Self-assembled monolayers of benzylmercaptan and para-cyanobenzylmercaptan on gold: Surface infrared spectroscopic characterization

Physical Chemistry Chemical Physics

Volumn 12, Issue 17, 2010, Pages 4390-4399

  Rajalingam, K ^a   Hallmann, L ^a   Strunskus, T ^a,b   Bashir, A ^b   Woll C ^b   Tuczek, F ^a  

^a UNIVERSITY OF KIEL   (Germany)

^b KARLSRUHE INSTITUTE OF TECHNOLOGY   (Germany)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 77951474215     PISSN: 14639076     EISSN: None     Source Type: Journal    
DOI: 10.1039/b923628g     Document Type: Article

References (48)

1. F. Hoffmann Infrared reflection-absorption spectroscopy of adsorbed molecules Surf. Sci. Rep. 1983 3 107 192
2. R. G. Greenler Infrared study of adsorbed molecules on metal surfaces by reflection techniques J. Chem. Phys. 1966 44 310 315
3. R. Arnold A. Terfort C. Wöll Determination of Molecular Orientation in Self-Assembled Monolayers Using IR Absorption Intensities: The Importance of Grinding Effects Langmuir 2001 17 4980 4989 (Pubitemid 35330222)
4. V. G. Gregoriou and S. E. Rodman, Vibrational Spectroscopy of Thin Organic Films, in Handbook of Vibrational Spectroscopy, ed., P. R. Griffiths, and, J. Chalmers, John Wiley & Sons Ltd, 2002, ch. 4, pp. 2670-2693
5. P. Hollins Surface infrared spectroscopy Vacuum 1994 45 705 714
6. C. A. Mirkin M. A. Ratner Molecular electronics Annu. Rev. Phys. Chem. 1992 43 719 754
7. J. M. Tour Molecular Electronics. Synthesis and Testing of Components Acc. Chem. Res. 2000 33 791 804
8. J. C. Love L. A. Estroff J. K. Kriebel R. G. Nuzzo G. M. Whitesides Self-Assembled Monolayers of Thiolates on Metals as a Form of Nanotechnology Chem. Rev. 2005 105 1103 1169
9. X. M. Li J. Huskens D. N. Reinhoudt Reactive self-assembled monolayers on flat and nanoparticle surfaces, and their application in soft and scanning probe lithographic nanofabrication technologies J. Mater. Chem. 2004 14 2954 2971
10. M. C. Daniel D. Astruc Gold Nanoparticles: Assembly Supramolecular Chemistry, Quantum-Size-Related Properties, and Applications toward Biology, Catalysis, and Nanotechnology Chem. Rev. 2004 104 293 346
11. V. Huc Transition metal catalysts for molecular motors: towards molecular lithography J. Phys.: Condens. Matter 2006 18 S1909 S1926
12. K. Hara R. Akiyama S. Takakusagi K. Uosaki T. Yoshino H. Kagi M. Sawamura Self-Assembled Monolayers of Compact Phosphanes with Alkanethiolate Pendant Groups: Remarkable Reusability and Substrate Selectivity in Rh Catalysis Angew. Chem. 2008 120 5709 5712
13. S. Berner S. Biela G. Ledung A. Gogoll J. Bäckvall C. Puglia S. Oscarsson Activity boost of a biomimetic oxidation catalyst by immobilization onto a gold surface J. Catal. 2006 244 86 91 (Pubitemid 44547940)
14. T. Belser M. Stöhr A. Pfaltz Immobilization of Rhodium Complexes at Thiolate Monolayers on Gold Surfaces: Catalytic and Structural Studies J. Am. Chem. Soc. 2005 127 8720 8731 (Pubitemid 40868255)
15. K. Hara K. Iwahashi S. Takakusagi K. Uosaki M. Sawamura Construction of self-assembled monolayer terminated with N-heterocyclic carbene-rhodium(I) complex moiety Surf. Sci. 2007 601 5127 5132 (Pubitemid 350046701)
16. J. R. deSousa I. C. N. Diogenes M. L. A. Temperini F. A. M. Sales S. O. Pinheiro R. N. C. Filho J. S. d. Junior I. S. Moreira Synthesis, characterization, and SAMs electroactivity of ruthenium complexes with sulfur containing ligands J. Organomet. Chem. 2007 692 3691 3699 (Pubitemid 47042811)
17. K. D. Dronavajjala R. Rajagopalan S. Uppili A. Sen D. L. Allara H. C. Foley A Simple Technique To Grow Polymer Brushes Using in situ Surface Ligation of an Organometallic Initiator J. Am. Chem. Soc. 2006 128 13040 13041 (Pubitemid 44527661)
18. T. Vallant W. Simanko H. Brunner U. Mayer H. Hoffmann R. Schmid K. Kirchner R. Svagera G. Schügerl M. Ebel Comparing Reactivities of Metal Complexes in Solution and on Surfaces by IR Spectroscopy and Time-Resolved in situ Ellipsometry Organometallics 1999 18 3744 3749
19. J. Luo S. S. Isied Ruthenium Tetraammine Chemistry of Self-Assembled Monolayers on Gold Surfaces: Substitution and Reactivity at the Monolayer Interface Langmuir 1998 14 3602 3606 (Pubitemid 128581294)
20. K. Rajalingam T. Strunskus A. Terfort R. A. Fischer C. Wöll Metallization of a Thiol-Terminated Organic Surface Using Chemical Vapor Deposition Langmuir 2008 24 7986 7994
21. 2 - Adrenergic Receptors Measured by Plasmonic Interactions of Functionalized Nanoparticles ACS Nano 2009 3 2329 2339
22. L. Hallmann A. Bashir T. Strunskus R. Adelung V. Staemmler C. Wöll F. Tuczek Self-Assembled Monolayers of Benzylmercaptan and p- Cyanobenzylmercaptan on Au(111) Surfaces: Structural and Spectroscopic Characterization Langmuir 2008 24 5726 5733
23. M. Bellas D. L. Tuleen L. Field Organic disulfides and related substances. XXII. Substituted benzyl 2-(N-decylamino) ethyl disulfide hydrochlorides. A possible neighboring-group effect involving sulfur J. Org. Chem. 1967 32 2591 2595
24. M. J. Frisch, G. W. Trucks, H. B. Schlegel, G. E. Scuseria, M. A. Robb, J. R. Cheeseman, J. A. Montgomery, T. Vreven, K. N. Kudin, J. C. Burant, J. M. Millam, S. S. Iyengar, J. Tomasi, V. Barone, B. Mennucci, M. Cossi, G. Scalmani, N. Rega, G. A. Petersson, H. Nakatsuji, M. Hada, M. Ehara, K. Toyota, R. Fukuda, J. Hasegawa, M. Ishida, T. Nakajima, Y. Honda, O. Kitao, H. Nakai, M. Klene, X. Li, J. E. Knox, H. P. Hratchian, J. B. Cross, C. Adamo, J. Jaramillo, R. Gomperts, R. E. Stratmann, O. Yazyev, A. J. Austin, R. Cammi, C. Pomelli, J. W. Ochterski, P. Y. Ayala, K. Morokuma, G. A. Voth, P. Salvador, J. J. Dannenberg, V. G. Zakrzewski, S. Dapprich, A. D. Daniels, M. C. Strain, O. Farkas, D. K. Malick, A. D. Rabuck, K. Raghavachari, J. B. Foresman, J. V. Ortiz, Q. Cui, A. G. Baboul, S. Clifford, J. Cioslowski, B. B. Stefanov, G. Liu, A. Liashenko, P. Piskorz, I. Komaromi, R. L. Martin, D. J. Fox, T. Keith, M. A. Al-Laham, C. Y. Peng, A. Nanayakkara, M. Challacombe, P. M. W. Gill, B. Johnson, W. Chen, M. W. Wong, C. Gonzalez and J. A. Pople, GAUSSIAN 03, Gaussian Inc., Pittsburgh PA, 2003
25. A. Frisch, A. B. Nielsen and A. J. Holder, Gaussview Users Manual, Gaussian Inc., 2000
26. C. Lee W. Yang R. G. Parr Development of the Colle-Salvetti correlation-energy formula into a functional of the electron density Phys. Rev. B: Condens. Matter 1988 37 785 789
27. A. D. Becke Density-functional thermochemistry. III. The role of exact exchange J. Chem. Phys. 1993 98 5648 5652
28. E. B. Wilson A Partial Interpretation of the Raman and Infrared Spectra of Benzene Phys. Rev. 1934 46 146 147
29. S. E. Wiberley S. C. Bunce W. H. Bauer Carbon-Hydrogen stretching frequencies Anal. Chem. 1960 32 217 221
30. J. Liu L. Stratmann S. Krakert M. Kind F. Olbrich A. Terfort C. Wöll IR spectroscopic characterization of SAMs made from a homologous series of pyridine disulfides J. Electron Spectrosc. Relat. Phenom. 2009 172 120 127
31. D. A. Zimmerman J. L. Koenig H. Ishida Infrared spectroscopic analysis of poly(p-phenylene sulfide) Spectrochim. Acta, Part A 1995 51 2397 2409
32. W. R. T. Barden S. Singh P. e. Kruse Roughening of Gold Atomic Steps Induced by Interaction with Tetrahydrofuran Langmuir 2008 24 2452 2458 (Pubitemid 351542642)
33. B. Berron G. K. Jennings Loosely Packed Hydroxyl-Terminated SAMs on Gold Langmuir 2006 22 7235 7240 (Pubitemid 44366421)
34. D. A. Krapchetov H. Ma A. K. Y. Jen D. A. Fischer Y. L. Loo Solvent-Dependent Assembly of Terphenyl- and Quaterphenyldithiol on Gold and Gallium Arsenide Langmuir 2005 21 5887 5893 (Pubitemid 40940621)
35. Y. Tai A. Shaporenko H. T. Rong M. Buck W. Eck M. Grunze M. Zharnikov Fabrication of Thiol-Terminated Surfaces Using Aromatic Self-Assembled Monolayers J. Phys. Chem. B 2004 108 16806 16810
36. E. D. Schmid R. D. Topsom Raman Intensity and Conjugation, 5. A Quantitative Relationship between Raman Intensity and the Length of Conjugation and an Analysis of the Raman Intensities of Some Substituted Benzenes and Biphenyls J. Am. Chem. Soc. 1981 103 1628 1632
37. I. K. Korobeinicheva O. M. Fugaeva G. G. Furin Influence of fluorine atoms on intensity of aromatic ring vibrations in raman spectra of fluorobenzenes and pentafluoro-substituted derivatives of benzene Bull. Acad. Sci. USSR, Div. Chem. Sci. (Engl. Transl.) 1987 36 1634 1637
38. -1 range Zhurnal Prikladnoi Spektroskopii 1968 8 825 829
39. T. Baunach D. M. Kolb The electrochemical characterisation of benzyl mercaptan-modified Au(111): Structure and copper deposition Anal. Bioanal. Chem. 2002 373 743 748 (Pubitemid 34994809)
40. F. Wrochem F. Scholz A. Yasuda J. M. Wessels Probing Structure and Molecular Conductance in Highly Ordered Benzyl Mercaptan Monolayers J. Phys. Chem. C 2009 113 12395 12401
41. H. H. Jung Y. D. Won S. Shin K. Kim Molecular Dynamics Simulation of Benzenethiolate and Benzyl Mercaptide on Au(111) Langmuir 1999 15 1147 1154
42. J. Y. Gui D. A. Stern D. G. Frank F. Lu D. C. Zapien A. T. Hubbard Adsorption and Surface Structural Chemistry of Thiophenol, Benzyl Mercaptan, and Alkyl Mercaptans. Comparative Studies at Ag(111) and Pt(111) Electrodes by Means of Auger Spectroscopy, Electron Energy Loss Spectroscopy, Low-Energy Electron Diffraction, and Electrochemistry Langmuir 1991 7 955 963
43. S. Joo Y. Kim Surface-enhanced Raman scattering study of benzyl mercaptide and benzyl isocyanide on gold and silver nanocolloid surfaces Colloids Surf., A 2004 234 117 122 (Pubitemid 38317237)
44. E. J. Sturrock Q. Chen P. H. Borchardt N. V. Richardson Coverage dependent change in orientation for the adsorption of benzyl mercaptan on Au(111) J. Electron Spectrosc. Relat. Phenom. 2004 135 127 134
45. N. Nishi D. Hobara M. Yamamoto T. Kakiuchi Orientation of o-, m-, and p-Methylbenzylmercaptans Adsorbed on Au(111) Probed by Broad-Bandwidth Sum Frequency Generation Spectroscopy Langmuir 2003 19 6187 6192
46. R. E. Holmlin R. Haag M. L. Chabinyc R. F. Ismagilov A. E. Cohen A. Terfort M. A. Rampi G. M. Whitesides Electron Transport through Thin Organic Films in Metal-Insulator-Metal Junctions Based on Self-Assembled Monolayers J. Am. Chem. Soc. 2001 123 5075 5085 (Pubitemid 32910235)
47. R. Liu S. H. Ke H. U. Baranger W. Yang Intermolecular effect in molecular electronics J. Chem. Phys. 2005 122 44703
48. Y. T. Tao C. C. Wu J. Y. Eu W. L. Lin K. C. Wu C. H. Chen Structure Evolution of Aromatic-Derivatized Thiol Monolayers on Evaporated Gold Langmuir 1997 13 4018 4023