Grafting of functionalized [Fe(III)(salten)] complexes to Au(111) surfaces via thiolate groups: Surface spectroscopic characterization and comparison of different linker designs

Langmuir

Volumn 29, Issue 27, 2013, Pages 8534-8543

  Jacob, Hanne ^a   Kathirvel, Ketheeswari ^a   Petersen, Finn ^a   Strunskus, Thomas ^a   Bannwarth, Alexander ^a   Meyer, Sven ^a   Tuczek, Felix ^a  

^a UNIVERSITY OF KIEL   (Germany)

Author keywords

[No Author keywords available]

Indexed keywords

ADSORBED MONOLAYERS; COORDINATION SPHERE; INFRARED REFLECTION ABSORPTION SPECTROSCOPY; MONONUCLEAR COMPLEXES; NEAR EDGE X RAY ABSORPTION FINE STRUCTURE; SPECTROSCOPIC CHARACTERIZATION; SPIN-CROSSOVER COMPLEXES; TRANSITION-METAL COMPLEX;

LIGANDS; METAL COMPLEXES; MONOLAYERS; PHOTOELECTRONS; X RAY PHOTOELECTRON SPECTROSCOPY;

IRON COMPOUNDS;

ETHYLENEDIAMINE DERIVATIVE; FERRIC ION; GOLD; N,N' DISALICYLIDENEETHYLENEDIAMINE; THIOL DERIVATIVE;

ARTICLE; CHEMICAL STRUCTURE; CHEMISTRY; COMPARATIVE STUDY; INFRARED SPECTROSCOPY; SPECTROPHOTOMETRY; SURFACE PROPERTY; X RAY; X RAY ABSORPTION SPECTROSCOPY;

ETHYLENEDIAMINES; FERRIC COMPOUNDS; GOLD; MOLECULAR STRUCTURE; SPECTROPHOTOMETRY; SPECTROSCOPY, FOURIER TRANSFORM INFRARED; SULFHYDRYL COMPOUNDS; SURFACE PROPERTIES; X-RAY ABSORPTION SPECTROSCOPY; X-RAYS;

EID: 84880166151     PISSN: 07437463     EISSN: 15205827     Source Type: Journal    
DOI: 10.1021/la400663y     Document Type: Article

References (49)

1. Alam, M. S.; Stocker, M.; Gieb, K.; Mueller, P.; Haryono, M.; Student, K.; Grohmann, A. Spin-State Patterns in Surface-Grafted Beads of Iron(II) Complexes Angew. Chem., Int. Ed. 2010, 49, 1159-1163
2. Kuck, S.; Chang, S.-H.; Klöckner, J.-P.; Prosenc, M. H.; Hoffmann, G.; Wiesendanger, R. Steering Two-Dimensional Molecular Growth via Dipolar Interaction ChemPhysChem 2009, 10, 2008-2011
3. + on Self-Assembled Monolayer Surfaces J. Phys. Chem. C 2010, 114, 5305-5311
4. Venkataramanan, N. S.; Kuppuraj, G.; Rajagopal, S. Metal-Salen Complexes as Efficient Catalysts for the Oxygenation of Heteroatom Containing Organic Compounds-Synthetic and Mechanistic Aspects Coord. Chem. Rev. 2005, 249, 1249-1268
5. Chiang, W.; Vanengen, D.; Thompson, M. E. Second-Order Non-Linear Optical Properties of Fe(Salen) Complexes Polyhedron 1996, 15, 2369-2376
6. Koley, M. K.; Manoharan, P. T.; Koley, A. P. Synthesis and Characterization of a Stable Paramagnetic Hexacoordinated Oxochromium(IV) Complex with Dianionic Tetradentate Schiff Base Ligand Salen Inorg. Chim. Acta 2010, 363, 3798-3802
7. Sarasukutty, S.; Prabhakaran, C. P. Studies on Iron(III) Thiocyanate Complexes of N,N′ Ethylene Bis (Salicylideneimine), N,N′ Bis o -Hydroxybenzylidene o -Phenylenediamine and N,N′ Propylene Bis (Salicylideneimine) J. Inorg. Nucl. Chem. 1977, 39, 374-376
8. 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
9. Wäckerlin, Ch.; Tarafder, K.; Siewert, D.; Girovsky, J.; Hählen, T.; Iacovita, Ch.; Kleibert, A.; Nolting, F.; Jung, T. A.; Oppeneer, P. M.; Ballav, N. On-Surface Coordination Chemistry of Planar Molecular Spin Systems: Novel Magnetochemical Effects Induced by Axial Ligands Chem. Sci. 2012, 3, 3154-3160
10. Silien, Ch.; Buck, M.; Goretzki, G.; Lahaye, D.; Champness, N. R.; Weidner, T.; Zharnikov, M. Self-Assembly of a Pyridine-Terminated Thiol Monolayer on Au(111) Langmuir 2009, 25, 959-967
11. Silien, Ch.; Lahaye, D.; Caffio, M.; Schaub, R.; Champness, N. R.; Buck, M. Electrodeposition of Palladium onto a Pyridine-Terminated Self-Assembled Monolayer Langmuir 2011, 27, 2567-2574
12. Darlatt, E.; Traulsen, Ch. H.-H.; Poppenberg, J.; Richter, S.; Kühn, J.; Schalley, Ch. A.; Unger, W. E. S. Evidence of Click and Coordination Reactions on a Self-Assembled Monolayer by Synchrotron Radiation Based XPS and NEXAFS J. Electron Spectrosc. Relat. Phenom. 2012, 185, 85-89
13. Poppenberg, J.; Richter, S.; Darlatt, E.; Traulsen, Ch. H.-H.; Min, H.; Unger, W. E. S.; Schalley, Ch. A. Successive Coordination of Palladium(II)-Ions and Terpyridine-Ligands to a Pyridyl-Terminated Self-Assembled Monolayer on Gold Surf. Sci. 2012, 606, 367-377
14. Kind, M.; Wöll, C. Organic Surfaces Exposed by Self-Assembled Organothiol Monolayers: Preparation, Characterization and Application Prog. Surf. Sci. 2009, 84, 230-278
15. Arnold, R.; Terfort, A.; Wöll, C. Determination of Molecular Orientation in Self-Assembled Monolayers Using IR Absorption Intensities: The Importance of Grinding Effects Langmuir 2001, 17, 4980-4989
16. Gregoriou, V. G.;; Rodman, S. E. Vibrational Spectroscopy of Thin Organic Films; Handbook of Vibrational Spectroscopy; J. Wiley: New York, 2006
17. Hollins, P. Surface Infrared Spectroscopy Vacuum 1994, 45, 705-714
18. Greenler, R. G. Infrared Study of Adsorbed Molecules on Metal Surfaces by Reflection Techniques J. Chem. Phys. 1966, 44, 310
19. Rajalingam, K.; Strunskus, T.; Terfort, A.; Fischer, R. A.; Wöll, C. Metallization of a Thiol-Terminated Organic Surface Using Chemical Vapor Deposition Langmuir 2008, 24, 7886-7994
20. Shekhah, O.; Wang, H.; Strunskus, T.; Cyganik, P.; Zacher, D.; Fischer, R.; Wöll, C. Layer-by-Layer Growth of Oriented Metal Organic Polymers on a Functionalized Organic Surface Langmuir 2007, 23, 7440-7442
21. Zawisza, I.; Wittstock, G.; Boukherroub, R.; Szunerits, S. PM IRRAS Investigation of Thin Silica Films Deposited on Gold. Part 1. Theory and Proof of Concept Langmuir 2007, 23, 9303-9309
22. Mayer, C. R.; Cucchiaro, G.; Jullien, J.; Dumur, F.; Marrot, J.; Dumas, E.; Sécheresse, F. Functionalization of Gold Nanoparticles by Iron(III) Complexes Derived from Schiff Base Ligands Eur. J. Inorg. Chem. 2008, 3614-3623
23. Hirose, S.; Hayami, S.; Maeda, Y. Magnetic Properties of Iron(III) Complexes with Photoisomerizable Ligands Bull. Chem. Soc. Jpn. 2000, 73, 2059-2066
24. Nemec, I.; Boča, R.; Gembický, M.; Dlhaň, L.; Herchel, R.; Renz, F. High-Spin Schiff Base Dinuclear Iron(III) Complexes Bridged by N-Oxide Ligands Inorg. Chim. Acta 2009, 362, 4754-4759
25. http://avogadro.openmolecules.net.
26. Becke, A. D. Density-Functional Exchange-Energy Approximation with Correct Asymptotic Behavior Phys. Rev. A: Gen. Phys. 1988, 38, 3098-3100
27. Perdew, J. P. Phys. Rev. B: Condens. Matter 1986, 157, 200-206
28. Schaefer, A.; Horn, H.; Ahlrichs, R. Fully Optimized Contracted Gaussian-Basis Sets for Atoms Li to Kr J. Chem. Phys. 1992, 97, 2571-2577
29. Schaefer, A.; Huber, C.; Ahlrichs, R. Fully Optimized Contracted Gaussian-Basis Sets of Triple Zeta Valence Quality for Atoms Li to Kr J. Chem. Phys. 1994, 100, 5829-5835
30. 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, Ö.; Foresman, J. B.; Ortiz, J. V.; Cioslowski, J.; Fox, D. J. Gaussian 09, revision A.1; Gaussian, Inc.: Wallingford, CT, 2009.
31. Casa XPS, casaxps.com; Casa Software Ltd., 2009.
32. Heister, K.; Zharnikov, M.; Grunze, M. Characterization of X-ray Induced Damage in Alkanethiolate Monolayers by High-Resolution Photoelectron Spectroscopy Langmuir 2001, 17, 8-11
33. 3+ Ions in Oxide Materials Appl. Surf. Sci. 2008, 254, 2441-2449
34. Stoch, J.; Capecki, A. Decomposition of 2p3/2 Bands in XPS Spectra of Fe, Co and Ni Compounds Surf. Interface Anal. 1990, 15, 206-210
35. Bannwarth, A.; Schmidt, S.-O.; Peters, G.; Sönnichsen, F. D.; Thimm, W.; Herges, R.; Tuczek, F. Fe(III) Spin Crossover Complexes with Photoisomerizable Ligands: Experimental and Theoretical Investigations on the LD-LISC Effect Eur. J. Inorg. Chem. 2012, 2776-2783
36. Boča, R.; Fukuda, Y.; Gembický, M.; Herchel, R.; Jaroščiak, R.; Linert, W.; Renz, F.; Yuzurihara, J. Spin Crossover in Mononuclear and Binuclear Iron(III) Complexes with Pentadentate Schiff Base Ligands Chem. Phys. Lett. 2000, 325, 411-419
37. Ohta, S.; Yoshimura, C.; Matsumoto, N.; Okawa, H.; Ohyoshi, A. The Synthesis, Magnetic, and Spectroscopic Properties of Binuclear Iron(III) Complexes bridged by Pyrazine, 1,1′-Tetramethylenebis(imidazol), or Bis(pyridine) Compounds Exhibiting a Spin-Equilibrium Behavior Bull. Chem. Soc. Jpn. 1986, 59, 155-159
38. Soomro, S. A.; Benmouna, R.; Berger, R.; Meier, H. Preparation and Photochemistry of Dendrimers with Isolated Stilbene Chromophores Eur. J. Org. Chem. 2005, 3586-3593
39. Wackerbarth, H.; Marie, R.; Grubb, M.; Zhang, J.; Hansen, A. G.; Chorkendorff, I.; Christensen, C. B. V.; Boisen, A.; Ulstrup, J. Thiol- and Disulfide-Modified Oligonucleotide Monolayer Structures on Polycrystalline and Single-Crystal Au(111) Surfaces J. Solid State Electrochem. 2004, 8, 474-481
40. Hallmann, L.; Bashir, A.; Strunskus, T.; Adelung, R.; Staemmler, V.; Wöll, Ch.; Tuczek, F. Self-Assembled Monolayers of Benzylmercaptan and p -Cyanobenzylmercaptan on Au(111) Surfaces: Structural and Spectroscopic Characterization Langmuir 2008, 24, 5726-5733
41. Castner, D. G. X-ray Photoelectron Spectroscopy Sulfur 2p Study of Organic Thiol and Disulfide Binding Interactions with Gold Surfaces Langmuir 1996, 12, 5083-5086
42. Vericat, C.; Vela, M. E.; Benitez, G.; Carro, P.; Salvarezza, R. C. Self-Assembled Monolayers of Thiols and Dithiols on Gold: New Challenges for a Well-Known System Chem. Soc. Rev. 2010, 39, 1805-1834
43. Cyganik, P.; Buck, M.; Strunskus, T.; Shaporenko, A.; Wilton-Ely, J. D. E. T.; Zharnikov, M.; Wöll, C. Competition as a Design Concept: Polymorphism in Self-Assembled Monolayers of Biphenyl-Based Thiols J. Am. Chem. Soc. 2006, 128, 13868-13878
44. 3S Monolayer on Au(111) Solved by the Interplay between Molecular Dynamics Calculations and Diffraction Measurements Phys. Rev. Lett. 2007, 98, 016102-1-016102-4
45. Grosvenor, A. P.; Kobe, B. A.; Biesinger, M. C.; McIntyre, N. S. Investigation of Multiplet Splitting of Fe 2p XPS Spectra and Bonding in Iron Compounds Surf. Interface Anal. 2004, 36, 1564-1574
46. Pippig, F.; Sarghini, S.; Hollaender, A.; Paulussen, S.; Terryn, H. TFAA Chemical Derivatization and XPS. Analysis of OH and NHx Polymers Surf. Interface Anal. 2009, 41, 421-429
47. 2 J. Electron Spectrosc. Relat. Phenom. 1980, 21, 249-256
48. Biebuyck, H. A.; Bain, C. D.; Whitesides, G. M. Comparison of Organic Monolayers on Polychristalline Gold Spontaneously Assembled from Solutions Containing Dialkyl Disulfides or Alkanethiols Langmuir 1994, 10, 1825-1831
49. Gopakumar, T. G.; Matino, F.; Naggert, H.; Bannwarth, A.; Tuczek, F.; Berndt, R. Electron-Induced Spin Crossover of Single Molecules in a Bilayer on Gold Angew. Chem., Int. Ed. 2012, 51, 6262-6266