H2O2 Generation by Decamethylferrocene at a Liquid|Liquid Interface†
Bin Su Dr.
Laboratoire d'Electrochimie Physique et Analytique, Ecole Polytechnique Fédérale de Lausanne (EPFL), Station 6, 1015 Lausanne, Switzerland, Fax: (+41) 21-693-3667 http://lepa.epfl.ch
Search for more papers by this authorRaheleh Partovi Nia
Laboratoire d'Electrochimie Physique et Analytique, Ecole Polytechnique Fédérale de Lausanne (EPFL), Station 6, 1015 Lausanne, Switzerland, Fax: (+41) 21-693-3667 http://lepa.epfl.ch
Search for more papers by this authorFei Li Dr.
Laboratoire d'Electrochimie Physique et Analytique, Ecole Polytechnique Fédérale de Lausanne (EPFL), Station 6, 1015 Lausanne, Switzerland, Fax: (+41) 21-693-3667 http://lepa.epfl.ch
Search for more papers by this authorMohamad Hojeij
Laboratoire d'Electrochimie Physique et Analytique, Ecole Polytechnique Fédérale de Lausanne (EPFL), Station 6, 1015 Lausanne, Switzerland, Fax: (+41) 21-693-3667 http://lepa.epfl.ch
Search for more papers by this authorMichel Prudent
Laboratoire d'Electrochimie Physique et Analytique, Ecole Polytechnique Fédérale de Lausanne (EPFL), Station 6, 1015 Lausanne, Switzerland, Fax: (+41) 21-693-3667 http://lepa.epfl.ch
Search for more papers by this authorClémence Corminboeuf Prof.
Laboratory for Computational Molecular Design, Ecole Polytechnique Fédérale de Lausanne (EPFL), BCH, 1015 Lausanne, Switzerland
Search for more papers by this authorZdenek Samec Prof.
Department of Electrochemistry, J. Heyrovsky Institute of Physical Chemistry, Academy of Sciences of the Czech Republic, Dolejskova 3, 18223 Prague 8, Czech Republic
Search for more papers by this authorHubert H. Girault Prof.
Laboratoire d'Electrochimie Physique et Analytique, Ecole Polytechnique Fédérale de Lausanne (EPFL), Station 6, 1015 Lausanne, Switzerland, Fax: (+41) 21-693-3667 http://lepa.epfl.ch
Search for more papers by this authorBin Su Dr.
Laboratoire d'Electrochimie Physique et Analytique, Ecole Polytechnique Fédérale de Lausanne (EPFL), Station 6, 1015 Lausanne, Switzerland, Fax: (+41) 21-693-3667 http://lepa.epfl.ch
Search for more papers by this authorRaheleh Partovi Nia
Laboratoire d'Electrochimie Physique et Analytique, Ecole Polytechnique Fédérale de Lausanne (EPFL), Station 6, 1015 Lausanne, Switzerland, Fax: (+41) 21-693-3667 http://lepa.epfl.ch
Search for more papers by this authorFei Li Dr.
Laboratoire d'Electrochimie Physique et Analytique, Ecole Polytechnique Fédérale de Lausanne (EPFL), Station 6, 1015 Lausanne, Switzerland, Fax: (+41) 21-693-3667 http://lepa.epfl.ch
Search for more papers by this authorMohamad Hojeij
Laboratoire d'Electrochimie Physique et Analytique, Ecole Polytechnique Fédérale de Lausanne (EPFL), Station 6, 1015 Lausanne, Switzerland, Fax: (+41) 21-693-3667 http://lepa.epfl.ch
Search for more papers by this authorMichel Prudent
Laboratoire d'Electrochimie Physique et Analytique, Ecole Polytechnique Fédérale de Lausanne (EPFL), Station 6, 1015 Lausanne, Switzerland, Fax: (+41) 21-693-3667 http://lepa.epfl.ch
Search for more papers by this authorClémence Corminboeuf Prof.
Laboratory for Computational Molecular Design, Ecole Polytechnique Fédérale de Lausanne (EPFL), BCH, 1015 Lausanne, Switzerland
Search for more papers by this authorZdenek Samec Prof.
Department of Electrochemistry, J. Heyrovsky Institute of Physical Chemistry, Academy of Sciences of the Czech Republic, Dolejskova 3, 18223 Prague 8, Czech Republic
Search for more papers by this authorHubert H. Girault Prof.
Laboratoire d'Electrochimie Physique et Analytique, Ecole Polytechnique Fédérale de Lausanne (EPFL), Station 6, 1015 Lausanne, Switzerland, Fax: (+41) 21-693-3667 http://lepa.epfl.ch
Search for more papers by this authorThis work was supported by the EPFL and European COST Action (D36/007/06). We thank Professors X. Hu and J. Waser for fruitful discussions. The technical assistance of V. Devaud is also acknowledged.
Graphical Abstract
Hydrogen peroxide generation at a liquid|liquid interface occurs with a yield of 20 % with respect to the concentration of reducing agent (decamethylferrocene). The liquid|liquid interface supplies electrons from the reducing agent and protons from the aqueous phase to drive the reduction of O2 into H2O2, which is extracted into the aqueous phase during the course of reaction (see picture; DCE=1,2-dichloroethane).
Supporting Information
Supporting information for this article is available on the WWW under http://www.wiley-vch.de/contents/jc_2002/2008/z801004_s.pdf or from the author.
Please note: The publisher is not responsible for the content or functionality of any supporting information supplied by the authors. Any queries (other than missing content) should be directed to the corresponding author for the article.
References
- 1
- 1aI. Yamanaka, T. Onizawa, S. Takenaka, K. Otsuka, Angew. Chem. 2003, 115, 3781–3783;
10.1002/ange.200351343 Google ScholarAngew. Chem. Int. Ed. 2003, 42, 3653–3655;
- 1bV. R. Choudhary, A. G. Gaikwad, S. D. Sansare, Angew. Chem. 2001, 113, 1826–1829;
10.1002/1521-3757(20010504)113:9<1826::AID-ANGE18260>3.0.CO;2-F Google ScholarAngew. Chem. Int. Ed. 2001, 40, 1776–1779;10.1002/1521-3773(20010504)40:9<1776::AID-ANIE17760>3.0.CO;2-C CAS PubMed Web of Science® Google Scholar
- 1cI. Yamanaka, T. Murayama, Angew. Chem. 2008, 120, 1926–1928;
10.1002/ange.200704431 Google ScholarAngew. Chem. Int. Ed. 2008, 47, 1900–1902;
- 1dK. Otsuka, I. Yamanaka, Electrochim. Acta 1990, 35, 319–322.
- 2W. Eul, A. Moeller, N. Steiner in Kirk–Othmer Encyclopedia of Chemical Technology, Vol. 14, 5th ed. ), Wiley, Hoboken, 2005, pp. 35–78.
- 3J. M. Campos-Martin, G. Blanco-Brieva, J. L. G. Fierro, Angew. Chem. 2006, 118, 7116–7139;
10.1002/ange.200503779 Google ScholarAngew. Chem. Int. Ed. 2006, 45, 6962–6984.
- 4W. R. Thiel, Angew. Chem. 1999, 111, 3349–3351;
10.1002/(SICI)1521-3757(19991102)111:21<3349::AID-ANGE3349>3.0.CO;2-P Google ScholarAngew. Chem. Int. Ed. 1999, 38, 3157–3158.10.1002/(SICI)1521-3773(19991102)38:21<3157::AID-ANIE3157>3.0.CO;2-E CAS PubMed Web of Science® Google Scholar
- 5J. H. Zagal, M. A. Paez, J. F. Silva in N4-Macrocyclic Metal Complexes (Eds.: ), Springer, New York, 2006, pp. 41–75.
10.1007/978-0-387-28430-9_2 Google Scholar
- 6
- 6aK. Tammeveski, K. Kontturi, R. J. Nichols, R. J. Potter, D. J. Schiffrin, J. Electroanal. Chem. 2001, 515, 101–112;
- 6bA. Sarapuu, K. Vaik, D. J. Schiffrin, K. Tammeveski, J. Electroanal. Chem. 2003, 541, 23–29;
- 6cF. Mirkhalaf, K. Tammeveski, D. J. Schiffrin, Phys. Chem. Chem. Phys. 2004, 6, 1321–1327;
- 6dK. Vaik, A. Sarapuu, K. Tammeveski, F. Mirkhalaf, D. J. Schiffrin, J. Electroanal. Chem. 2004, 564, 159–166;
- 6eK. Vaik, D. J. Schiffrin, K. Tammeveski, Electrochem. Commun. 2004, 6, 1–5;
- 6fJ. R. T. Johnsson Wass, E. Ahlberg, I. Panas, D. J. Schiffrin, Phys. Chem. Chem. Phys. 2006, 8, 4189–4199.
- 7
- 7aR. Prins, A. G. T. G. Kortbeek, J. Organomet. Chem. 1971, 33, C 33–C34;
- 7bT. E. Bitterwolf, A. C. Ling, J. Organomet. Chem. 1972, 40, C 29–C32.
- 8J. Lubach, W. Drenth, Recl. Trav. Chim. Pays-Bas 1973, 92, 586–592.
- 9V. J. Cunnane, G. Geblewicz, D. J. Schiffrin, Electrochim. Acta 1995, 40, 3005–3014.
- 10V. M. Fomin, Russ. J. Gen. Chem. 2007, 77, 954–960.
- 11A. Sabela, V. Marecek, Z. Samec, R. Fuoco, Electrochim. Acta 1992, 37, 231–235.
- 12R. O. Rahn, M. I. Stefan, J. R. Bolton, E. Goren, P.-S. Shaw, K. R. Lykke, Photochem. Photobiol. 2003, 78, 146–152.
- 13D. J. Fermin, R. Lahtinen, Surfactant Sci. Ser. 2001, 95, 179–227.