Electrografting of calix[4]arenediazonium salts to form versatile robust platforms for spatially controlled surface functionalization

Nature Communications

Volumn 3, Issue , 2012, Pages

  Mattiuzzi, Alice ^a   Jabin, Ivan ^a   Mangeney, Claire ^b   Roux, Clément ^c   Reinaud, Olivia ^d   Santos, Luis ^e   Bergamini, Jean François ^e   Hapiot, Philippe ^e   Lagrost, Corinne ^e  

^a UNIVERSITÉ LIBRE DE BRUXELLES   (Belgium)

^b UNIVERSITÉ PARIS DIDEROT   (France)

^c UNIVERSITY OF CANTERBURY   (New Zealand)

^d UNIVERSITÉ PARIS DESCARTES   (France)

^e UNIVERSITÉ DE RENNES 1   (France)

Author keywords

[No Author keywords available]

Indexed keywords

ANILINE DERIVATIVE; CALIX[4]ARENEDIAZONIUM; CALIXARENE; CARBON; DIAZONIUM COMPOUND; GOLD; SODIUM CHLORIDE; UNCLASSIFIED DRUG;

ACCURACY ASSESSMENT; CARBON; CHEMICAL COMPOSITION; CHEMISTRY; GOLD; INTERFACE; LAYER; MOLECULAR ANALYSIS; SALT; SUBSTRATE;

ARTICLE; CHEMICAL COMPOSITION; CYCLIC POTENTIOMETRY; ELECTROCHEMISTRY; MONOLAYER CULTURE; SOLID;

TETRA;

EID: 84869386194     PISSN: None     EISSN: 20411723     Source Type: Journal    
DOI: 10.1038/ncomms2121     Document Type: Article

References (57)

1. Simao, C. et al. A robust molecular platform for non-volatile memory devices with optical and magnetic responses. Nat Chem. 3, 359-364 (2011).
2. Areephong, J., Browne, W. R., Katsonis, N. & Feringa, B. L. Photo-and electro-chromism of diarylethene modifed ITO electrodes-towards molecular based read-write-erase information storage. Chem. Commun. 3930-3932 (2006). (Pubitemid 44423472)
3. Amatore, C., Genovese, D., Maisonhaute, E., Raouaf, N. & Schollhorn, B. Electrochemically driven release of picomole amounts of calcium ions with temporal and spatial resolution. Angewandte Chem. Int. Ed. 47, 5211-5214 (2008).
4. Lahann, J. et al. A reversibly switching surface. Science 299, 371-374 (2003). (Pubitemid 36120035)
5. Kim, B. S. et al. Temperature and length dependence of charge transport in redox-active molecular wires incorporating ruthenium(II) bis (σ-arylacetylide) complexes. J. Phys. Chem. C 111, 7521-7526 (2007).
6. Willner, I. Biomaterials for sensors,fuel cells, and circuitry. Science 298, 2407-2408 (2002).
7. Choi, H. J., Kim, N. H., Chung, B. H. & Seong, G. H. Micropatterning of biomolecules on glass surfaces modifed with various functional groups using photoactivatable biotin. Anal. Biochem. 347, 60-66 (2005). (Pubitemid 41608568)
8. Adams, D. M. et al. Charge Transfer on the nanoscale: current status, J. Phys. Chem. B 107, 6668-6697 (2003).
9. Finklea, H. O. Electrochemistry of organized monolayers of thiols and related molecules on electrodes. in Electroanalytical chemistry, Vol 19 (eds Bard A.J. and Rubinstein) 109-337 (Marcel Dekker, Inc. New York, 1996).
10. Gooding, J. J. Advances in interfacial design for electrochemical biosensors and sensors: aryl diazonium salts for modifying carbon and metal electrodes. Electroanalysis 20, 573-582 (2008).
11. Gooding, J. J. & Ciampi, S. The molecular level modifcation of surfaces: from self-assembled monolayers to complex molecular assemblies. Chem. Soc. Rev. 40, 2704-2718 (2011).
12. Love, C. J., Estrof, L. A., Kriebel, J. K., Nuzzo, R. G. & Whitesides, G. M. Self-assembeld monolayers of thiolates on metal as a form of nanotechnology Chem. Rev. 105, 1103-1169 (2005). (Pubitemid 40600878)
13. Vericat, C., Vela, M. E., Benitez, G., Carro, P. & Salvarezza, R. C. Self-assembled monolayers of thiols and dithiols on gold: new challenges for a well-known system. Chem. Soc. Rev. 39, 1805-1834 (2010).
14. Kind, M. & Wöll, C. Organic surfaces exposed by self-assembled organothiol monolayers: preparation, characterization, and application. Progr. Surf. Sci. 84, 230-278 (2009).
15. Sullivan, T. P. & Huck, W. T. S. Reactions on monolayers: organic synthesis in two dimensions. Eur. J. Org. Chem. 17-23 (2003).
16. Bain, C. D. & Whitesides, G. M. Formation of monolayers by the coadsorption of thiols on gold: variation in the length of the alkylchain. J. Am. Chem. Soc. 111, 7164-7175 (1989).
17. 2OH terminal groups. Langmuir 8, 1330-1341 (1992).
18. Stranick, S. J., Parikh, A. N., Tao, Y. T., Allara, D. L. & Weiss, P. S. Phase separation of mixed-composition self assembled monolayers into nanometer scale molecular domains. J. Phys. Chem. 98, 7636-7646 (1994).
19. Tamada, K., Akiyama, H., Wei, T. X. & Kim, S. A. Photoisomerization reaction of unsymmetrical azobenzene disulfde self-assembled monolayers: modifcation of azobenzene dyes to improve thermal endurance for photoreaction. Langmuir 19, 2306-2312 (2003).
20. Downard, A. J. Electrochemically assisted covalent modifcation of carbon electrodes. Electroanalysis. 11, 1085-1096 (2000).
21. Pinson, J. & Podvorica, F. Attachment of organic layers to conductive or semiconductive surfaces by reduction of diazonium salts. Chem. Soc. Rev. 34, 429-439 (2005). (Pubitemid 40720488)
22. Pinson, J. & Bélanger, D. Electrografing: a powerful method for surface modifcation. Chem. Soc. Rev. 40, 3995-4048 (2011).
23. Mahouche-Chergui, S., Gam-Derouich, S., Mangeney, C. & Chehimi, M. H. Aryl diazonium salts: a new class of coupling agent for bonding polymers, biomacromolecules and nanoparticles to surfaces. Chem. Soc. Rev. 40, 4143-4166 (2011).
24. Aryl Diazonium Salts. New Coupling Agents in Polymer and Surface Science (ed. Chehimi, M.M.), (Wiley-VCH, Weinheim, 2012).
25. Gui, A. L. et al. A comparative study of modifying gold and carbon electrode with 4-sulfophenyl diazonium salt. Electroanalysis 22, 1283-1289 (2010).
26. Zigah, D., Noel, J. M., Lagrost, C. & Hapiot, P. Charge transfer electroactive species immobilized on carbon surfaces by aryl diazonium reduction. SECM investigations. J. Phys. Chem. C 114, 3075-3081 (2010).
27. Combellas, C., Kanouf, F., Pinson, J. & Podvorica, F. I. Sterically hindered diazonium salts for the grafing of a monolayer on metals. J. Am. Chem. Soc. 130, 8576-8577 (2008). (Pubitemid 351962475)
28. Leroux, Y. R., Fei, H., Noel, J.-M., Roux, C. & Hapiot, P. Efcient covalent modifcation of a carbon Surface: Use of a silyl protecting group to form an active monolayer. J. Am. Chem. Soc. 132, 14039-14041 (2010).
29. Malmos, K. et al. Using a hydrazone-protected benzenediazonium salt to introduce a near-monolayer of benzaldehyde on glassy carbon surfaces. J. Am. Chem. Soc. 131, 4928-4938 (2009).
30. Nielsen, L. T. et al. Electrochemical approach for constructing a monolayer of thiophenolates from grafed multilayers of diaryl disulfdes. J. Am. Chem. Soc. 129, 1888-1889 (2007).
31. Peng, Z., Holm, A. H., Nielsen, L. T., Pedersen, S. U. & Daasberg, K. Covalent sidewall functionalization of carbon nanotubes by a "formation-degradation" approach. Chem. Mater. 20, 6068-6075 (2008).
32. Marshall, N. & Locklin, J. Reductive electrografing of benzene (p-bisdiazonium hexafuorophosphate): a simple and efective protocol for creating diazonium-functionalized thin flms. Langmuir 27, 13367-13373 (2011).
33. Gutsche, C. D. in Calixarenes Revisited, Monographs in Supramolecular Chemistry (ed. Stoddart, J.F.), (The Royal Society of Chemistry, Cambridge, 1998).
34. Kim, H. J., Lee, M. H., Mutihac, L., Vicens, J. & Kim, J. S. Host-guest sensing by calixarenes on the surface. Chem. Soc. Rev. 41, 1173-1190 (2012).
35. Sansone, F., Chierici, E., Casnati, A. & Ungaro, R. Tiourea-linked upper rim calix[4]arene neoglycoconjugates: synthesis, conformations and binding properties. Org Biomol. Chem. 1, 1802-1809 (2003).
36. Baranton, S. & Bélanger, D. Electrochemical derivatization of carbon surface by reduction of in situ generated diazonium cations. J. Phys. Chem. B 109, 24401-24410 (2005). (Pubitemid 43063688)
37. Delamar, M., Hitmi, R., Pinson, J. & Savéant, J.-M. Covalent modifcation of carbon surfaces by grafing of functionalized aryl radicals produced from electrochemical reduction of diazonium salts. J. Am. Chem. Soc. 114, 5883-5884 (1992).
38. DuVall, S. H. & McCreery, R. L. Control of catechol and hydroquinone electron-transfer kinetics on native and modifed glassy carbon electrodes. Anal. Chem. 71, 4594-4602 (1999).
39. DuVall, S. H. & McCreery, R. L. Self-catalysis by catechols and Quinones during heterogeneous electron transfer at carbon electrodes. J. Am. Chem. Soc. 122, 6759-6764 (2000). (Pubitemid 30489998)
40. Cygan, M. T. et al. Calixarene monolayers as quartz crystal microbalance sensing element in aqueous solution. Anal. Chem. 71, 142-148 (1999). (Pubitemid 29029518)
41. Zhang, S., Song, F. & Echegoyen, L. Synthesis, self-assembled monolayers and alkaline earth metal ion recognition of p-tert-butylcalix[4]arene derivatives. Eur. J. Org Chem. 2936-2943 (2004).
42. Toupin, M. & Bélanger, D. Termal stability study of aryl modifed carbon black in situ generated diazonium salt. J. Phys. Chem. C 111, 5394-5401 (2007). (Pubitemid 46723962)
43. Saby C., Ortiz, B., Champagne, G. Y. & Bélanger, D. Electrochemical modifcation of glassy carbon electrode using aromatic diazonium salt. Blocking efect of 4-nitrophenyl and 4-carboxyphenyl groups. Langmuir 13, 6805-6813 (1997). (Pubitemid 127592107)
44. Lyskawa, J. & Bélanger, D. Direct modifcation of a gold electrode with aminophenyl groups by electrochemical reduction of in situ generated aminophenyl monodiazonium cations. Chem. Mater. 18, 4755-4763 (2006). (Pubitemid 44626799)
45. Hurley B. L. & McCreery R. L. Covalent bonding of organic molecules to Cu and Al alloy 2024 T3 surfaces via diazonium ion reduction. J. Electrochem. Soc. 151, B252-B259 (2004).
46. Doppelt, P., Hallais, G., Pinson, J., Podvorica, F. & Verneyre, S. Surface modifcation of conducting substrates. Existence of azo bonds in the structure of organic layers obtained from diazonium salts. Chem. Mater. 19, 4570-4575 (2007). (Pubitemid 47441897)
47. Ranganathan, S. & McCreery R. L. Electroanalytical performance of carbon flms with near-atomic fatness. Anal. Chem. 73, 893-900 (2001). (Pubitemid 32204902)
48. Anariba, F., DuVall, S. H. & McCreery R. L. Mono-and multilayer formation by diazonium reduction on carbon surfaces monitored with atomic force microscopy 'scratching'. Anal. Chem. 75, 3837-3844 (2003). (Pubitemid 36962119)
49. Dahoumane, S. A et al. Protein-functionalized hairy diamond nanoparticles. Langmuir 25, 9633-9638 (2009).
50. Kim, J.-H., Kim, Y.-G., Lee, K.-H., Kang, S.-W. & Koh, K.-N. Size selective molecular recognition of calix[4]arenes in Langmuir-Blodgett monolayers. Synth. Met. 117, 145-148 (2001). (Pubitemid 32264128)
51. Noel, J.-M., et al. Flexible strategy for immobilizing redox-active compounds using in situ generation of diazonium salts. Investigation of the blocking and catalytic properties of the layers. Langmuir 25, 12742-12749 (2009).
52. Chen, H. et al. Comparative study of protein immobilization properties on calixarenes monolayers. Sensors 7, 1091-1107 (2007).
53. Cormode, D. P., Evans, A. J., Davis, J. J. & Beer, P. D. Amplifcation of anion sensing by disulfde functionalized ferrocene and ferrocene-calixarene receptors adsorbed onto gold surfaces. Dalton Trans. 39, 6532-6541 (2010).
54. Notestein, J. M., Katz, A. & Iglesia, E. Energetics of small molecule and water complexation in hydrophobic calixarene cavities. Langmuir 22, 4004-4014 (2006).
55. Seo, K., Jeon, I. C. & Yoo, D. J. Electrochemical characteristics of ferrocenecarboxylate-coupled aminoundecylthiol self-assembled monolayers. Langmuir 20, 4147-4154 (2004).
56. Mattiuzzi, A., Jabin, I., Reinaud, O., Hapiot, P. & Lagrost, C. European patent EP 12164038 (2012).
57. Brooksby P. A. & Downard, A. J. Electrochemical and atomic force microscopy study of carbon surface modifcation via diazonium reduction in aqueous and acetonitrile solutions. Langmuir 20, 5038-5045 (2004).