Unraveling the mechanism of the covalent coupling between terminal alkynes on a noble metal

Journal of Physical Chemistry C

Volumn 118, Issue 6, 2014, Pages 3181-3187

  Björk, Jonas ^a   Zhang, Yi Qi ^b   Klappenberger, Florian ^b   Barth, Johannes V ^b   Stafström, Sven ^a  

^a LINKÖPING UNIVERSITY   (Sweden)

^b TECHNICAL UNIVERSITY OF MUNICH   (Germany)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 84894039612     PISSN: 19327447     EISSN: 19327455     Source Type: Journal    
DOI: 10.1021/jp5002918     Document Type: Article

References (53)

1. Sakamoto, J.; van Heijst, J.; Lukin, O.; Schlüter, A. D. Two-Dimensional Polymers: Just a Dream of Synthetic Chemists? Angew. Chem., Int. Ed. 2009, 48, 1030-1069
2. Franc, G.; Gourdon, A. Covalent Networks Through On-Surface Chemistry in Ultra-High Cacuum: State-of-the-Art and Recent Developments Phys. Chem. Chem. Phys. 2011, 13, 14283-14292
3. Colson, J. W.; Dichtel, W. R. Rationally Synthesized Two-Dimensional Polymers Nat. Chem. 2013, 5, 453-465
4. Lafferentz, L.; Ample, F.; Yu, H.; Hecht, S.; Joachim, C.; Grill, L. Conductance of a Single Conjugated Polymer as a Continuous Function of Its Length Science 2009, 323, 1193-1198
5. Bieri, M.; Treier, M.; Cai, J.; Aït-Mansour, K.; Ruffieux, P.; Gröning, O.; Gröning, P.; Kastler, M.; Rieger, R.; Feng, X. Porous Graphenes: Two-Dimensional Polymer Synthesis with Atomic Precision Chem. Commun. 2009, 6919-6921
6. Cai, J.; Ruffieux, P.; Jaafar, R.; Bieri, M.; Braun, T.; Blankenburg, S.; Muoth, M.; Seitsonen, A. P.; Saleh, M.; Feng, X. Atomically Precise Bottom-Up Fabrication of Graphene Nanoribbons Nature 2010, 466, 470-473
7. Bieri, M.; Blankenburg, S.; Kivala, M.; Pignedoli, C. A.; Ruffieux, P.; Müllen, K.; Fasel, R. Surface-Supported 2D Heterotriangulene Polymers Chem. Commun. 2011, 47, 10239-10241
8. Treier, M.; Pignedoli, C. A.; Laino, T.; Rieger, R.; Müllen, K.; Passerone, D.; Fasel, R. Surface-Assisted Cyclodehydrogenation Provides a Synthetic Route Towards Easily Processable and Chemically Tailored Nanographenes Nat. Chem. 2011, 3, 61-67
9. Fan, Q.; Wang, C.; Han, Y.; Zhu, J.; Hieringer, W.; Kuttner, J.; Hilt, G.; Gottfried, J. M. Surface-Assisted Organic Synthesis of Hyperbenzene Nanotroughs Angew. Chem., Int. Ed. 2013, 52, 4668-4672
10. Sun, Q.; Zhang, C.; Li, Z.; Kong, H.; Tan, Q.; Hu, A.; Xu, W. On-Surface Formation of One-Dimensional Polyphenylene through Bergman Cyclization J. Am. Chem. Soc. 2013, 135, 8448-8451
11. Novoselov, K. S.; Fal'ko, V. I.; Colombo, L.; Gellert, P. R.; Schwab, M. G.; Kim, K. A Roadmap for Graphene Nature 2012, 490, 192-200
12. Diederich, F.; Kivala, M. All-Carbon Scaffolds by Rational Design Adv. Mater. 2010, 22, 803-812
13. Grill, L.; Dyer, M.; Lafferentz, L.; Persson, M.; Peters, M. V.; Hecht, S. Nano-Architectures by Covalent Assembly of Molecular Building Blocks Nat. Nanotechnol. 2007, 2, 687-691
14. Björk, J.; Hanke, F.; Stafström, S. Mechanisms of Halogen-Based Covalent Self-Assembly on Metal Surfaces J. Am. Chem. Soc. 2013, 135, 5768-5775
15. Wang, W.; Shi, X.; Wang, S.; Van Hove, M. A.; Lin, N. Single-Molecule Resolution of an Organometallic Intermediate in a Surface-Supported Ullmann Coupling Reaction J. Am. Chem. Soc. 2011, 133, 13264-13267
16. Wang, S.; Wang, W.; Lin, N. Visualization and Manipulation of Individual Dopant States in Single Conjugated Oligomers ACS Nano 2012, 6, 3404-3410
17. Zhang, Y.-Q.; Kepčija, N.; Kleinschrodt, M.; Diller, K.; Fischer, S.; Papageorgiou, A. C.; Allegretti, F.; Björk, J.; Klyatskaya, S.; Klappenberger, F. Homo-Coupling of Terminal Alkynes on a Noble Metal Surface Nat. Commun 2012, 3, 1286
18. Gao, H.-Y.; Wagner, H.; Zhong, D.; Franke, J.-H.; Studer, A.; Fuchs, H. Glaser Coupling at Metal Surfaces Angew. Chem., Int. Ed. 2013, 52, 4024-4028
19. Eichhorn, J.; Heckl, W. M.; Lackinger, M. On-Surface Polymerization of 1,4-diethynylbenzene on Cu(111) Chem. Commun. 2013, 49, 2900-2902
20. Cirera, B.; Zhang, Y.-Q.; Klyatskaya, S.; Ruben, M.; Klappenberger, F.; Barth, J. V. Surface-Assisted Two Dimensional Self-Assembly and Catalytic Homo-Coupling of the Terminal Alkyne 1,4-Bis(3,5-bisethynylphenyl)butadiyne-1,3 on Ag(111) ChemCatChem 2013, 5, 3281-3288
21. Matena, M.; Stöhr, M.; Riehm, T.; Björk, J.; Martens, S.; Dyer, M. S.; Persson, M.; Lobo-Checa, J.; Müller, K.; Enache, M. Aggregation and Contingent Metal/Surface Reactivity of 1,3,8,10-Tetraazaperopyrene (TAPP) on Cu(111) Chem.-Eur. J. 2010, 16, 2079-2091
22. Hanke, F.; Haq, S.; Raval, R.; Persson, M. Heat to Connect: Surface Commensurability Directs Organometallic One-Dimensional Self-Assembly ACS Nano 2011, 5, 9093-9103
23. Nguyen, M.-T.; Pignedoli, C. A.; Passerone, D. An ab Initio Insight into the Cu(111)-Mediated Ullmann Reaction Phys. Chem. Chem. Phys. 2011, 13, 154-160
24. Blankenburg, S.; Cai, J.; Ruffieux, P.; Jaafar, R.; Passerone, D.; Feng, X.; Fasel, R.; Pignedoli, C. A. Intraribbon Heterojunction Formation in Ultranarrow Graphene Nanoribbons ACS Nano 2012, 2020-2025
25. Björk, J.; Hanke, F. Towards Design Rules for Covalent Nanostructures on Metal Surfaces Chem.-Eur. J. 2014, 20, 928-934
26. Glaser, C. Beiträge zur Kenntnis des Acetenylbenzols Ber. Dtsch. Chem. Ges. 1869, 2, 422-424
27. Hay, A. S. Oxidative Coupling of Acetylenes 0.2 J. Org. Chem. 1962, 27, 3320-3321
28. Halbes-Letinois, U.; Weibel, J.-M.; Pale, P. The Organic Chemistry of Silver Acetylides Chem. Soc. Rev. 2007, 36, 759-769
29. Long, N. J.; Williams, C. K. Metal Alkynyl Sigma Complexes: Synthesis and Materials Angew. Chem., Int. Ed. 2003, 42, 2586-2617
30. Yamamoto, Y. Silver-Catalyzed C(sp)-H and C(sp)-Si Bond Transformations and Related Processes Chem. Rev. 2008, 108, 3199-3222
31. Siemsen, P.; Livingston, R.; Diederich, F. Acetylenic Coupling: A Powerful Tool in Molecular Construction Angew. Chem., Int. Ed. 2000, 39, 2632-2657
32. Montoya, A.; Schlunke, A.; Haynes, B. S. Reaction of Hydrogen With Ag(111): Binding States, Minimum Energy Paths, and Kinetics J. Phys. Chem. B 2006, 110, 17145-17154
33. Zhou, X.; White, J.; Koel, B. Chemisorption of Atomic Hydrogen on Clean and Cl-Covered Ag(111) Surf. Sci. 1989, 218, 201-210
34. Gao, H.-Y.; Franke, J.-H.; Wagner, H.; Zhong, D.; Held, P.-A.; Studer, A.; Fuchs, H. Effect of Metal Surfaces in On-Surface Glaser Coupling J. Phys. Chem. C 2013, 117, 18595-18602
35. Fomina, L.; Vazquez, B.; Tkatchouk, E.; Fomine, S. The Glaser Reaction Mechanism. A DFT Study Tetrahedron 2002, 58, 6741-6747
36. Vilhelmsen, M. H.; Jensen, J.; Tortzen, C. G.; Nielsen, M. B. The Glaser-Hay Reaction: Optimization and Scope Based on 13 C NMR Kinetics Experiments Eur. J. Org. Chem. 2013, 701-711
37. van Gelderen, L.; Rothenberg, G.; Roberto Calderone, V.; Wilson, K.; Raveendran Shiju, N. Efficient Alkyne Homocoupling Catalysed by Copper Immobilized on Functionalized Silica Appl. Organomet. Chem. 2013, 27, 23-27
38. Kresse, G.; Furthmüller, J. Efficient Iterative Schemes for ab Initio Total-Energy Calculations Using a Plane-Wave Basis Set Phys. Rev. B 1996, 54, 11169-11186
39. Blöchl, P. E. Projector Augmented-Wave Method Phys. Rev. B 1994, 50, 17953-17979
40. Kresse, G.; Joubert, D. From Ultrasoft Pseudopotentials to the Projector Augmented-Wave Method Phys. Rev. B 1999, 59, 1758-1775
41. Dion, M.; Rydberg, H.; Schröder, E.; Langreth, D. C.; Lundqvist, B. I. Van der Waals Density Functional for General Geometries Phys. Rev. Lett. 2004, 92, 246401-246404
42. Klimeš, J.; Bowler, D.; Michaelides, A. Van der Waals density Functionals Applied to Solids Phys. Rev. B 2011, 83, 195131-195143
43. Henkelman, G.; Uberuaga, B. P.; Jónsson, H. A Climbing Image Nudged Elastic Band Method for Finding Saddle Points and Minimum Energy Paths J. Chem. Phys. 2000, 113, 9901-9904
44. Henkelman, G.; Jónsson, H. Improved Tangent Estimate in the Nudged Elastic Band Method for Finding Minimum Energy Paths and Saddle Points J. Chem. Phys. 2000, 113, 9978-9985
45. Henkelman, G.; Jónsson, H. A Dimer Method for Finding Saddle Points on High Dimensional Potential Surfaces Using Only First Derivatives J. Chem. Phys. 1999, 111, 7010-7022
46. Kästner, J.; Sherwood, P. Superlinearly Converging Dimer Method for Transition State Search J. Chem. Phys. 2008, 128, 014106-014111
47. Tersoff, J.; Hamann, D. R. Theory and Application for the Scanning Tunneling Microscope Phys. Rev. Lett. 1983, 50, 1998-2001
48. Lorente, N.; Persson, M. Theoretical Aspects of Tunneling-Current-Induced Bond Excitation and Breaking at Surfaces Faraday Discuss. 2000, 277-290
49. Kepčija, N.; Zhang, Y.-Q.; Kleinschrodt, M.; Björk, J.; Klyatskaya, S.; Klappenberger, F.; Ruben, M.; Barth, J. V. Steering On-Surface Self-Assembly of High-Quality Hydrocarbon Networks with Terminal Alkynes J. Phys. Chem. C 2013, 117, 3987-3995
50. Jensen, F. Introduction to Computational Chemistry; John Wiley & Sons, Ltd.: New York, 1999.
51. Mittendorfer, F.; Garhofer, A.; Redinger, J.; Klimeš, J.; Harl, J.; Kresse, G. Graphene on Ni(111): Strong Interaction and Weak Adsorption Phys. Rev. B 2011, 84, 201401-201404
52. Perdew, J.; Burke, K.; Ernzerhof, M. Generalized Gradient Approximation Made Simple Phys. Rev. Lett. 1996, 77, 3865-3868
53. Di Giovannantonio, M.; El Garah, M.; Lipton-Duffin, J.; Meunier, V.; Cardenas, L.; Fagot Revurat, Y.; Cossaro, A.; Verdini, A.; Perepichka, D. F.; Rosei, F. Insight into Organometallic Intermediate and Its Evolution to Covalent Bonding in Surface-Confined Ullmann Polymerization ACS Nano 2013, 7, 8190-8198