Photochemical control of conductivity of polythiophenes with photochromic moieties

Abstract

The synthesis, optical and electrical properties of azobenzene-substituted polythiophene derivatives at the 3-position are reported: one without flexible spacer (PT0) and the other with a hexamethylene spacer (PT6). Photoirradiation of PT6 at 366 nm caused trans-cis isomerization of the azobenzene moiety and this photochromic reaction induced a change in conductivity of the thin film of PT6: the conductivity was 1.1×10^–7 S cm^–1 before irradiation and 8.3×10^–7 S cm^–1 after photoirradiation. After annealing, the conductivity of the film returned to the initial value. The conductivity of a compound without the azobenzene moiety, α-terthienyl (αT3), showed no change on photoirradiation at 366 nm.

References

1. J. Roncali, Chem. Rev., 1992, 92, 711.
2. Handbook of Conducting Polymers, ed. T. A. Skotheim, Dekker:New York, 1986, Vol. 1 and 2.
3. R. D. McCullough and S. P. Williams, J. Am. Chem. Soc., 1993, 115, 11608.
4. R. D. McCullough, R. D. Lowe, M. Jayaraman and D. L. Anderson, J. Org. Chem., 1993, 58, 904.
5. T.-A. Chen and R. D. Rieke, J. Am. Chem. Soc., 1992, 114, 10087.
6. C. A. Sandstedt, R. D. Rieke and C. J. Eckhardt, Chem. Mater., 1995, 7, 1057.
7. K. Faid, M. Frechette, M. Ranger, L. Mazerolle, I. Levesque, M. Leclerc, T.-A. Chen and R. D. Rieke, Chem. Mater., 1995, 7, 1390.
8. G. H. Brown, Photochromism, Techniques of Chemistry, Vol. III, Wiley Interscience, 1971.
9. M. Irie, M. Miyatake, K. Uchida and T. Eriguchi, J. Am. Chem. Soc., 1994, 116, 9894.
10. T. Saika, M. Irie and T. Shimidzu, J. Chem. Soc., Chem. Commun., 1994, 2123.
11. K. Uchida and M. Irie, J. Am. Chem. Soc., 1993, 115, 6442.
12. K. Sayo and M. Irie, J. Phys. Chem., 1992, 96, 7671.
13. G. M. Tsivgoulis and J.-M. Lehn, Angew. Chem., Int. Ed. Engl., 1995, 34, 1119.
14. A. Yassar, C. Moustrou, H. Korri-Youssoufi, A. Samat, R. Gugliemetti and F. Garnier, Macromolecules, 1995, 28, 4548.
15. I. Levesque and M. Leclerc, Macromolecules, 1997, 30, 4347.
16. L. M. Goldenberg, M. R. Bryce, S. Wegener, M. C. Petty, J. P. Cresswell, I. K. Lednev, R. E. Hester and J. N. Moore, J. Mater. Chem., 1997, 7, 2033.
17. S. A. Chen and C. S. Liao, Synth. Met., 1993, 55–57, 4950.
18. S. A. Chen and C. S. Liao, Makromol. Chem. Rapid Commun., 1993, 14, 69.
19. T. Ikeda, T. Miyamoto, S. Kurihara, M. Tsukada and S. Tazuke, Mol. Cryst. Liq. Cryst., 1991, 182B, 357.
20. A. Hassner and V. Alexanian, Tetrahedron Lett., 1989, 19, 307.
21. K. Yoshino, S. Hayashi and R. Sugimoto, Jpn. J. Appl. Phys., 1984, 23, L899.
22. T. Yamamoto, K. Sanechika and A. Yamamoto, Bull. Chem. Soc. Jpn., 1983, 56, 1497, 1503.
23. T. Yamamoto, J. Synth. Org. Chem. Jpn., 1995, 53, 77.
24. M. R. Anderson, D. Selse, H. Jarvinen, T. Hjertberg, O. Inganas, O. Wennerstorm and J. E. Osterholm, Macromolecules, 1994, 27, 6503.
25. R. M. S. Maior, K. Hinkelmann, H. Eckent and F. Wudl, Macromolecules, 1990, 23, 1268.
26. M. Sato and H. Morii, Macromolecules, 1991, 24, 1196.
27. M. Leclerc, M. F. Diaz and G. Wegner, Makromol. Chem., 1989, 190, 3105.
28. T. Yamamoto, D. Komarudin, M. Arai, B. L. Lee, H. Suganuma, N. Asakawa, Y. Inoue, K. Kubota, S. Sasaki, T. Fukuda and H. Matsuda, J. Am. Chem. Soc., 1998, 120, 2047.
29. R. D. McCullough, R. D. Lowe, M. Jayaraman and D. L. Anderson, J. Org. Chem., 1993, 58, 904.
30. G. Barbarella, A. Bongini and M. Zambianchi, Macromolecules, 1994, 27, 3039.
31. Y. Miyazaki and T. Yamamoto, Synth. Met., 1994, 64, 69.
32. P. L. Burtlett and K. Birkin, Synth. Met., 1993, 61, 15.
33. T. M. Sweger and M. J. Marsella, Adv. Mater., 1994, 6, 595.
34. T.-A. Chen, X. Wu and R. D. Rieke, J. Am. Chem. Soc., 1995, 117, 233.
35. R. D. McCullough and S. P. Williams, J. Am. Chem. Soc., 1993, 115, 4910.