Switching on/off the chemisorption of thioctic-based self-assembled monolayers on gold by applying a moderate cathodic/anodic potential

Langmuir

Volumn 29, Issue 17, 2013, Pages 5360-5368

  Sahli, Rihab ^a,c   Fave, Claire ^a,b   Raouafi, Noureddine ^c   Boujlel, Khaled ^c   Schöllhorn, Bernd ^a,b   Limoges, Benoiît ^a  

^a UNIVERSITÉ PARIS DIDEROT   (France)

^b UNIVERSITÉ PARIS DIDEROT   (France)

^c UNIVERSITY OF TUNIS EL MANAR   (Tunisia)

Author keywords

[No Author keywords available]

Indexed keywords

ADSORPTION/DESORPTION; CATHODIC POTENTIALS; ELECTROCHEMICAL METHODS; ELECTRODE POLARIZATIONS; INTRAMOLECULAR CYCLIZATIONS; POLYCRYSTALLINE GOLD; SATURATED MONOLAYERS; TEMPORAL RESOLUTION;

CYCLIZATION; GOLD; ORGANOMETALLICS; POLARIZATION; POWER QUALITY; SELF ASSEMBLED MONOLAYERS; SELF ASSEMBLY; SULFUR COMPOUNDS; SURFACE REACTIONS;

ELECTROCHEMICAL ELECTRODES;

GOLD; THIOCTIC ACID;

ARTICLE; CHEMICAL STRUCTURE; CHEMISTRY; ELECTROCHEMICAL ANALYSIS; ELECTRODE; TIME;

ELECTROCHEMICAL TECHNIQUES; ELECTRODES; GOLD; MOLECULAR STRUCTURE; THIOCTIC ACID; TIME FACTORS;

EID: 84877079266     PISSN: 07437463     EISSN: 15205827     Source Type: Journal    
DOI: 10.1021/la401117u     Document Type: Article

References (60)

1. Schreiber, F. Structure and growth of self-assembling monolayers Prog. Surf. Sci. 2000, 65, 151-256
2. 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
3. Eckermann, A. L.; Feld, D. J.; Shaw, J. A.; Meade, T. J. Electrochemistry of redox-active self-assembled monolayers Coord. Chem. Rev. 2010, 254, 1769-1802
4. Mandler, D.; Kraus-Ophir, S. Self-assembled monolayers (SAMs) for electrochemical sensing J. Solid State Electrochem. 2011, 15, 1535-1558
5. Finklea, H. O. In Electroanalytical Chemistry; Bard, A. J.; Rubinstein, I., Eds.; Marcel Dekker Inc.: New York, 1996; Vol. 19, pp 110-335.
6. Bensebaa, F.; Voicu, R.; Huron, L.; Ellis, T. H. Kinetics of formation of long-chain n-alkanethiolate monolayers on polycrystalline gold Langmuir 1997, 13, 5335-5340
7. Voicu, R.; Ellis, T. H.; Ju, H.; Leech, D. Adsorption and desorption of electroactive self-assembled thiolate monolayers on gold Langmuir 1999, 15, 8170-8177
8. Bain, C. D.; Troughton, E. B.; Tao, Y. Y.; 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
9. Pan, W.; Durning, C. J.; Turro, N. J. Kinetics of alkanethiol adsorption on gold Langmuir 1996, 12, 4469-4473
10. Peterlinz, K. A.; Georgiadis, R. In situ kinetics of self-assembly by surface plasmon resonance spectroscopy Langmuir 1996, 12, 4731-4740
11. Shon, Y.-S.; Lee, T. R. A steady-state kinetic model can be used to describe the growth of self-assembled monolayers (SAMs) on gold J. Phys. Chem. B 2000, 104, 8182-8191
12. Ma, F.; Lennox, R. B. Potential-assisted deposition of alkanethiols on Au: Controlled preparation of single- and mixed-component SAMs Langmuir 2000, 16, 6188-6190
13. Meunier-Prest, R.; Legay, G.; Raveau, S.; Chiffot, N.; Finot, E. Potential-assisted deposition of mixed alkanethiol self-assembled monolayers Electrochim. Acta 2010, 55, 2712-2720
14. Diao, P.; Hou, Q.; Guo, M.; Xiang, M.; Zhang, Q. Effect of substrate potentials on the structural disorders of alkanethiol monolayers prepared by electrochemically directed assembly J. Electroanal. Chem. 2006, 597, 103-110
15. Riepl, M.; Mirsky, V. M.; Wolfbeis, O. S. Electrical control of alkanethiols self-assembly on a gold surface as an approach for preparation of microelectrode arrays Mikrochim. Acta 1999, 131, 29-34
16. Paik, W.; Eu, S.; Lee, K.; Chon, S.; Kim, M. Electrochemical reactions in adsorption of organosulfur molecules on gold and silver: Potential dependent adsorption Langmuir 2000, 16, 10198-10205
17. Chon, S.; Paik, W. Adsorption of self-assembling sulfur compounds through electrochemical reactions: Effects of potential, acid and oxidizing agents Phys. Chem. Chem. Phys. 2001, 3, 3405-3410
18. Chinwangso, P.; Jamison, A. C.; Lee, T. R. Multidentate adsorbates for self-assembled monolayer films Acc. Chem. Res. 2011, 44, 511-519
19. Uyeda, H. T.; Medintz, I. L.; Jaiswal, J. K.; Simon, S. M.; Mattoussi, H. Synthesis of compact multidentate ligands to prepare stable hydrophilic quantum dot fluorophores J. Am. Chem. Soc. 2005, 127, 3870-3878
20. Sharma, J.; Chhabra, R.; Andersen, C. S.; Gothelf, K. V.; Yan, H.; Liu, Y. Toward reliable gold nanoparticle patterning on self-assembled DNA nanoscaffold J. Am. Chem. Soc. 2008, 130, 7820-7821
21. Mei, B. C.; Oh, E.; Susumu, K.; Farrell, D.; Mountziaris, T. J.; Mattoussi, H. Effects of ligand coordination number and surface curvature on the stability of gold nanoparticles in aqueous solutions Langmuir 2009, 25, 10604-10611
22. Hong, H.-G.; Park, W. A study of adsorption kinetics and thermodynamics of ω-mercaptoalkylhydroquinone self-assembled monolayer on a gold electrode Electrochim. Acta 2005, 51, 579-587
23. Bretz, R. L.; Abruña, H. D. Synthesis of adsorbable redox-active osmium thiol monolayers and the effects of the working electrode potential during deposition J. Electroanal. Chem. 1995, 388, 123-132
24. Rouhana, L. L.; Moussallem, M. D.; Schlenoff, J. B. Adsorption of short-chain thiols and disulfides onto gold under defined mass transport conditions: Coverage, kinetics, and mechanism J. Am. Chem. Soc. 2011, 133, 16080-16091
25. Dannenberger, O.; Buck, M.; Grunze, M. Self-assembly of n-alkanethiols: A kinetic study by second harmonic generation J. Phys. Chem. B 1999, 103, 2202-2213
26. Balland, V.; Lecomte, S.; Limoges, B. Characterization of the electron transfer of a ferrocene redox probe and a histidine-tagged hemoprotein specifically bound to a nitrilotriacetic-terminated self-assembled monolayer Langmuir 2009, 25, 6532-6542
27. Antonello, S.; Benassi, R.; Gavioli, G.; Taddei, F.; Maran, F. Theoretical and electrochemical analysis of dissociative electron transfers proceeding through formation of loose radical anion species: Reduction of symmetrical and unsymmetrical disulfides J. Am. Chem. Soc. 2002, 124, 7529-7538
28. Grogger, C.; Fattakhov, S. G.; Jouikov, V. V.; Shulaeva, M. M.; Reznik, V. S. Primary steps of oxidation and electronic interactions in anodic cleavage of α,ω-diisocyanurate substituted dialkyl disulfides Electrochim. Acta 2004, 49, 3185-3194
29. Chidsey, C. E. D.; Bertozzi, C. R.; Putvinski, T. M.; Mujsce, A. M. Coadsorption of ferrocene-terminated and unsubstituted alkanethiols on gold: Electroactive self-assembled monolayers J. Am. Chem. Soc. 1990, 112, 4301-4306
30. Laviron, E. General expression of the linear potential sweep voltammogram in the case of diffusionless electrochemical systems J. Electroanal. Chem. 1979, 101, 19-28
31. Lyons, M. E. G.; O'Brien, R.; Kinsella, M.; Mc Gloinn, C.; Scully, P. N. Magnetic field effects in ferrocenealkane thiol self assembled monolayer modified electrodes Int. J. Electrochem. Sci 2010, 5, 1310-1341
32. Alvarado, R. J.; Mukherjee, J.; Pacsial, E. J.; Alexander, D.; Raymo, F. M. Self-assembling bipyridinium multilayers J. Phys. Chem. B 2005, 109, 6164-6173
33. Widrig, C. A.; Chung, C.; Porter, M. D. The electrochemical desorption of n-alkanethiol monolayers from polycrystalline Au and Ag electrodes J. Electroanal. Chem. 1991, 310, 335-359
34. Yang, D. F.; Wilde, C. P.; Morin, M. Electrochemical desorption and adsorption of nonyl mercaptan at gold single crystal electrode surfaces Langmuir 1996, 12, 6570-6577
35. Zhong, C.-J.; Zak, J.; Porter, M. D. Voltammetric reductive desorption characteristics of alkanethiolate monolayers at single crystal Au(111) and (110) electrode surfaces J. Electroanal. Chem. 1997, 421, 9-13
36. Beulen, M. W. J.; Kastenberg, M. I.; Van Veggel, F. C. J. M.; Reinhoudt, D. N. Electrochemical stability of self-assembled monolayers on gold Langmuir 1998, 14, 7463-7467
37. Sumi, T.; Uosaki, K. Electrochemical oxidative formation and reductive desorption of a self-assembled monolayer of decanethiol on a Au(111) surface in KOH ethanol solution J. Phys. Chem. B 2004, 108, 6422-6428
38. Ron, H.; Rubinstein, I. Self-assembled monolayers on oxidized metals. 3. Alkylthiol and dialkyl disulfide assembly on gold under electrochemical conditions J. Am. Chem. Soc. 1998, 120, 13444-13452
39. Collman, J. P.; Hosseini, A.; Eberspacher, T. A.; Chidsey, C. E. D. Selective anodic desorption for assembly of different thiol monolayers on the individual electrodes of an array Langmuir 2009, 25, 6517-6521
40. Everett, W. R.; Fritsch-Faules, I. Factors that influence the stability of self-assembled organothiols on gold under electrochemical conditions Anal. Chim. Acta 1995, 307, 253-268
41. Jung, C.; Dannenberger, O.; Xu, Y.; Buck, M.; Grunze, M. Self-assembled monolayers from organosulfur compounds: A comparison between sulfides, disulfides, and thiols Langmuir 1998, 14, 1103-1107
42. 7 Langmuir 2002, 18, 10202-10212
43. Subramanian, R.; Lakshminarayanan, V. A study of kinetics of adsorption of alkanethiols on gold using electrochemical impedance spectroscopy Electrochim. Acta 2000, 45, 4501-4509
44. Kondo, T.; Takechi, M.; Sato, Y.; Uosaki, K. Adsorption behavior of functionalized ferrocenylalkane thiols and disulfide onto Au and ITO and electrochemical properties of modified electrodes: Effects of acyl and alkyl groups attached to the ferrocene ring J. Electroanal. Chem. 1995, 381, 203-209
45. Bain, C. D.; Biebuyck, H. A.; Whitesides, G. M. Comparison of self-assembled monolayers on gold: coadsorption of thiols and disulfides Langmuir 1989, 5, 723-727
46. Biebuyck, H. A.; Bain, C. D.; Whitesides, G. M. Comparison of organic monolayers on polycrystalline gold spontaneously assembled from solutions containing dialkyl disulfides or alkanethiols Langmuir 1994, 10, 1825-1831
47. Ishida, T.; Yamamoto, S.; Mizutani, W.; Motomatsu, M.; Tokumoto, H.; Hokari, H.; Azehara, H.; Fujihira, M. Langmuir 1997, 13, 3261-3265
48. Schlenoff, J. B.; Li, M.; Ly, H. Stability and self-exchange in alkanethiol monolayers J. Am. Chem. Soc. 1995, 117, 12528-12536
49. Campbell, G. A.; Mutharasan, R. Monitoring of the self-assembled monolayer of 1-hexadecanethiol on a gold surface at nanomolar concentration using a piezo-excited millimeter-sized cantilever sensor Langmuir 2005, 21, 11568-11573
50. Schessler, H. M.; Karpovich, D. S.; Blanchard, G. J. Quantitating the balance between enthalpic and entropic forces in alkanethiol/gold monolayer self assembly J. Am. Chem. Soc. 1996, 118, 9645-9651
51. Balss, K. M.; Coleman, B. D.; Lansford, C. H.; Haasch, R. T.; Bohn, P. W. Active spatiotemporal control of electrochemical reactions by coupling to in-plane potential gradients J. Phys. Chem. B 2001, 105, 8970-8978
52. Terrill, R. H.; Balss, K. M.; Zhang, Y.; Bohn, P. W. Dynamic monolayer gradients: Active spatiotemporal control of alkanethiol coatings on thin gold films J. Am. Chem. Soc. 2000, 122, 988-989
53. Wittstock, G.; Hesse, R.; Schuhmann, W. Patterned self-assembled alkanethiolate monolayers on gold. Patterning and imaging by means of scanning electrochemical microscopy Electroanalysis 1997, 9, 746-750
54. Ross, C. B.; Sun, L.; Crooks, R. M. Scanning probe lithography. 1. Scanning tunneling microscope induced lithography of self-assembled n-alkanethiol monolayer resists Langmuir 1993, 9, 632-636
55. Niu, L.; Knoll, W. Electrochemically addressable functionalization and parallel readout of a DNA biosensor array Anal. Chem. 2007, 79, 2695-2702
56. Hsueh, C.-C.; Lee, M.-T.; Freund, M. S.; Ferguson, G. S. Electrochemically directed self-assembly on gold Angew. Chem., Int. Ed. 2000, 39, 1227-1230
57. Labukas, J. P.; Ferguson, G. S. Direct route to well-defined, chemically diverse electrode arrays Langmuir 2011, 27, 3219-3223
58. Tender, L. M.; Worley, R. L.; Fan, H. Y.; Lopez, G. P. Electrochemical patterning of self-assembled monolayers onto microscopic arrays of gold electrodes fabricated by laser ablation Langmuir 1996, 12, 5515-5518
59. Fairbanks, B. D.; Singh, S. P.; Bowman, C. N.; Anseth, K. S. Photodegradable, photoadaptable hydrogels via radical-mediated disulfide fragmentation reaction Macromolecules 2011, 44, 2444-2450
60. Krysinski, P.; Chamberlain, R. V., II; Majda, M. Partial electron transfer in octadecanethiol binding to gold Langmuir 1994, 10, 4286-4294