Synthesis and Electronic Properties of Aldehyde End-Capped Thiophene Oligomers and Other α,ω-Substituted Sexithiophenes

Chemistry of Materials

Volumn 8, Issue 11, 1996, Pages 2659-2666

  Wei, Yen ^a   Yang, Yun ^a   Yeh, Jui Ming ^a  

^a DREXEL UNIVERSITY   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 0000593523     PISSN: 08974756     EISSN: None     Source Type: Journal    
DOI: 10.1021/cm960182p     Document Type: Article

References (57)

1. (a) Tourillon, G. In Handbook of Conducting Polymers; Skotheim, T. A., Ed.; Marcel Dekker: New York, 1986; Vol. 1, p 293.
2. (b) Roncali, J. Chem. Rev. 1992, 92, 711.
3. (a) Garnier, F.; Horowitz, G.; Peng, X. Z.; Fichou, D. Adv. Mater. 1990, 2, 592.
4. (b) Garnier, F.; Horowitz, X. Z.; Fichou, D. Synth. Met. 1989, 28, 705.
5. (c) Zhao, M. T.; Singh, B. P.; Prasad, P. N. J. Chem. Phys. 1988, 89, 5535.
6. (d) Zotti, G.; Berlin, A.; Pagani, G.; Schiavon, G.; Zecchin, S. Adv. Mater. 1994, 6, 231.
7. (a) Torsi, L.; Dodableapur, A.; Katz, H. E. Polym. Mater. Sci. Eng. 1995, 72, 569.
8. (b) Servet, B.; Horowitz, G.; Ries, S.; Lagorsse, O.; Alnot, P.; Yassar, A.; Deloffre, F.; Srivastava, P.; Hajlaoui, R.; Lang, P.; Garnier, F. Chem. Mater. 1994, 6, 1809.
9. (c) Garnier, F.; Hajlaoui, R.; Yassar, A.; Srivasyava, P. Science 1994, 265, 1684.
10. (d) Garnier, F.; Horowitz, G.; Peng, X. Z.; Fichou, D. Synth. Met. 1991, 45, 163.
11. (e) Horowitz, G.; Fichou, D.; Peng, X. Z.; Garnier, F. Synth. Met. 1991, 41-43, 1127.
12. (a) Horowitz, G.; Delannoy, P.; Bouchriha, H.; Deloffre, F.; Fave, J. L.; Garnier, F.; Hajlaoui, R.; Heyman, M.; Kouki, F.; Valat, P.; Wintgens, V.; Yassar, A. Adv. Mater. 1994, 6, 752.
13. (b) Uchiyama, K.; Akimichi, H.; Hotta, S.; Noge, H.; Sakaki, H. Synth. Met. 1994, 63, 57-59.
14. (c) Geiger, F.; Stoldt, M.; Schweizer, H.; Bäuerle, P.; Umbach, E. Adv. Mater. 1993, 5, 922.
15. (d) Grem, G.; Leditzky, G.; Ulrich, B.; Leising, G. Adv. Mater. 1992, 4, 36.
16. (e) Braun, D.; Heeger, A. J. Appl. Phys. Lett. 1991, 58, 1989.
17. (f) Burroughes, J. H.; Bradley, D. C. C.; Brown, A. R.; Marks, R. N.; Mcklay, K.; Friend, R. H. Nature 1990,
18. Noma, N.; Tsuzuki, T.; Shirota, Y. Adv. Mater. 1995, 7, 647.
19. For a review, see: Nakayama, J.; Konishi, T.; Hoshino, M. Heterocycles 1988, 27, 1731.
20. (a) Yu, Y.; Gunice, E.; Zinger, B.; Miller, L. L. J. Am. Chem. Soc. 1996, 118, 1013.
21. (b) Herrema, J. K.; Wildeman, J.; van Bolhuis, F.; Hadziioannou, G. Synth. Met. 1993, 60, 239.
22. (c) Bäuerle, P.; Pfau, F.; Schlupp, H.; Wüthner, F.; Gaudl, K.-U; Karo, B.-M.; Fischer, P. J. Chem. Soc., Perkin Trans. 2 1993, 489.
23. (d) Yassar, A.; Delabouglise, D.; Hmyene, M.; Nessak, B.; Horowitz, G.; Garnier, F. Adv. Mater. 1992, 4, 490.
24. (e) Tour, J. M.; Wu, R. Macromolecules 1992, 25, 1901.
25. (f) Ten Hoeve, W.; Wynberg, H.; Havinga, E. E.; Meijer, E. W. J. Am. Chem. Soc. 1991, 113, 5887.
26. (g) Havinga, E. E.; Rotte, I.; Meijer, E. W.; Ten Hoeve, W.; Wynberg, H. Synth. Met. 1991, 43-43, 473.
27. (h) Xu, Z.; Fichou, D.; Horowitz, G.; Garnier, F. J. Electroanal. Chem. 1989, 267, 339.
28. (i) Van Pham, C.; Burkhardt, A.; Shabana, R.; Cunningham, D. D.; Mark, H. B., Jr.; Zimmer, H. Phosphorous, Sulfur Silicon 1989, 46, 153.
29. (a) Katz, H. E.; Dodabalapur, A.; Torsi, L.; Elder, D. Chem. Mater. 1995, 7, 2238.
30. (b) Yassar, A.; Garnier, F.; Doloffre, F.; Horowitz, G.; Ricard, L. Adv. Mater. 1994, 6, 660.
31. (c) Garnier, F.; Yassar, A.; Hajlaoui, R.; Horowitz, G.; Deloffre, F.; Servet, B.; Ries, S.; Alnot, P. J. Am. Chem. Soc. 1993, 115, 8716.
32. (d) Deatri, S.; Mascherpa, M.; Porzio, W. Synth. Met. 1995, 69, 287.
33. (e) Bäuerle, P. Adv. Mater. 1992, 4, 102.
34. (f) Hotta, S.; Waragai, K. J. Phys. Chem. 1993, 97, 7427.
35. (g) Zotti, G.; Schiavon, G.; Berlin, A.; Pagani, G. Synth. Met. 1993, 61, 81.
36. (a) Wei, Y.; Jang, G.-W.; Chan, C.-C. J. Polym. Sci., Part C 1990, 28, 219.
37. (b) Wei, Y.; Jang, G.-W.; Chan, C.-C.; Tian, J. Chem. Mater. 1991, 3, 888.
38. (c) Wei, Y.; Tian, J. Macromolecules 1993, 26, 457.
39. (d) Wei, Y.; Tian, J.; Glahn, D.; Wang, B.; Chu, D. J. Phys. Chem. 1993, 97, 12842.
40. (e) Wei, Y.; Tian, J.; Hsueh, K. F. Polym. Mater. Sci. Eng. 1994, 71, 586.
41. max value is given in the present article (Table 1, compound 10).
42. (a) Stille, J. K. Angew. Chem., Int. Ed. Engl. 1986, 25, 508.
43. (b) Mckean, D. R.; Perrinello, G.; Renaldo, A. F.; Stille, J. K. J. Org. Chem. 1987, 52, 422.
44. (a) Colon, I.; Kelsey, D. R. J. Org. Chem. 1986, 51, 2627.
45. (b) Nakayama, J.; Konishi, T.; Murabayashi, S.; Hoshino, M. Heterocycles 1987, 26, 1793.
46. (a) Bao, Z.; Chan, W. K.; Yu, L. J. Am. Chem. Soc. 1995, 117, 12426 and references therein.
47. (b) McCullough, R. D.; Williams, S. P. J. Am. Chem. Soc. 1993, 115, 11608.
48. (c) McCullough, R. D.; Lowe, R. D.; Jayaraman, M,; Anderson, D. L. J. Org. Chem. 1993, 58, 904.
49. (d) Swager, T. M.; Marsella, M. J.; Zhou, Q.; Goldfinger, M. B. J. Macromol. Sci. Pure Appl. Chem. 1994, A31, 1893.
50. 3) showed 2,5-dideuteriothiophene, δ 6.99 (s), to be the only product.
51. 3) showed 5,5′-dideuterium-2,2′-bithiophene, δ 7.01 (d, J = 3.5 Hz, 2H), 7.17 (d, J = 3.5 Hz, 2H), to be the only product.
52. (a) Tsumura, A.; Koezuka, H.; Ando, T. Synth. Met. 1988, 25, 11.
53. (b) Roncali, J.; Garnier, F.; Lemaire, M.; Garreau, R. Synth. Met. 1986, 15, 323.
54. Paloheimo, J.; Kuivalainen, P.; Stubb, H.; Vuorimaa, E.; Yli-Lahti, P. Appl. Phys. Lett. 1990, 56, 1157.
55. Bäuerle, P.; Götz, G.; Hiller, M.; Scheib, S.; Fischer, T.; Segelbacher, U.; Bennati, M.; Grupp, A.; Mehring, M.; Schmelzer, M.; Roth, S.; Egelhaaf, H. J.; Oelkrug, D.; Emele, P.; Port, H. Synth. Met. 1993, 61, 71.
56. Lescot, E., Jr.; Bûû-Hoi, N. P.; Xuong, N. D. J. Chem. Soc. 1959, 3234.
57. D'Auria, M.; De Mico, A.; D'Onofrio, F.; Piancatelli, G. J. Org. Chem. 1987, 52, 5243.