A generic platform for the addressable functionalisation of electrode surfaces through self-induced "electroclick"

Chemistry - A European Journal

Volumn 18, Issue 2, 2012, Pages 594-602

  Orain, Christophe ^a   Le Poul, Nicolas ^a   Gomila, Antoine ^a   Kerbaol, Jean Michel ^a   Cosquer, Nathalie ^a   Reinaud, Olivia ^b   Conan, Françoise ^a   Le Mest, Yves ^a  

^a UNIVERSITÉ DE BRETAGNE OCCIDENTALE   (France)

^b UNIVERSITÉ PARIS DESCARTES   (France)

Author keywords

click chemistry; copper; electrode functionalisation; N ligands; self assembly

Indexed keywords

ALKANETHIOLS; AMINE DERIVATIVES; BIPHASIC CONDITIONS; CLICK CHEMISTRY; COPPER COMPLEXES; COPPER IONS; ELECTROCHEMICAL GRAFTING; ELECTROCHEMICAL PROBE; ELECTROCHEMICAL RESPONSE; ELECTRODE SURFACES; ELECTRON TRANSFER; ELECTRON-TRANSFER REACTIONS; ETHYNYL; FERROCENE MOIETY; FERROCENES; FUNCTIONAL OBJECT; FUNCTIONALISATION; GENERIC PLATFORMS; GOLD ELECTRODES; HUISGEN CYCLOADDITION; IMMOBILISATION; IN-SITU; MOLECULAR PLATFORM; N LIGANDS; PYRIDYL; REDOX-ACTIVE; SURFACE COVERAGES; TAGGED OBJECT; VOLTAMMETRIC;

COPPER; COPPER COMPOUNDS; ELECTRODES; FUNCTIONAL GROUPS; GRAFTING (CHEMICAL); IRON COMPOUNDS; METAL IONS; ORGANOMETALLICS; SURFACES;

SELF ASSEMBLED MONOLAYERS;

COORDINATION COMPOUND; COPPER; FERROCENE; FERROUS ION; GOLD; THIOL DERIVATIVE;

ARTICLE; CHEMISTRY; CYCLIZATION; ELECTROCHEMICAL ANALYSIS; ELECTRODE; INSTRUMENTATION; KINETICS; SURFACE PROPERTY;

COORDINATION COMPLEXES; COPPER; CYCLIZATION; ELECTROCHEMICAL TECHNIQUES; ELECTRODES; FERROUS COMPOUNDS; GOLD; KINETICS; SULFHYDRYL COMPOUNDS; SURFACE PROPERTIES;

EID: 84855301789     PISSN: 09476539     EISSN: 15213765     Source Type: Journal    
DOI: 10.1002/chem.201102620     Document Type: Article

References (60)

1. A. Pron, P. Gawrys, M. Zagorska, D. Djurado, R. Demadrillea, Chem. Soc. Rev. 2010, 39, 2577-2632
2. M. Grätzel, Inorg. Chem. 2005, 44, 6841-6851
3. B. Ulgut, H. D. Abruna, Chem. Rev. 2008, 108, 2721-2736.
4. J. Chen, W. Zhang, D. Officer, G. F. Swiegers, G. G. Wallace, Chem. Commun. 2007, 3353-3355
5. I. Willner, E. Katz, Angew. Chem. 2000, 112, 1230-1269
6. L. Shen, Z. Chen, Y. Li, S. He, S. Xie, X. Xu, Z. Liang, X. Meng, Q. Li, Z. Zhu, M. Li, X. C. Le, Y. Shao, Anal. Chem. 2008, 80, 6323-6328
7. D. Nkosi, J. Pillay, K. I. Ozoemena, K Nouneh, M. Oyama, Phys. Chem. Chem. Phys. 2010, 12, 604-613
8. E. Bakker, Y. Qin, Anal. Chem. 2006, 78, 3965-3983.
9. J. A. Cracknell, K. A. Vincent, F. A. Armstrong, Chem. Rev. 2008, 108, 2439-2461.
10. A. Heller, Curr. Opin. Chem. Biol. 2006, 10, 664-672
11. C. Bunte, O. Prucker, T. König, J. Rühe, Langmuir 2010, 26, 6019-6027
12. B. A. Gregg, A. Heller, J. Phys. Chem. 1991, 95, 5976-5980
13. S. Cosnier, Biosens. Bioelectron. 1999, 14, 443-456.
14. G. Decher, Science 1997, 277, 1232-1237
15. J. Hodak, R. Etchenique, E. J. Calvo, K. Singhal, P. N. Bartlett, Langmuir 1997, 13, 2708-2716
16. V. Flexer, E. S. Forzani, E. J. Calvo, S. J. Luduena, L. I. Pietrasanta, Anal. Chem. 2006, 78, 399-407.
17. J. C. Love, L. A. Estroff, J. K. Kriebel, R. G. Nuzzo, G. M. Whitesides, Chem. Rev. 2005, 105, 1103-1169.
18. C. E. D. Chidsey, C. R. Bertozzi,., T. M. Putvinski, A. M. Mujsce, J. Am. Chem. Soc. 1990, 112, 4301-4306
19. C. E. D. Chidsey, Science 1991, 251, 919-922.
20. C. Amatore, S. Gazard, E. Maisonhaute, C. Pebay, B. Schöllhorn, J.-L. Syssa-Magalé, J. Wadhawan, Eur. J. Inorg. Chem. 2007, 4035-4042.
21. J. Sumner, S. E. Creager, J. Phys. Chem. B. 2001, 105, 8739-8745
22. H. O. Finklea, D. D. Hanshaw, J. Am. Chem. Soc. 1992, 114, 3173-3181
23. D. A. Brevnov, H. O. Finklea, H. Van Ryswyk, J. Electroanal. Chem. 2001, 500, 100-107
24. L. Tender, M. T. Carter, R. W. Murray, Anal. Chem. 1994, 66, 3173-3181.
25. O. Alévêque, P.-Y. Blanchard, C. Gautier, M. Dias, T. Breton, E. Levillain, Electrochem. Commun. 2010, 12, 1462-1466
26. S. J. Green, N. Le Poul, P. P. Edwards, G. Peacock, J. Am. Chem. Soc. 2003, 125, 3686-3687.
27. A. L. Eckermann, D. J. Feld, J. A. Shaw, T. J. Meade, Coord. Chem. Rev. 2010, 254, 1769-1802
28. E. Tran, M. A. Rampi, G. M. Whitesides, Angew. Chem. 2004, 116, 3923-3927
29. Angew. Chem. Int. Ed. 2004, 43, 3835-3839.
30. B. T. Houseman, E. S. Gawalt, M. Mrksich, Langmuir 2003, 19, 1522-1531
31. E. A. Smith, W. D. Thomas, Y. Cheng, S. V. P. Barreira, A. G. Frutos, R. M. Corn, Langmuir 2001, 17, 2502-2507.
32. G. J. Wegner, H. J. Lee, R. M. Corn, Anal. Chem. 2002, 74, 5161-5168.
33. E. A. Smith, W. D. Thomas, L. L. Kiessling, R. M. Corn, J. Am. Chem. Soc. 2003, 125, 6140-6148.
34. The immobilisation of redox proteins onto thioalkane-modified electrodes is not considered here as they specifically bind through non-covalent modes. See, for example:, M. J. Tarlov, E. F. Bowden, J. Am. Chem. Soc. 1991, 113, 1847-1849.
35. V. V. Rostovtsev, L. G. Green, V. V. Fokin, K. B. Sharpless, Angew. Chem. 2002, 114, 2708-2711
36. Angew. Chem. Int. Ed. 2002, 41, 2596-2599.
37. J. P. Collman, N. K. Devaraj, C. E. D. Chidsey, Langmuir 2004, 20, 1051-1053
38. J. P. Collman, N. K. Devaraj, T. P. A. Eberspacher, C. E. D. Chidsey, Langmuir 2006, 22, 2457-2464
39. N. K. Devaraj, R. A. Decreau, W. Ebina, J. P. Collman, C. E. D. Chidsey, J. Phys. Chem. B. 2006, 110, 15955-15962.
40. N. K. Devaraj, P. H. Dinolfo, C. E. D. Chidsey, J. P. Collman, J. Am. Chem. Soc. 2006, 128, 1794-1795.
41. J. P. Collman, N. K. Devaraj, R. A. Decreau, Y. Yang, Y.-L. Yan, W. Ebina, T. A. Eberspacher, C. E. D. Chidsey, Science 2007, 315, 1565-1568.
42. N. K. Devaraj, G. P. Miller, W. Ebina, B. Kakaradov, J. P. Collman, E. T. Kool, C. E. D. Chidsey, J. Am. Chem. Soc. 2005, 127, 8600-8601
43. Y. Zhang, S. Luo, Y. Tang, L. Yu, K.-Y. Hou, J.-P. Cheng, X. Zeng, P. G. Wang, Anal. Chem. 2006, 78, 2001-2008
44. J. F. Lutz, Angew. Chem. 2007, 119, 1036-1043
45. Angew. Chem. Int. Ed. 2007, 46, 1018-1025.
46. T. S. Hansen, A. E. Daugaard, S. Hvilsted, N. B. Larsen, Adv. Mater. 2009, 21, 4483-4486.
47. A. Gomila, N. Le Poul, N. Cosquer, J.-M. Kerbaol, J.-M. NoÃl, M. T. Reddy, I. Jabin, O. Reinaud, F. Conan, Y. Le Mest, Dalton Trans. 2010, 39, 11516-11518.
48. N. Le Poul, B. Douziech, J. Zeitouny, G. Thiabaud, H. Colas, F. Conan, N. Cosquer, I. Jabin, C. Lagrost, P. Hapiot, O. Reinaud, Y. Le Mest, J. Am. Chem. Soc. 2009, 131, 17800-17808.
49. A. J. Bard, L. R. Faulkner, Electrochemical Methods: Fundamentals and Applications, 2 nd ed., John Wiley & Sons, New York, 2001, pp. 580-631.
50. J.-M. Savéant, Elements of Molecular and Biomolecular Electrochemistry, John Wiley & Sons, Hoboken, 2006, pp. 1-77.
51. E. Laviron, J. Electroanal. Chem. 1979, 101, 19-28.
52. C. Amatore, E. Maisonhaute, B. Schöllhorn, J. Wadhawan, ChemPhysChem 2007, 8, 1321-1329.
53. D. Evrard, F. Lambert, C. Policar, V. Balland, B. Limoges, Chem. Eur. J. 2008, 14, 9286-9291.
54. C. C. L. McCrory, A. Devadoss, X. Ottenwaelder, R. D. Lowe, T. D. Stack, C. E. D. Chidsey, J. Am. Chem. Soc. 2011, 133, 3696-3699.
55. B. Giese, M. Spichty, ChemPhysChem 2000, 1, 195-198
56. G. B. Schuster, Acc. Chem. Res. 2000, 33, 253-260.
57. E. M. Boon, D. M. Ceres, T. G. Drummond, M. G. Hill, J. K. Barton, Nat. Biotechnol. 2000, 18, 1096-1100.
58. M. Merkel, D. Schnieders, S. M. Baldeau and B. Krebs, Eur. J. Inorg. Chem. 2004, 783-790.
59. J. M. Casas-Solvas, A. Vargas-Berenguel, L. F. Capitan-Vallvey, F. Santo-Gonzalez, Org. Lett. 2004, 6, 3687-3690.
60. G. Colombano, C. Travelli, U. Galli, A. Caldarelli, M. G. Chini, P. L. Canonico, G. Sorba, G. Bifulco, G. C. Tron, A. A. Genazzani, J. Med. Chem. 2010, 53, 616-623.