q. Fan, C. Wang, Y. Han, J. Zhu, J. Kuttner, G. Hilt, J.M. Gottfried: Surface-assisted formation, assembly, and dynamics of planar organometallic macrocycles and zigzag shaped polymer chains with C–Cu–C bonds, ACS Nano 8, 709–718 (2014)

    Google Scholar 

  66. M.O. Blunt, J.C. Russell, N.R. Champness, P.H. Beton: Templating molecular adsorption using a covalent organic framework, Chem. Commun. 46, 7157–7159 (2010)

    Google Scholar 

  67. J. Eichhorn, T. Strunskus, A. Rastgoo-Lahrood, D. Samanta, M. Schmittel, M. Lackinger: On-surface Ullmann polymerization via intermediate organometallic networks on Ag(111), Chem. Commun. 50, 7680–7682 (2014)

    Google Scholar 

  68. P. Ruffieux, J. Cai, N.C. Plumb, L. Patthey, D. Prezzi, A. Ferretti, E. Molinari, X. Feng, K. Müllen, C.A. Pignedoli, R. Fasel: Electronic structure of atomically precise graphene nanoribbons, ACS Nano 6, 6930–6935 (2012)

    Google Scholar 

  69. K.A. Simonov, N.A. Vinogradov, A.S. Vinogradov, A.V. Generalov, E.M. Zagrebina, N. Mårtensson, A.A. Cafolla, T. Carpy, J.P. Cunniffe, A.B. Preobrajenski: Effect of substrate chemistry on the bottom-up fabrication of graphene nanoribbons: Combined core-level spectroscopy and STM study, J. Phys. Chem. C 118, 12532–12540 (2014)

    Google Scholar 

  70. P. Han, K. Akagi, F. Federici Canova, H. Mutoh, S. Shiraki, K. Iwaya, P.S. Weiss, N. Asao, T. Hitosugi: Bottom-up graphene-nanoribbon fabrication reveals chiral edges and enantioselectivity, ACS Nano 8, 9181–9187 (2014)

    Google Scholar 

  71. X. Li, X. Wang, L. Zhang, S. Lee, H. Dai: Chemically derived, ultrasmooth graphene nanoribbon semiconductors, Science 319, 1229–1232 (2008)

    ADS  Google Scholar 

  72. L. Jiao, L. Zhang, X. Wang, G. Diankov, H. Dai: Narrow graphene nanoribbons from carbon nanotubes, Nature 458, 877–880 (2009)

    ADS  Google Scholar 

  73. K.A. Simonov, N.A. Vinogradov, A.S. Vinogradov, A.V. Generalov, E.M. Zagrebina, G.I. Svirskiy, A.A. Cafolla, T. Carpy, J.P. Cunniffe, T. Taketsugu, A. Lyalin, N. Mårtensson, A.B. Preobrajenski: From graphene nanoribbons on Cu(111) to nanographene on Cu(110): Critical role of substrate structure in the bottom-up fabrication strategy, ACS Nano 9, 8997–9011 (2015)

    Google Scholar 

  74. C. Zhang, Q. Sun, H. Kong, L. Wang, Q. Tana, W. Xu: On-surface synthesis of organometallic complex via metal–alkene interactions, Chem. Commun. 50, 15924–15927 (2014)

    Google Scholar 

  75. M. Chen, J. Xiao, H.-P. Steinrück, S. Wang, W. Wang, N. Lin, W. Hieringer, J.M. Gottfried: Combined photoemission and scanning tunneling microscopy study of the surface-assisted Ullmann coupling reaction, J. Phys. Chem. C 118, 6820–6830 (2014)

    Google Scholar 

  76. A. Kimouche, M.M. Ervasti, R. Drost, S. Halonen, A. Harju, P.M. Joensuu, J. Sainio, P. Liljeroth: Ultra-narrow metallic armchair graphene nanoribbons, Nat. Commun. 6, 10177 (2015)

    ADS  Google Scholar 

  77. F. Schulz, P.H. Jacobse, F. Federici Canova, J. van der Lit, D.Z. Gao, A. van den Hoogenband, P. Han, R.J.M. Klein Gebbink, M.-E. Moret, P.M. Joensuu, I. Swart, P. Liljeroth: Precursor geometry determines the growth mechanism in graphene nanoribbons, J. Phys. Chem. C 121, 2896–2904 (2017)

    Google Scholar 

  78. H. Huang, D. Wei, J. Sun, S.L. Wong, Y.P. Feng, A.H. Castro Neto, A.T.S. Wee: Spatially resolved electronic structures of atomically precise armchair graphene nanoribbons, Sci. Rep. 2, 983 (2012)

    Google Scholar 

  79. F. Hanke, S. Haq, R. Raval, M. Persson: Heat-to-connect: Surface commensurability directs organometallic one-dimensional self-assembly, ACS Nano 5, 9093–9103 (2011)

    Google Scholar 

  80. P. Maksymovych, O. Voznyy, D.B. Dougherty, D.C. Sorescu, J.T. Yates: Gold adatom as a key structural component in self-assembled monolayers of organosulfur molecules on Au(111), Prog. Surf. Sci. 85, 206–240 (2010)

    ADS  Google Scholar 

  81. D.P. Woodruff: The interface structure of n-alkylthiolate self-assembled monolayers on coinage metal surfaces, Phys. Chem. Chem. Phys. 10, 7211–7221 (2008)

    Google Scholar 

  82. E. Pensa, E. Cortés, G. Corthey, P. Carro, C. Vericat, M.H. Fonticelli, G. Benítez, A.A. Rubert, R.C. Salvarezza: The chemistry of the sulfur–gold interface: In search of a unified model, Acc. Chem. Res. 45, 1183–1192 (2012)

    Google Scholar 

  83. T. Bürgi: Properties of the gold–sulphur interface: From self-assembled monolayers to clusters, Nanoscale 7, 15553–15567 (2015)

    ADS  Google Scholar 

  84. M. Smerieri, L. Vattuone, D. Costa, F. Tielens, L. Savio: Self-assembly of (S)-glutamic acid on Ag(100): A combined LT-STM and ab initio investigation, Langmuir 26, 7208–7215 (2010)

    Google Scholar 

  85. A. Dmitriev, N. Lin, J. Weckesser, J.V. Barth, K. Kern: Supramolecular assemblies of trimesic acid on a Cu(100) surface, J. Phys. Chem. B 106, 6907–6912 (2002)

    Google Scholar 

  86. L.J. Prins, D.N. Reinhoudt, P. Timmerman: Noncovalent synthesis using hydrogen bonding, Angew. Chem. Int. Ed. 40, 2382–2426 (2001)

    Google Scholar 

  87. T. Yokoyama, T. Kamikado, S. Yokoyama, S. Mashiko: Conformation selective assembly of carboxyphenyl substituted porphyrins on Au (111), J. Chem. Phys. 121, 11993–11997 (2004)

    ADS  Google Scholar 

  88. J. Weckesser, A. De Vita, J.V. Barth, C. Cai, K. Kern: Mesoscopic correlation of supramolecular chirality in one-dimensional hydrogen-bonded assemblies, Phys. Rev. Lett. 87, 961011–961014 (2001)

    Google Scholar 

  89. N. Muskal, I. Turyan, D. Mandler: Self-assembled monolayers on mercury surfaces, J. Electroanal. Chem. 409, 131–136 (1996)

    Google Scholar 

  90. A. Iakovlev, D. Bedrov, M. Müller: Molecular dynamics simulation of alkylthiol self-assembled monolayers on liquid mercury, Langmuir 33, 744–754 (2017)

    Google Scholar 

  91. H. Häkkinen: The gold–sulfur interface at the nanoscale, Nat. Chem. 4, 443–455 (2012)

    Google Scholar 

  92. W.C. Bigelow, D.L. Pickett, W.A. Zisman: Oleophobic monolayers, J. Colloid Sci. 1, 513–538 (1946)

    Google Scholar 

  93. R.G. Nuzzo, D.L. Allara: Adsorption of bifunctional organic disulfides on gold surfaces, J. Am. Chem. Soc. 105, 4481–4483 (1983)

    Google Scholar 

  94. R.G. Nuzzo, F.A. Fusco, D.L. Allara: Spontaneously organized molecular assemblies. 3. Preparation and properties of solution adsorbed monolayers of organic disulfides on gold surfaces, J. Am. Chem. Soc. 109, 2358–2368 (1987)

    Google Scholar 

  95. A. Ulman: An Introduction to Ultrathin Organic Films: From Langmuir–Blodgett to Self-Assembly (Academic Press, San Diego 1991)

    Google Scholar 

  96. C.D. Bain, E.B. Troughton, Y.T. Tao, J. Evall, G.M. Whitesides, R.G. Nuzzo: Formation of monolayer films by the spontaneous assembly of organic thiols from solution onto gold, J. Am. Chem. Soc. 111, 321–335 (1989)

    Google Scholar 

  97. H. Hamoudi, V.A. Esaulov: Selfassembly of α , ω-dithiols on surfaces and metal dithiol heterostructures, Ann. Phys. 528, 242–263 (2016)

    Google Scholar 

  98. H.-J. Himmel, K. Weiss, B. Jäger, O. Dannenberger, M. Grunze, C. Wöll: Ultrahigh vacuum study on the reactivity of organic surfaces terminated by OH and COOH groups prepared by self-assembly of functionalized alkanethiols on Au substrates, Langmuir 13, 4943–4947 (1997)

    Google Scholar 

  99. S.M. Mendoza, I. Arfaoui, S. Zanarini, F. Paolucci, P. Rudolf: Improvements in the characterization of the crystalline structure of acid-terminated alkanethiol self-assembled monolayers on Au(111), Langmuir 23, 582–588 (2007)

    Google Scholar 

  100. J. Pflaum, G. Bracco, F. Schreiber, R. Colorado Jr., O.E. Shmakova, T.R. Lee, G. Scoles, A. Kahn: Structure and electronic properties of CH3- and CF3-terminated alkanethiol monolayers on Au(111): A scanning tunneling microscopy, surface x-ray and helium scattering study, Surf. Sci. 498, 89–104 (2002)

    ADS  Google Scholar 

  101. W.A. Marmisollé, D.A. Capdevila, E. de la Llave, F.J. Williams, D.H. Murgida: Self-assembled monolayers of NH2-terminated thiolates: Order, pKa, and specific adsorption, Langmuir 29, 5351–5359 (2013)

    Google Scholar 

  102. M.J. Esplandiú, H. Hagenström, D.M. Kolb: Functionalized self-assembled alkanethiol monolayers on Au(111) electrodes: 1. Surface structure and electrochemistry, Langmuir 17, 828–838 (2001)

    Google Scholar 

  103. F. Schreiber: Structure and growth of self-assembling monolayers, Prog. Surf. Sci. 65, 151–256 (2000)

    ADS  Google Scholar 

  104. H.A. Biebuyck, C.D. Bain, G.M. Whitesides: Comparison of organic monolayers on polycrystalline gold spontaneously assembled from solutions containing dialkyl disulfides or alkanethiols, Langmuir 10, 1825–1831 (1994)

    Google Scholar 

  105. G.E. Poirier: Coverage-dependent phases and phase stability of decanethiol on Au(111), Langmuir 15, 1167–1175 (1999)

    Google Scholar 

  106. G.E. Poirier, W.P. Fitts, J.M. White: Two-dimensional phase diagram of decanethiol on Au(111), Langmuir 17, 1176–1183 (2001)

    Google Scholar 

  107. R. Colorado Jr., T.R. Lee: Thiol-based self-assembled monolayers: Formation and organization. In: Encyclopedia of Materials: Science and Technology, ed. by K.H.J. Buschow, R.W. Cahn, M.C. Flemings, B. Ilschner, E.J. Kramer, S. Mahajan, P. Veyssière (Elsevier, Oxford 2001) pp. 9332–9344

    Google Scholar 

  108. N.K. Chaki, K. Vijayamohanan: Self-assembled monolayers as a tunable platform for biosensor applications, Biosens. Bioelectron. 17, 1–12 (2002)

    Google Scholar 

  109. G. Heimel, L. Romaner, E. Zojer, J.-L. Bredas: The interface energetics of self-assembled monolayers on metals, Acc. Chem. Res. 41, 721–729 (2008)

    Google Scholar 

  110. J. Gao, L. Tang, S. Holmes, F. Li, R.E. Palmer, Q. Guo: Surface-induced symmetry reduction in molecular switching: Asymmetric cis–trans switching of CH3S–Au–SCH3 on Au(111), Nanoscale 8, 19787–19793 (2016)

    Google Scholar 

  111. E. Ostuni, R.G. Chapman, R.E. Holmlin, S. Takayama, G.M. Whitesides: A survey of structure–property relationships of surfaces that resist the adsorption of protein, Langmuir 17, 5605–5620 (2001)

    Google Scholar 

  112. I. Solano, P. Parisse, F. Gramazio, O. Cavalleri, G. Bracco, M. Castronovo, L. Casalis, M. Canepa: Spectroscopic ellipsometry meets AFM nanolithography: About hydration of bio-inert oligo(ethylene glycol)-terminated self-assembled monolayers on gold, Phys. Chem. Chem. Phys. 17, 28774–28781 (2015)

    Google Scholar 

  113. Y. Xia, G.M. Whitesides: Soft lithography, Annu. Rev. Mater. Sci. 28, 153–184 (1998)

    ADS  Google Scholar 

  114. G.-Y. Liu, S. Xu: Nanometer scale fabrication of self-assembled monolayers: Nanoshaving and nanografting. In: Inorganic Materials Synthesis, ACS Symposium Series, Vol. 727 (American Chemical Society, Washington 1999) pp. 199–208

    Google Scholar 

  115. K. Salaita, Y. Wang, C.A. Mirkin: Applications of dip-pen nanolithography, Nat. Nanotechnol. 2, 145–155 (2007)

    ADS  Google Scholar 

  116. S. Iannotta, T. Toccoli, F. Biasioli, A. Boschetti, M. Ferrari: Highly ordered films of quaterthiophene grown by seeded supersonic beams, Appl. Phys. Lett. 76, 1845–1847 (2000)

    ADS  Google Scholar 

  117. E. Albayrak, S. Karabuga, G. Bracco, M.F. Danışman: Investigation of the deposition and thermal behavior of striped phases of unsymmetric disulfide self-assembled monolayers on Au(111): The case of 11-hydroxyundecyl decyl disulfide, J. Chem. Phys. 142, 014703 (2015)

    ADS  Google Scholar 

  118. R. Yamada, K. Uosaki: In situ, real time monitoring of the self-assembly process of decanethiol on Au(111) in liquid phase. A scanning tunneling microscopy investigation, Langmuir 13, 5218–5221 (1997)

    Google Scholar 

  119. R. Yamada, K. Uosaki: In situ scanning tunneling microscopy observation of the self-assembly process of alkanethiols on gold(111) in solution, Langmuir 14, 855–861 (1998)

    Google Scholar 

  120. S. Xu, S.J.N. Cruchon-Dupeyrat, J.C. Garno, G.-Y. Liu, G.K. Jennings, T.-H. Yong, P.E. Laibinis: In situ studies of thiol self-assembly on gold from solution using atomic force microscopy, J. Chem. Phys. 108, 5002–5012 (1998)

    ADS  Google Scholar 

  121. F. Ma, R.B. Lennox: Potential-assisted deposition of alkanethiols on Au: Controlled preparation of single- and mixed-component SAMs, Langmuir 16, 6188–6190 (2000)

    Google Scholar 

  122. R. Yamada, H. Wano, K. Uosaki: Effect of temperature on structure of the self-assembled monolayer of decanethiol on Au(111) surface, Langmuir 16, 5523–5525 (2000)

    Google Scholar 

  123. E. Delamarche, B. Michel, H. Kang, C. Gerber: Thermal stability of self-assembled monolayers, Langmuir 10, 4103–4108 (1994)

    Google Scholar 

  124. U. Harten, A.M. Lahee, J.P. Toennies, C. Wöll: Observation of a soliton reconstruction of Au(111) by high-resolution helium-atom diffraction, Phys. Rev. Lett. 54, 2619–2622 (1985)

    ADS  Google Scholar 

  125. A.R. Sandy, S.G.J. Mochrie, D.M. Zehner, K.G. Huang, D. Gibbs: Structure and phases of the Au(111) surface: X-ray-scattering measurements, Phys. Rev. B 43, 4667–4687 (1991)

    ADS  Google Scholar 

  126. E. Torres, G.A. DiLabio: A density functional theory study of the reconstruction of gold(111) surfaces, J. Phys. Chem. C 118, 15624–15629 (2014)

    Google Scholar 

  127. G.E. Poirier: Mechanism of formation of Au vacancy islands in alkanethiol monolayers on Au(111), Langmuir 13, 2019–2026 (1997)

    Google Scholar 

  128. G. Yang, G. Liu: New insights for self-assembled monolayers of organothiols on Au(111) revealed by scanning tunneling microscopy, J. Phys. Chem. B 107, 8746–8759 (2003)

    Google Scholar 

  129. P. Maksymovych, D.C. Sorescu, J.T. Yates: Gold-adatom-mediated bonding in self-assembled short-chain alkanethiolate species on the Au(111) surface, Phys. Rev. Lett. 97, 146103 (2006)

    ADS  Google Scholar 

  130. G.E. Poirier: Characterization of organosulfur molecular monolayers on Au(111) using scanning tunneling microscopy, Chem. Rev. 97, 1117–1128 (1997)

    Google Scholar 

  131. P. Schwartz, F. Schreiber, P. Eisenberger, G. Scoles: Growth kinetics of decanethiol monolayers self-assembled on Au(111) by molecular beam deposition: An atomic beam diffraction study, Surf. Sci. 423, 208–224 (1999)

    ADS  Google Scholar 

  132. F. Schreiber, A. Eberhardt, T.Y.B. Leung, P. Schwartz, S.M. Wetterer, D.J. Lavrich, L. Berman, P. Fenter, P. Eisenberger, G. Scoles: Adsorption mechanisms, structures, and growth regimes of an archetypal self-assembling system: Decanethiol on Au(111), Phys. Rev. B 57, 12476–12481 (1998)

    ADS  Google Scholar 

  133. L.H. Dubois, B.R. Zegarski, R.G. Nuzzo: Molecular ordering of organosulfur compounds on Au(111) and Au(100): Adsorption from solution and in ultrahigh vacuum, J. Chem. Phys. 98, 678–688 (1993)

    ADS  Google Scholar 

  134. N. Camillone III, P. Eisenberger, T.Y.B. Leung, P. Schwartz, G. Scoles, G.E. Poirier, M.J. Tarlov: New monolayer phases of n-alkane thiols self-assembled on Au(111): Preparation, surface characterization, and imaging, J. Chem. Phys. 101, 11031–11036 (1994)

    ADS  Google Scholar 

  135. N. Camillone, T.Y.B. Leung, P. Schwartz, P. Eisenberger, G. Scoles: Chain length dependence of the striped phases of alkanethiol monolayers self-assembled on Au(111): An atomic beam diffraction study, Langmuir 12, 2737–2746 (1996)

    Google Scholar 

  136. F. Balzer, R. Gerlach, G. Polanski, H.-G. Rubahn: Chain length dependence of the structure of alkane thiol films on Au(111), Chem. Phys. Lett. 274, 145–151 (1997)

    ADS  Google Scholar 

  137. R. Gerlach, G. Polanski, H.-G. Rubahn: Structural manipulation of ultrathin organic films on metal surfaces: The case of decane thiol/Au(111), Appl. Phys. A 65, 375–377 (1997)

    ADS  Google Scholar 

  138. H. Kondoh, C. Kodama, H. Sumida, H. Nozoye: Molecular processes of adsorption and desorption of alkanethiol monolayers on Au(111), J. Chem. Phys. 111, 1175–1184 (1999)

    ADS  Google Scholar 

  139. K. Sotthewes, H. Wu, A. Kumar, G.J. Vancso, P.M. Schön, H.J.W. Zandvliet: Molecular dynamics and energy landscape of decanethiolates in self-assembled monolayers on Au(111) studied by scanning tunneling microscopy, Langmuir 29, 3662–3667 (2013)

    Google Scholar 

  140. G.E. Poirier, M.J. Tarlov, H.E. Rushmeier: Two-dimensional liquid phase and the p × √3 phase of alkanethiol self-assembled monolayers on Au(111), Langmuir 10, 3383–3386 (1994)

    Google Scholar 

  141. R. Staub, M. Toerker, T. Fritz, T. Schmitz-Hübsch, F. Sellam, K. Leo: Flat lying pin-stripe phase of decanethiol self-assembled monolayers on Au(111), Langmuir 14, 6693–6698 (1998)

    Google Scholar 

  142. R.G. Nuzzo, L.H. Dubois, D.L. Allara: Fundamental studies of microscopic wetting on organic surfaces. 1. Formation and structural characterization of a self-consistent series of polyfunctional organic monolayers, J. Am. Chem. Soc. 112, 558–569 (1990)

    Google Scholar 

  143. P. Fenter, A. Eberhardt, K.S. Liang, P. Eisenberger: Epitaxy and chainlength dependent strain in self-assembled monolayers, J. Chem. Phys. 106, 1600–1608 (1997)

    ADS  Google Scholar 

  144. N. Camillone, C.E.D. Chidsey, G. Liu, G. Scoles: Superlattice structure at the surface of a monolayer of octadecanethiol self-assembled on Au(111), J. Chem. Phys. 98, 3503–3511 (1993)

    ADS  Google Scholar 

  145. P. Fenter, P. Eisenberger, K.S. Liang: Chain-length dependence of the structures and phases of CH3(CH2)n–1SH self-assembled on Au(111), Phys. Rev. Lett. 70, 2447–2450 (1993)

    ADS  Google Scholar 

  146. F. Schreiber: Self-assembled monolayers: From simple model systems to biofunctionalized interfaces, J. Phys. Condens. Matter 16, R881–R900 (2004)

    ADS  Google Scholar 

  147. G.E. Poirier, M.J. Tarlov: The c(4 × 2) superlattice of n-alkanethiol monolayers self-assembled on Au(111), Langmuir 10, 2853–2856 (1994)

    Google Scholar 

  148. G. Yang, G. Liu: New insights for self-assembled monolayers of organothiols on Au(111) revealed by scanning tunneling microscopy, J. Phys. Chem. B 107, 8746–8759 (2003)

    Google Scholar 

  149. P. Fenter, A. Eberhardt, P. Eisenberger: Self-assembly of n-alkyl thiols as disulfides on Au(111), Science 266, 1216–1218 (1994)

    ADS  Google Scholar 

  150. P. Fenter, F. Schreiber, L. Berman, G. Scoles, P. Eisenberger, M.J. Bedzyk: On the structure and evolution of the buried S/Au interface in self-assembled monolayers: X-ray standing wave results, Surf. Sci. 412/413, 213–235 (1998)

    ADS  Google Scholar 

  151. Y. Kitajimaa, S. Yagi, T. Yokoyama, A. Imanishi, S. Takenaka, T. Ohta: Surface structures of SNi(111) in (√3 × √3)R30∘ and (5√3 × 2) phases studied by surface extended x-ray absorption fine structure spectroscopy, Surf. Sci. 320, L89–L94 (1994)

    ADS  Google Scholar 

  152. M.H. Dishner, J.C. Hemminger, F.J. Feher: Direct observation of substrate influence on chemisorption of methanethiol adsorbed from the gas phase onto the reconstructed Au(111) surface, Langmuir 13, 2318–2322 (1997)

    Google Scholar 

  153. M.F. Danışman, L. Casalis, G. Bracco, G. Scoles: Structural investigation of monolayers prepared by deposition of (CH3S)2 on the (111) face of single-crystal gold, J. Phys. Chem. B 106, 11771–11777 (2002)

    Google Scholar 

  154. H. Kondoh, H. Nozoye: Low-temperature ordered phase of methylthiolate monolayers on Au(111), J. Phys. Chem. B 103, 2585–2588 (1999)

    Google Scholar 

  155. V. De Renzi, R. Di Felice, D. Marchetto, R. Biagi, U. del Pennino, A. Selloni: Ordered (3 × 4) high-density phase of methylthiolate on Au(111), J. Phys. Chem. B 108, 16–20 (2004)

    Google Scholar 

  156. D. Cavanna, G. Bracco, V. De Renzi, V. Corradini, R. Biagi, U. del Pennino: Ordered phases and temperature behaviour of CH3S self-assembled monolayers on Au(111), J. Phys. Condens. Matter 19, 305019 (2007)

    Google Scholar 

  157. L. Tang, F. Li, W. Zhou, Q. Guo: The structure of methylthiolate and ethylthiolate monolayers on Au(111): Absence of the (√3 × √3)R30∘ phase, Surf. Sci. 606, L31–L35 (2012)

    ADS  Google Scholar 

  158. R. Mazzarello, A. Cossaro, A. Verdini, R. Rousseau, L. Casalis, M.F. Danisman, L. Floreano, S. Scandolo, A. Morgante, G. Scoles: Structure of a CH3S monolayer on Au(111) solved by the interplay between molecular dynamics calculations and diffraction measurements, Phys. Rev. Lett. 98, 16102 (2007)

    ADS  Google Scholar 

  159. O. Voznyy, J.J. Dubowski, J.T. Yates, P. Maksymovych: The role of gold adatoms and stereochemistry in self-assembly of methylthiolate on Au(111), J. Am. Chem. Soc. 131, 12989–12993 (2009)

    Google Scholar 

  160. X. Fan, X. Fang, R. Ran, W. Ming Lau: Density functional theory study of the adsorption of methanthiol on Au(111): Role of gold adatoms, Physica E Low Dimens. Syst. Nanostruct. 59, 248–253 (2014)

    ADS  Google Scholar 

  161. J. Lee, J.S. Boschen, T.L. Windus, P.A. Thiel, D.-J. Liu: Stabilization of X–Au–X complexes on the Au(111) surface: A theoretical investigation and comparison of X = S, Cl, CH3S, and SiH3S, J. Phys. Chem. C 121, 3870–3879 (2017)

    Google Scholar 

  162. N.A. Kautz, S.A. Kandel: Alkanethiol/Au(111) self-assembled monolayers contain gold adatoms: Scanning tunneling microscopy before and after reaction with atomic hydrogen, J. Am. Chem. Soc. 130, 6908–6909 (2008)

    Google Scholar 

  163. F.-S. Li, W. Zhou, Q. Guo: Uncovering the hidden gold atoms in a self-assembled monolayer of alkanethiol molecules on Au(111), Phys. Rev. B 79, 113412 (2009)

    ADS  Google Scholar 

  164. Q. Guo, F. Li: Self-assembled alkanethiol monolayers on gold surfaces: Resolving the complex structure at the interface by STM, Phys. Chem. Chem. Phys. 16, 19074 (2014)

    Google Scholar 

  165. M. Kawasaki, H. Nagayama: Observation of highly ordered 3 × 4 phase of ethanethiol self-assembled monolayer on Au(111), Chem. Lett. 30, 942–943 (2001)

    Google Scholar 

  166. J. Gao, F. Li, Q. Guo: Balance of forces in self-assembled monolayers, J. Phys. Chem. C 117, 24985–24990 (2013)

    Google Scholar 

  167. A. Chaudhuri, D.C. Jackson, T.J. Lerotholi, R.G. Jones, T.-L. Lee, B. Detlefs, D.P. Woodruff: Structural investigation of Au(111)/butylthiolate adsorption phases, Phys. Chem. Chem. Phys. 12, 3229–3238 (2010)

    Google Scholar 

  168. M. Yu, N. Bovet, C.J. Satterley, S. Bengió, K.R.J. Lovelock, P.K. Milligan, R.G. Jones, D.P. Woodruff, V. Dhanak: True nature of an archetypal self-assembly system: Mobile Au-thiolate species on Au(111), Phys. Rev. Lett. 97, 166102 (2006)

    ADS  Google Scholar 

  169. P. Maksymovych, J.T. Yates: Au adatoms in self-assembly of benzenethiol on the Au(111) surface, J. Am. Chem. Soc. 130, 7518–7519 (2008)

    Google Scholar 

  170. P.D. Jadzinsky, G. Calero, C.J. Ackerson, D.A. Bushnell, R.D. Kornberg: Structure of a thiol monolayer-protected gold nanoparticle at 1.1 Å resolution, Science 318, 430–433 (2007)

    ADS  Google Scholar 

  171. E. Pensa, A.A. Rubert, G. Benitez, P. Carro, A. González Orive, A. Hernández Creus, R.C. Salvarezza, C. Vericat: Are 4-mercaptobenzoic acid self-assembled monolayers on Au(111) a suitable system to test adatom models?, J. Phys. Chem. C 116, 25765–25771 (2012)

    Google Scholar 

  172. X. Zhao, R.G. Zhao, W.S. Yang: Adsorption of alanine on Cu(001) studied by scanning tunneling microscopy, Surf. Sci. 442, L995–L1000 (1999)

    ADS  Google Scholar 

  173. J. Reichert, A. Schiffrin, W. Auwärter, A. Weber-Bargioni, M. Marschall, M. Dell’Angela, D. Cvetko, G. Bavdek, A. Cossaro, A. Morgante, J.V. Barth: L-tyrosine on Ag(111): Universality of the amino acid 2D zwitterionic bonding scheme?, ACS Nano 4, 1218–1226 (2010)

    Google Scholar 

  174. Y. Izumi: Modified Raney nickel (MRNi) catalyst: Heterogeneous enantio-differentiating (asymmetric) catalyst. In: Advances in Catalysis, Vol. 32, ed. by D.D. Eley, H. Pines, P.B. Weisz (Academic Press, New York 1983) pp. 215–271

    Google Scholar 

  175. G. Webb, P.B. Wells: Asymmetric hydrogenation, Catal. Today 12, 319–337 (1992)

    Google Scholar 

  176. M. Mahapatra, L. Burkholder, Y. Bai, M. Garvey, J.A. Boscoboinik, C. Hirschmugl, W.T. Tysoe: Formation of chiral self-assembled structures of amino acids on transition-metal surfaces: Alanine on Pd(111), J. Phys. Chem. C 118, 6856–6865 (2014)

    Google Scholar 

  177. G. Feng, L. Zhenjun, W. Yilin, L. Burkholder, W.T. Tysoe: Chemistry of glycine on Pd(111): Temperature-programmed desorption and x-ray photoelectron spectroscopic study, J. Phys. Chem. C 111, 9981–9991 (2007)

    Google Scholar 

  178. P. Löfgren, A. Krozer, J. Lausmaa, B. Kasemo: Glycine on Pt(111): A TDS and XPS study, Surf. Sci. 370, 277–292 (1997)

    ADS  Google Scholar 

  179. K.E. Wilson, C.J. Baddeley: Chiral assemblies of nickel lysinate via the corrosive adsorption of (S)-lysine on Ni/Au{111}, Surf. Sci. 629, 102–107 (2014)

    ADS  Google Scholar 

  180. T.E. Jones, A.E. Rekatas, C.J. Baddeley: Influence of modification pH and temperature on the interaction of methylacetoacetate with (S)-glutamic acid-modified Ni{111}, J. Phys. Chem. C 111, 5500–5505 (2007)

    Google Scholar 

  181. E.M. Marti, C. Methivier, C.M. Pradier: (S)-Cysteine chemisorption on Cu(110), from the gas or liquid phase: An FT-RAIRS and XPS study, Langmuir 20, 10223–10230 (2004)

    Google Scholar 

  182. T. Eralp, A. Shavorskiy, G. Held: The adsorption geometry and chemical state of lysine on Cu{110}, Surf. Sci. 605, 468–472 (2011)

    ADS  Google Scholar 

  183. T. Eralp, A. Cornish, A. Shavorskiy, G. Held: The study of chiral adsorption systems using synchrotron-based structural and spectroscopic techniques: Stereospecific adsorption of serine on Au-modified chiral Cu{531} surfaces, Top. Catal. 54, 1414–1428 (2011)

    Google Scholar 

  184. R.B. Rankin, D.S. Sholl: Assessment of heterochiral and homochiral glycine adlayers on Cu(110) using density functional theory, Surf. Sci. 548, 301–308 (2004)

    ADS  Google Scholar 

  185. Z.V. Zheleva, T. Eralp, G. Held: Complete experimental structure determination of the p(3 × 2) phase of glycine on Cu{110}, J. Phys. Chem. C 116, 618–625 (2012)

    Google Scholar 

  186. V. Humblot, C. Méthivier, R. Raval, C.M. Pradier: Amino acid and peptides on Cu(1 1 0) surfaces: Chemical and structural analyses of L-lysine, Surf. Sci. 601, 4189–4194 (2007)

    ADS  Google Scholar 

  187. G. Jones, L.B. Jones, F. Thibault-Starzyk, E.A. Seddon, R. Raval, S.J. Jenkins, G. Held: The local adsorption geometry and electronic structure of alanine on Cu{1 1 0}, Surf. Sci. 600, 1924–1935 (2006)

    ADS  Google Scholar 

  188. S. Haq, A. Massey, N. Moslemzadeh, A. Robin, S.M. Barlow, R. Raval: Racemic versus enantiopure alanine on Cu(110): An experimental study, Langmuir 23, 10694–10700 (2007)

    Google Scholar 

  189. T.E. Jones, C.J. Baddeley, A. Gerbi, L. Savio, M. Rocca, L. Vattuone: Molecular ordering and adsorbate induced faceting in the Ag{110}-(S)-glutamic acid system, Langmuir 21, 9468–9475 (2005)

    Google Scholar 

  190. R.B. Rankin, D.S. Sholl: Structure of enantiopure and racemic alanine adlayers on Cu(110), Surf. Sci. 574, L1–L8 (2005)

    ADS  Google Scholar 

  191. D.I. Sayago, M. Polcik, G. Nisbet, C.L.A. Lamont, D.P. Woodruff: Local structure determination of a chiral adsorbate: Alanine on Cu(1 1 0), Surf. Sci. 590, 76–87 (2005)

    ADS  Google Scholar 

  192. A. Kühnle, T.R. Linderoth, B. Hammer, F. Besenbacher: Chiral recognition in dimerization of adsorbed cysteine observed by scanning tunnelling microscopy, Nature 415, 891–893 (2002)

    ADS  Google Scholar 

  193. T. Eralp, A. Shavorskiy, Z.V. Zheleva, G. Held, N. Kalashnyk, Y. Ning, T.R. Linderoth: Global and local expression of chirality in serine on the Cu{110} surface, Langmuir 26, 18841–18851 (2010)

    Google Scholar 

  194. Y. Yun, A.J. Gellman: Enantiospecific adsorption of amino acids on naturally chiral Cu{3,1,17}R&S Surfaces, Langmuir 31, 6055–6063 (2015)

    Google Scholar 

  195. H.S. Song, J.W. Han: Tuning the surface chemistry of chiral Cu(531)S for enhanced enantiospecific adsorption of amino acids, J. Phys. Chem. C 119, 15195–15203 (2015)

    Google Scholar 

  196. T. Eralp, A. Ievins, A. Shavorskiy, S.J. Jenkins, G. Held: The importance of attractive three-point interaction in enantioselective surface chemistry: Stereospecific adsorption of serine on the intrinsically chiral Cu{531} surface, J. Am. Chem. Soc. 134, 9615–9621 (2012)

    Google Scholar 

  197. Y. Wang, S. Yang, M. Fuentes-Cabrera, S. Li, W. Liu: Enhancing enantiomeric separation with strain: The case of serine on Cu(531), J. Am. Chem. Soc. 139, 8167–8173 (2017)

    Google Scholar 

  198. M. Smerieri, L. Vattuone, M. Rocca, L. Savio: Spectroscopic evidence for neutral and anionic adsorption of (S)-glutamic acid on Ag(111), Langmuir 29, 6867–6875 (2013)

    Google Scholar 

  199. D. Costa, M. Smerieri, I. Tranca, L. Savio, L. Vattuone, F. Tielens: DFT atomistic thermodynamics applied to elucidate the driving force behind glutamic acid self-assemblies on silver (100) surface, J. Phys. Chem. C 118, 29874–29879 (2014)

    Google Scholar 

  200. V. Humblot, S. Haq, C. Muryn, W.A. Hofer, R. Raval: From local adsorption stresses to chiral surfaces: (R,R)-Tartaric acid on Ni(110), J. Am. Chem. Soc. 124, 503–510 (2002)

    Google Scholar 

  201. T.E. Jones, C.J. Baddeley: A RAIRS, STM and TPD study of the Ni/R,R-tartaric acid system: Modelling the chiral modification of Ni nanoparticles, Surf. Sci. 513, 453–467 (2002)

    ADS  Google Scholar 

  202. T.E. Jones, M.E. Urquhart, C.J. Baddeley: An investigation of the influence of temperature on the adsorption of the chiral modifier, (S)-glutamic acid, on Ni{1 1 1}, Surf. Sci. 587, 69–77 (2005)

    ADS  Google Scholar 

  203. A.G. Trant, T.E. Jones, T.C.Q. Noakes, P. Bailey, C.J. Baddeley: Adsorption of (S)-glutamic acid induces segregation of Ni at bimetallic Au/Ni surfaces, Surf. Sci. 604, 300–307 (2010)

    ADS  Google Scholar 

  204. A.G. Trant, T.E. Jones, C.J. Baddeley: Thermal treatment of glutamic acid-modified nickel nanoclusters on Au{111} leads to the formation of one-dimensional metal-organic coordination networks, J. Phys. Chem. C 111, 10534–10540 (2007)

    Google Scholar 

  205. T.E. Jones, C.J. Baddeley: Investigating the mechanism of chiral surface reactions: The interaction of methylacetoacetate with (S)-glutamic acid modified Ni{111}, Langmuir 22, 148–152 (2006)

    Google Scholar 

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Authors and Affiliations

  1. Dipartimento di Fisica, Università di Genova, Genova, Italy

    Gianangelo Bracco

  2. Istituto dei Materiali per l’Elettronica ed il Magnetismo, Consiglio Nazionale delle Ricerche, Genova, Italy

    Marco Smerieri

  3. Istituto dei Materiali per l’Elettronica ed il Magnetismo, Consiglio Nazionale delle Ricerche, Genova, Italy

    Letizia Savio

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  1. Dipt. di Fisica, Università di Genova, Genova, Italy

    Mario Rocca

  2. Department of Physics, University of Central Florida, Orlando, FL, USA

    Talat S. Rahman

  3. Dipt. di Fisica, Università di Genova and IMEM-CNR Unità di Genova, Genova, Italy

    Luca Vattuone

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Bracco, G., Smerieri, M., Savio, L. (2020). Self-assembly of Organic Molecules at Metal Surfaces. In: Rocca, M., Rahman, T.S., Vattuone, L. (eds) Springer Handbook of Surface Science. Springer Handbooks. Springer, Cham. https://doi.org/10.1007/978-3-030-46906-1_29

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