Electrochemical remote control for dithienylethene-ferrocene switches

Journal of Physical Chemistry C

Volumn 111, Issue 6, 2007, Pages 2770-2776

  Guirado, Gonzalo ^a,b   Coudret, Christophe ^a   Launay, Jean Pierre ^a  

^a CEMES CNRS   (France)

^b UNIVERSITAT AUTÒNOMA DE BARCELONA   (Spain)

Author keywords

[No Author keywords available]

Indexed keywords

CHARGE TRANSFER; ELECTROCHROMISM; ELECTRON TRANSITIONS; ISOMERS; OXIDANTS; PHOTOCHEMICAL REACTIONS; REMOTE CONTROL;

DIFERROCENYL COMPOUNDS; DITHIENYLETHENE-FERROCENE SWITCHES; PHOTOELECTROCHROMIC CORE; REACTIVITY;

SINGLE CRYSTALS;

EID: 34248644006     PISSN: 19327447     EISSN: 19327455     Source Type: Journal    
DOI: 10.1021/jp066571g     Document Type: Article

References (35)

1. Feringa, B.L., Ed. In Molecular Switches; Wiley-VCH: Weinheim, Germany, 2001.
2. Launay, J. P. Joachim, C.; Coudret, C. Molecular Switches. In Dekker Encyclopedia of Nanoscience and Nanotechnology; Marcel Dekker: New York, 2004; p 2145.
3. (a) Irie, M. Chem. Rev. 2000, 100, 1685
4. (b) Tian, H.; Yang, S. Chem. Soc. Rev. 2004, 33, 85.
5. Fraysse, S.; Coudret, C.; Launay, J.-P. Eur. J. Inorg. Chem. 2000, 1581.
6. (a) Dulic, C.; van der Molen, S. J.; Kudernal, T.; Jonkman, H. T.; De Jong, J. J. D.; Bowden, T. N.; van Esch, J.; Feringa, B. L.; van Wees, B. J. Phys. Rev. Letter. 2003, 91, 207402.
7. (b) He, J.; Chen, F.; Liddell, P. A.; Andr'easson, J.; Straight, S. D.; Gust, D.; Moore, T. A.; Moore, A. L.; Li, J.; Sankey, O. F.; Lindsay, S. M. Nanotech. 2005, 16, 695.
8. Guirado, G.; Coudret, C.; Hliwa, M.; Launay, J.-P. J. Phys. Chem. B 2005, 109(37), 1744.
9. (a) Gorodetsky, B.; Samachetty, H. D.; Donkers, R. L.; Workentin, M. S.; Branda, N. R. Angew. Chem., Int. Ed. Engl. 2004, 43, 2812
10. (b) Peters, A.; Branda, N. R. J. Am. Chem. Soc. 2003, 125, 3404
11. (c) Peters, A.; Branda, N. R.; Chem. Commun. 2003, 954
12. (d) : Zhou, X. H.; Zhang, F. S.; Yuang, P.; Sun, F.; Pu, S. Z.; Zhao, F. Q.; Tung, C. H. Chem. Lett. 2004, 33, 1006
13. (e) Moriyama, Y.; Matsuda, K.; Tanafuji, N.; Iries, S.; Irie, M. Org. Lett. 2005, 15, 3315
14. (f) Baron, R.; Onopriyenko, A.; Katz, E.; Lioubashevski, O.; Willner, I.; Wang, S.; Tian, H. Chem Comm. 2006, 2147.
15. The ferrocene groups incorporated to related systems have the same oxidation potential regardless of the structure. For more information on ferrocene in supramolecular systems, see Kaifer, A. E.; G'omez-Kaifer, M. Supramolecular Electrochemistry: Wiley-VCH: Weinheim, Germany, 1999.
16. Malaun, M.; Reeves, Z. R.; Paul, R. L.; Jeffery, J. C.; McCleverty, J. A.; Ward, M. D.; Asselberghs, I.; Clays, K.; Persoons, A. Chem. Commun. 2001, 49.
17. (a) Lützen, A.; Hapke, M.; Meyer, S. Synthesis, 2002, 15, 2289
18. (b) Liltzen, A.; Thiemann, F.; Meyer, S. Synthesis 2002, 15, 2771.
19. Justin Thomas, K. R.; Lin, J. T.; Wen, S. Y. Organometallics 2002, 19, 1008.
20. Nakamura, K.; Okubo, H.; Yamaguchi, M. Synlett 1999, 5, 549.
21. 1H NMR, which allows determining the compositions of all photostationary states. The closed-open isomers were purified prior to perform electrochemical and spectroelectrochemical experiments using TLC-semipreparative techniques.
22. ΔE° was obtained by differential pulse voltammetry with a rotating glassy carbon electrode (1000 rev/min) with pulses of 70 ms duration and 25 mV amplitude, see D.E. Richardson, H. Taube, Inorg. Chem. 1981, 20, 1278.
23. Ribou, C.; Launay, J.-P.; Sachtleben, M. L.; Li, H.; Spangler, C. W. Inorg. Chem. 1996, 35, 3735
24. a) Das, N.; Arif, A. M.; Stang, P. J.; Sieger, M.; Sarkar, B.; Kaim, W.; Fiedler, J. Inorg. Chem. 2005, 44, 5798.
25. b) Mukherjee, P. S.; Das, N.; Kryschenko, Y. K.; Arif, A. M.; Stang, P. J. J. Am. Chem. Soc. 2004, 126, 2464.
26. c) Prins, R. J. Chem. Soc. Chem. Commun. 1970, 280.
27. d) Sohn, Y. S.; Hendrickson, D. N.; Gray, H. B. J. Am. Chem. Soc. 1971, 93, 3603.
28. Gilat, S. L.; Kawai, S. H.; Lehn, J.-M. Chem. Eur. J. 1995, 1, 275.
29. Launay, J.-P.; Fraysse, S.; Coudret, C. Mol. Cryst. Liquid Cryst. 2000, 344, 125.
30. (a) Nadjo, L.; Savéant, J.-M. J. Electonanal. Chem. 1973, 48, 113.
31. (b) Andrieux C. P.; Savéant, J.-M. Electrochemical Reactions. In Investigation of Rates and Mechanism of Reactions, Techniques of Chemistry; Bernasconi, C. F., Ed.; Wiley: New York, 1986; p 305.
32. closed unit is partly destabilized by one ferrocenium site.
33. Similar results were obtained by R.H. Mitchell et. al. for similar compounds, see Mitchell, R. H.; Brkic, Z.; Sauro, V. A.; Berg, D. J. J. Am. Chem. Soc. 2003, 125, 7581.
34. Wu, S. W.; Nazin, G. V.; Chen, X.; Qiu, X. H. Phys. Rev. Lett. 2004, 93, 236802.
35. Repp, J.; Meyer, G.; Stojkovic, S.; Gourdon, A.; Joachim, C. Phys. Rev. Lett. 2005, 94, 026803.