Indirect grafting of acetonitrile-derived films on metallic substrates

Chemistry of Materials

Volumn 22, Issue 9, 2010, Pages 2962-2969

  Berisha, Avni ^a,b   Combellas, Catherine ^a   Kanoufi, Frédéric ^a   Pinson, Jean ^a   Ustaze, Stéphane ^c   Podvorica, Fetah I ^a,b  

^a CNRS   (France)

^b UNIVERSITY OF PRISHTINA   (Serbia)

^c Alchimer   (France)

Author keywords

[No Author keywords available]

Indexed keywords

AMINO GROUP; HYDROGEN ATOMS; IR SPECTROSCOPY; METALLIC SUBSTRATE; ORGANIC FILMS; SILICON SURFACES; SPONTANEOUS REACTIONS; WATER CONTACT ANGLE;

ACETONITRILE; CONTACT ANGLE; GRAFTING (CHEMICAL); SCANNING ELECTRON MICROSCOPY; SUBSTRATES; SURFACE REACTIONS;

CYCLIC VOLTAMMETRY;

EID: 77951951619     PISSN: 08974756     EISSN: 15205002     Source Type: Journal    
DOI: 10.1021/cm100295n     Document Type: Article

References (77)

1. Pinson, J.; Podvorica, F. Chem. Soc. Rev. 2005, 34, 429
2. Barrière, F.; Downard, A. J. Solid State Electrochem. 2008, 12, 1231
3. McCreery, R., L. Chem. Rev. 2008, 108, 2646
4. Gooding, J. J. Electroanalysis 2008, 20, 582
5. Delamar, M.; Hitmi, R.; Pinson, J.; Savéant, J.-M. J. Am. Chem. Soc. 1992, 114, 5883
6. Allongue, P.; Delamar, M.; Desbat, B.; Fagebaume, O.; Hitmi, R.; Pinson, J.; Savéant, J.-M. J. Am. Chem. Soc. 1997, 119, 201
7. Henry de Villeneuve, C.; Pinson, J.; Bernard, M. C.; Allongue, P. J. Phys. Chem. B 1997, 101, 2415
8. Allongue, P.; Henry de Villeneuve, C.; Pinson, J.; Ozanam, F.; Chazalviel, J. N.; Wallart, X. Electrochim. Acta 1998, 43, 2791
9. Adenier, A.; Bernard, M. C.; Chehimi, M. M.; Cabet-Deliry, E.; Desbat, B.; Fagebaume, O.; Pinson, J.; Podvorica, F. J. Am. Chem. Soc. 2001, 123, 4541
10. Chaussé, A.; Chehimi, M. M.; Karsi, N.; Pinson, J.; Podvorica, F.; Vautrin-Ul, C. Chem. Mater. 2002, 14, 392
11. Adenier, A.; Cabet-Deliry, E.; Lalot, T.; Pinson, J.; Podvorica, F. Chem. Mater. 2002, 14, 4576
12. Bernard, M. C.; Chaussé, A.; Cabet-Deliry, E.; Chehimi, M. M.; Pinson, J.; Podvorica, F.; Vautrin-Ul, C. Chem. Mater. 2003, 15, 3450
13. Allongue, P.; Henry de Villeneuve, C.; Cherouvrier, G.; Cortes, R. J. Electroanal. Chem. 2003, 550, 161
14. Combellas, C.; Kanoufi, F.; Pinson, J.; Podvorica, F. I. Langmuir 2005, 21, 280
15. Adenier, A.; Cabet-Deliry, E.; Chaussé, A.; Griveau, S.; Mercier, F.; Pinson, J.; Vautrin-Ul, C. Chem. Mater. 2005, 17, 491
16. Combellas, C.; Kanoufi, F.; Pinson, J.; Podvorica, F. I. Chem. Mater. 2005, 17, 3968
17. Combellas, C.; Kanoufi, F.; Pinson, J.; Podvorica, F. I. Chem. Mater. 2006, 18, 2021
18. Adenier, A.; Barré, N.; Cabet-Deliry, E.; Chaussé, A.; Griveau, S.; Mercier, F.; Pinson, J.; Vautrin-Ul, C. Surf. Sci. 2006, 600, 4801
19. Podvorica, F. I.; Kanoufi, F.; Pinson, J.; Combellas, C. Electrochim. Acta 2009, 54, 2164
20. Liu, Y. C.; McCreery, R. L. J. Am. Chem. Soc. 1995, 117, 11254
21. Liu, Y. C.; McCreery, R. L. Anal. Chem. 1997, 69, 2091
22. DuVall, S. H.; McCreery, R. L. J. Am. Chem. Soc. 2000, 122, 6759
23. Ranganathan, S.; Steidel, I.; Anariba, F.; McCreery, R. L. Nano Lett. 2001, 1, 491
24. Itoh, T.; McCreery, R. L. J. Am. Chem. Soc. 2002, 124, 1089
25. Anariba, F.; DuVall, S. H.; McCreery, R. L. Anal. Chem. 2003, 75, 3837
26. Hurley, B. L.; McCreery, R. L. J. Electrochem. Soc. 2004, 151, B252
27. Anariba, F.; Viswanathan, U.; Bocian, D. F.; McCreery, R. L. Anal. Chem. 2006, 78, 3104
28. Mahmoud, A. M.; Bergren, A. J.; McCreery, R. L. Anal. Chem. 2009, 81, 6972
29. Saby, C.; Ortiz, B.; Champagne, G. Y.; Bélanger, D. Langmuir 1997, 13, 3837
30. D'Amours, M.; Bélanger, D. J. Phys. Chem B 2003, 107, 4811
31. Baranton, S.; Bélanger, D. J. Phys. Chem B 2005, 109, 24401
32. Chamoulaud, G.; Bélanger, D. Langmuir 2004, 20, 4989
33. Toupin, B.; Bélanger, D. Langmuir 2008, 24, 1910
34. Cougnon, C.; Mauzeroll, J.; Bélanger, D. Angew. Chem., Int. Ed. 2009, 48, 7395
35. Downard, A. J. Langmuir 2000, 16, 9680
36. Downard, A. J.; Prince, M. J. Langmuir 2001, 17, 5581
37. Brooksby, P. A.; Downard, A. J. Langmuir 2004, 20, 5038
38. Paulik, M. G.; Brooksby, P. A.; Abell, A. D.; Downard, A. J. J. Phys. Chem. C 2007, 111, 7808
39. Downard, A. J.; Garrett, D. J.; Tan, E. S. Q. Langmuir 2006, 22, 10739
40. Lehr, J.; Williamson, B. E.; Flavel, B. S.; Downard, A. J. Langmuir 2009, 25, 13503
41. Nielsen, L. T.; Vase, K. H.; Dong, M.; Besenbacher, F.; Pedersen, S. U.; Daasbjerg, K. J. Am. Chem. Soc. 2007, 129, 1888
42. Peng, Z.; Holm, A. H.; Nielsen, L. T.; Pedersen, S. U.; Daasbjerg, K. Chem. Mater. 2008, 20, 6068
43. Malmos, K.; Iruthayaraj, J.; Pedersen, S. U.; Daasbjerg, K. J. Am. Chem. Soc. 2009, 131, 13926
44. Kariuki, J. K.; McDermott, M. T. Langmuir 1999, 15, 6534
45. Kariuki, J. K.; McDermott, M. T. Langmuir 2001, 17, 5947
46. Shewchuk, D. M.; McDermott, M. T. Langmuir 2009, 25, 4556
47. Vase, K. H.; Holm, A. H.; Norman, K.; Pedersen, S. U.; Daasbjerg, K. Langmuir 2007, 23, 3786
48. Matrab, T.; Combellas, C.; Kanoufi, F. Electrochem. Commun. 2008, 10, 1230
49. Andrieux, C.; Pinson, J. J. Am. Chem. Soc. 2003, 125, 14801
50. Wildgoose, G. G.; Pandurangappa, M.; Lawrence, N. S.; Jiang, L.; Jones, T. G. J.; Compton, R. G. Talanta 2003, 60, 887
51. Bureau, C.; Pinson, J. Fr Pat 0510914, PCT WO2007048894 (to Alchimer).
52. Gomberg, M.; Bachmann, W. E. J. Am. Chem. Soc. 1924, 45, 2339
53. M'Halla, F.; Pinson, J.; Savéant, J.-M. J. Am. Chem. Soc. 1980, 102, 4120
54. Doppelt, P.; Hallais, G.; Pinson, J.; Podvorica, F.; Verneyre, S. Chem. Mater. 2007, 19, 4570
55. Combellas, C.; Kanoufi, F.; Pinson, J.; Podvorica, F. I. J. Am. Chem. Soc. 2008, 130, 8576
56. Combellas, C.; Jiang, D.; Kanoufi, F.; Pinson, J.; Podvorica, F. I. Langmuir 2009, 25, 286
57. Smith, M. B.; March, J. March's Advanced Organic Chemistry, 5th ed.; Wiley Interscience: New York, 2001; p 510.
58. 2 correction indicates that, in any case, the CN band should not exceed the background noise.
59. Socrates, G. Infrared and Raman Characteristic Group Frequencies, 3rd ed.; John Wiley & Sons: New York, 2008.
60. The increase in the current observed during the chronopotentiometry is most likely related to the increasing concentration of the cyanomethyl radical in the solution.
61. Isse, A. A.; Gennaro, A. J. Phys. Chem. A 2004, 108, 4180
62. p = -0.95 V/SCE. The reduction potential of the 2,6-dimethyl phenyl radical should be slightly more negative because of the effect of the methyl groups.
63. Andrieux, C. P.; Pinson, J. J. Am. Chem. Soc. 2003, 125, 14801
64. Vase, K. Ph.D. Thesis, University of Aarhus, Aarhus, Denmark, 2007.
65. The pKa of acetonitrile is 31.3 (21b) and that of phenyllitium is about 43; (21c) therefore, the 2,6-dimethylbezene anion should be able to deprotonate acetonitrile to give the cyanomethyl anion.
66. Rossi, L.; Feroci, M.; Inesi, A. Mini-Rev. Org. Chem. 2005, 2, 79
67. Smith, M. B.; March, J. March's Advanced Organic Chemistry, 5th ed.; Wiley Interscience: New York, 2001; p 331.
68. Smith, M. B.; March, J. March's Advanced Organic Chemistry, 5th ed.; Wiley Interscience: New York, 2001; p 1238.
69. Lund, H. Reduction of Azomethines in Organic Electrochemistry, 4th ed.; Lund, H.; Hammerich, O., Eds.; Marcel Dekker: New York, 2001, p 435.
70. Reed, R. C.; Wightman, R. M. In Encyclopedia of Electrochemistry of the Elements; Bard, A. J.; Lund, H., Eds.; Marcel Dekker: New York, Vol. XV.1, pp 54.
71. Largeron, M.; Fleury, M.-B. Org. Lett. 2009, 11, 883
72. Largeron, M.; Chiaroni, A.; Fleury, M.-B. Chem. Eur. J. 2008, 14, 996
73. th ed.; Wiley Interscience: New York, 2001; p 1177.
74. Tsubota, T.; Shintaro, I.; Osamu, H.; Nagaoka, S.; Masanori, M.; Yasumichi, M. Phys. Chem. Chem. Phys. 2002, 4, 3881
75. Deniau, G.; Azoulay, L.; Bougerolles, L.; Palacin, S. Chem. Mater. 2006, 18, 5421
76. Tessier, L.; Deniau, G.; Charleux, B.; Palacin, S. Chem. Mater. 2009, 21, 4261
77. Kim, J.; Cho, J.; Seidler, P.; Kurland, N.; Yadavalli, V. Langmuir 2010, 26, 2599