Temperature gating of the ring-opening process in diarylethene molecular switches

Advanced Materials

Volumn 19, Issue 19, 2007, Pages 2898-2902

  Dulić, Diana ^a,c   Kudernac, Tibor ^b   Pužys, Audrius ^a,d   Feringa, Ben L ^b   Van Wees, Bart J ^a  

^a UNIVERSITY OF GRONINGEN   (Netherlands)

^b UNIVERSITY OF GRONINGEN   (Netherlands)

^c SERVICE DE PHYSIQUE DE L ETAT CONDENSÉ   (France)

^d VIENNA UNIVERSITY OF TECHNOLOGY   (Austria)

Author keywords

[No Author keywords available]

Indexed keywords

ABSORPTION SPECTROSCOPY; ACTIVATION ENERGY; AROMATIC COMPOUNDS; LIGHT SOURCES; RING OPENING POLYMERIZATION; THERMAL EFFECTS;

DITHIENYLCYCLOPENTENES; MOLECULAR SWITCHES; RING-OPENING PROCESS;

MOLECULAR ELECTRONICS;

EID: 35348979217     PISSN: 09359648     EISSN: None     Source Type: Journal    
DOI: 10.1002/adma.200700161     Document Type: Article

References (54)

1. a) M. Irie, Chem. Rev. 2000, 100, 1685.
2. b) B. L. Feringa, Molecular Switches, WILEY-VCH, Weinheim, Germany 2001.
3. c) J.-M. Lehn, in Supramolecular Chemistry-Concepts and Perspectives, Wiley-VCH, Weinheim, Germany 1995, Ch. 8.
4. a) A. Fernandez-Asebes, J.-M. Lehn, Adv. Mater. 1999, 11, 910.
5. b) M. Morimoto, S. Kobatake, M. Irie, Adv. Mater. 2002, 14, 1027.
6. c) K. Uchida, M. Saito, A. Murakami, T. Kobayashi, S. Nakamura, M. Irie, Chem. Eur. J. 2005, 534.
7. a) T. Kawai, Y. Nakashima, M. Irie, Adv. Mater. 2005, 17, 309.
8. b) A. J. Myles, Z. Zhang, G. Liu, N. R. Branda, Org. Lett. 2000, 2, 2749.
9. c) H. Nakashima, M. Irie, Macromol. Chem. Phys. 1999, 200, 684.
10. J. C. Crano, R. X Guglielmeti, Organic Photochromic and Thermochromic compounds. Vol. 2, Plenum Press, New York 1999.
11. a) M. Irie, T. Fukaminato, T. Sasaki, N. Tamai, T. Kawai, Nature 2002, 420, 759.
12. b) J. J. D. de Jong, L. N. Lucas, R. M. Kellogg, J. H. van Esch, B. L. Feringa, Science 2004, 304, 278.
13. c) H. Miyasaka. T. Nobuto, A. Itaya, N. Tamai, M. Irie, Chem. Phys. Lett. 1997, 269, 281.
14. d) J. C. Owrutsky, H. H. Nelson, A. P. Baronavski, O.-K. Kim, G. M. Tsivgoulis, S. L. Gilat, J.-M. Lehn, Chem. Phys. Lett. 1998, 293, 555.
15. a) K. Koshido, T. Kawai, T. Yoshino, Synth. Met. 1995, 73, 275.
16. b) Y. Kaneuchi, T. Kawai, K. Yoshino, M. Irie, Jpn. J. Appl. Phys., Part 1 1997, 36, 3736.
17. a) G. M. Tsivogulis, J. -M. Lehn, Angew. Chem. Int. Eng. Ed. 1995, 34, 1119.
18. b) A. Fernardez-Acebes, J.-M. Lehn, Chem. Eur. J. 1999, 5, 3285.
19. a) T. Norsten, N. R. Branda, J. Am. Chem. Soc. 2001, 123. 1784.
20. b) A. X Myles, N. R. Branda, Macromolecules 2003, 36, 298.
21. a) T. Kawai, T. Sasaki, M. Irie, Chem. Commun. 2001, 711.
22. b) M.-S. Kim, T. Kawai, M. Irie, Chem. Lett. 2001, 30, 702.
23. c) M. Irie, T. Fukaminato, T. Saski, N. Tamai, T. Kawai, Nature 2002, 420, 759.
24. J. Giordano, T. M. Jovin, M. Irie, E. A. Jares-Erijman, J. Am. Chem. Soc. 2002, 124, 7481.
25. A. Osuka, D. Fujikane, H. Shinmori, S. Kobatake, M. Irie, J. Org. Chem. 2001, 66, 5419.
26. H. Cho, E. Kim, Macromolecules 2002, 35, 8684.
27. a) H. Tian, B. Chen, H. Tu, K. Mullen, Adv. Mater. 2002, 14, 918.
28. b) Q. F. Luo, B. Z. Chen, M. Z. Wang, H. Tian, Adv. Func. Mater. 2003, 3, 233.
29. c) H. Tian, B. Qin, R. Yao, X. Zhao, S. Yang, Adv. Mater. 2003, 15, 2104.
30. a) T. Kawai, T. Koshido, M. Nakazono, K. Yoshino, Chem. Lett. 1993, 697.
31. b) S. L. Gilat, S. H. Kawai, J.-M. Lehn, Chem. Eur. J. 1995, 1, 275.
32. c) A. Peters, N. R. Branda, J. Am. Chem. Soc. 2003, 125, 3404.
33. d) W. R. Browne, J. J. D. de Jong, T. Kudernac, M. Walko, L. N. Lucas, K. Uchida, J. H. van Esch, B. L. Feringa, Chem. Eur. J. 2005, 11, 6414.
34. e) W. R. Browne, J. J. D. de Jong, T. Kudernac, M. Walko, L. N. Lucas, K. Uchida, J. H. van Esch, B. L. Feringa, Chem. Eur. J. 2005, 11, 6430.
35. f) J. Areephong, W. R. Browne, N. Katsonis, B. L. Feringa, Chem. Commun. 2006, 3930.
36. a) Y. Yokoyama, H. Shiraishi, Y. Tani, Y. Yokoyama, Y. Yamaguchi, J. Am. Chem. Soc. 2003, 125, 7194.
37. b) E. Murguly, T. B. Norsten, N. R. Branda, Angew. Chem. Int. Ed. 2001, 40, 1752.
38. c) C. Denekamp, B. L. Feringa, Adv. Mater. 1998, 10, 1080.
39. a) K. Matsuda, M. Irie, J. Am. Chem. Soc. 2000, 122, 7195.
40. b) K. Matsuda, M. Matsuo, S. Mizoguti, K. Higashiguchi, M. Irie, J. Phys. Chem. 2002, 106, 11 218.
41. a) S. Fraysse, C. Coudret, J. P. Launay, Eur. J. Inorg. Chem. 2000, 1581.
42. b) X M. Endtner, F. Effenberger, A. Hartschuh, H. Port, J Am. Chem. Soc. 2000, 122, 3037.
43. a) N. Katsonis, T. Kudernac, M. Walko, S. J. van der Molen, B. J. van Wees, B. L. Feringa, Adv. Mater. 2006, 18, 1397.
44. b) D. Dulic, S. J. van der Molen, T. Kudernac, H. T. Jonkman, J. J. D. De Jong, T. N. Bowden, J van Esch, B. L. Feringa, B. J. van Wees, Phys. Rev. Lett. 2003, 91, 207402.
45. c) S. J. van der Molen, H. Van der Vegte, T. Kudernac, I. Amin, B. L. Feringa, B. J. van Wees, Nanotechnology 2006, 77, 310.
46. d) J. He, F. Chen, P. A. Liddell, J. Andréasoon, S. D. Straight, D. Gust, T. A. Moore, A. L. Moore, J. Li, O. F. Sankey, S. M. Lindsay, Nanotechnology 2005, 16, 695.
47. a) M. Irie, T. Eriguchi, T. Takada, K. Uchida, Tetrahedron 1997, 53, 12263.
48. b) K. Kuldová, K. Tsyganenko, A. Corval, H. P. Trommsdorff, A. T. Bens, C. Kryschi, Synth. Met. 2000, 115, 163.
49. J. Reichert, H. B. Weber, M. Mayor, H. v. Löhneysen, Appl. Phys. Lett. 2003, 82, 4137.
50. Both forms (open and closed) are photoactive when UV light is employed.
51. J. Areephong, W. R. Browne, B. L. Feringa, Orig. Biomol Chem. 2007, 5, 1170.
52. a) Perhydro: T. Kudernac, D. Dulic, S. J. van der Molen, B. J. van Wees, B. L. Feringa, Mol. Cryst. Liq. Cryst. 2005, 430, 205.
53. b) Perfluoro: T. Kudernac, unpublished.
54. At room temperature the photostationary state corresponds to more than 99 % of the switch in the closed form. At low temperatures the content of the closed form should not change, because the ring closure is not affected, and ring opening is diminishing.