Understanding electrochromic processes initiated by dithienylcyclopentene cation-radicals

Journal of Physical Chemistry B

Volumn 109, Issue 37, 2005, Pages 17445-17459

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

^a CEMES CNRS   (France)

^b FACULTÉ DES SCIENCES BEN M SIK   (Morocco)

Author keywords

[No Author keywords available]

Indexed keywords

ELECTROCHROMISM; ISOMERS; ORGANIC COMPOUNDS; OXIDATION;

PERHYDRO CYCLOPENTENE RING; PHENYLTHIO; THIOPHENE RING;

FREE RADICALS;

EID: 25844461239     PISSN: 15206106     EISSN: None     Source Type: Journal    
DOI: 10.1021/jp052459r     Document Type: Article

References (68)

1. For an overview of electrochromism and its applications, see: (a)Monk, P. M. S.; Mortimer, R. J.; Rosseinky, D. R. Electrochromism: Fundamentals and Applications; VCH: New York, 1995.
2. (b) Bechinger, C.; Ferrere, S.; Zaban, A.; Sprague, J.; Gregg, B. A. Nature 1996, 383, 608.
3. (a) Irie, M. Chem. Rev. 2000, 100, 1685.
4. (b) Tian, H.; Yang, S. Chem. Soc. Rev. 2004, 33, 85.
5. Frigoli, M.; Mehl, G. H. Chem. Eur. J. 2004, 10, 5240.
6. (a) Uchida, K.; Saito, M.; Murakami, A.; Nakamura, S.; Irie, M. Chem. Phys. Chem. 2003, 4, 11124.
7. (b) Uchida, K.; Saito, M.; Murakami, A.; Nakamura, S.; Irie, M. Adv. Mater. 2003, 15, 121.
8. Molinari, E.; Bertarelli, C.; Bianco, A.; Bortoletto, F.; Conconi, P.; Crimi, G.; Gallazzi, M. C.; Giro, E.; Lucotti, A.; Pernechele, C.; Zerbi, F. M.; Zerbi, G. Proc. SPIE - Int. Soc. Opt. Eng. 2003, 4842, 335-342.
9. Dulic, D.; van der Molen, S. J.; Kudenac, T.; Jonkman, H. T.; de Jong, J. J. D.; Bowden, T. N.; van Esch, J.; Feringa, B. L.; van Wees, B. J. Phys. Chem. Lett. 2003, 91, 207402-1.
10. Irie, M.; Fukaminato, T.; Sasaki, T.; Tamai, N.; Kawai, T. Nature 2002, 420, 759.
11. (a) Matsuda, K.; Matsuo, M.; Mizoguti, S.; Higashiguchi, K.; Irie, M. J. Phys. Chem. B 2000, 7, 1581.
12. (b) Matsuda, K.; Matsuo, M.; Irie, M. J. Org. Chem. 2001, 66, 8799.
13. Fraysse, S.; Coudret, C.; Launay, J.-P. Eur. J. Inorg. Chem. 2000, 1581.
14. (a) Fernandez-Acebes, A.; Lehn, J.-M. Chem. Eur. J. 1999, 5, 3285.
15. (b) Kawai, S. H.; Gilat, S. L.; Lehn, J.-M. Eur. J. Org. Chem. 1999, 2359.
16. (c) Tsivgoulis, G. M.; Lehn, J.-M. Chem. Eur. J. 1996, 2, 1399.
17. (d) Kawai, S. H.; Gilat, S. L.; Ponsinet, R.; Lehn, J.-M. Chem. Eur. J. 1995, 1, 285.
18. (a) Gorodetsky, B.; Samachetty, H. D.; Donkers, R. L.; Workentin, M. S.; Branda, N. R. Angew. Chem., Int. Ed. . 2004, 43, 2812.
19. (b) Peters, A.; Branda, N. R. J. Am. Chem. Soc. 2003, 125, 3404.
20. (c) Peters, A.; Branda, N. R. Chem. Commun. 2003, 954.
21. (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.
22. (a) Roncali, J. Chem. Rev. 1992, 92, 711.
23. (b) Audebert, P.; Catel, J.-M.; Le Coustumer, G.; Duchenet, V.; Hapiot, P. J. Phys. Chem. 1995, 99, 11923.
24. (c) Martínez, F.; Retuert, J.; Neculqueo, G. Int. J. Polym. Mater. 1995, 28, 51.
25. (d) Krische, B.; Hellberg J.; Lilja, C. J. Chem. Soc., Chem. Commun. 1987, 1476.
26. (a) Peglow, T.; Blechert, S.; Steckhan, E. Chem. Eur. J. 1998, 4, 107 and references therein.
27. (b) Chiba, K.; Miura, T.; Kim, S.; Kitano, Y.; Tada, M. J. Am. Chem. Soc. 2001, 123, 11314.
28. Carell, T.; Epple, R.; Gramblich, V. Angew. Chem., Int. Ed. Engl. 1996, 35, 620.
29. (a) Saettel, N. J.; Oxgaard, J.; Wiest, O. Eur. J. Org. Chem. 2001, 1429.
30. (b) Radosevich, A. T.; Wiest, O. J. Org. Chem. 2001, 66, 5808.
31. (a) Nadjo, L.; Savéant, J.-M. J. Electroanal. Chem. 1973, 48, 113.
32. (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; Vol. 6, Ch. 2.1, p 305.
33. (a) Lucas, L. N.; de Jong, J. J. D.; van Esch, J. H.; Kellogg, R. M.; Feringa, B. L. Eur. J. Org. Chem. 2003, 1555.
34. (b) Lucas, L. N.; van Esch, J. H.; Kellogg, R. M.; Feringa, B. L. Chem. Commun. 1998, 2313.
35. Fürstner, A.; Huppers, A. J. Am. Chem. Soc. 1995, 117, 4468.
36. Tsivgoulis, G. M.; Lehn, J.-M. Angew. Chem., Int. Ed. Engl. 1995, 34, 1119.
37. (a) Myles, A. J.; Branda, N. R. Macromolecule 2003, 36, 298.
38. (b) Norsten, T. B.; Branda, N. R. J. Am. Chem. Soc. 2001, 123, 1784.
39. Negishi, E.; Liu F. In Metal-Catalyzed Cross Coupling Reactions; Diederich, F., Stang, P. J., Eds.; Wiley-WCH; New York, 1998; p 32.
40. 1H NMR and cyclic voltammetry were used to determine the compositions of all photostationary states.
41. (e) Smie, A.; Synowczyk, A.; Heinze, J.; Alle, R.; Tschuncky, P.; Gotz, G.; Bauerle, P. J. Electroanal. Chem. 1998, 452, 87.
42. β,β-Dimerization can take place when the α-positions in the thiophene ring positions are blocked. For recently published examples see (a) Raimundo, J. M.; Levillain, E.; Gallego-Planas, N.; Roncali, J. Electrochem. Commun. 2000, 211.
43. (b) Salhi, F.; Lee, B.; Metz, C.; Bottomley, L. A.; Collard, D. M. Org. Lett. 2002, 4 (19), 3195.
44. 3]. UV/Vis: Open form: 317 nm; closed form: 535 nm (blue). It is important to remark that similar red-shifts (from 240 to 317 nm, open form, and from 450 to 535) have been found in the literature between monomers and dimers in their open and closed forms for covalently link double 1,2-dithienylethenes, see references: (a) Stellacci, F.; Toscano, F.; Gallazi, M. C.; Zerbi, G. Synth. Met. 1999, 979.
45. (b) Stellacci, F.; Bertarelli, C.; Toscano, F.; Gallazi, M. C.; Zotti, G.; Zerbi, G. Adv. Mater. 1999, 11, 292.
46. (c) Peters, A.; Branda, N. R. Adv. Mater. Opt. Electron. 2000, 10, 245.
47. (a) Moore, A. J.; Bryce, M. R.; Batanov, A. S.; Green, A.; Howard, J. A. K.; McKervey, M. A.; McGuigan, P.; Ledoux, I.; Orti, E.; Viruela, R.; Viruela, P. M.; Tarbit, B. J. Mater. Chem. 1998, 8, 1173.
48. (b) ΔE was obtained for 2c by differential pulse voltammetry with a rotating glassy carbon electrode (1000 rev/min) with pulses of 70 ms duration and 25 mV amplitude, see: Richardson, D. E.; Taube, H. Inorg. Chem. 1981, 20, 1278.
49. •+, the present work does not give any evidence to solve the uncertainty of ECE/DISP1 in the last step of the mechanism. For further information, see: Amatore, C.; Saveant, J.-M. J. Electroanal. Chem. 1979, 21, 102.
50. To determine, with better accuracy, the kinetic constant value, numerical simulations of the voltammograms were performed with the commercial BAS Digisim Simulator 2.1.
51. (a) Andrieux, C. P.; Saveant, J.-M.; Tallec, A.; Tardivel, R.; Tardy, C. J. Am. Chem. Soc. 1996, 118, 9788.
52. (b) Andrieux, C. P.; Saveant, J.-M.; Tallec, A.; Tardivel, R.; Tardy, C. J. Am. Chem. Soc. 1997, 119, 2420.
53. (c) Pause L.; Robert, M.; Saveant, J.-M. J. Am. Chem. Soc. 1999, 121, 7158.
54. (d) Pause L.; Robert, M.; Saveant, J.-M. J. Am. Chem. Soc. 2001, 123, 4886.
55. (e) Holder, G. N.; McClure, L. L.; Farrar, D. G. Chem. Educator 2002, 7, 74 and references therein.
56. The same result was obtained for compound 10c. Controlled potential electrolysis at 1.8 V vs SCE of a solution in ACN of ring-closed isomer 10c after the passage of IF leads to the open isomer as the mechanistic study predicts (see Supporting Information) and in contrast to a recent study published in the literature (see ref lie). The contradiction might be due to the potential applied in the above-mentioned publication, which could have been too low for oxidizing the closed isomer. Compound 10c is very difficult to oxidize due to the presence of the perfluorocyclo-pentene ring and of the acceptor aldehyde substituents.
57. Zhi, J. F.; Baba, R.; Hashimiyo, K.; Fujishima, A. J. Photochem. Photobiol. A: Chemistry 1995, 92, 91.
58. Bally, T.; Borden, W. T. Rev. Comput. Chem. 1999, 13, 1.
59. Garoufalis, C. S.; Zdetsis, A. D. Phys. Rev. Lett. 2001, 87, 276402-1.
60. Guo, J. D.; Luo, Y.; Himo, F. Chem. Phys. Lett. 2002, 366, 73.
61. Schmidt, M. W.; Balbrige, K. K.; Boatz, J. A.; Elbert, S. T.; Gordon, M. S.; Jensen, J. H.; Koseki, K.; Matsunaga, N.; Nguyen, K. A.; Su, S.; Windus, T. L.; Depuis M.; Montgomery, J. A. J. Comput. Chem. 1993, 14, 1347.
62. (a) Becke, A. D. J. Chem. Phys. 1993, 98, 5648.
63. (b) Lee, C.; Yang, W.; Parr, R. G. Phys. Rev. 1988, B37, 785.
64. (a) Stevens, W. J.; Basch, H.; Krauss, M. J. Chem. Phys. 1984, 87, 6026.
65. (b) Stevens, W. J.; Krauss, M.; Basch, H.; Jasien, P. G. Can. J. Chem. 1992, 70, 612.
66. (c) Cundari, T. R.; Stevens, W. J. J. Chem. Phys. 1993, 98, 5555.
67. Rappe, A. K.; Casewit, C. J.; Colwell, K. S.; Goddard, W. A., III; Skiff, W. M. J. Am. Chem. Soc. 1992, 114, 10024.
68. 2, Accelrys, San Diego, CA, www.accelrys.com.