Covalent attachment of porphyrins and ferrocenes to electrode surfaces through direct anodic oxidation of terminal ethynyl groups

Angewandte Chemie - International Edition

Volumn 52, Issue 49, 2013, Pages 12897-12900

  Sheridan, Matthew V ^a   Lam, Kevin ^b   Geiger, William E ^a  

^a UNIVERSITY OF VERMONT   (United States)

^b NAZARBAYEV UNIVERSITY   (Kazakhstan)

Author keywords

electrochemistry; electrodes; oxidation; porphyrins; surface chemistry

Indexed keywords

COVALENT ATTACHMENT; DIRECT OXIDATION; ELECTRODE MODIFICATION; ELECTRODE SURFACES; FERROCENES; GRAFTING ONTO; INDIUM TIN OXIDE; TERMINAL ALKYNE;

ANODIC OXIDATION; ELECTROCHEMISTRY; ELECTRODES; HYDROCARBONS; OXIDATION; SURFACE CHEMISTRY;

PORPHYRINS;

EID: 84888598384     PISSN: 14337851     EISSN: 15213773     Source Type: Journal    
DOI: 10.1002/anie.201307453     Document Type: Article

References (30)

1. F. Lissel, T. Fox, O. Blacque, W. Polit, R. F. Winter, K. Venkatesan, H. Berke, J. Am. Chem. Soc. 2013, 135, 4051-4060
2. F. Gendron, A. Burgun, B. W. Skelton, A. H. White, T. Roisnel, M. I. Bruce, J.-F. Halet, C. Lapinte, K. Costuas, Organometallics 2012, 31, 6796-6811
3. H. N. Roberts, N. J. Brown, R. Edge, E. C. Fitzgerald, Y. T. Ta, D. Collison, P. J. Low, M. W. Whiteley, Organometallics 2012, 31, 6322-6335
4. S. Szafert, J. A. Gladysz, Chem. Rev. 2006, 106, PR 1 -PR 33
5. T. Ren, Organometallics 2005, 24, 4854-4870.
6. M. V. Sheridan, K. Lam, W. E. Geiger, J. Am. Chem. Soc. 2013, 135, 2939-2942.
7. Acetylene Chemistry (Eds.:, F. Diederich, P. J. Stang, R. R. Tykwinski,), Wiley-VCH, Weinheim, 2005.
8. D. Bélanger, J. Pinson, Chem. Soc. Rev. 2011, 40, 3995-4048.
9. P. Aschwanden, E. M. Carreira, Acetylene Chemistry (Eds.:, F. Diederich, P. J. Stang, R. R. Tykwinski,), Wiley-VCH, Weinheim, 2005, p. 101.
10. Ox1.
11. The oxidation potentials of alkynes are typically 1 V vs. ferrocene or slightly higher. See Y. Fu, L. Liu, H.-Z. Yu, Y.-M. Wang, Q.-X. Guo, J. Am. Chem. Soc. 2005, 127, 7227-7234
12. M. Katz, H. Wendt, Electrochim. Acta 1976, 21, 215-218
13. R. Bauer, H. Wendt, J. Electroanal. Chem. 1977, 80, 395-399.
14. -2. See, K. Seo, I. C. Jeon, D. J. Yoo, Langmuir 2004, 20, 4147-4154.
15. S. Drouet, S. Ballut, J. Rault-Berthelot, P. Turban, C. Paul-Roth, Thin Solid Films 2009, 517, 5474-5481
16. C. Paul-Roth, J. Rault-Berthelot, G. Simonneaux, C. Poriel, M. Abdalilah, J. Letessier, J. Electroanal. Chem. 2006, 597, 19-27
17. J. Rault-Berthelot, C. Paul-Roth, C. Poriel, S. Juillard, S. Ballut, S. Drouet, G. Simmoneaux, J. Electroanal. Chem. 2008, 623, 204-214.
18. J. E. Huthchinson, T. A. Postlethwaite, C.-H. Chen, K. W. Hathcock, R. S. Ingram, W. Ou, R. W. Linton, R. W. Murrary, D. A. Tyvoll, L. L. Chng, J. P. Collman, Langmuir 1997, 13, 2143-2148
19. H. H. De Paz, C. Médard, M. Morin, J. Electroanal. Chem. 2010, 648, 163-168.
20. S. Ssenyange, F. Anariba, D. F. Bocian, R. L. McCreery, Langmuir 2005, 21, 11105-11112.
21. A. R. McDonald, N. Franssen, G. P. M. van Klink, G. van Koten, J. Organomet. Chem. 2009, 694, 2153-2162
22. P. K. B. Palomaki, P. H. Dinolfo, Langmuir 2010, 26, 9677-9685.
23. M. Picot, I. Nicolas, C. Poriel, J. Rault-Berthelot, F. Barrière, Electrochem. Commun. 2012, 20, 167-170
24. A. J. Gross, C. Bucher, L. Coche-Guerente, P. Labbé, A. J. Downard, J.-C. Moutet, Electrochem. Commun. 2011, 13, 1236-1239.
25. K. M. Kadish, E. Van Caemelbecke, J. Solid State Electrochem. 2003, 7, 254-258.
26. D. A. Van Galen, M. Majda, Anal. Chem. 1988, 60, 1549-1553.
27. D.-J. Qian, C. Nakamura, T. Ishida, S.-O. Wenk, T. Wakayama, S. Takeda, J. Miyake, Langmuir 2002, 18, 10237-10242
28. P. K. B. Palomaki, P. H. Dinoflo, ACS Appl. Mater. Interfaces 2011, 3, 4703-4713.
29. D. Clark, M. Fleischmann, D. Pletcher, J. Electroanal. Chem. 1972, 36, 137-146
30. D. B. Clark, M. Fleischmann, D. Pletcher, J. Electroanal. Chem. 1973, 42, 133-138.