Electrochemical approach for constructing a monolayer of thiophenolates from grafted multilayers of diaryl disulfides

Journal of the American Chemical Society

Volumn 129, Issue 7, 2007, Pages 1888-1889

  Nielsen, Lasse T ^a   Vase, Karina H ^a   Dong, Mingdong ^a   Besenbacher, Flemming ^a   Pedersen, Steen U ^a   Daasbjerg, Kim ^a  

^a AARHUS UNIVERSITY   (Denmark)

Author keywords

[No Author keywords available]

Indexed keywords

BENZENE DERIVATIVE; DIAZONIUM COMPOUND; DISULFIDE; PHENOL DERIVATIVE; THIOL DERIVATIVE;

ARTICLE; CHEMICAL MODIFICATION; CHEMICAL STRUCTURE; CYCLIC POTENTIOMETRY; ELECTROCHEMICAL ANALYSIS; OXIDATION; OXIDATION REDUCTION REACTION; POLYMERIZATION; SURFACE PROPERTY; X RAY PHOTOELECTRON SPECTROSCOPY;

EID: 33847292365     PISSN: 00027863     EISSN: None     Source Type: Journal    
DOI: 10.1021/ja0682430     Document Type: Article

References (23)

1. Delamar, M.; Hitmi, R.; Pinson, J.; Savéant, J.-M. J. Am. Chem. Soc. 1992, 114, 5883-5884.
2. Allongue, P.; Delamar, M.; Desbat, B.; Fagebaume, O.; Hitmi, R.; Pinson, J.; Savéant, J.-M. J. Am. Chem. Soc. 1997, 119, 201-207.
3. Downard, A. J. Electroanalysis 2000, 12, 1085-1096.
4. Kariuki, J. K.; McDermott, M. T. Langmuir 2001, 17, 5947-5951.
5. Itoh, T.; McCreery, R. L. J. Am. Chem. Soc. 2002, 124, 10894-10902.
6. Nowak, A. M.; McCreery, R. L. J. Am. Chem. Soc. 2004, 126, 16621-16631.
7. Pinson, J.; Podvorica, F. Chem. Soc. Rev. 2005, 34, 429-439.
8. Holm, A. H.; Møller, R.; Vase, K. H.; Dong, M.; Norrman, K.; Besenbacher, F.; Pedersen, S. U.; Daasbjerg, K. New J. Chem. 2005, 29, 659-666.
9. Brooksby, P. A.; Downard, A. J. Langmuir 2005, 21, 1672-1675.
10. Baranton, S.; Bélanger, D. J. Phys. Chem. B 2005, 109, 24401-24410.
11. Brooksby, P. A.; Downard, A. J. J. Phys. Chem. B 2005, 109, 8791-8798.
12. Anariba, F.; Viswanathan, U.; Bocian, D. F.; McCreery, R. L. Anal. Chem. 2006, 78, 3104-3112.
13. Ricci, A.; Bonazzola, C.; Calvo, E. J. Phys. Chem. Chem. Phys. 2006, 8, 4297-4299.
14. The bond cleavage can be accomplished using various chemical approaches, but an electrochemical procedure exploiting the high conductivity of GC seems straightforward.
15. Harnisch, J. A.; Pris, A. D.; Porter, M. D. J. Am. Chem. Soc. 2001, 123, 5829-5830.
16. +/H.
17. a.c versus log v are 0.87 and 0.92. respectively.
18. - appears at a less extreme potential than the solution counterpart (Supporting Information). This might be attributed to an effect such as charge repulsion between the surface-confined thiophenolate ions. The possibility that the inner ring A has been attacked by aryl radicals during the grafting process to produce the biphenyl bis(thiolate) system after degradation cannot be excluded.
19. Liu, Y.-C.; McCreery, R. L. J. Am. Chem. Soc. 1995, 117, 11254-11259.
20. Calculations are based on an optimization of the structure using DFT and assuming a perpendicular orientation of the molecules.
21. Brooksby, P. A.; Downard, A. J. Langmuir 2004, 20, 5038-5045.
22. Traynham, J. G. Chem. Rev. 1979, 79, 323-330.
23. 4.21