Substrate, molecular structure, and solvent effects in 2D self-assembly via hydrogen and halogen bonding

Journal of Physical Chemistry C

Volumn 118, Issue 44, 2014, Pages 25505-25516

  Gatti, Riccardo ^a   MacLeod, Jennifer M ^a   Lipton Duffin, Josh A ^a   Moiseev, Andrey G ^b   Perepichka, Dmitrii F ^b   Rosei, Federico ^a  

^a INRS EMT   (Canada)

^b MCGILL UNIVERSITY   (Canada)

Author keywords

[No Author keywords available]

Indexed keywords

BENZENE; DENSITY FUNCTIONAL THEORY; HYDROGEN; HYDROGEN BONDS; MOLECULES; PHASE INTERFACES; SCANNING TUNNELING MICROSCOPY; SELF ASSEMBLY; SINGLE CRYSTALS; SUPRAMOLECULAR CHEMISTRY;

ADSORPTION ENERGIES; AMBIENT CONDITIONS; HIGHLY ORIENTED PYROLYTIC GRAPHITE; LIQUID-SOLID INTERFACES; MOLECULAR BUILDING BLOCKS; MOLECULAR NETWORKS; SUPRAMOLECULAR STRUCTURE; TWO-DIMENSIONAL SUPRAMOLECULAR ASSEMBLIES;

SOLVENTS;

EID: 84908611830     PISSN: 19327447     EISSN: 19327455     Source Type: Journal    
DOI: 10.1021/jp507729w     Document Type: Article

References (110)

1. Whitesides, G. M.; Mathias, J. P.; Seto, C. T. Molecular Self-Assembly and Nanochemistry - A Chemical Strategy for the Synthesis of Nanostructures. Science 1991, 254, 1312-1319.
2. Whitesides, G. M.; Grzybowski, B. Self-Assembly at All Scales. Science 2002, 295, 2418-2421.
3. Barth, J. V.; Costantini, G.; Kern, K. Engineering Atomic and Molecular Nanostructures at Surfaces. Nature 2005, 437, 671-679.
4. Barth, J. V. Molecular Architectonic on Metal Surfaces. Annu. Rev. Phys. Chem. 2007, 58, 375-407.
5. Mali, K. S.; Adisoejoso, J.; Ghijsens, E.; De Cat, I.; De Feyter, S. Exploring the Complexity of Supramolecular Interactions for Patterning at the Liquid-Solid Interface. Acc. Chem. Res. 2012, 45, 1309-1320.
6. Rosei, F. Nanostructured Surfaces: Challenges and Frontiers in Nanotechnology. J. Phys. Condens. Matter. 2004, 16, S1373-S1436.
7. Otero, R.; Maria Gallego, J.; Vazquez de Parga, A. L.; Martìn, N.; Miranda, R. Molecular Self-Assembly at Solid Surfaces. Adv. Mater. 2011, 23, 5148-5176.
8. Rosei, F.; Schunack, M.; Naitoh, Y.; Jiang, P.; Gourdon, A.; Laegsgaard, E.; Stensgaard, I.; Joachim, C.; Besenbacher, F. Properties of Large Organic Molecules on Metal Surfaces. Prog. Surf. Sci. 2003, 71, 95-146.
9. Kühnle, A. Self-Assembly of Organic Molecules at Metal Surfaces. Curr. Opin. Colloid Interface Sci. 2009, 14, 157-168.
10. De Feyter, S.; De Schryver, F. C. Two-Dimensional Supramolecular Self-Assembly Probed by Scanning Tunneling Microscopy. Chem. Soc. Rev. 2003, 32, 139-150.
11. De Feyter, S.; De Schryver, F. C. Self-Assembly at the Liquid/Solid Interface: STM Reveals. J. Phys. Chem. B 2005, 109, 4290-4302.
12. Baris, B.; Luzet, V.; Duverger, E.; Sonnet, P.; Palmino, F.; Cherioux, F. Robust and Open Tailored Supramolecular Networks Controlled by the Template Effect of a Silicon Surface. Angew. Chem., Int. Ed. 2011, 50, 4094-8.
13. Gutzler, R.; Cardenas, L.; Rosei, F. Kinetics and Thermodynamics in Surface-Confined Molecular Self-Assembly. Chem. Sci. 2011, 2, 2290-2300.
14. Lehn, J.-M. Toward Complex Matter: Supramolecular Chemistry and Self-Organization. Proc. Natl. Acad. Sci. U.S.A. 2002, 99, 4763-4768.
15. Theobald, J. A.; Oxtoby, N. S.; Phillips, M. A.; Champness, N. R.; Beton, P. H. Controlling Molecular Deposition and Layer Structure with Supramolecular Surface Assemblies. Nature 2003, 424, 1029-1031.
16. Yokoyama, T.; Yokoyama, S.; Kamikado, T.; Okuno, Y.; Mashiko, S. Selective Assembly on a Surface of Supramolecular Aggregates with Controlled Size and Shape. Nature 2001, 413, 619-621.
17. Xie, R.; Song, Y.; Wan, L.; Yuan, H.; Li, P.; Xiao, X.; Liu, L.; Ye, S.; Lei, S.; Wang, L. Two-Dimensional Polymerization and Reaction at the Solid/Liquid Interface: Scanning Tunneling Microscopy Study. Anal. Sci. 2011, 27, 129-138.
18. Cardenas, L.; Lipton-Duffin, J.; Rosei, F. Transformations of Molecular Frameworks by Host-Guest Response: Novel Routes toward Two-Dimensional Self-Assembly at the Solid-Liquid Interface. Jpn. J. Appl. Phys. 2011, 50, 08LA02.
19. Forrest, S. R. The Path to Ubiquitous and Low-Cost Organic Electronic Appliances on Plastic. Nature 2004, 428, 911-918.
20. Whitesides, G. M.; Boncheva, M. Beyond Molecules: Self-Assembly of Mesoscopic and Macroscopic Components. Proc. Natl. Acad. Sci. U.S.A. 2002, 99, 4769-74.
21. Aldaye, F. A.; Palmer, A. L.; Sleiman, H. F. Assembling Materials with DNA as the Guide. Science 2008, 321, 1795-1799.
22. MacLeod, J. M.; Rosei, F. Expanding the Scope of Molecular Self-Organization Studies through Temperature Control at the Solution/Solid Interface. Aust. J. Chem. 2011, 64, 1297-1298.
23. Mali, K. S.; Lava, K.; Binnemans, K.; De Feyter, S. Hydrogen Bonding versus van der Waals Interactions: Competitive Influence of Noncovalent Interactions on 2D Self-Assembly at the Liquid-Solid Interface. Chem. - Eur. J. 2010, 16, 14447-58.
24. Nath, K. G.; Ivasenko, O.; MacLeod, J. M.; Miwa, J. A.; Wuest, J. D.; Nanci, A.; Perepichka, D. F.; Rosei, F. Crystal Engineering in Two Dimensions: An Approach to Molecular Nanopatterning. J. Phys. Chem. C 2007, 111, 16996-17007.
25. Bléger, D.; Bocheux, A.; Kreher, D.; Mathevet, F.; Attias, A.-J.; Metgé, G.; Douillard, L.; Fiorini-Debuisschert, C.; Charra, F. An Optimized Alkyl Chain-Based Binding Motif for 2d Self-Assembly: A Comprehensive Crystallographic Approach. Nanoscale 2013, 5, 1452-1455.
26. Grimme, S. Do Special Noncovalent Pi-Pi Stacking Interactions Really Exist? Angew. Chem., Int. Ed. 2008, 47, 3430-4.
27. Macleod, J. M.; Ivasenko, O.; Perepichka, D. F.; Rosei, F. Stabilization of Exotic Minority Phases in a Multicomponent Self-Assembled Molecular Network. Nanotechnology 2007, 18, 424031-424039.
28. Lackinger, M.; Griessl, S.; Heckl, W. M.; Hietschold, M.; Flynn, G. W. Self-Assembly of Trimesic Acid at the Liquid-Solid Interfaces - A Study of Solvent-Induced Polymorphism. Langmuir 2005, 21, 4984-4988.
29. Nath, K. G.; Ivasenko, O.; Miwa, J. A.; Dang, H.; Wuest, J. D.; Nanci, A.; Perepichka, D. F.; Rosei, F. Rational Modulation of the Periodicity in Linear Hydrogen-Bonded Assemblies of Trimesic Acid on Surfaces. J. Am. Chem. Soc. 2006, 128, 4212-4213.
30. El Garah, M.; Lipton-Duffin, J.; Macleod, J. M.; Gutzler, R.; Palmino, F.; Luzet, V.; Cherioux, F.; Rosei, F. Self-Assembly of a Halogenated Molecule on Oxide-Passivated Cu(110). Chem. - Asian. J. 2013, 8, 1-6.
31. Gutzler, R.; Ivasenko, O.; Fu, C.; Brusso, J. L.; Rosei, F.; Perepichka, D. F. Halogen Bonds as Stabilizing Interactions in a Chiral Self-Assembled Molecular Monolayer. Chem. Commun. 2011, 47, 9453-5.
32. Gutzler, R.; Fu, C.; Dadvand, A.; Hua, Y.; MacLeod, J. M.; Rosei, F.; Perepichka, D. F. Halogen Bonds in 2D Supramolecular Self-Assembly of Organic Semiconductors. Nanoscale 2012, 4, 5965-71.
33. Müller, T.; Werblowsky, T. L.; Florio, G. M.; Berne, B. J.; Flynn, G. W. Ultra-High Vacuum Scanning Tunneling Microscopy and Theoretical Studies of 1-Halohexane Monolayers on Graphite. Proc. Natl. Acad. Sci. U.S.A. 2005, 102, 5315-22.
34. Florio, G. M.; Werblowsky, T. L.; Ilan, B.; Müller, T.; Berne, B. J.; Flynn, G. W. Chain-Length Effects on the Self-Assembly of Short 1-Bromoalkane and N-Alkane Monolayers on Graphite. J. Phys. Chem. C 2008, 112, 18067-18075.
35. Yoon, J. K.; Son, W.-j.; Chung, K.-H.; Kim, H.; Han, S.; Kahng, S.-J. Visualizing Halogen Bonds in Planar Supramolecular Systems. J. Phys. Chem. C 2011, 115, 2297-2301.
36. Desiraju, G. R.; Ho, P. S.; Kloo, L.; Legon, A. C.; Marquardt, R.; Metrangolo, P.; Politzer, P.; Resnati, G.; Rissanen, K. Definition of the Halogen Bond (IUPAC Recommendations 2013). Pure Appl. Chem. 2013, 85, 1711-1713.
37. Bui, T. T. T.; Dahaoui, S.; Lecomte, C.; Desiraju, G. R.; Espinosa, E. The Nature of Halogen⋯Halogen Interactions: A Model Derived from Experimental Charge-Density Analysis. Angew. Chem., Int. Ed. 2009, 48, 3838-3841.
38. Reddy, C. M.; Kirchner, M. T.; Gundakaram, R. C.; Padmanabhan, K. A.; Desiraju, G. R. Isostructurality, Polymorphism and Mechanical Properties of Some Hexahalogenates Benzenes: The Nature of Halogen⋯Halogen Interactions. Chem. - Eur. J. 2006, 12, 2222-2234.
39. Metrangolo, P.; Meyer, F.; Pilati, T.; Resnati, G.; Terraneo, G. Halogen Bonding in Supramolecular Chemistry. Angew. Chem., Int. Ed. 2008, 47, 6114-27.
40. Clark, T.; Hennemann, M.; Murray, J. S.; Politzer, P. Halogen Bonding: The Sigma-Hole. Proceedings of "Modeling Interactions in Biomolecules II", Prague, September 5-9, 2005. J. Mol. Model. 2007, 13, 291-6.
41. Gutzler, R.; Walch, H.; Eder, G.; Kloft, S.; Heckl, W. M.; Lackinger, M. Surface Mediated Synthesis of 2d Covalent Organic Frameworks: 1,3,5-Tris(4-bromophenyl)benzene on Graphite(001), Cu(111), and Ag(110). Chem. Commun. 2009, 4456-8.
42. Walch, H.; Gutzler, R.; Sirtl, T.; Eder, G.; Lackinger, M. Material- and Orientation-Dependent Reactivity for Heterogeneously Catalyzed Carbon-Bromine Bond Homolysis. J. Phys. Chem. C 2010, 114, 12604-12609.
43. Blunt, M. O.; Russell, J. C.; Champness, N. R.; Beton, P. H. Templating Molecular Adsorption Using a Covalent Organic Framework. Chem. Commun. 2010, 46, 7157-9.
44. Russell, J. C.; Blunt, M. O.; Garfitt, J. M.; Scurr, D. J.; Alexander, M.; Champness, N. R.; Beton, P. H. Dimerization of Tri(4-bromophenyl)benzene by Aryl-Aryl Coupling from Solution on a Gold Surface. J. Am. Chem. Soc. 2011, 133, 4220-3.
45. Baris, B.; Jeannoutot, J.; Luzet, V.; Palmino, F.; Rochefort, A.; Chérioux, F. Noncovalent Bicomponent Self-Assemblies on a Silicon Surface. ACS Nano 2012, 6, 6905-6911.
46. Eder, G.; Smith, E. F.; Cebula, I.; Heckl, W. M.; Beton, P. H.; Lackinger, M. Solution Preparation of Two-Dimensional Covalently Linked Networks by Polymerization of 1,3,5-Tri(4-iodophenyl)-benzene on Au(111). ACS Nano 2013, 7, 3014-3021.
47. Schlögl, S.; Heckl, W. M.; Lackinger, M. On-Surface Radical Addition of Triply Iodinated Monomers on Au(111) - The Influence of Monomer Size and Thermal Post-Processing. Surf. Sci. 2012, 606, 999-1004.
48. Makoudi, Y.; Baris, B.; Jeannoutot, J.; Palmino, F.; Grandidier, B.; Cherioux, F. Tailored Molecular Design for Supramolecular Network Engineering on a Silicon Surface. Chemphyschem 2013, 14, 900-904.
49. Silly, F. Selecting Two-Dimensional Halogen-Halogen Bonded Self-Assembled 1,3,5-Tris(4-iodophenyl)benzene Porous Nanoarchitectures at the Solid-Liquid Interface. J. Phys. Chem. C 2013, 117, 20244-20249.
50. Cicoira, F.; Santato, C.; Rosei, F. Two-Dimensional Nanotemplates as Surface Cues for the Controlled Assembly of Organic Molecules. Top. Curr. Chem. 2008, 285, 203-267.
51. Levlin, M.; Laakso, A.; Niemi, H. E.-M.; Hautojärvi, P. Evaporation of Gold Thin Films on Mica: Effect of Evaporations Parameters. Appl. Surf. Sci. 1997, 115, 31-38.
52. Wöll, C.; Chiang, S.; Wilson, R. J.; Lippel, P. H. Determination of Atom Positions at Stacking-Fault Dislocations on Au(111) by Scanning Tunneling Microscopy. Phys. Rev. B 1989, 39, 7988-7991.
53. Barth, J. V.; Brune, H.; Ertl, G.; Behm, R. J. Scanning Tunneling Microscopy Observations on the Reconstructed Au(111) Surface: Atomic Structure, Long-Range Superstructure, Rotational Domains, and Surface Defects. Phys. Rev. B 1990, 42, 9307-9318.
54. Horcas, I.; Fernandez, R.; Gomez-Rodriguez, J. M.; Colchero, J.; Gomez-Herrero, J.; Baro, A. M. WSXM: A Software for Scanning Probe Microscopy and a Tool for Nanotechnology. Rev. Sci. Instrum. 2007, 78, 013705.
55. Frisch, M. J.; Trucks, G. W.; Schlegel, H. B.; Scuseria, G. E.; Robb, M. A.; Cheeseman, J. R.; Scalmani, G.; Barone, V.; Mennucci, B.; Petersson, G. A.; Nakatsuji, H.; Caricato, M.; Li, X.; Hratchian, H. P.; Izmaylov, A. F.; Bloino, J.; Zheng, G.; Sonnenberg, J. L.; Hada, M.; Ehara, M.; Toyota, K.; Fukuda, R.; Hasegawa, J.; Ishida, M.; Nakajima, T.; Honda, Y.; Kitao, O.; Nakai, H.; Vreven, T.; Montgomery, J. A., Jr.; Peralta, J. E.; Ogliaro, F.; Bearpark, M.; Heyd, J. J.; Brothers, E.; Kudin, K. N.; Staroverov, V. N.; Kobayashi, R.; Normand, J.; Raghavachari, K.; Rendell, A.; Burant, J. C.; Iyengar, S. S.; Tomasi, J.; Cossi, M.; Rega, N.; Millam, J. M.; Klene, M.; Knox, J. E.; Cross, J. B.; Bakken, V.; Adamo, C.; Jaramillo, J.; Gomperts, R.; Stratmann, R. E.; Yazyev, O.; Austin, A. J.; Cammi, R.; Pomelli, C.; Ochterski, J. W.; Martin, R. L.; Morokuma, K.; Zakrzewski, V. G.; Voth, G. A.; Salvador, P.; Dannenberg, J. J.; Dapprich, S.; Daniels, A. D.; Farkas, O.; Foresman, J. B.; Ortiz, J. V.; Cioslowski, J.; Fox, D. J. Gaussian 09, revision B.01; Gaussian, Inc.: Wallingford, CT, 2009.
56. Becke, A. D. Density-Functional Thermochemistry. III. The Role of Exact Exchange. J. Chem. Phys. 1993, 98, 5648-5652.
57. Becke, A. D. Density-Functional Exchange-Energy Approximation with Correct Asymptotic Behavior. Phys. Rev. A 1988, 38, 3098-3100.
58. Stephens, P. J.; Devlin, F. J.; Chabalowski, C. F.; Frisch, M. J. Ab Initio Calculation of Vibrational Absorption and Circular Dichroism Spectra Using Density Functional Force Fields. J. Phys. Chem. 1994, 98, 11623-11627.
59. Lee, C.; Yang, W.; Parr, R. G. Development of the Colle-Salvetti Correlation-Energy Formula into a Functional of the Electron Density. Phys. Rev. B 1988, 37, 785-789.
60. Zhao, Y.; Truhlar, D. G. The M06 Suite of Density Functionals for Main Group Thermochemistry, Thermochemical Kinetics, Noncovalent Interactions, Excited States, and Transition Elements: Two New Functionals and Systematic Testing of Four M06-Class Functionals and 12 Other Functionals. Theor. Chem. Acc. 2008, 120, 215-241.
61. Zhao, Y.; Truhlar, D. G. A New Local Density Functional for Main-Group Thermochemistry, Transition Metal Bonding, Thermochemical Kinetics, and Noncovalent Interactions. J. Chem. Phys. 2006, 125, 194101(18).
62. Zhao, Y.; Truhlar, D. G. Density Functionals with Broad Applicability in Chemistry. Acc. Chem. Res. 2008, 41, 157-167.
63. Perdew, J. P.; Ruzsinszky, A.; Tao, J.; Staroverov, V. N.; Scuseria, G. E.; Csonka, G. I. Prescription for the Design and Selection of Density Functional Approximations: More Constraint Satisfaction with Fewer Fits. J. Chem. Phys. 2005, 123, 62201(9).
64. Lu, Y.; Zou, J.; Wang, H.; Yu, Q.; Zhang, H.; Jiang, Y. Triangular Halogen Trimers. A DFT Study of the Structure, Cooperativity, and Vibrational Properties. J. Phys. Chem. A 2005, 109, 11956-11961.
65. Bondi, A. Van der Waals Volumes and Radii. J. Phys. Chem. 1964, 68, 441-451.
66. Fourmigué, M.; Batail, P. Activation of Hydrogen- and Halogen-Bonding Interactions in Tetrathiafulvalene-Based Crystalline Molecular Conductors. Chem. Rev. 2004, 104, 5379-5418.
67. Björk, J.; Hanke, F.; Palma, C.-A.; Samorì, P.; Cecchini, M.; Persson, M. Adsorption of Aromatic and Anti-aromatic Systems on Graphene through Π-Π Stacking. J. Phys. Chem. Lett. 2010, 1, 3407-3412.
68. Zacharia, R.; Ulbricht, H.; Hertel, T. Interlayer Cohesive Energy of Graphite from Thermal Desorption of Polyaromatic Hydrocarbons. Phys. Rev. B 2004, 69, 155406(8).
69. Palma, C. A.; Cecchini, M.; Samorì, P. Predicting Self-Assembly: From Empirism to Determinism. Chem. Soc. Rev. 2012, 41, 3713-30.
70. Ivasenko, O.; Perepichka, D. F. Mastering Fundamentals of Supramolecular Design with Carboxylic Acids. Common Lessons from X-ray Crystallography and Scanning Tunneling Microscopy. Chem. Soc. Rev. 2011, 40, 191-206.
71. Macleod, J. M.; Ivasenko, O.; Fu, C.; Taerum, T.; Rosei, F.; Perepichka, D. F. Supramolecular Ordering in Oligothiophene-Fullerene Monolayers. J. Am. Chem. Soc. 2009, 131, 16844-16850.
72. Bartels, L.; Meyer, G.; Rieder, K.-H. Controlled Vertical Manipulation of Single Co Molecules with the Scanning Tunneling Microscope: A Route to Chemical Contrast. Appl. Phys. Lett. 1997, 71, 213-215.
73. Ernst, K.-H. Molecular Chirality at Surfaces. Phys. Status Solidi B 2012, 249, 2057-2088.
74. Ortega Lorenzo, M.; Baddeley, C. J.; Muryn, C.; Raval, R., Extended Surface Chirality from Supramolecular Assemblies of Adsorbed Chiralmolecules. Nature 2000, 404.
75. Ronci, F.; Gatti, R.; Caponi, G.; Colonna, S.; Galeotti, G.; Catone, D.; Turchini, S.; Prosperi, T.; Zema, N.; Palma, A.; Gori, P.; Contini, G. Organizational Chirality Expression as a Function of the Chirality Measure of Simple Amino Alcohols on Cu(100). Surf. Sci. 2014, 629, 41-47.
76. Optimization was performed using constraints to maintain the 2D lattice planar while enabling out-of-plane rotation of the bromophenyl side groups. Constraints were also applied to the molecular unit cell, to account for a SAMN rotationally and translationally commensurate with the HOPG substrate (see also SI).
77. Elemans, J. A.; Lei, S.; De Feyter, S. Molecular and Supramolecular Networks on Surfaces: From Two-Dimensional Crystal Engineering to Reactivity. Angew. Chem., Int. Ed. 2009, 48, 7298-7332.
78. Adisoejoso, J.; Tahara, K.; Okuhata, S.; Lei, S.; Tobe, Y.; De Feyter, S. Two-Dimensional Crystal Engineering: A Four-Component Architecture at a Liquid-Solid Interface. Angew. Chem., Int. Ed. 2009, 48, 7353-7.
79. Poirier, G. E.; Pylant, E. D. The Self-Assembly Mechanism of Alkanethiols on Au (111). Science 1996, 272, 1145-1148.
80. Jewell, A. D.; Tierney, H. L.; Sykes, E. C. H. Gently Lifting Gold's Herringbone Reconstruction: Trimethylphosphine on Au(111). Phys. Rev. B 2010, 82, 205401(6).
81. Iski, E. V.; Jewell, A. D.; Tierney, H. L.; Kyriakou, G.; Sykes, E. C. H. Controllable Restructuring of a Metal Substrate: Tuning the Surface Morphology of Gold. Surf. Sci. 2012, 606, 536-541.
82. Min, B.; Deng, X.; Pinnaduwage, D.; Schalek, R.; Friend, C. Oxygen-Induced Restructuring with Release of Gold Atoms from Au(111). Phys. Rev. B 2005, 72, 121410(4).
83. Poirier, G. E. Characterization of Organosulfur Molecular Monolayers on Au(111) Using Scanning Tunneling Microscopy. Chem. Rev. 1997, 97, 1117-1127.
84. Maksymovych, P.; Sorescu, D.; Yates, J., Gold-Adatom-Mediated Bonding in Self-Assembled Short-Chain Alkanethiolate Species on the Au(111) Surface. Phys. Rev. Lett. 2006, 97.
85. Jewell, A. D.; Kyran, S. J.; Rabinovich, D.; Sykes, E. C. Effect of Head-Group Chemistry on Surface-Mediated Molecular Self-Assembly. Chemistry 2012, 18, 7169-78.
86. Bellisario, D. O.; Jewell, A. D.; Tierney, H. L.; Baber, A. E.; Sykes, E. C. H. Adsorption, Assembly, and Dynamics of Dibutyl Sulfide on Au{111}. J. Phys. Chem. C 2010, 114, 14583-14589.
87. Jewell, A. D.; Tierney, H. L.; Zenasni, O.; Lee, T. R.; Sykes, E. C. H. Asymmetric Thioethers as Building Blocks for Chiral Monolayers. Top. Catal. 2011, 54, 1357-1367.
88. Rossel, F.; Brodard, P.; Patthey, F.; Richardson, N. V.; Schneider, W.-D. Modified Herringbone Reconstruction on Au(111) Induced by Self-Assembled Azure a Islands. Surf. Sci. 2008, 602, L115-L117.
89. Jewell, A. D.; Sykes, E. C. H.; Kyriakou, G. Molecular-Scale Surface Chemistry of a Common Metal Nanoparticle Capping Agent: Triphenylphosphine on Au(111). ACS Nano 2012, 6, 3545-3552.
90. We first computed the α phase, and starting from this geometry we computed the β phase freezing the interactions along the u′ vector, given that the only difference between the two polymorphs is between neighboring rows.
91. Han, P.; Mantooth, B. A.; Sykes, E. C. H.; Donhauser, Z. J.; Weiss, P. S. Benzene on Au{111} at 4 K: Monolayer Growth and Tip-Induced Molecular Cascades. J. Am. Chem. Soc. 2004, 126, 10787-10793.
92. Hanke, F.; Björk, J. Structure and Local Reactivity of the Au(111) Surface Reconstruction. Phys. Rev. B 2013, 87, 235422(6).
93. Zhang, J.; Li, B.; Cui, X.; Wang, B.; Yang, J.; Hou, J. G. Spontaneous Chiral Resolution in Supramolecular Assembly of 2,4,6-Tris(2-Pyridyl)-1,3,5-Triazine on Au(111). J. Am. Chem. Soc. 2009, 131, 5885-5890.
94. Peköz, R.; Johnston, K.; Donadio, D. Adsorption of Dichlorobenzene on Au and Pt Stepped Surfaces Using Van Der Waals Density Functional Theory. J. Phys. Chem. C 2012, 116, 20409-20416.
95. Björk, J.; Hanke, F.; Stafström, S. Mechanisms of Halogen-Based Covalent Self-Assembly on Metal Surfaces. J. Am. Chem. Soc. 2013, 135, 5768-75.
96. Kamna, M. M.; Stranick, S. J.; Weiss, P. S. Imaging Substrate-Mediated Interactions. Science 1996, 274, 118-119.
97. Sykes, E. C. H.; Han, P.; Kandel, S. A.; Kelly, K. F.; McCarthy, G. S.; Weiss, P. S. Substrate-Mediated Interactions and Intermolecular Forces between Molecules Adsorbed on Surfaces. Acc. Chem. Res. 2003, 36, 945-953.
98. 2 Interaction with Friedel Oscillations on Au{111}. J. Phys. Chem. B 2003, 107, 5016-5021.
99. Somorjai, G. A. The Flexible Surface: New Techniques for Molecular Level Studies of Time Dependent Changes in Metal Surface Structure and Adsorbate Structure During Catalytic Reactions. J. Mol. Catal. A 1996, 107, 39-53.
100. Stranick, S. J.; Kamna, M. M.; Weiss, P. S. Atomic-Scale Dynamics of a Two-Dimensional Gas-Solid Interface. Science 1996, 266, 99-102.
101. Fujita, D.; Amemiya, K.; Yakabe, T.; Nejoh, H. Anisotropic Standing-Wave Formation on an Au (111)-(23x√3) Reconstructed Surface. Phys. Rev. Lett. 1997, 78, 3904-3907.
102. Goyhenex, C.; Bulou, H., Theoretical Insight in the Energetics of Co Adsorption on a Reconstructed Au(111) Substrate. Phys. Rev. B 2001, 63.
103. Chen, W.; Madhavan, V.; Jamneala, T.; Crommie, M. F. Scanning Tunneling Microscopy Observation of an Electronic Superlattice at the Surface of Clean Gold. Phys. Rev. Lett. 1998, 80, 1469-1472.
104. Bürgi, L.; Brune, H.; Kern, K. Imaging of Electron Potential Landscapes on Au(111). Phys. Rev. Lett. 2002, 89, 176801(4).
105. Mantooth, B. A.; Sykes, E. C. H.; Han, P.; Moore, A. M.; Donhauser, Z. J.; Crespi, V. H.; Weiss, P. S. Analyzing the Motion of Benzene on Au{111}: Single Molecule Statistics from Scanning Probe Images. J. Phys. Chem. C 2007, 111, 6167-6182.
106. Sykes, E. C. H.; Mantooth, B. A.; Han, P.; Donhauser, Z. J.; Weiss, P. S. Substrate-Mediated Intermolecular Interactions: A Quantitative Single Molecule Analysis. J. Am. Chem. Soc. 2005, 127, 7255-7260.
107. Kirakosian, A.; Comstock, M.; Cho, J.; Crommie, M. Molecular Commensurability with a Surface Reconstruction: Stm Study of Azobenzene on Au(111). Phys. Rev. B 2005, 71, 113409.
108. Cheng, Z. H.; Gao, L.; Deng, Z. T.; Jiang, N.; Liu, Q.; Shi, D. X.; Du, S. X.; Guo, H. M.; Gao, H.-J. Adsorption Behavior of Iron Phthalocyanine on Au(111) Surface at Submonolayer Coverage. J. Phys. Chem. C 2007, 111, 9240-9244.
109. Cheng, Z. H.; Gao, L.; Deng, Z. T.; Liu, Q.; Jiang, N.; Lin, X.; He, X. B.; Du, S. X.; Gao, H.-J. Epitaxial Growth of Iron Phthalocyanine at the Initial Stage on Au(111) Surface. J. Phys. Chem. C 2007, 111, 2656-2660.
110. Silly, F.; Shaw, A. Q.; Briggs, G. A. D.; Castell, M. R. Epitaxial Ordering of a Perylenetetracarboxylic Diimide-Melamine Supramolecular Network Driven by the Au(111)-(22x√3) Reconstruction. Appl. Phys. Lett. 2008, 92, 023102.