Multifunctional Diarylethenes

Molecular Switches, Second Edition

Volumn 1, Issue , 2011, Pages 1-35

  Warford, C Chad ^a   Lemieux, Vincent ^a   Branda, Neil R ^a  

^a SIMON FRASER UNIVERSITY   (Canada)

Author keywords

Dithienylethene; Electrochemical behaviour; Gated photochromism; Photoisomers; Photoswitching; Ring closing; Ring opening

Indexed keywords

EID: 84886034175     PISSN: None     EISSN: None     Source Type: Book    
DOI: 10.1002/9783527634408.ch1     Document Type: Chapter

References (81)

1. Irie, M. (2000) Chem. Rev., 100, 1685-1716.
2. Irie, M., Sakemura, K., Okinaka, M. and Uchida, K. (1995) J. Org. Chem., 60, 8305-8309.
3. Nakayama, Y., Hayashi, K. and Irie, M. (1991) Bull. Chem. Soc. Jpn., 64, 789-795.
4. Nakagawa, T., Hasegawa, Y. and Kawai, T. (2008) J. Phys. Chem. A, 112, 5096-5103.
5. Fernandez-Acebes, A. and Lehn, J.-M. (1999) Chem. Eur. J., 5, 3285-3292.
6. Murguly, E., Norsten, T. and Branda, N.R. (2001) Angew. Chem. Int. Ed., 40, 1752-1755.
7. Zhao, H., Al-Atar, U., Pace, T., Bohne, C. and Branda, N. (2008) J. Photochem. Photobiol., 200, 74-82.
8. Yamaguchi, T., Uchida, K. and Irie, M. (1997) J. Am. Chem. Soc., 119, 6066-6071.
9. Kodani, T., Matsuda, K., Yamada, T., Kobatake, S. and Irie, M. (2000) J. Am. Chem. Soc., 122, 9631-9637.
10. Yamamoto, S., Matsuda, K. and Irie, M. (2003) Org. Lett., 5, 1769-1772.
11. Matsuda, K., Yamamoto, S. and Irie, M. (2001) Tetrahedron Lett., 42, 7291-7293.
12. Yamagchi, T., Nomiyama, K., Isayama, M. and Irie, M. (2004) Adv. Mater., 16, 643-645.
13. Matsuda, K. and Irie, M. (2005) Polyhedron, 24, 2477-2483.
14. Tanifuji, N., Irie, M. and Matsuda, K. (2005) J. Am. Chem. Soc., 127, 13344-13353.
15. Sun, L. and Tian, H. (2006) Tetrahedron Lett., 47, 9227-9231.
16. Dulic, D., van der Molen, S.J., Kudernac, T., Jonkman, H.T., de Jong, J.J.D., Bowden, T.N., van Esch, J., Feringa, B.L. and van Wees, B.J. (2003) Phys. Rev. Lett., 91, 207402.
17. Matsuda, K., Yamaguchi, H., Sakano, T., Ikeda, M., Tanifuji, N. and Irie, M. (2008) J. Phys. Chem.C, 112, 17005-17010.
18. Kronemeijer, A.J., Akkerman, H.B., Kudernac, T., van Wees, B.J., Feringa, B.L., Blom, P.W.M. and de Boer, B. (2008) Adv. Mater., 20, 1467-1473.
19. Whalley, A.C., Steigerwald, M.L., Guo, X. and Nuckolls, C. (2007) J. Am. Chem. Soc., 129, 12590-12591.
20. Gorodetsky, B. (2008) The design of dual-mode photochromic and electrochromic 1,2-Dithienylcyclopentene dyes. Ph.D. thesis. Department of Chemistry, Simon Fraser University. Burnaby, BC, Canada.
21. Jeong, Y.C., Yang, S.I., Kim, E. and Ahn, K.H. (2006) Tetrahedron, 62, 5855-5861.
22. Irie, M., Fukaminato, T., Sasaki, T., Tamai, N. and Kawai, T. (2002) Nature, 420, 759-760.
23. Jeong, Y.C., Yang, S.I., Kim, E. and Ahn, K.H. (2006) Macromol. Rapid Commun., 27, 1769-1773.
24. Finden, J., Kunz, T., Branda, N.R. and Wolf, M.O. (2008) Adv. Mater., 20, 1998-2002.
25. Choi, H., Lee, H., Kang, Y.J., Kim, E., Kang, S.O. and Ko, J. (2005) J. Org. Chem., 70, 8291-8297.
26. Ikeda, M., Tanifuji, N., Yamaguchi, H., Irie, M. and Matsuda, K. (2007) Chem. Commun., 13, 1355-1357.
27. Tsuijioka, T., Hamada, Y., Shibata, K., Taniguchi, A. and Fuyuki, T. (2001) Appl. Phys. Lett., 78, 2282-2284.
28. Matsuda, K. and Irie, M. (2005) Polyhedron, 24, 2477-2483.
29. Yokoyama, Y., Shiozawa, T., Tani, Y. and Ubukata, T. (2009) Angew. Chem. Int. Ed., 48, 4521-4523.
30. Wigglesworth, T.J., Sud, D., Norsten, T.B., Lekhi, V.S. and Branda, N.R. (2005) J. Am. Chem. Soc., 127, 7272-7273.
31. Tsujika, T., Sesumi, Y., Tagaki, R., Masui, K., Yokojima, S., Uchida, K. and Nakamura, S. (2008) J. Am. Chem. Soc., 130, 10740-10747.
32. de Jong, J.J.D., Tiemersma-Wegman, T.D., van Esch, J.H. and Feringa, B.L. (2005) J. Am. Chem. Soc., 127, 13804-13805.
33. Tian, H. and Wang, S. (2007) Chem. Commun., 8, 781-792.
34. Cusido, J., Deniz, E. and Raymo, F.M. (2009) Eur. J. Org. Chem., 13, 2031-2045.
35. Raymo, F.M. Tomasulo M. (2005) Chem. Soc. Rev., 34, 327-336.
36. Odo, Y., Fukaminato, T. and Irie, M. (2007) Chem. Lett., 36, 240-241.
37. Koshido, T., Kawai, T. and Yoshino, K. (1995) J. Phys. Chem., 99, 6110-6114.
38. Gorodetsky, B. and Branda, N.R. (2007) Adv. Funct. Mater., 17, 786-796.
39. Gorodetsky, B., Samachetty, H., Donkers, R.L., Workentin, M.S. and Branda, N.R. (2004) Angew. Chem. Int. Ed., 43, 2812-2815.
40. Fraysse, S., Coudret, C. and Launey, J.P. (2000) Eur. J. Inorg. Chem., 7, 1581-1590.
41. Peters, A. and Branda, N.R. (2003) J. Am. Chem. Soc., 125, 3404-3405.
42. Peters, A. and Branda, N.R. (2003) Chem. Commun., 8, 954-955.
43. Guirado, G., Coudret, C., Hliwa, M. and Launay, J.-P. (2005) J. Phys. Chem. B, 109, 17445-17459.
44. Zhou, X.-H., Zhang, F.-S., Yuan, P., Sun, F., Pu, S.-Z., Zhao, F.-Q. and Tung, C.-H. (2004) Chem. Lett., 33, 1006-1007.
45. Areephong, J., Browne, W.R., Katsonis, N. and Feringa, B.L. (2006) Chem. Commun., 37, 3930-3932.
46. Moriyama, Y., Matsuda, K., Tanifuji, N., Irie, S. and Irie, M. (2005) Org. Lett., 7, 3315-3318.
47. Browne, W.R., de Jong, J.J.D., Kudernac, T., Walko, M., Lucas, L.N., Uchida, K., van Esch, J.H. and Feringa, B.L. (2005) Chem. Eur. J., 11, 6414-6429.
48. Browne, W.R., de Jong, J.J.D., Kudernac, T., Walko, M., Lucas, L.N., Uchida, K., van Esch, J.H. and Feringa, B.L. (2005) Chem. Eur. J., 11, 6430-6441.
49. Takeshita, M., Uchida, K. and Irie, M. (1996) Chem. Commun., 15, 1807-1808.
50. Takeshita, M. and Irie, M. (1998) Tetrahedron Lett., 39, 613-616.
51. Takeshita, M. and Irie, M. (1998) J. Org. Chem., 63, 6643-6649.
52. Kawai, S.H. (1998) Tetrahedron Lett., 39, 4445-4448.
53. Takeshita, M., Soong, C.F. and Irie, M. (1998) Tetrahedron Lett., 39, 7717-7720.
54. Mulder, A., Jukovic, A.A., van Leeuwen, F.W.B., Kooijman, H., Spek, A.L., Huskens, J. and Reinhoudt, D.N. (2004) Chem. Eur. J., 10, 1114-1123.
55. Sud, D., Norsten, T.B. and Branda, N.R. (2005) Angew. Chem. Int. Ed., 44, 2019-2021.
56. Vomasta, D., Hogner, C., Branda, N.R. and Konig, B. (2008) Angew. Chem. Int. Ed., 47, 7644-7647.
57. Kawai, S.H., Gilat, S.L. and Lehn, J.-M. (1999) Eur. J. Org. Chem., 9, 2359-2366.
58. Odo, Y., Matsuda, K. and Irie, M. (2006) Chem. Eur. J., 12, 4283-4288.
59. Malval, J.-P., Gosse, I., Morand, J.-P. and Lapouyade, R. (2002) J. Am. Chem. Soc., 124, 904-905.
60. Samachetty, H.D. and Branda, N.R. (2005) Chem. Commun., 22, 2840-2842.
61. Samachetty, H.D. and Branda, N.R. (2006) Pure Appl. Chem., 78, 2351-2359.
62. Samachetty, H.D. (2007) Modulation of chemical reactivity using photoresponsive dithienylethene. Ph.D. thesis. Department of Chemistry, Simon Fraser University. Burnaby, BC, Canada.
63. Lemieux, V., Spantulescu, M.D., Baldridge, K.K. and Branda, N.R. (2008) Angew. Chem. Int. Ed., 120, 5112-5115.
64. Sud, D., Wigglesworth, T.J. and Branda, N.R. (2007) Angew. Chem. Int. Ed., 46, 8017-8019.
65. Nicolaou, K.C., Zuccarello, G., Riemer, C., Estevez, V.A. and Dai, W.M. (1991) Angew. Chem. Int. Ed. Engl., 30, 1387-1416.
66. Compiled by McNaught, A. D. and Wilkinson, A. (eds) (1997) IUPAC compendium of chemical terminology, The ''Gold Book'', 2nd edn, Blackwell Scientific Publications, Oxford, 169.
67. Irie, M., Miyatake, O., Uchida, K. and Eriguchi, T. (1994) J. Am. Chem. Soc., 116, 9894-9900.
68. Irie, M., Miyatake, O. and Uchida, K. (1992) J. Am. Chem. Soc., 114, 8715-8716.
69. Irie, M., Miyatake, O., Sumiya, R., Hanazawa, M., Horikawa, Y. and Uchida, K. (1994) Mol. Cryst. Liq. Cryst., 246, 155-158.
70. Walko, M. and Feringa, B.L. (2005) Mol. Cryst. Liq. Cryst., 431, 249-253.
71. Qin, B., Yao, R., Zhao, X. and Tian, H. (2003) Org. Biomol. Chem., 1, 2187-2191.
72. Sud, D., Norsten, T.B. and Branda, N.R. (2004) Angew. Chem. Int. Ed., 44, 2019-2021.
73. Kawai, S.H., Gilat, S.L. and Lehn, J.-M. (1994) J. Chem. Soc., Chem. Commun., 8, 1011-1013.
74. Kawai, S.H., Gilat, S.L., Ponsinet, R. and Lehn, J.-M. (1995) Chem. Eur. J., 1, 285-293.
75. Ohsumi, M., Fukaminato, T. and Irie, M. (2005) Chem. Commun., 31, 3921-3923.
76. Kuhni, J. and Belser, P. (2007) Org. Lett., 9, 1915-1918.
77. Uchida, K., Matsuoka, T., Kobatake, S., Yamaguchi, T. and Irie, M. (2001) Tetrahedron, 57, 4559-4565.
78. Chen, Z., Zhao, S., Li, Z., Zhang, Z. and Zhang, F. (2007) Sci. China Ser. B-Chem., 50, 581-586.
79. Lemieux, V., Gauthier, S., Branda, N.R. (2006) Angew. Chem. Int. Ed., 45, 6820-6824.
80. Lemieux, V. and Branda, N.R. (2005) Org. Lett., 7, 2969-2972.
81. Raymond Bonnett (2000) Chemical Aspects of Photodynamic Therapy., Gordon and Breach Science Publishers, Amsterdam.