Locally induced and self-induced "electroclick" onto a self-assembled monolayer: Writing and reading with SECM under unbiased conditions

Langmuir

Volumn 30, Issue 15, 2014, Pages 4501-4508

  Lhenry, Sébastien ^a   Leroux, Yann R ^a   Orain, Christophe ^b   Conan, Francoise ^b   Cosquer, Nathalie ^b   Poul, Nicolas Le ^b   Reinaud, Olivia ^c   Mest, Yves Le ^b   Hapiot, Philippe ^a  

^a UNIVERSITÉ DE RENNES 1   (France)

^b UNIVERSITÉ DE BRETAGNE OCCIDENTALE   (France)

^c UNIVERSITÉ PARIS DESCARTES   (France)

Author keywords

[No Author keywords available]

Indexed keywords

CATALYSTS; ORGANIC POLYMERS; SCANNING ELECTRON MICROSCOPY; SCANNING PROBE MICROSCOPY; SELF ASSEMBLED MONOLAYERS; TWO DIMENSIONAL;

CATALYTIC EFFICIENCIES; CATALYTIC MODIFICATIONS; COUPLING REACTION; FUNCTIONAL MOIETIES; METALLIC COPPER; MICROMETER SCALE; SCANNING ELECTROCHEMICAL MICROSCOPY; UNBIASED CONDITIONS;

COPPER COMPOUNDS;

CATALYSIS; MICROSCOPY; PROCEDURES;

CATALYSIS; MICROSCOPY;

EID: 84899426703     PISSN: 07437463     EISSN: 15205827     Source Type: Journal    
DOI: 10.1021/la405005f     Document Type: Article

References (31)

1. 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
2. Collman, J. P.; Devaraj, N. K.; Eberspacher, T. P. A.; Chidsey, C. E. D. Mixed Azide-Terminated Monolayers: A Platform for Modifying Electrode Surfaces Langmuir 2006, 22, 2457-2464
3. Kolb, H. C.; Finn, M. G.; Sharpless, K. B. Click Chemistry: Diverse Chemical Function from a Few Good Reactions Angew. Chem., Int. Ed. 2001, 40, 2004-2021
4. Hawker, C. J.; Fokin, V. V.; Finn, M. G.; Sharpless, K. B. Bringing Efficiency to Materials Synthesis: The Philosophy of Click Chemistry Aust. J. Chem. 2007, 60, 381-383
5. Devaraj, N. K.; Decreau, R. A.; Ebina, W.; Collman, J. P.; Chidsey, C. E. D. Rate of Interfacial Electron Transfer through the 1,2,3-Triazole Linkage J. Phys. Chem. B 2006, 110, 15955-15962
6. Leroux, Y. R.; Fei, H.; Noël, J.-M.; Roux, C.; Hapiot, P. Efficient Covalent Modification of a Carbon Surface: Use of a Silyl Protecting Group To Form an Active Monolayer J. Am. Chem. Soc. 2010, 132, 14039-14041
7. Devaraj, N. K.; Dinolfo, P. H.; Chidsey, C. E. D.; Collman, J. P. Selective Functionalization of Independently Addressed Microelectrodes by Electrochemical Activation and Deactivation of a Coupling Catalyst J. Am. Chem. Soc. 2006, 128, 1794-1795
8. Hansen, T. S.; Daugaard, A. E.; Hvilsted, S.; Larsen, N. B. Spatially Selective Unctionalization of Conducting Polymers by "Electroclick" Chemistry Adv. Mater. 2009, 21, 4483-4486
9. Shida, N.; Ishiguro, Y.; Atobe, M.; Fuchigami, T.; Inagi, S. Electroclick Modification of Conducting Polymer Surface Using CuI Species Generated on a Bipolar Electrode in a Gradient Manner ACS Macro Lett. 2012, 1, 656-659
10. Ku, S.-Y.; Wong, K.-T.; Bard, A. J. Surface Patterning with Fluorescent Molecules Using Click Chemistry Directed by Scanning Electrochemical Microscopy J. Am. Chem. Soc. 2008, 130, 2392-2393
11. Bard, A. J.; Mirkin, M. V. Scanning Electrochemical Microscopy; Marcel Dekker: New York, 2001.
12. Wittstock, G.; Burchardt, M.; Sascha, E. P.; Shen, Y.; Zhao, C. Scanning Electrochemical Microscopy for Direct Imaging of Reaction Rates Angew. Chem., Int. Ed. 2007, 46, 1584-1617
13. Amemiya, S.; Bard, A. J.; Fan, F. R. F.; Mirkin, M. V.; Unwin, P. R. Scanning Electrochemical Microscopy Annu. Rev. Anal. Chem. 2008, 1, 95-131
14. Stoica, L.; Neugebauer, S.; Schuhmann, W. Scanning Electrochemical Microscopy (SECM) as a Tool in Biosensor Research Adv. Biochem Eng. Biotechnol. 2008, 109, 455-92
15. Ktari, N.; Combellas, C.; Kanoufi, F. Local Oxidation of Polystyrene by Scanning Electrochemical Microscopy J. Phys. Chem. C 2011, 115, 17891-17897
16. Noël, J. M.; Latus, A.; Lagrost, C.; Volanschi, E.; Hapiot, P. Evidence for OH Radical Production during Electrocatalysis of Oxygen Reduction on Pt Surfaces: Consequences and Application J. Am. Chem. Soc. 2012, 134, 2835-2841
17. Quinton, D.; Maringa, A.; Griveau, S.; Nyokong, T.; Bedioui, F. Surface Patterning Using Scanning Electrochemical Microscopy to Locally Trigger a "Click" Chemistry Reaction Electrochem. Commun. 2013, 31, 112-115
18. Le Poul, N.; Douziech, B.; Zeitouny, J.; Thiabaud, G.; Colas, H.; Conan, F.; Cosquer, N.; Jabin, I.; Lagrost, C.; Hapiot, P.; Reinaud, O.; Le Mest, Y. Mimicking the Protein Access Channel to a Metal Center: Effect of a Funnel Complex on Dissociative versus Associative Copper Redox Chemistry J. Am. Chem. Soc. 2009, 131, 17800-17807
19. Gomila, A.; Le Poul, N.; Cosquer, N.; Kerbaol, J.-M.; Noël, J.-M.; Reddy, M. T.; Jabin, I.; Reinaud, O.; Conan, F.; Le Mest, Y. Self-Induced "Electroclick" Immobilization of Copper Complex onto Self-Assembled Monolayers on a Gold Electrode Dalton Trans. 2010, 39, 11516-11518
20. Orain, C.; Porras-Gutiérrez, A. G.; Evoung Evoung, F.; Charles, C.; Cosquer, N.; Gomila, A.; Conan, F.; Le Mest, Y.; Le Poul, N. Electrocatalytic Reduction of Nitrite Ions by a Copper Complex Attached as SAMs on Gold by "Self-Induced Electroclick": Enhancement of the Catalytic Rate by Surface Coverage Decrease Electrochem. Commun. 2013, 34, 204-207
21. Heuft, M. A.; Collins, S. K.; Yap, G. P. A.; Fallis, A. G. Synthesis of Diynes and Tetraynes from in Situ Desilylation/Dimerization of Acetylenes Org. Lett. 2001, 3, 2883-2886
22. Meldal, M.; Tornøe, C. W. Cu-Catalyzed Azide-Alkyne Cycloaddition Chem. Rev. 2008, 108, 2952-3015
23. Sklyan, O.; Wittstock, G.; Numes Kirchner, C.; Leash, A. SECMX software. http://www.wittstock.chemie.uni-oldenburg.de/de/research/secm/SECMx.html.
24. Wackerbarth, H.; Grubb, M.; Zhang, J.; Hansen, A. G.; Ulstrup, J. Long-Range Order of Organized Oligonucleotide Monolayers on Au(111) Electrodes Langmuir 2004, 20, 1647-1655
25. Amatore, C.; Savéant, J.-M.; Tessier, D. Charge Transfer at Partially Blocked Surfaces: A Model for the Case of Microscopic Active and Inactive Sites J. Electroanal. Chem. 1983, 147, 39-51
26. Oleinick, A. I.; Battistel, D.; Daniele, S.; Svir, I.; Amatore, C. Simple and Clear Evidence for Positive Feedback Limitation by Bipolar Behavior during Scanning Electrochemical Microscopy of Unbiased Conductors Anal. Chem. 2011, 83, 4887
27. Chailapakul, O.; Crooks, R. M. Interactions between Organized, Surface-Confined Monolayers and Liquid-Phase Probe Molecules. 4. Synthesis and Characterization of Nanoporous Molecular Assemblies: Mechanism of Probe Penetration Langmuir 1995, 11, 1329-1340
28. Chen, P.; McCreery, R. L. Control of Electron Transfer Kinetics at Glassy Carbon Electrodes by Specific Surface Modification Anal. Chem. 1996, 68, 3958-3965
29. Lhenry, S.; Leroux, Y. R.; Hapiot, P. Use of Cathechol As Selective Redox Mediator in Scanning Electrochemical Microscopy Investigations Anal. Chem. 2012, 84, 7518-7524
30. Lewis, W. G.; Magallon, F. G.; Fokin, V. V.; Finn, M. G. Discovery and Characterization of Catalysts for Azide-Alkyne Cycloaddition by Fluorescence Quenching J. Am. Chem. Soc. 2004, 126, 9152-9153
31. Hazimeh, H.; Nunige, S.; Cornut, R.; Lefrou, C.; Combellas, C.; Kanoufi, F. Surface Reactivity from Electrochemical Lithography: Illustration in the Steady-State Reductive Etching of Perfluorinated Surfaces Anal. Chem. 2011, 83, 6106-6113