Self-metalation of 2H-tetraphenylporphyrin on Cu(111) studied with XSW: Influence of the central metal atom on the adsorption distance

Journal of Physical Chemistry C

Volumn 118, Issue 25, 2014, Pages 13659-13666

  Burker C ^a   Franco Canellas A ^a   Broch, K ^a   Lee, T L ^b   Gerlach, A ^a   Schreiber, F ^a  

^a UNIVERSITY OF TÜBINGEN   (Germany)

^b DIAMOND LIGHT SOURCE LTD   (United Kingdom)

Author keywords

[No Author keywords available]

Indexed keywords

ADSORPTION; ATOMS; CARBON; CHEMICAL BONDS; CHEMICAL REACTIONS; COPPER COMPOUNDS; METALS; MOLECULES; NITROGEN;

BONDING DISTANCES; CARBON AND NITROGEN; CONJUGATED MOLECULES; STRONG INTERACTION; SUBSTRATE SURFACE; TETRAPHENYL PORPHYRINS; THERMALLY ACTIVATED; X-RAY STANDING WAVES;

STANDING WAVE METERS;

EID: 84920685539     PISSN: 19327447     EISSN: 19327455     Source Type: Journal    
DOI: 10.1021/jp503046w     Document Type: Article

References (51)

1. Heimel, G.; Duhm, S.; Salzmann, I.; Gerlach, A.; Strozecka, A.; Niederhausen, J.; Búrker, C.; Hosokai, T.; Fernandez-Torrente, I.; Schulze, G.; et al. Charged and Metallic Molecular Monolayers through Surface-Induced Aromatic Stabilization. Nat. Chem. 2013, 5, 187-194.
2. Stadler, C.; Hansen, S.; Kröger, I.; Kumpf, C.; Umbach, E. Tuning Intermolecular Interaction in Long-Range-Ordered Submonolayer Organic Films. Nat. Phys. 2009, 5, 153-158.
3. Koch, N.; Gerlach, A.; Duhm, S.; Glowatzki, H.; Heimel, G.; Vollmer, A.; Sakamoto, Y.; Suzuki, T.; Zegenhagen, J.; Rabe, J. P.; et al. Adsorption Induced Intramolecular Dipole: Correlating Molecular Conformation and Interface Electronic Structure. J. Am. Chem. Soc. 2008, 130, 7300-7304.
4. Yamane, H.; Gerlach, A.; Duhm, S.; Tanaka, Y.; Hosokai, T.; Mi, Y. Y.; Zegenhagen, J.; Koch, N.; Seki, K.; Schreiber, F. Site-Specific Geometric and Electronic Relaxations at OrganicMetal Interfaces. Phys. Rev. Lett. 2010, 105, 0461031-0461034.
5. Rakow, N. A.; Suslick, K. S. A Colorimetric Sensor Array for Odour Visualization. Nature 2000, 406, 710-713.
6. Meunier, B. Metalloporphyrins as Versatile Catalysts for Oxidation Reactions and Oxidative DNA Cleavage. Chem. Rev. 1992, 92, 1411-1456.
7. Bhugun, I.; Lexa, D.; Savéant, J.-M. Homogeneous Catalysis of Electrochemical Hydrogen Evolution by Iron(0) Porphyrins. J. Am. Chem. Soc. 1996, 118, 3982-3983.
8. 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.
9. Baldo, M. A.; O'Brien, D. F.; You, Y.; Shoustikov, A.; Sibley, S.; Thompson, M. E.; Forrest, S. R. Highly Efficient Phosphorescent Emission from Organic Electroluminescent Devices. Nature 1998, 395, 151-154.
10. Imahori, H.; Fukuzumi, S. Porphyrin-and Fullerene-Based Molecular Photovoltaic Devices. Adv. Funct. Mater. 2004, 14, 525-536.
11. Koiry, S.; Jha, P.; Aswal, D.; Nayak, S.; Majumdar, C.; Chattopadhyay, S.; Gupta, S.; Yakhmi, J. Diodes Based on Bilayers Comprising of Tetraphenyl Porphyrin Derivative and Fullerene for Hybrid Nanoelectronics. Chem. Phys. Lett. 2010, 485, 137-141.
12. Scheybal, A.; Ramsvik, T.; Bertschinger, R.; Putero, M.; Nolting, F.; Jung, T. Induced Magnetic Ordering in a Molecular Monolayer. Chem. Phys. Lett. 2005, 411, 214-220.
13. 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.
14. Wáckerlin, C.; Chylarecka, D.; Kleibert, A.; Múller, K.; Iacovita, C.; Nolting, F.; Jung, T. A.; Ballav, N. Controlling Spins in Adsorbed Molecules by a Chemical Switch. Nat. Commun. 2010, 1, 1-7.
15. Panighel, M.; Di Santo, G.; Caputo, M.; Lal, C.; Taleatu, B.; Goldoni, A. Review of 2H-Tetraphenylporphyrins Metalation in Ultra-High Vacuum on Metal Surfaces. J. Phys.: Conf. Ser. 2013, 470, 0120121-0120126.
16. 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. A.; et al. Following the Metalation Process of Protoporphyrin IX with Metal Substrate Atoms at Room Temperature. J. Phys. Chem. C 2011, 115, 6849-6854.
17. Doyle, C. M.; Krasnikov, S. A.; Sergeeva, N. N.; Preobrajenski, A. B.; Vinogradov, N. A.; Sergeeva, Y. N.; Senge, M. O.; Cafolla, A. A. Evidence for the Formation of an Intermediate Complex in the Direct Metalation of Tetra(4-bromophenyl)-porphyrin on the Cu(111) Surface. Chem. Commun. 2011, 47, 12134-12136.
18. 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.
19. 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.
20. Diller, K.; Klappenberger, F.; Allegretti, F.; Papageorgiou, A. C.; Fischer, S.; Wiengarten, A.; Joshi, S.; Seufert, K.; Ecija, D.; Auwárter, 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 1-9.
21. Nowakowski, J.; Wáckerlin, C.; Girovsky, J.; Siewert, D.; Jung, T. A.; Ballav, N. Porphyrin Metalation Providing an Example of a Redox Reaction Facilitated by a Surface Reconstruction. Chem. Commun. 2013, 49, 2347-2349.
22. Diller, K.; Klappenberger, F.; Marschall, M.; Hermann, K.; Nefedov, A.; Wöll, C.; Barth, J. V. Self-Metalation of 2HTetraphenylporphyrin on Cu(111): An X-ray Spectroscopy Study. J. Chem. Phys. 2012, 136, 0147051-01470513.
23. Xiao, J.; Ditze, S.; Chen, M.; Buchner, F.; Stark, M.; Drost, M.; Steinrúck, H.-P.; Gottfried, J. M.; Marbach, H. Temperature-Dependent Chemical and Structural Transformations from 2H Tetraphenylporphyrin to Copper(II)-Tetraphenylporphyrin on Cu(111). J. Phys. Chem. C 2012, 116, 12275-12282.
24. Shubina, T. E.; Marbach, H.; Flechtner, K.; Kretschmann, A.; Jux, N.; Buchner, F.; Steinrúck, 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.
25. Buchner, F.; Xiao, J.; Zillner, E.; Chen, M.; Röckert, M.; Ditze, S.; Stark, M.; Steinrúck, H.-P.; Gottfried, J. M.; Marbach, H. Diffusion, Rotation, and Surface Chemical Bond of Individual 2H-Tetraphenylporphyrin Molecules on Cu(111). J. Phys. Chem. C 2011, 115, 24172-24177.
26. Upon metalation, the remaining N 1s peak has a binding energy slightly shifted with respect to the nonmetalated iminic peak. However, for simplicity, we refer to those nitrogen atoms equally coordinated to the central Cu atom, which yield the single N 1s XPS peak, as iminic as well.
27. Ditze, S.; Stark, M.; Drost, M.; Buchner, F.; Steinrúck, H.-P.; Marbach, H. Activation Energy for the Self-Metalation Reaction of 2HTetraphenylporphyrin on Cu(111). Angew. Chem., Int. Ed. 2012, 51, 10898-10901.
28. Röckert, M.; Ditze, S.; Stark, M.; Xiao, J.; Steinrúck, H.-P.; Marbach, H.; Lytken, O. Abrupt Coverage-Induced Enhancement of the Self-Metalation of Tetraphenylporphyrin with Cu(111). J. Phys. Chem. C 2014, 118, 1661-1667.
29. Rojas, G.; Simpson, S.; Chen, X.; Kunkel, D. A.; Nitz, J.; Xiao, J.; Dowben, P. A.; Zurek, E.; Enders, A. Surface State Engineering of MoleculéMolecule Interactions. Phys. Chem. Chem. Phys. 2012, 14, 4971-4976.
30. Stark, M.; Ditze, S.; Drost, M.; Buchner, F.; Steinrúck, H.-P.; Marbach, H. Coverage Dependent Disorder Order Transition of 2HTetraphenylporphyrin on Cu(111). Langmuir 2013, 29, 4104-4110.
31. Rojas, G.; Chen, X.; Bravo, C.; Kim, J.-H.; Kim, J.-S.; Xiao, J.; Dowben, P. A.; Gao, Y.; Zeng, X. C.; Choe, W.; et al. Self-Assembly and Properties of Nonmetalated Tetraphenyl-Porphyrin on Metal Substrates. J. Phys. Chem. C 2010, 114, 9408-9415.
32. Brede, J.; Linares, M.; Kuck, S.; Schwbel, J.; Scarfato, A.; Chang, S.-H.; Hoffmann, G.; Wiesendanger, R.; Lensen, R.; Kouwer, P. H. J.; et al. Dynamics of Molecular Self-Ordering in Tetraphenyl Porphyrin Monolayers on Metallic Substrates. Nanotechnology 2009, 20, 275602/ 1-27560210.
33. Buchner, F.; Kellner, I.; Hieringer, W.; Görling, A.; Steinrúck, H.-P.; Marbach, H. Ordering Aspects and Intramolecular Conformation of Tetraphenylporphyrins on Ag(111). Phys. Chem. Chem. Phys. 2010, 12, 13082-13090.
34. Duhm, S.; Gerlach, A.; Salzmann, I.; Bröcker, B.; Johnson, R.; Schreiber, F.; Koch, N. PTCDA on Au(111), Ag(111) and Cu(111): Correlating Bonding Distance and Interfacial Charge Transfer. Org. Electron. 2008, 9, 111-118.
35. Búrker, C.; Ferri, N.; Tkatchenko, A.; Gerlach, A.; Niederhausen, J.; Hosokai, T.; Duhm, S.; Zegenhagen, J.; Koch, N.; Schreiber, F. Exploring the Bonding of Large Hydrocarbons on Noble Metals: Diindoperylene on Cu(111), Ag(111), and Au(111). Phys. Rev. B 2013, 87, 1654431-1654435.
36. Stadtmúller, B.; Kröger, I.; Reinert, F.; Kumpf, C. Submonolayer Growth of CuPc on Noble Metal Surfaces. Phys. Rev. B 2011, 83, 0854161-08541610.
37. Hauschild, A.; Karki, K.; Cowie, B. C. C.; Rohlfing, M.; Tautz, F. S.; Sokolowski, M. Molecular Distortions and Chemical Bonding of a Large -Conjugated Molecule on a Metal Surface. Phys. Rev. Lett. 2005, 94, 0361061-0361064.
38. Gerlach, A.; Hosokai, T.; Duhm, S.; Kera, S.; Hofmann, O. T.; Zojer, E.; Zegenhagen, J.; Schreiber, F. Orientational Ordering of Nonplanar Phthalocyanines on Cu(111): Strength and Orientation of the Electric Dipole Moment. Phys. Rev. Lett. 2011, 106, 1561021-1561024.
39. Henze, S. K. M.; Bauer, O.; Lee, T.-L.; Sokolowski, M.; Tautz, F. S. Vertical Bonding Distances of PTCDA on Au(111) and Ag(111): Relation to the Bonding Type. Surf. Sci. 2007, 601, 1566-1573.
40. Kilian, L.; Hauschild, A.; Temirov, R.; Soubatch, S.; Schöll, A.; Bendounan, A.; Reinert, F.; Lee, T.-L.; Tautz, F. S.; Sokolowski, M.; et al. Role of Intermolecular Interactions on the Electronic and Geometric Structure of a Large -Conjugated Molecule Adsorbed on a Metal Surface. Phys. Rev. Lett. 2008, 100, 1361031-1361034.
41. Gerlach, A.; Búrker, C.; Hosokai, T.; Schreiber, F. In The MoleculéMetal Interface; Koch, N., Ueno, N., Wee, A., Eds.; WILEY VCH Verlag: New York, 2013.
42. Zegenhagen, J. Surface-Structure Determination with X-ray Standing Waves. Surf. Sci. Rep. 1993, 18, 199-271.
43. Woodruff, D. P.; Seymour, D. L.; McConville, C. F.; Riley, C. E.; Crapper, M. D.; Prince, N.; Jones, R. G. A Simple X-ray Standing Wave Technique for Surface Structure Determination Theory and an Application. Surf. Sci. 1988, 195, 237-254.
44. Cheng, L.; Fenter, P.; Bedzyk, M. J.; Sturchio, N. C. Fourier-Expansion Solution of Atom Distributions in a Crystal Using X-ray Standing Waves. Phys. Rev. Lett. 2003, 90, 2555031-2555034.
45. Touloukian, Y. S.; Kirby, R. K.; Taylor, R. E.; Desai, P. D. Thermophysical Properties of Matter. Vol. 12: Thermal Expansion-Metallic Elements and Alloys; IFI Plenum: NewYork, Washington, DC, 1975.
46. See the Supporting Information. It contains the desorption spectrum of a CuTPP monolayer, the details of the metalation reaction due to hard X-rays exposure, and the details of the calculation of the bending angles for the phenyl groups.
47. Buchner, F.; Zillner, E.; Röckert, M.; Gláßel, S.; Steinrúck, H.-P.; Marbach, H. Substrate-Mediated Phase Separation of Two Porphyrin Derivatives on Cu(111). Chem. Eur. J. 2011, 17, 10226-10229.
48. 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.
49. Kröger, I.; Bayersdorfer, P.; Stadtmúller, B.; Kleimann, C.; Mercurio, G.; Reinert, F.; Kumpf, C. Submonolayer Growth of H2-Phthalocyanine on Ag(111). Phys. Rev. B 2012, 86, 1954121-1954129.
50. Duhm, S.; Búrker, C.; Niederhausen, J.; Salzmann, I.; Hosokai, T.; Duvernay, J.; Kera, S.; Schreiber, F.; Koch, N.; Ueno, N.; et al. Pentacene on Ag(111): Correlation of Bonding Distance with Intermolecular Interaction and Order. ACS Appl. Mater. Interfaces 2013, 5, 9377-9381.
51. Kröger, I.; Stadtmúller, B.; Kleimann, C.; Rajput, P.; Kumpf, C. Normal-Incidence X-ray Standing-Wave Study of Copper Phthalocyanine Submonolayers on Cu(111) and Au(111). Phys. Rev. B 2011, 83, 1954141-1954149.