Electrochemical and spectroscopic study of the self-assembling mechanism of normal and chelating alkanethiols on copper

Langmuir

Volumn 28, Issue 17, 2012, Pages 6857-6865

  Dilimon, V S ^a   Denayer, J ^a   Delhalle, J ^a   Mekhalif, Z ^a  

^a UNIVERSITY OF NAMUR   (Belgium)

Author keywords

[No Author keywords available]

Indexed keywords

ALIPHATIC THIOLS; ALKANETHIOLS; DITHIOCARBOXYLIC ACIDS; DITHIOLS; EIS STUDIES; ELECTROCHEMICAL IMPEDANCE SPECTROSCOPIES (EIS); EX SITU; H-BASED; IN-SITU; LINEAR SWEEP VOLTAMMETRY; OXIDE REDUCTION; PM-IRRAS; POLARIZATION MODULATION INFRARED REFLECTION ABSORPTION SPECTROSCOPY; REAL TIME; SAMS; SELF-ASSEMBLING; SPECTROSCOPIC STUDIES;

ADSORPTION; ELECTROCHEMICAL IMPEDANCE SPECTROSCOPY; MONOLAYERS; PHOTOELECTRONS; SELF ASSEMBLY; SPECTROSCOPIC ANALYSIS; SULFUR; X RAY PHOTOELECTRON SPECTROSCOPY;

COPPER;

EID: 84860491232     PISSN: 07437463     EISSN: 15205827     Source Type: Journal    
DOI: 10.1021/la300021g     Document Type: Article

References (42)

1. Love, J. C.; Estroff, L. A.; Kriebel, J. K.; Nuzzo, R. G.; Whitesides, G. M. Self-Assembled Monolayers of Thiolates on Metals as a Form of Nanotechnology Chem. Rev. 2005, 105, 1103-1169 (Pubitemid 40600878)
2. Ulman, A. Formation and Structure of Self-Assembled Monolayers Chem. Rev. 1996, 96, 1533-1554 (Pubitemid 126639367)
3. Laibinis, P. E.; Whitesides, G. M. Self-Assembled Monolayers on n -Alkanethiolates on Copper Are Barrier Films That Protect the Metal against Oxidation by Air J. Am. Chem. Soc. 1992, 114, 9022-9028
4. Ron, H.; Cohen, H.; Matlis, S.; Rappaport, M.; Rubinstein, I. Self-Assembled Monolayers on Oxidized Metals. 4. Superior n -Alkanethiol Monolayers on Copper J. Phys. Chem. B 1998, 102, 9861-9869 (Pubitemid 128605078)
5. Hosseinpour, S.; Hedberg, J.; Baldelli, S.; Leygraf, C.; Johnson, M. Initial Oxidation of Alkanethiol-Covered Copper Studied by Vibrational Sum Frequency Spectroscopy J. Phys. Chem. C 2011, 115, 23871-23879
6. Sung, M. M.; Sung, K.; Kim, C. G.; Lee, S. S.; Kim, Y. Self-Assembled Monolayers of Alkanethiols on Oxidized Copper Surfaces J. Phys. Chem. B 2000, 104, 2273-2277
7. 25X Molecules Adsorption on Copper Sheets, X (-SH, -S-S-, -SeH and -Se-Se-) Electrochim. Acta 2010, 55, 1557-1567
8. Keller, H.; Simak, P.; Schrepp, W.; Dembowski, J. Surface Chemistry of Thiols on Copper: An Efficient Way of Producing Multilayers Thin Solid Films 1994, 244, 799-805
9. Laibinis, P. E.; Whitesides, G. M.; Allara, D. L.; Tao, Y.-T.; Parikh, A. N.; Nuzzo, R. G. Comparison of the Structures and Wetting Properties of Self-Assembled Monolayers of n- Alkanethiols on the Coinage Metal Surfaces, Cu, Ag, Au J. Am. Chem. Soc. 1991, 113, 7152-7167
10. Lee, T.-C.; Hounihan, D. J.; Colorado, R., Jr.; Park, J.-S.; Lee, T. R. Stability of Aliphatic Dithiocarboxylic Acid Self-Assembled Monolayers on Gold J. Phys. Chem. B 2004, 108, 2648-2653
11. Kumar, A.; Whitesides, G. M. Patterned Condensation Figures as Optical Diffraction Gratings Science 1994, 263, 60-62 (Pubitemid 24077280)
12. Aizenberg, J.; Black, A. J.; Whitesides, G. M. Controlling Local Disorder in Self-Assembled Monolayers by Patterning the Topography of Their Metallic Supports Nature 1998, 394, 868-871 (Pubitemid 28410903)
13. Green, J.-B. D.; McDermott, M. T.; Porter, M. D. Nanometer-Scale Mapping of Chemically Distinct Domains at Well-Defined Organic Interfaces Using Frictional Force Microscopy J. Phys. Chem. 1995, 99, 10960-10965
14. Colorado, R., Jr.; Villazana, R. J.; Lee, T. R. Self-Assembled Monolayers on Gold Generated from Aliphatic Dithiocarboxylic Acids Langmuir 1998, 14, 6337-6340 (Pubitemid 128633864)
15. Garg, N; Friedman, J. M.; Lee, T. R. Adsorption Profiles of Chelating Aromatic Dithiols and Disulfides: Comparison to Those of Normal Alkanethiols and Disulfides Langmuir 2000, 16, 4266-4271
16. Shon, Y.-S.; Lee, T. R. Chelating Self-Assembled Monolayers on Gold Generated from Spiroalkanedithiols Langmuir 1999, 15, 1136-1140
17. Wang, W.; Zhang, S.; Chinwangso, P.; Advincula, R. C.; Lee, T. R. Electric Potential Stability and Ionic Permeability of SAMs on Gold Derived from Bidentate and Tridentate Chelating Alkanethiols J. Phys. Chem. C 2009, 113, 3717-3725
18. Park, J.-S.; Smith, A. C.; Lee, T. R. Loosely Packed Self-Assembled Monolayers on Gold Generated from 2-Alkyl-2-methylpropane-1,3-dithiols Langmuir 2004, 20, 5829-5836
19. Shon, Y.-S.; Colorado, R., Jr.; Williams, C. T.; Bain, C. D.; Lee, T. R. Low-Density Self-Assembled Monolayers on Gold Derived from Chelating 2-Monoalkylpropane-1,3-dithiols Langmuir 2000, 16, 541-548 (Pubitemid 32211249)
20. Shon, Y.-S.; Lee, S.; Colorado, R., Jr.; Perry, S. S.; Lee, T. R. Spiroalkanedithiol-Based SAMs Reveal Unique Insight into the Wettabilities and Frictional Properties of Organic Thin Films J. Am. Chem. Soc. 2000, 122, 7556-7563 (Pubitemid 30641554)
21. Park, J.-S.; Vo, A. N.; Barriet, D.; Shon, Y.-S.; Lee, T. R. Systematic Control of the Packing Density of Self-Assembled Monolayers Using Bidentate and Tridentate Chelating Alkanethiols Langmuir 2005, 21, 2902-2911 (Pubitemid 40448955)
22. Lee, S.; Shon, Y.-S.; Colorado, R., Jr.; Rebecca, L. G.; Lee, T. R.; Perry, S. S. The Influence of Packing Densities and Surface Order on the Frictional Properties of Alkanethiol Self-Assembled Monolayers (SAMs) on Gold: A Comparison of SAMs Derived from Normal and Spiroalkanedithiols Langmuir 2000, 16, 2220-2224 (Pubitemid 30572969)
23. Srisombat, L; Shishan, Z.; Lee, T. R. Thermal Stability of Mono-, Bis-, and Tris-Chelating Alkanethiol Films Assembled on Gold Nanoparticles and Evaporated "Flat" Gold Langmuir 2010, 26, 41-46
24. Chinwangso, P.; Jamison, A. C.; Lee, T. R. Multidentate Adsorbates for Self-Assembled Monolayer Films Acc. Chem. Res. 2011, 44, 511-519
25. Denayer, J.; Delhalle, J.; Mekhalif, Z. Comparative Study of Copper Surface Treatment with Self-Assembled Monolayers of Aliphatic Thiol, Dithiol and Dithiocarboxylic Acid J. Electroanal. Chem. 2009, 637, 43-49
26. Maho, A.; Denayer, A.; Delhalle, J.; Mekhalif, Z. Electro-Assisted Assembly of Aliphatic Thiol, Dithiol and Dithiocarboxylic Acid Monolayers on Copper Electrochim. Acta 2011, 56, 3954-3962
27. Dilimon, V. S.; Fonder, G.; Delhalle, J.; Mekhalif, Z. Self-Assembled Monolayer Formation on Copper: A Real Time Electrochemical Impedance Study J. Phys. Chem. C 2011, 115, 18202-18207
28. 2O Reduction J. Phys. Chem. C 2010, 114, 3945-3957
29. Subramanian, R.; Lakshminarayanan, V. A Study of Kinetics of Adsorption of Alkanethiols on Gold Using Electrochemical Impedance Spectroscopy Electrochim. Acta 2000, 45, 4501-4509
30. Bain, C. D.; Troughton, E. B.; Tao, Y.-T.; Evall, J.; Whitesides, G. M.; Nuzzo, R. G. Formation of Monolayer Films by the Spontaneous Assembly of Organic Thiols from Solution onto Gold J. Am. Chem. Soc. 1989, 111, 321-335
31. 3+ Redox Reactions J. Phys. Chem. B 2005, 109, 16372-16381 (Pubitemid 41321459)
32. Assaf, F. H.; Ayman, M. Z.; Abd El-Rehim, S. S. Cyclic Voltammetric Studies of the Electrochemical Behaviour of Copper-Silver Alloys in NaOH Solution Appl. Surf. Sci. 2002, 187, 18-27 (Pubitemid 34201449)
33. Abd El-Rehim, S. S.; Foad, E. E. Effect of Halide Anions on Anodic Behaviour and Passivation of Copper in Alkaline Media Collect. Czech. Chem. Commun. 1996, 61, 85-92
34. Karim-Nezhad, G.; Hasanzadesh, M.; Saghatforoush, L.; Ershad, S.; Shadjou, N. Kinetic Study of the Electro-Catalytic Oxidation of Acetaldehyde on Copper Electrode J. Chin. Chem. Soc. 2009, 56, 554-560
35. Tacconi, N. R.; Rajeshwar, K.; Lezna, R. O. Study of Copper Sulfide Film Formation by Voltammetry Combined with Electrochemical Quartz Crystal Microgravimetry/Coulometry and Optical Spectroscopy J. Phys. Chem. 1996, 100, 18234-18239 (Pubitemid 126788784)
36. Marioli, J. M.; Kuwana, T. Electrochemical Characterization of Carbohydrate Oxidation at Copper Electrodes Electrochim. Acta 1992, 37, 1187-1197
37. Jennings, G. K.; Munro, J. C.; Yong, T.-H.; Laibinis, P. E. Effect of Chain Length on the Protection of Copper by n -Alkanethiols Langmuir 1998, 14, 6130-6139 (Pubitemid 128612938)
38. Porter, M. D.; Bright, T. B.; Allara, D. L.; Chidsey, C. E. D. Spontaneously Organized Molecular Assemblies. 4. Structural Characterization of n -Alkyl Thiol Monolayers on Gold by Optical Ellipsometry, Infrared Spectroscopy, and Electrochemistry J. Am. Chem. Soc. 1987, 109, 3559-3568
39. Krylova, V.; Andrulevičius, M. Optical, XPS and XRD Studies of Semiconducting Copper Sulfide Layers on a Polyamide Film Int. J. Photoenergy 2009, 2009, 1-8
40. Fonder, G.; Laffineur, F.; Delhalle, J.; Mekhalif, Z. Alkanethiol-Oxidized Copper Interface: The Critical Influence of Concentration J. Colloid Interface Sci. 2008, 326, 333-338
41. Shon, Y.-S.; Lee, T. R. Desorption and Exchange of Self-Assembled Monolayers (SAMs) on Gold Generated from Chelating Alkanedithiols J. Phys. Chem. B 2000, 104, 8192-8200
42. Sung, M. M.; Yun, W. J.; Lee, S. S.; Kim, Y. Thermal Decomposition of Octanethiolate Self-Assembled Monolayers on Cu(111) in UHV Bull. Korean Chem. Soc. 2003, 24, 610-612