Synthesis and application of a triazene?ferrocene modifier for immobilization and characterization of oligonucleotides at electrodes

Journal of Organic Chemistry

Volumn 75, Issue 8, 2010, Pages 2474-2481

  Hansen, Majken N ^a   Farjami, Elaheh ^a   Kristiansen, Martin ^a   Clima, Lilia ^a   Pedersen, Steen Uttrup ^a   Daasbjerg, Kim ^a   Ferapontova, Elena E ^a   Gothelf, Kurt V ^a  

^a AARHUS UNIVERSITY   (Denmark)

Author keywords

[No Author keywords available]

Indexed keywords

ACTIVATED ESTER; ALKANETHIOLS; DIAZONIUM SALTS; DIMETHYL SULFATES; DNA IMMOBILIZATION; ELECTROCHEMICAL GRAFTING; ELECTROCHEMICAL STUDIES; FERROCENES; GC ELECTRODE; GOLD ELECTRODES; METHYLENE BLUE; MODIFIED DNA; REDOX POTENTIALS; TRIAZENES;

ACTIVATED CARBON; CARBOXYLIC ACIDS; DNA; ELECTROCHEMICAL ELECTRODES; ESTERIFICATION; ESTERS; GENES; GLASSY CARBON; IRON COMPOUNDS; OLIGONUCLEOTIDES; ORGANIC ACIDS; ORGANIC POLYMERS; REDOX REACTIONS; SECONDARY BATTERIES; SYNTHESIS (CHEMICAL);

GRAFTING (CHEMICAL);

CARBON; DNA; FERROCENE DERIVATIVE; GOLD; OLIGONUCLEOTIDE; TRIAZENE DERIVATIVE;

ARTICLE; DNA DENATURATION; DNA HYBRIDIZATION; DNA MODIFICATION; ELECTROCHEMISTRY; ELECTRODE; IMMOBILIZATION; REACTION ANALYSIS; SYNTHESIS;

CARBON; DNA; ELECTROCHEMISTRY; ELECTRODES; FERROUS COMPOUNDS; GOLD; MODELS, MOLECULAR; NUCLEIC ACID CONFORMATION; NUCLEIC ACID HYBRIDIZATION; OLIGONUCLEOTIDES; TRIAZENES;

EID: 77950999625     PISSN: 00223263     EISSN: 15206904     Source Type: Journal    
DOI: 10.1021/jo9024368     Document Type: Article

References (38)

1. Campas, M.; Katakis, I. Trends Anal. Chem. 2004, 23, 49-62
2. Sassolas, A.; Leca-Bouvier, B. D.; Blum, L. Chem. Rev. 2008, 108, 109-139
3. Davis, F.; Higson, S. J. Biosens. Bioelectron. 2005, 21, 1-20
4. Drummond, T. G.; Hill, M. G.; Barton, J. K Nat. Biotechnol. 2003, 21, 1192-1199
5. Odenthal, K. J.; Gooding, J. J. Analyst 2007, 132, 603-610
6. Lucarelli, F.; Marrazza, G.; Turner, A. P. F.; Mascini, M. Biosens. Bioelectron. 2004, 19, 515-530
7. Schlein, J.; Grassl, B.; Krause, J.; Schulze, C.; Kugler, C.; Mller, P.; Bertling, W. M.; Hassmann, J. Talanta 2002, 56, 875-885
8. Herne, T. M.; Tarlov, M. J. J. Am. Chem. Soc. 1997, 119, 8916-8920
9. Steel, A. B.; Herne, T. M.; Tarlov, M. J. Anal. Chem. 1998, 70, 4670-4677
10. Bain, C. D.; Troughton, E. B.; Tao, Y. T.; Evall, J.; Whitesides, G. M.; Nuzzo, R. G. J. Am. Chem. Soc. 1989, 111, 321-335
11. Beulen, M. W.; Kastenberg, M. I.; van Veggel, C. J.; Reinhoudt, D. N. Langmuir 1998, 14, 7463-7467
12. Finklea, H. O. In Electroanalytical Chemistry: A Series of Advances; Bard, A. J.; Rubinstein, I., Eds.; Marcel Dekker: New York, 1996; Vol. 19, pp 109 ? 335.
13. Ravenscroft, M. S.; Finklea, H. O. J. Phys. Chem. 1994, 98, 3843-3850
14. Lee, C.-S.; Baker, S. E.; Marcus, M. S.; Yang, W.; Eriksson, M. A.; Hamers, R. J. Nano Lett. 2004, 4, 1713-1716
15. Shabani, A.; Mak, A. W. H.; Gerges, I.; Cuccia, L. A.; Lawrence, M. F. Talanta 2006, 70, 615-623
16. Shin, D.; Tokuda, N.; Rezek, B.; Nebel, C. E. Electrochem. Commun. 2006, 8, 844-850
17. Harper, J. C.; Polsky, R.; Wheeler, D. R.; Brozik, S. M. Langmuir 2008, 24, 2206-2211
18. Dolan, P. L.; Wu, Y.; Ista, L. K.; Metzenberg, R. L.; Nelson, M. A.; Lopez, G. P. Nucleic Acids Res. 2001, 29, e107
19. Pinson, J.; Podvorica, F. Chem. Soc. Rev. 2005, 34, 429-439
20. Tamm, C.; Hodes, M. E.; Chargaff, E. J. Biol. Chem. 1952, 195, 49-63
21. Delamar, M.; Hitmi, R.; Pinson, J.; Savant, J.-M. J. Am. Chem. Soc. 1992, 114, 5883-5884
22. Chen, B.; Flatt, A. K.; Jian, H.; Hudson, J. L.; Tour, J. M. Chem. Mater. 2005, 17, 4832-4836
23. Lu, M.; Chen, B.; He, T.; Li, Y.; Tour, J. M. Chem. Mater. 2007, 19, 4447-4453
24. Hudson, J. L.; Jian, H.; Leonard, A. D.; Stephenson, J. J.; Tour, J. M. Chem. Mater. 2006, 18, 2766-2770
25. In a separate study we are investigating the reaction mechanism of the acid and dimethylsulfate activation of triazenes for generation of diazonium salts.
26. Ferapontova, E. E.; Olsen, E. M.; Gothelf, K. V. J. Am. Chem. Soc. 2008, 130, 4256-4258
27. Barii?, L.; Rapi?, V.; Pritzkow, H.; Pavlovi?, G.; Nemet, I. J. Organomet. Chem. 2003, 682, 131-142
28. van Staveren, D. R.; Metzler-Nolte, N. Chem. Rev. 2004, 104, 5931-5985
29. nd ed.; Wiley: New York, 2000.
30. Petrovykh, D. Y.; Kimura-Suda, H.; Whitman, L. J.; Tarlov, M. J. J. Am. Chem. Soc. 2003, 125, 5219-5226
31. Laviron, E. J. Electroanal. Chem. 1979, 101, 19-28
32. Liu, G.; Liu, J.; Bcking, T.; Eggers, P. K.; Gooding, J. J. Chem. Phys. 2005, 319, 136-146
33. Rayner-Canham, G. Descriptive Inorganic Chemistry, 2 nd ed.; W. H. Freeman: New York, 2000.
34. Ferapontova, E. E.; Gothelf, K. V. Electroanalysis 2009, 21, 1261-1266
35. Ferapontova, E. E.; Ruzgas, T.; Gorton, L. Anal. Chem. 2003, 75, 4841-4850
36. Hoare, J. P. J. Electrochem. Soc. 1984, 131, 1808-1815
37. Rand, D. A. J.; Woods, R. J. Electroanal. Chem. 1971, 31, 29-38
38. Anjo, D. M.; Kahr, M.; Khodabakhsh, M. M.; Nowinski, S.; Wanger, M. Anal. Chem. 1989, 61, 2603-2608