Self-terminating protocol for an interfacial complexation reaction in vacuo by metal-organic chemical vapor deposition

ACS Nano

Volumn 7, Issue 5, 2013, Pages 4520-4526

  Papageorgiou, Anthoula C ^a   Fischer, Sybille ^a   Oh, Seung Cheol ^a   Saǧlam, Özge ^a   Reichert, Joachim ^a   Wiengarten, Alissa ^a   Seufert, Knud ^a   Vijayaraghavan, Saranyan ^a   Écija, David ^a   Auwärter, Willi ^a   Allegretti, Francesco ^a   Acres, Robert G ^b   Prince, Kevin C ^b   Diller, Katharina ^a   Klappenberger, Florian ^a   Barth, Johannes V ^a  

^a TECHNICAL UNIVERSITY OF MUNICH   (Germany)

^b SINCROTRONE TRIESTE   (Italy)

Author keywords

chemical vapor deposition; interfaces; monolayers; porphyrins; silver surface; surface chemistry

Indexed keywords

COMPLEXATION REACTION; COORDINATION COMPOUNDS; COORDINATION ENVIRONMENT; CYCLODEHYDROGENATION; METAL-ORGANIC COMPLEXES; METAL-ORGANIC INTERFACE; SILVER SURFACE; SINGLE-SITE CATALYSIS;

BYPRODUCTS; CARBONYLATION; CHEMICAL VAPOR DEPOSITION; COMPLEXATION; COORDINATION REACTIONS; DEHYDROGENATION; INTERFACES (MATERIALS); METALLORGANIC CHEMICAL VAPOR DEPOSITION; MONOLAYERS; PORPHYRINS; RUBIDIUM COMPOUNDS; SCANNING TUNNELING MICROSCOPY; SILVER; SURFACE CHEMISTRY; VAPORS; X RAY SPECTROSCOPY;

RUTHENIUM;

EID: 84878279370     PISSN: 19360851     EISSN: 1936086X     Source Type: Journal    
DOI: 10.1021/nn401171z     Document Type: Article

References (56)

1. Copéret, C. C-H Bond Activation and Organometallic Intermediates on Isolated Metal Centers on Oxide Surfaces Chem. Rev. 2010, 110, 656-680
2. Hulsken, B.; Van Hameren, R.; Gerritsen, J. W.; Khoury, T.; Thordarson, P.; Crossley, M. J.; Rowan, A. E.; Nolte, R. J. M.; Elemans, J. A. A. W.; Speller, S. Real-Time Single-Molecule Imaging of Oxidation Catalysis at a Liquid-Solid Interface Nat. Nanotechnol. 2007, 2, 285-289
3. Sedona, F.; Di Marino, M.; Forrer, D.; Vittadini, A.; Casarin, M.; Cossaro, A.; Floreano, L.; Verdini, A.; Sambi, M. Tuning the Catalytic Activity of Ag(110)-Supported Fe Phthalocyanine in the Oxygen Reduction Reaction Nat. Mater. 2012, 11, 970-977
4. Hagfeldt, A.; Boschloo, G.; Sun, L.; Kloo, L.; Pettersson, H. Dye-Sensitized Solar Cells Chem. Rev. 2010, 110, 6595-6663
5. Yella, A.; Lee, H.-W.; Tsao, H. N.; Yi, C.; Chandiran, A. K.; Nazeeruddin, M. K.; Diau, E. W.-G.; Yeh, C.-Y.; Zakeeruddin, S. M.; Grätzel, M. Porphyrin-Sensitized Solar Cells with Cobalt (II/III)-Based Redox Electrolyte Exceed 12% Efficiency Science 2011, 334, 629-634
6. Makiura, R.; Motoyama, S.; Umemura, Y.; Yamanaka, H.; Sakata, O.; Kitagawa, H. Surface Nano-architecture of a Metal-Organic Framework Nat. Mater. 2010, 9, 565-571
7. Shekhah, O.; Wang, H.; Paradinas, M.; Ocal, C.; Schupbach, B.; Terfort, A.; Zacher, D.; Fischer, R. A.; Wöll, Ch. Controlling Interpenetration in Metal-Organic Frameworks by Liquid-Phase Epitaxy Nat. Mater. 2009, 8, 481-484
8. Seufert, K.; Bocquet, M.-L.; Auwärter, W.; Weber-Bargioni, A.; Reichert, J.; Lorente, N.; Barth, J. V. cis -Dicarbonyl Binding at Cobalt and Iron Porphyrins with Saddle-Shape Conformation Nat. Chem. 2011, 3, 114-119
9. Hieringer, W.; Flechtner, K.; Kretschmann, A.; Seufert, K.; Auwärter, W.; Barth, J. V.; Görling, A.; Steinrück, H.-P.; Gottfried, J. M. The Surface Trans Effect: Influence of Axial Ligands on the Surface Chemical Bonds of Adsorbed Metalloporphyrins J. Am. Chem. Soc. 2011, 133, 6206-6222
10. Barth, J. V. Fresh Perspectives for Surface Coordination Chemistry Surf. Sci. 2009, 603, 1533-1541
11. Seufert, K.; Auwärter, W.; Barth, J. V. Discriminative Response of Surface-Confined Metalloporphyrin Molecules to Carbon and Nitrogen Monoxide J. Am. Chem. Soc. 2010, 132, 18141-18146
12. Wende, H.; Bernien, M.; Luo, J.; Sorg, C.; Ponpandian, N.; Kurde, J.; Miguel, J.; Piantek, M.; Xu, X.; Eckhold, P. et al. Substrate-Induced Magnetic Ordering and Switching of Iron Porphyrin Molecules Nat. Mater. 2007, 6, 516-520
13. Wäckerlin, C.; Chylarecka, D.; Kleibert, A.; Müller, K.; Iacovita, C.; Nolting, F.; Jung, T. A.; Ballav, N. Controlling Spins in Adsorbed Molecules by a Chemical Switch Nat. Commun. 2010, 1, 61
14. Umbach, T. R.; Bernien, M.; Hermanns, C. F.; Krüger, A.; Sessi, V.; Fernandez-Torrente, I.; Stoll, P.; Pascual, J. I.; Franke, K. J.; Kuch, W. Ferromagnetic Coupling of Mononuclear Fe Centers in a Self-Assembled Metal-Organic Network on Au(111) Phys. Rev. Lett. 2012, 109, 267207
15. Komeda, T.; Isshiki, H.; Liu, J.; Katoh, K.; Shirakata, M.; Breedlove, B. K.; Yamashita, M. Variation of Kondo Peak Observed in the Assembly of Heteroleptic 2,3-Naphthalocyaninato Phthalocyaninato Tb(III) Double-Decker Complex on Au(111) ACS Nano 2013, 7, 1092-1099
16. Miyamachi, T.; Gruber, M.; Davesne, V.; Bowen, M.; Boukari, S.; Joly, L.; Scheurer, F.; Rogez, G.; Yamada, T. K.; Ohresser, P. et al. Robust Spin Crossover and Memristance across a Single Molecule Nat. Commun. 2012, 3, 938
17. Mohn, F.; Repp, J.; Gross, L.; Meyer, G.; Dyer, M. S.; Persson, M. Reversible Bond Formation in a Gold-Atom-Organic-Molecule Complex as a Molecular Switch Phys. Rev. Lett. 2010, 105, 266102
18. Leoni, T.; Guillermet, O.; Walch, H.; Langlais, V.; Scheuermann, A.; Bonvoisin, J.; Gauthier, S. Controlling the Charge State of a Single Redox Molecular Switch Phys. Rev. Lett. 2011, 106, 216103
19. écija, D.; Auwärter, W.; Vijayaraghavan, S.; Seufert, K.; Bischoff, F.; Tashiro, K.; Barth, J. V. Assembly and Manipulation of Rotatable Cerium Porphyrinato Sandwich Complexes on a Surface Angew. Chem., Int. Ed. 2011, 50, 3872-3877
20. Komeda, T.; Isshiki, H.; Liu, J.; Zhang, Y.-F.; Lorente, N.; Katoh, K.; Breedlove, B. K.; Yamashita, M. Observation and Electric Current Control of a Local Spin in a Single-Molecule Magnet Nat. Commun. 2011, 2, 217
21. Lin, N.; Stepanow, S.; Ruben, M.; Barth, J. V. Surface-Confined Supramolecular Coordination Chemistry. In Templates in Chemistry III, Broekmann, P.; Dötz, K.-H.; Schalley, C. A., Eds.; Springer: Berlin, 2009; Vol. 287, pp 1-44.
22. Auwärter, W.; Weber-Bargioni, A.; Brink, S.; Riemann, A.; Schiffrin, A.; Ruben, M.; Barth, J. V. Controlled Metalation of Self-Assembled Porphyrin Nanoarrays in Two Dimensions ChemPhysChem 2007, 8, 250-254
23. écija, D.; Trelka, M.; Urban, C.; de Mendoza, P.; Mateo-Martí, E.; Rogero, C.; Martín-Gago, J. A.; Echavarren, A. M.; Otero, R.; Gallego, J. M. et al. Molecular Conformation, Organizational Chirality, and Iron Metalation of meso -Tetramesitylporphyrins on Copper(100) J. Phys. Chem. C 2008, 112, 8988-8994
24. Di Santo, G.; Castellarin-Cudia, C.; Fanetti, M.; Taleatu, B.; Borghetti, P.; Sangaletti, L.; Floreano, L.; Magnano, E.; Bondino, F.; Goldoni, A. Conformational Adaptation and Electronic Structure of 2H-Tetraphenylporphyrin on Ag(111) during Fe Metalation J. Phys. Chem. C 2011, 115, 4155-4162
25. Gottfried, J. M.; Flechtner, K.; Kretschmann, A.; Lukasczyk, T.; Steinrück, H.-P. Direct Synthesis of a Metalloporphyrin Complex on a Surface J. Am. Chem. Soc. 2006, 128, 5644-5645
26. Di Santo, G.; Sfiligoj, C.; Castellarin-Cudia, C.; Verdini, A.; Cossaro, A.; Morgante, A.; Floreano, L.; Goldoni, A. Changes of the Molecule-Substrate Interaction upon Metal Inclusion into a Porphyrin Chem.-Eur. J. 2012, 18, 12619-12623
27. Shubina, T. E.; Marbach, H.; Flechtner, K.; Kretschmann, A.; Jux, N.; Buchner, F.; Steinrück, H.-P.; Clark, T.; Gottfried, J. M. Principle and Mechanism of Direct Porphyrin Metalation: Joint Experimental and Theoretical Investigation J. Am. Chem. Soc. 2007, 129, 9476-9483
28. Chen, M.; Feng, X.; Zhang, L.; Ju, H.; Xu, Q.; Zhu, J.; 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
29. Weber-Bargioni, A.; Reichert, J.; Seitsonen, A. P.; Auwärter, W.; Schiffrin, A.; Barth, J. V. Interaction of Cerium Atoms with Surface-Anchored Porphyrin Molecules J. Phys. Chem. C 2008, 112, 3453-3455
30. 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
31. González-Moreno, R.; Sánchez-Sánchez, C.; Trelka, M.; Otero, R.; Cossaro, A.; Verdini, A.; Floreano, L.; Ruiz-Bermejo, M.; García-Lekue, A.; Martín-Gago, J. á. et al. Following the Metalation Process of Protoporphyrin IX with Metal Substrate Atoms at Room Temperature J. Phys. Chem. C 2011, 115, 6849-6854
32. Diller, K.; Klappenberger, F.; Marschall, M.; Hermann, K.; Nefedov, A.; Wöll, Ch.; Barth, J. V. Self-Metalation of 2H-Tetraphenylporphyrin on Cu(111): An X-ray Spectroscopy Study J. Chem. Phys. 2012, 136, 014705
33. Nowakowski, J.; Wäckerlin, C.; Girovsky, J.; Siewert, D.; Jung, T.; Ballav, N. Porphyrin Metalation Providing an Example of a Redox Reaction Facilitated by a Surface Reconstruction Chem. Commun. 2013, 49, 2347-2349
34. Diller, K.; Klappenberger, F.; Allegretti, F.; Papageorgiou, A. C.; Fischer, S.; Wiengarten, A.; Joshi, S.; Seufert, K.; écija, D.; Auwärter, W. et al. Investigating the Molecule-Substrate Interaction of Prototypic Tetrapyrrole Compounds: Adsorption and Self-Metalation of Porphine on Cu(111) J. Chem. Phys. 2013, 138, 154710
35. Goldoni, A.; Pignedoli, C. A.; Di Santo, G.; Castellarin-Cudia, C.; Magnano, E.; Bondino, F.; Verdini, A.; Passerone, D. Room Temperature Metalation of 2H-TPP Monolayer on Iron and Nickel Surfaces by Picking up Substrate Metal Atoms ACS Nano 2012, 6, 10800-10807
36. Che, C.-M.; Lo, V. K.-Y.; Zhou, C.-Y.; Huang, J.-S. Selective Functionalisation of Saturated C-H Bonds with Metalloporphyrin Catalysts Chem. Soc. Rev. 2011, 40, 1950-1975
37. Tour, J. M. Molecular Electronics. Synthesis and Testing of Components Acc. Chem. Res. 2000, 33, 791-804
38. Di Natale, C.; Salimbeni, D.; Paolesse, R.; Macagnano, A.; D'Amico, A. Porphyrins-Based Opto-electronic Nose for Volatile Compounds Detection Sens. Actuators, B 2000, 65, 220-226
39. Guldi, D. M. Fullerene-Porphyrin Architectures; Photosynthetic Antenna and Reaction Center Models Chem. Soc. Rev. 2002, 31, 22-36
40. Yu, J.; Mathew, S.; Flavel, B. S.; Johnston, M. R.; Shapter, J. G. Ruthenium Porphyrin Functionalized Single-Walled Carbon Nanotube Arrays-A Step toward Light Harvesting Antenna and Multibit Information Storage J. Am. Chem. Soc. 2008, 130, 8788-8796
41. Fackler, P.; Huber, S. M.; Bach, T. Enantio- and Regioselective Epoxidation of Olefinic Double Bonds in Quinolones, Pyridones, and Amides Catalyzed by a Ruthenium Porphyrin Catalyst with a Hydrogen Bonding Site J. Am. Chem. Soc. 2012, 134, 12869-12878
42. Che, C.-M.; Huang, J.-S. Ruthenium and Osmium Porphyrin Carbene Complexes: Synthesis, Structure, and Connection to the Metal-Mediated Cyclopropanation of Alkenes Coord. Chem. Rev. 2002, 231, 151-164
43. Kulkarni, A.; Lobo-Lapidus, R. J.; Gates, B. C. Metal Clusters on Supports: Synthesis, Structure, Reactivity, and Catalytic Properties Chem. Commun. 2010, 46, 5997-6015
44. Eaton, G. R.; Eaton, S. S. Reversible Carbon Monoxide Binding by Ruthenium Carbonyl Porphyrins J. Am. Chem. Soc. 1975, 97, 235-236
45. 3 C-H Bonds Adjacent to a Nitrogen Atom in Alkylamines with Alkenes J. Am. Chem. Soc. 2001, 123, 10935-10941
46. Auwärter, W.; Seufert, K.; Bischoff, F.; écija, D.; Vijayaraghavan, S.; Joshi, S.; Klappenberger, F.; Samudrala, N.; Barth, J. V. A Surface-Anchored Molecular Four-Level Conductance Switch Based on Single Proton Transfer Nat. Nanotechnol. 2012, 7, 41-46
47. Di Santo, G.; Blankenburg, S.; Castellarin-Cudia, C.; Fanetti, M.; Borghetti, P.; Sangaletti, L.; Floreano, L.; Verdini, A.; Magnano, E.; Bondino, F. et al. Supramolecular Engineering through Temperature-Induced Chemical Modification of 2H-Tetraphenylporphyrin on Ag(111): Flat Phenyl Conformation and Possible Dehydrogenation Reactions Chem.-Eur. J. 2011, 17, 14354-14359
48. Wagner, C. D.; Riggs, W. M.; Davis, L. E.; Moulder, J. F.; Muilenberg, G. E. Handbook of X-ray Photoelectron Spectroscopy: A Reference Book of Standard Data for Use in X-ray Photoelectron Spectroscopy; Perkin-Elmer Corporation: Eden Prairie, MN, 1979.
49. Auwärter, W.; Seufert, K.; Klappenberger, F.; Reichert, J.; Weber-Bargioni, A.; Verdini, A.; Cvetko, D.; Dell'Angela, M.; Floreano, L.; Cossaro, A. et al. Site-Specific Electronic and Geometric Interface Structure of Co-tetraphenyl-porphyrin Layers on Ag(111) Phys. Rev. B 2010, 81, 245403
50. 4P-Mn(III)Cl on Ag(100) J. Am. Chem. Soc. 2009, 131, 1910-1914
51. Turner, M.; Vaughan, O. P. H.; Kyriakou, G.; Watson, D. J.; Scherer, L. J.; Papageorgiou, A. C.; Sanders, J. K. M.; Lambert, R. M. Deprotection, Tethering, and Activation of a One-Legged Metalloporphyrin on a Chemically Active Metal Surface: NEXAFS, Synchrotron XPS, and STM Study of [SAc]P-Mn(III)Cl on Ag(100) J. Am. Chem. Soc. 2009, 131, 14913-14919
52. Fanetti, M.; Calzolari, A.; Vilmercati, P.; Castellarin-Cudia, C.; Borghetti, P.; Di Santo, G.; Floreano, L.; Verdini, A.; Cossaro, A.; Vobornik, I. et al. Structure and Molecule-Substrate Interaction in a Co-octaethyl Porphyrin Monolayer on the Ag(110) Surface J. Phys. Chem. C 2011, 115, 11560-11568
53. Seah, M. P.; Gilmore, I. S.; Beamson, G. XPS: Binding Energy Calibration of Electron Spectrometers 5-Re-evaluation of the Reference Energies Surf. Interface Anal. 1998, 26, 642-649
54. Outka, D. A.; Stöhr, J. Curve Fitting Analysis of Near-Edge Core Excitation Spectra of Free, Adsorbed, and Polymeric Molecules J. Chem. Phys. 1988, 88, 3539-3554
55. Grevels, F. W.; Reuvers, J. G. A.; Takats, J. (.eta.2-Olefin) tetracarbonylruthenium Complexes: Photochemical Syntheses from Dodecacarbonyltriruthenium and Quantum Yield Determinations J. Am. Chem. Soc. 1981, 103, 4069-4073
56. 12 Deposition on Au(111) Surf. Sci. 2003, 538, 76-88