Surface-assisted formation, assembly, and dynamics of planar organometallic macrocycles and zigzag shaped polymer chains with C-Cu-C bonds

ACS Nano

Volumn 8, Issue 1, 2014, Pages 709-718

  Fan, Qitang ^a   Wang, Cici ^a   Han, Yong ^a   Zhu, Junfa ^a   Kuttner, Julian ^b   Hilt, Gerhard ^b   Gottfried, J Michael ^b  

^a UNIVERSITY OF SCIENCE AND TECHNOLOGY OF CHINA   (China)

^b PHILIPPS UNIVERSITY MARBURG   (Germany)

Author keywords

copper; hyperbenzene; organometallic chemistry; photoelectron spectroscopy; scanning probe microscopy; surface chemistry; Ullmann reaction

Indexed keywords

BOND SCISSIONS; HYPERBENZENE; ORDERED STRUCTURES; ORGANOMETALLIC CHEMISTRY; ORGANOMETALLIC POLYMER; POLYMER CHAINS; ROOM TEMPERATURE; ULLMANN REACTION;

CHAINS; COPPER; PHOTOELECTRON SPECTROSCOPY; PHOTOELECTRONS; POLYMERS; SCANNING PROBE MICROSCOPY; SCANNING TUNNELING MICROSCOPY; SURFACE CHEMISTRY; X RAY PHOTOELECTRON SPECTROSCOPY;

ORGANOMETALLICS;

EID: 84893515650     PISSN: 19360851     EISSN: 1936086X     Source Type: Journal    
DOI: 10.1021/nn405370s     Document Type: Article

References (37)

1. Barth, J. V.; Costantini, G.; Kern, K. Engineering Atomic and Molecular Nanostructures at Surfaces Nature 2005, 437, 671-679
2. Lee, J.; Farha, O. K.; Roberts, J.; Scheidt, K. A.; Nguyen, S. T.; Hupp, J. T. Metal-Organic Framework Materials as Catalysts Chem. Soc. Rev. 2009, 38, 1450-1459
3. Murray, L. J.; Dinca, M.; Long, J. R. Hydrogen Storage in Metal-Organic Frameworks Chem. Soc. Rev. 2009, 38, 1294-1314
4. Kurmoo, M. Magnetic Metal-Organic Frameworks Chem. Soc. Rev. 2009, 38, 1353-1379
5. Heim, D.; Ecija, D.; Seutert, K.; Auwärter, W.; Aurisicchio, C.; Fabbro, C.; Bonifazi, D.; Barth, J. V. Self-Assembly of Flexible One-Dimensional Coordination Polymers on Metal Surfaces J. Am. Chem. Soc. 2010, 132, 6783-6790
6. Haq, S.; Hanke, F.; Dyer, M. S.; Persson, M.; Iavicoli, P.; Amabilino, D. B.; Raval, R. Clean Coupling of Unfunctionalized Porphyrins at Surfaces To Give Highly Oriented Organometallic Oligomers J. Am. Chem. Soc. 2011, 133, 12031-12039
7. Shi, Z.; Lin, N. Porphyrin-Based Two-Dimensional Coordination Kagome Lattice Self-Assembled on a Au(111) Surface J. Am. Chem. Soc. 2009, 131, 5376-5377
8. Wang, L.; Kong, H.; Chen, X.; Du, X.; Chen, F.; Liu, X.; Wang, H. Conformation-Induced Self-Assembly of Rubrene on Au(111) Surface Appl. Phys. Lett. 2009, 95, 093102-1-093102-3
9. Buchner, F.; Flechtner, K.; Bai, Y.; Zillner, E.; Kellner, I.; Steinrück, H.-P.; Marbach, H.; Gottfried, J. M. Coordination of Iron Atoms by Tetraphenylporphyrin Monolayers and Multilayers on Ag(111) and Formation of Iron-Tetraphenylporphyrin J. Phys. Chem. C 2008, 112, 15458-15465
10. Barth, J. V.; Weckesser, J.; Trimarchi, G.; Vladimirova, M.; De Vita, A.; Cai, C. Z.; Brune, H.; Gunter, P.; Kern, K. 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. 2002, 124, 7991-8000
11. Gourdon, A. On-Surface Covalent Coupling in Ultrahigh Vacuum Angew. Chem., Int. Ed. 2008, 47, 6950-6953
12. Shi, Z.; Lin, N. Structural and Chemical Control in Assembly of Multicomponent Metal-Organic Coordination Networks on a Surface J. Am. Chem. Soc. 2010, 132, 10756-10761
13. Li, Y.; Xiao, J.; Shubina, T. E.; Chen, M.; Shi, Z.; Schmid, M.; Steinrück, H.-P.; Gottfried, J. M.; Lin, N. Coordination and Metalation Bifunctionality of Cu with 5,10,15,20-Tetra(4-pyridyl)porphyrin: Toward a Mixed-Valence Two-Dimensional Coordination Network J. Am. Chem. Soc. 2012, 134, 6401-6408
14. Lin, N.; Dmitriev, A.; Weckesser, J.; Barth, J. V.; Kern, K. Real-Time Single-Molecule Imaging of the Formation and Dynamics of Coordination Compounds Angew. Chem., Int. Ed. 2002, 41, 4779-4783
15. Gambardella, P.; Stepanow, S.; Dmitriev, A.; Honolka, J.; de Groot, F. M. F.; Lingenfelder, M.; Sen Gupta, S.; Sarma, D. D.; Bencok, P.; Stanescu, S. et al. Supramolecular Control of the Magnetic Anisotropy in Two-Dimensional High-Spin Fe Arrays at a Metal Interface Nat. Mater. 2009, 8, 189-193
16. Stepanow, S.; Lin, N.; Payer, D.; Schlickum, U.; Klappenberger, F.; Zoppellaro, G.; Ruben, M.; Brune, H.; Barth, J. V.; Kern, K. Surface-Assisted Assembly of 2D Metal-Organic Networks that Exhibit Unusual Threefold Coordination Symmetry Angew. Chem., Int. Ed. 2007, 46, 710-713
17. Ullmann, F.; Bielecki, J. Synthesis in the Biphenyl Series Ber. Deutsch. Chem. Ges. 1901, 34, 2174-2185
18. 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. et al. Insight into Organometallic Intermediate and Its Evolution to Covalent Bonding in Surface-Confined Ullmann Polymerization ACS Nano 2013, 7, 8190-8198
19. Wang, W. H.; Shi, X. Q.; Wang, S. Y.; 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
20. 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
21. Blunt, M. O.; Russell, J. C.; Champness, N. R.; Beton, P. H. Templating Molecular Adsorption Using a Covalent Organic Framework Chem. Commun. 2010, 46, 7157-7159
22. Fan, Q.; Wang, C.; Han, Y.; Zhu, J. F.; Hieringer, W.; Kuttner, J.; Hilt, G.; Gottfried, J. M. Surface-Assisted Organic Synthesis of Hyperbenzene Nanotroughs Angew. Chem., Int. Ed. 2013, 52, 4668-4672
23. 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
24. Tait, S. L.; Langner, A.; Lin, N.; Stepanow, S.; Rajadurai, C.; Ruben, M.; Kern, K. One-Dimensional Self-Assembled Molecular Chains on Cu(100): Interplay Between Surface-Assisted Coordination Chemistry and Substrate Commensurability J. Phys. Chem. C 2007, 111, 10982-10987
25. Klappenberger, F.; Weber-Bargioni, A.; Auwärter, W.; Marschall, M.; Schiffrin, A.; Barth, J. V. Temperature Dependence of Conformation, Chemical State, and Metal-Directed Assembly of Tetrapyridyl-Porphyrin on Cu(111) J. Chem. Phys. 2008, 129, 214702-1-214702-10
26. Classen, T.; Fratesi, G.; Costantini, G.; Fabris, S.; Stadler, F. L.; Kim, C.; de Gironcoli, S.; Baroni, S.; Kern, K. Templated Growth of Metal-Organic Coordination Chains at Surfaces Angew. Chem., Int. Ed. 2005, 44, 6142-6145
27. Park, J.; Kim, K. Y.; Chung, K.-H.; Yoon, J. K.; Kim, H.; Han, S.; Kahng, S.-J. Interchain Interactions Mediated by Br Adsorbates in Arrays of Metal-Organic Hybrid Chains on Ag(111) J. Phys. Chem. C 2011, 115, 14834-14838
28. Chung, K.-H.; Koo, B.-G.; Kim, H.; Yoon, J. K.; Kim, J.-H.; Kwon, Y.-K.; Kahng, S.-J. Electronic Structures of One-Dimensional Metal-Molecule Hybrid Chains Studied Using Scanning Tunneling Microscopy and Density Functional Theory Phys. Chem. Chem. Phys. 2012, 14, 7304-7308
29. Villagomez, C. J.; Sasaki, T.; Tour, J. M.; Grill, L. Bottom-up Assembly of Molecular Wagons on a Surface J. Am. Chem. Soc. 2010, 132, 16848-16854
30. 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
31. Xi, M.; Bent, B. E. Mechanisms of The Ullmann Coupling Reaction in Adsorbed Monolayers J. Am. Chem. Soc. 1993, 115, 7426-7433
32. Yoon, J. K.; Jung, G. E.; Kim, H.; Chung, K. H.; Kahng, S. J. Two-Dimensional Vacancy Islands Induced by the Growth of Cr on Cu(111) Thin Solid Films 2010, 519, 1375-1379
33. Icking-Konert, G. S.; Giesen, M.; Ibach, H. Decay of Cu Adatom Islands on Cu(111) Surf. Sci. 1998, 398, 37-48
34. Repp, J.; Moresco, F.; Meyer, G.; Rieder, K. H.; Hyldgaard, P.; Persson, M. Substrate Mediated Long-Range Oscillatory Interaction Between Adatoms: Cu/Cu(111) Phys. Rev. Lett. 2000, 85, 2981-2984
35. Eyring, H. The Activated Complex in Chemical Reactions J. Chem. Phys. 1935, 3, 107
36. L. Rossa, F. V. Synthesis of Medio- and Macrocyclic Compounds by High Dilution Principle Techniques. In Cyclophanes I, Topics in Current Chemistry; Vögtle, F., Ed.; Springer: Berlin, Heidelberg, 2013; Vol. 113, p 1.
37. Chen, M.; Feng, X.; Zhang, L.; Ju, H.; Xu, Q.; Zhu, J. F.; Gottfried, J. M.; Ibrahim, K.; Qian, H.; Wang, J. Direct Synthesis of Nickel(II) Tetraphenylporphyrin and Its Interaction with a Au(111) Surface: A Comprehensive Study J. Phys. Chem. C 2010, 114, 9908-9916