Grafting of nitrophenyl groups on carbon and metallic surfaces without electrochemical induction

Chemistry of Materials

Volumn 17, Issue 3, 2005, Pages 491-501

  Adenier, Alain ^c   Cabet Deliry, Eva ^b   Chaussé, Annie ^a   Griveau, Sophie ^a   Mercier, Florence ^a   Pinson, Jean ^d   Vautrin Ul, Christine ^a  

^a UNIVERSITÉ D EVRY VAL D ESSONNE   (France)

^b UNIVERSITÉ PARIS DIDEROT   (France)

^c UNIVERSITÉ PARIS DIDEROT   (France)

^d Alchimer SA   (France)

Author keywords

[No Author keywords available]

Indexed keywords

ACETONITRILE; CARBON; COATINGS; CYCLIC VOLTAMMETRY; ELECTROCHEMISTRY; MULTILAYERS;

ELECTROCHEMICAL INDUCTION; GLASSY CARBON (GC); METALLIC SURFACES; TETRAFLUOROBORATE SALTS;

GRAFTING (CHEMICAL);

4 NITROBENZENE DIAZONIUM TETRAFLUOROBORATE; 4 NITROPHENOL; ACETONITRILE; CARBON; COPPER; DIAZONIUM COMPOUND; IRON; METAL; NICKEL; POLYCYCLIC AROMATIC HYDROCARBON DERIVATIVE; UNCLASSIFIED DRUG; ZINC;

ARTICLE; ATOMIC FORCE MICROSCOPY; CYCLIC POTENTIOMETRY; ELECTROCHEMICAL ANALYSIS; ELECTROCHEMISTRY; IMMERSION; INFRARED SPECTROSCOPY; MATERIAL COATING; SURFACE PROPERTY; X RAY PHOTOELECTRON SPECTROSCOPY;

EID: 13444304306     PISSN: 08974756     EISSN: None     Source Type: Journal    
DOI: 10.1021/cm0490625     Document Type: Article

References (113)

1. Downard, A. J. Electroanalysis 2000, 12, 1085.
2. Maeda, H.; Yamauchi, Y.; Ohmori, H. Curr. Top. Anal. Chem. 2001, 2, 121.
3. Andrieux, C. P.; Gonzalez, F.; Savéant, J.-M. J. Am. Chem. Soc. 1997, 119, 4292.
4. Hayes, M. A.; Kuhr, W. G. Anal. Chem. 1999, 71, 1720.
5. (a) Lécayon, G.; Bouizem, Y.; Le Gressus, C.; Reynaud, C.; Boiziau, C.; Juret, C. Chem Phys. Lett. 1982, 91, 506.
6. (b) Deniau, G.; Lécayon, G.; Viel, P.; Hennico, G.; Delhalle, J. Langmuir 1992, 8, 267.
7. (c) Viel, P.; de Cayeux, S.; Lécayon, G. Surf. Interface Anal. 1993, 20, 468.
8. (d) Bureau, C.; Defranscheschi, M.; Delhalle, J.; Deniau, G.; Tanguy, J.; Lécayon, G. Surf. Sci. 1994, 311, 349.
9. (e) Tanguy, J.; Viel, P.; Deniau, G.; Lécayon, G. Electrochim. Acta 1993, 38, 175.
10. (f) Tanguy, J.; Deniau, G.; Augé, C.; Zalczer, G.; Lécayon, G. J. Electroanal. Chem. 1994, 377, 115.
11. (g) Tanguy, J.; Deniau, G.; Zalczer, G.; Lécayon, G. J. Electroanal Chem. 1996, 417, 175.
12. (h) Deniau, G.; Lécayon, G.; Bureau, C.; Tanguy J. In Protective Coatings and Thin Films; Pauleau, Y., Barna, P. B., Eds.; Kluwer Academic: Amsterdam, 1997; p 265.
13. (i) Bureau, C.; Deniau, G.; Viel, P.; Lécayon, G. Macromolecules 1997, 30, 333.
14. (j) Deniau, G.; Thome, T.; Gaudin, D.; Bureau, C.; Lécayon, G. J. Electroanal. Chem. 1998, 451, 145.
15. (k) Charlier, J.; Bureau, C.; Lécayon, G. J. Electroanal. Chem. 1999, 465, 200.
16. (l) Viel, P.; Bureau, C.; Deniau, G.; Zalczer, G.; Lécayon, G. J. Electroanal. Chem. 1999, 470, 14.
17. (m) Jerôme, C.; Geskin, V.; Lazzaroni, R.; Bredas, J. L.; Thibault, A.; Calberg, C.; Bodart, I.; Mertens, M.; Martinot, L.; Rodrigue, D.; Riga, J.; Jerôme, R. Chem. Mater. 2001, 13, 1656.
18. (n) Baute, N.; Martinet, L.; Jerôme, R. J. Electroanal. Chem. 1999, 472, 83 and references therein.
19. (o) Mertens, M.; Calberg, C.; Baute, N.; Jerôme, R.; Martinot, L. J. Electroanal. Chem. 1998, 441, 237.
20. (p) Calberg, C.; Mertens, M.; Jerôme R.; Arys, X.; Jonas, A. M.; Legras, R. Thin Solid Films 1997, 310, 148.
21. (q) Doneux, C.; Caudano, R.; Delhalle, J.; Leonard-Stibbe, E.; Charlier, J.; Bureau, C.; Tanguy, G.; Lécayon, G. Langmuir 1997, 13, 4898.
22. (r) Calberg, C.; Kroonen, D.; Mertens, M.; Jerôme, R.; Martinot, L. Polymer 1998, 39, 23.
23. (a) Delamar, M.; Hitmi, R.; Pinson, J.; Savéant, J.-M. J: Am. Chem. Soc. 1992, 114, 5883.
24. (b) Allongue, P.; Delamar, M.; Desbat, B.; Fagebaume, O.; Hitmi, R.; Pinson, J.; Savéant, J.-M. J. Am. Chem. Soc. 1997, 119, 201.
25. (c) Delamar, M.; Désarmot, G.; Fagebaume, O.; Hitmi, R.; Pinson, J.; Savéant: J.-M. Carbon 1997, 35, 801.
26. (d) Bourdillon, C.; Delamar, M.; Demaille, C.; Moiroux, J.; Pinson, J. J. Electroanal. Chem. 1992, 336, 5883.
27. (e). Coulon, E.; Pinson, J.; Bourzat, J.-D.; Commerçon, A.; Pulicani, J.-P. Langmuir 2001, 17, 7102.
28. (f) Coulon, E.; Pinson, J.; Bourzat, J.-D.; Commerçon, A.; Pulicani, J.-P. J. Org. Chem. 2002, 67, 8513.
29. (g) Andrieux, C. P.; Pinson, J. J. Am. Chem. Soc. 2003, 125, 14801.
30. (a) Saby, C.; Ortiz, B.; Champagne, G. Y.; Bélanger, D. Langmuir 1997, 13, 6803.
31. (b) Ortiz, B.; Saby, C.; Champagne G. Y.; Bélanger, D. J. Electroanal. Chem. 1998, 455, 75.
32. (c) D'Amours, M.; Bélanger, D. J. Phys. Chem. B 2003, 107, 4811.
33. (a) Liu, Y. C.; McCreery, R. L. J. Am. Chem. Soc. 1995, 117, 11254.
34. (b) Liu, Y. C.; McCreery, R. L. Anal. Chem. 1997, 69, 2091.
35. (c) Chen, P.; McCreery, R. L. Anal. Chem. 1996, 68, 3958.
36. (d) Ray, K., III; McCreery, R. L. Anal. Chem. 1997, 69, 4680.
37. (e) DuVall, S. H.; McCreery, R. L. Anal. Chem. 1999, 71, 4594.
38. (f) Kuo, T.-C.; McCreery, R. L. Anal. Chem. 1999, 71, 1553.
39. (g) Yang, H.-H.; McCreery, R. L. Anal. Chem. 1999, 71, 408.
40. (h) Kuo, T.-C.; McCreery, R. L.; Swain R. L. Electrochem Solid State Lett. 1999, 2, 288.
41. (i) DuVall, S. H.; McCreery, R. L. J. Am. Chem. Soc. 2000, 122, 6759.
42. (j) Ranganathan, S.; McCreery, R. L. Anal. Chem. 2001, 73, 893.
43. (k) Ranganathan, S.; Steidel, I.; Anariba, F.; McCreery, R. L. Nano Lett. 2001, 1, 491.
44. (l) Itoh, T.; McCreery, R. L. J. Am. Chem. Soc. 2002, 124, 1089.
45. (n) Anariba, F.; McCreery, R. L. J. Phys. Chem. B 2002, 106, 10335.
46. (o) Solak, A. O.; Ranganathan, S.; Itoh, T.; McCreery, R. L. Electrochem Solid State Lett. 2002, 5, E-43.
47. (p) Anariba, F.; DuVall, S. H.; McCreery, R. L. Anal. Chem. 2003, 75, 3837.
48. (q) Solak, A. O.; Eichorst, L. R.; Clark, W. J.; McCreery, R. L. Anal. Chem. 2003, 75, 296.
49. (a) Downard, A. J.; Roddick, A. D. Electroanalysis 1995, 7, 376.
50. (b) Downard, A. J.; Roddick, A. D.; Bond, A. M. Anal. Chim. Acta 1995, 317, 303.
51. (c) Downard, A. J.; Roddick, A. D. Electroanalysis 1997, 9, 693.
52. (d) Downard, A. J. Langmuir 2000, 16, 9680.
53. (e) Downard, A. J.; Prince; M. J. Langmuir 2001, 17, 5581.
54. (f) Brooksby, P. A.; Downard, A. J. Langmuir 2004, 20, 5038.
55. (a) Kariuki, J. K.; McDermott, M. T. Langmuir 1999, 15, 6534.
56. (b) Kariuki, J. K.; McDermott, M. T. Langmuir 2001, 17, 5947.
57. (a) Harnisch, J. A.; Gazda, D. B.; Anderegg, J. W.; Porter, M. D. Anal. Chem. 2001, 73, 3954.
58. (b) Harnisch, J. A.; Pritt, A. D.; Porter, M. D. J. Am. Chem. Soc. 2001, 123, 6759.
59. Dequaire, M.; Degrand, C.; Limoges, B. J. Am. Chem. Soc. 1999, 121, 6946.
60. Combellas, C.; Kanoufi, F.; Mazouzi, D.; Thiébault, A.; Bertrand, P.; Médard, N. Polymer 2003, 44, 19.
61. (a) Liu, S.; Tang, Z.; Shi, Z.; Niu, L.; Wang, E.; Dong, S. Langmuir 1999, 15, 7268.
62. (b) Liu, J.; Cheng, L.; Song, Y.; Liu, B.; Dong, S. Langmuir 2001, 17, 6747.
63. (c) Chen, X.; Liu, S.; Song, Y.; Dong, S. Chem. Lett. 2002, 5, 552.
64. Bath, B. D.; Martin, H. B.; Whightman, R. M.; Anderson, M. R. Langmuir 2001, 17, 7268.
65. (a) Tammeveski, T., Kontturi, K.; Nichols, R. J.; Potter, R. J.; Schiffrin, D. J. J. Electroanal. Chem. 2001, 515, 101.
66. (b) Sarapuu, A.; Vaik, K.; Schiffrin, D. J.; Tammeveski, K. J. Electroanal. Chem. 2003, 541, 23.
67. Yang, X.; Hall, S. B.; Burell, A. K.; Officer, D. Chem. Comm. 2001, 2628.
68. Smith, D. M.; Maskara, A.; Boes, U. J. Non-Cryst. Solids 1998, 225, 254.
69. (a) Bahr, J. L.; Tour, J. M. Chem. Mater. 2001, 13, 3823.
70. (b) Bahr, J. L.; Yang, J.; Kosynkin, D. V.; Bronikowski, M. J.; Smalley, R. E.; Tour, J. M. J. Am. Chem. Soc. 2001, 123, 6536.
71. (c) Dyke, C. A.; Tour, J. M. J. Am. Chem. Soc. 2003, 125, 1156.
72. (d) Dyke, C. A.; Tour, J. M. Nano Lett. 2003, 3, 1215.
73. (e) Strano, M. C.; Dyke, C. A.; Ursa, M. L.; Barone, P. W.; Allen, M. J.; Shan, H.; Kittrell, C.; Hauge, R. H.; Tour, J. M.; Smalley, R. E. Science 2003, 301, 1519.
74. (f) Fan, F.-R. F.; Yang, J.; Lintao, C.; Price, D. W.; Dirk, S. M.; Kosynkin, D. V.; Yao, Y.; Rawlett, A. M.; Tour, J. M.; Bard, A. J. J. Am. Chem. Soc. 2002, 124, 5550.
75. (g) Stewart, M. P.; Maya, F.; Kosynkin, D. M.; Dirk, S. M.; Stapleton, J. J.; McGuiness, C. L.; Allara, D. L.; Tour, J. M. J. Am. Chem. Soc. 2004, 126, 370.
76. Kooi, S. E.; Schlecht, U.; Burghard, M.; Kern, K. Angew. Chem. Int. Ed. 2002, 41, 1353.
77. (a) Belmont, J. A.; Amici, R. M.; Galloway, P. Patent PCT Int. Appl. WO 96 18688 A1 (to Cabot Corp.).
78. (b) Belmont, J. A. Patent PCT Int. Appl. WO 96 18690 A1 (to Cabot Corp.).
79. (c) Belmont, J. A.; Reed, T. F. Patent PCT Int. Appl. WO 96 18674 A1 (to Cabot Corp.).
80. (d) Belmont, J. A. Johnson, J. E.; Adams, C. E. Patent PCT Int. Appl. WO 96 18695 A1 (to Cabot Corp.).
81. (e) Belmont, J. A. Patent US 5672198 (to Cabot Corp.).
82. (f) Johnson, J. E.; Belmont, J. A. Patent PCT Int. Appl. WO 97 47692 A1 (to Cabot Corp.).
83. (g) Belmont, J. A.; Adams, C. E. Patent US 57 13988 A (to Cabot Corp.).
84. (h) Mahmud, K.; Belmont, J. A.; Adams, C. E.; Foster, J. K. Patent PCT Int. Appl. WO 97 47698 A1 (to Cabot Corp.).
85. (i) Reed, T. F.; Mahmud, K. Patent PCT Int. Appl. WO 98 34960 A1 (to Cabot Corp.).
86. (j) Adams, C. E.; Belmont, J. A.; Amici, R. M. Patent US 56 98016 A (to Cabot Corp.).
87. (k) Belmont, J. A.; Amici, R. M.; Galloway, C. P. Patent US 5851280 (to Cabot Corp).
88. (l) Belmont, J. A.; Adams, C. E. Patent PCT Int. Appl. WO 9907,794 (to Cabot Corp.).
89. (m) Adams, C. E.; Belmont, J. A. Patent US 5885355 (to Cabot Corp.).
90. (n) Whitehouse, R. S.; Devonport, W.; Warley, R. L.; Rawalpally, T. R.; Tu, H. Patent PCT Int Appl. WO 99 23,174 (to Cabot Corp.).
91. (o) Palumbo, S. P. Patent PCT Int. Appl. WO 0053681A1 (to Cabot Corp.).
92. (p) Cooke, J. M.; Galloway, C. P.; Bissell, M. A.; Adams, C. E.; Yu, M. C.; Belmont, J. A.; Amici, M. R. Patent US 61 109994 A (to Cabot Corp.).
93. (a) Adenier, A.; Bernard, M.-C.; Chehimi, M. M.; Cabet-Deliry, E.; Desbat, B.; Fagebaume, O.; Pinson, J.; Podovorica, F. J. Am. Chem. Soc. 2001, 123, 4541.
94. (b) Pinson, J.; Fagebaume, O.; Podvorica, F. Patent PCT Int Appl. WO 01 59178 (to Université Paris 7.).
95. (c) Chaussé, A.; Chehimi, M. M.; Karsi, N.; Pinson, J.; Podvorica, F.; Vautrin-Ul, C. Chem. Mater. 2002, 14, 392
96. (d) Bernard, M. C.; Chaussé, A.; Cabet-Deliry, E.; Chehimi, M. M.; Pinson, J.; Podvorica, F.; Vautrin-Ul, C. Chem. Mater. 2003, 15, 3450.
97. (e) Boukerma, K.; Chehimi, M. M.; Pinson, J.; Blomfield, C. Langmuir 2003, 19, 6333.
98. Bureau, C.; Levy, E.; Viel, P. PCT Int. Appl. 2003, WO 03018212.
99. Levesque, L.; Lawrence, M. F.; Bourguignon, B.; Leclerc, G. PCT Int. Appl. 2002 WO 02066092.
100. (a) Henry de Villeneuve, C.; Pinson, J.; Allongue, P. J. Phys Chem. 1997, 101, 2415.
101. (b) Allongue, P.; Henry de Villeneuve, C.; Pinson, J.; Ozanam, F.; Chazalviel, J. N.; Wallart, X. Electrochim. Acta 1998, 43, 2791.
102. (c) Allongue, P.; Henry de Villeneuve, C.; Pinson, J. Electrochim. Acta 2000, 45, 3241.
103. Hartig, P.; Dittrich, T.; Rappich J. Eur. Pat. Appl. 2003, EP 1271633.
104. Hurley, B. L.; McCreery, R. L. J. Electrochem. Soc. 2004, 151, B252.
105. (a) Nyquist, R. A. Interpreting Infrared, Roman and Nuclear Magnetic Spectra; Academic Press: New York, 2001; Volume 2, p 173.
106. (b) Socrates, G. Infrared Characteristic Group Frequencies, Tables and Charts; Wiley: New York, 1994.
107. (c) Bellamy, L. J. Advances in Infrared Group Frequencies; Methuen & Co: London, 1968; p 228.
108. (a) Mendes, P.; Belloni, M.; Ashworth, M.; Hardy, C.; Nikitin, K.; Fitzmaurice, D.; Critchley, K.; Evans, S.; Preece, J. Chem. Phys. Chem. 2003, 4, 884.
109. (b) Nakayama, Y.; Takahagi, T.; Soeda, F.; Ishitani, A.; Shimomura, M.; Okuyama, K.; Kunitake, T. Appl. Surf. Sci. 1988, 33/34, 1307.
110. Alchemy 2000; Tripos, Inc: St Louis, MO.
111. Cabet-Deliry, E.; Chaussé, A.; Griveau, S.; Mercier, F.; Pinson, J.; Vautrin-Ul, C. Submitted to J. Mater. Chem.
112. Dekanski, A.; Stevanović, J.; Stevanović, R.; Nikolića, B. Z.; Jovanović, V. M. Carbon 2001, 39, 119.
113. Zollinger, H. Acc. Chem. Res. 1973, 6, 335.