Influence of alkyl chain length on the structure of dialkyldithiophosphinic acid self-assembled monolayers on gold

Langmuir

Volumn 28, Issue 37, 2012, Pages 13253-13260

  San Juan, Ronan R ^a   Miller, Michael S ^a   Ferrato, Michael Anthony ^a   Carmichael, Tricia Breen ^a  

^a UNIVERSITY OF WINDSOR   (Canada)

Author keywords

[No Author keywords available]

Indexed keywords

ALKYL CHAIN; ALKYL CHAIN LENGTHS; ALKYL GROUPS; GOLD SUBSTRATES; MONODENTATES; PACKING DENSITY; REFLECTION ABSORPTION INFRARED SPECTROSCOPY; SAMS;

ADSORBATES; CHAIN LENGTH; CONTACT ANGLE; CRYSTALLINE MATERIALS; ELECTROCHEMICAL IMPEDANCE SPECTROSCOPY; GRAIN BOUNDARIES; INFRARED SPECTROSCOPY; PHOTOELECTRONS; SELF ASSEMBLED MONOLAYERS; SUBSTRATES; X RAY PHOTOELECTRON SPECTROSCOPY;

GOLD;

GOLD; PHOSPHINIC ACID DERIVATIVE;

ARTICLE; CHEMICAL STRUCTURE; CHEMISTRY; SURFACE PROPERTY; SYNTHESIS;

GOLD; MOLECULAR STRUCTURE; PHOSPHINIC ACIDS; SURFACE PROPERTIES;

EID: 84866387719     PISSN: 07437463     EISSN: 15205827     Source Type: Journal    
DOI: 10.1021/la302564u     Document Type: Article

References (41)

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
2. Xia, Y.; Whitesides, G. M. Soft Lithography Angew. Chem., Int. Ed. 1998, 37, 550-575
3. Ostuni, E.; Chapman, R. G.; Holmlin, E.; Takayama, S.; Whitesides, G. M. A Survey of Structure-Property Relationships of Surfaces that Resist the Adsorption of Protein Langmuir 2001, 17, 5605-5620
4. Herrwerth, S.; Eck, W.; Reinhardt, S.; Grunze, M. Factors that Determine the Protein Resistance of Oligoether Self-Assembled Monolayers - Internal Hydrophilicity, Terminal Hydrophilicity, and Lateral Packing Density J. Am. Chem. Soc. 2003, 125, 9359-9366
5. Akkerman, H. B.; Blom, P. W. M.; de Leeuw, D. M.; de Boer, B. Towards molecular electronics with large-area molecular junctions Nature 2006, 441, 69-72
6. Chiechi, R. C.; Weiss, E. A.; Dickey, M. D.; Whitesides, G. M. Eutectic Gallium-Indium (EGaIn): A Moldable Liquid Metal for Electrical Characterization of Self-Assembled Monolayers Angew. Chem., Int. Ed. 2008, 47, 142-144
7. Chinwangso, P.; Jamison, A. C.; Lee, T. R. Multidentate Adsorbates for Self-Assembled Monolayer Films Acc. Chem. Res. 2011, 44, 511-519
8. Srisombat, L.; Zhang, S.; 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
9. 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
10. 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
11. Shon, Y. -S.; Lee, T. R. Chelating Self-Assembled Monolayers on Gold Generated from Spiroalkanedithiols Langmuir 1999, 15, 1136-1140
12. Shon, Y. -S.; Lee, S.; Perry, S. S.; Lee, T. R. The Adsorption of Unsymmetrical Spiroalkanedithiols onto Gold Affords Multi-Component Interfaces that Are Homogeneously Mixed at the Molecular Level J. Am. Chem. Soc. 2000, 122, 1278-1281
13. 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
14. 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
15. Lee, S.; Shon, Y. -S.; Colorado, R., Jr.; Guenard, R. L.; 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
16. 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
17. Zhao, Y.; Perez-Segarra, W.; Shi, Q.; Wei, A. Dithiocarbamate Assembly on Gold J. Am. Chem. Soc. 2005, 127, 7328-7329
18. Morf, P.; Raimondi, F.; Nothofer, H. -G.; Schnyder, B.; Yasuda, A.; Wessels, J. M.; Jung, T. A. Dithiocarbamates: Functional and Versatile Linkers for the Formation of Self-Assembled Monolayers Langmuir 2006, 22, 658-663
19. Weinstein, R. D.; Richards, J.; Thai, S. D.; Omiatek, D. M.; Bessel, C. A.; Faulkner, C. J.; Othman, S.; Jennings, G. K. Characterization of Self-assembled Monolayers from Lithium Dialkyldithiocarbamate Salts Langmuir 2007, 23, 2887-2891
20. Von Wrochem, F.; Gao, D.; Scholz, F.; Nothofer, H. -G.; Nelles, G.; Wessels, J. M. Efficient electronic coupling and improved stability with dithiocarbamate-based molecular junctions Nat. Nanotechnol. 2010, 5, 618-624
21. Miller, M. S.; San Juan, R. R.; Ferrato, M. -A.; Carmichael, T. B. New Dialkyldithiophosphinic Acid Self-Assembled Monolayers (SAMs): Influence of Gold Substrate Morphology on Adsorbate Binding and SAM Structure Langmuir 2011, 27, 10019-10026
22. Moulder, J. F.; Stickle, W. F.; Sobol, P. E.; Bomben, K. D. Handbook of X-Ray Photoelectron Spectroscopy; Physical Electronics: Eden Prairie, MN, 1995.
23. Schoenfisch, M. H.; Pemberton, J. E. Air Stability of Alkanethiol Self-Assembled Monolayers on Silver and Gold Surfaces J. Am. Chem. Soc. 1998, 120, 4502-4513
24. Lusk, A. T.; Jennings, G. K. Characterization of Self-Assembled Monolayers Formed from Sodium S -Alkyl Thiosulfates on Copper Langmuir 2001, 17, 7830-7836
25. Castner, D. G.; Hinds, K.; Grainger, D. W. X-ray Photoelectron Spectroscopy Sulfur 2p Study of Organic Thiol and Disulfide Binding Interactions with Gold Surfaces Langmuir 1996, 12, 5083-5086
26. Ishida, T.; Choi, N.; Mizutani, W.; Tokumoto, H.; Kojima, I.; Azehara, H.; Hokari, H.; Akiba, U.; Fujihira, M. High-Resolution X-ray Photoelectron Spectra of Organosulfur Monolayers on Au(111): S(2p) Spectral Dependence on Molecular Species Langmuir 1999, 15, 6799-6806
27. Beattie, D. A.; Kempson, I. M.; Fan, L. -J.; Skinner, W. M. Synchrotron XPS studies of collector adsorption and co-adsorption on gold and gold:silver alloy surfaces Int. J. Miner. Process. 2009, 92, 162-168
28. Menoyo, B.; Elizalde, M. P.; Almela, A. Determination of the Degradation Compounds Formed by the Oxidation of Thiophosphinic Acids and Phosphine Sulfides with Nitric Acid Anal. Sci. 2002, 18, 799-804
29. Hutt, D. A.; Leggett, G. J. Influence of Adsorbate Ordering on Rates of UV Photooxidation of Self-Assembled Monolayers J. Phys. Chem. 1996, 100, 6657-6662
30. 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
31. Bubert, H.; Jenett, H. Surface and Thin Film Analysis; Wiley-VCH: Weinham, 2002; p 250.
32. Ulman, A. An Introduction to Ultrathin Organic Films; Academic: Boston, 1991.
33. 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 Solutions onto Gold J. Am. Chem. Soc. 1989, 111, 321-335
34. Bain, C. D.; Whitesides, G. M. Formation of Monolayers by the Coadsorption of Thiols on Gold: Variation in the Length of the Alkyl Chain J. Am. Chem. Soc. 1989, 111, 7164-7175
35. Yan, D.; Saunders, J. A.; Jennings, G. K. Enhanced Chain Densities of n -Alkanethiolate Self-Assembled Monolayers on Gold from Aqueous Micellar Solutions Langmuir 2000, 16, 7562-7565
36. Yan, D.; Jennings, G. K.; Weinstein, R. D. Controlling the Properties of n -Alkanethiolate Self-Assembled Monolayers on Gold by Using Supercritical Carbon Dioxide-Ethanol Mixtures as Solvents Ind. Eng. Chem. Res. 2002, 41, 4528-4533
37. Diao, P.; Guo, M.; Tong, R. Characterization of defects in the formation process of self-assembled thiol monolayers by electrochemical impedance spectroscopy J. Electroanal. Chem. 2001, 495, 98-105
38. Barsoukov, E.; Macdonald, J. R. Impedance Spectroscopy, 2 nd ed; Wiley & Sons: Hoboken, NJ, 2005.
39. Peterlinz, K. A.; Georgiadis, R. In Situ Kinetics of Self-Assembly by Surface Plasmon Resonance Spectroscopy Langmuir 1996, 12, 4731-4740
40. Finklea, H. O.; Snider, D. A.; Fedyk, J.; Sabatani, E.; Gafni, Y.; Rubinstein, I. Characterization of Octadecanethiol-Coated Gold Electrodes as Microarray Electrodes by Cyclic Voltammetry and ac Impedance Spectroscopy Langmuir 1993, 9, 3660-3667
41. 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