Regiocontrolled Synthesis of Poly(3-alkylthiophenes) Mediated by Rieke Zinc: Their Characterization and Solid-State Properties

Journal of the American Chemical Society

Volumn 117, Issue 1, 1995, Pages 233-244

  Chen, Tian An ^a   Wu, Xiaoming ^a   Rieke, Reuben D ^a  

^a UNIVERSITY OF NEBRASKA LINCOLN   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 0001714999     PISSN: 00027863     EISSN: 15205126     Source Type: Journal    
DOI: 10.1021/ja00106a027     Document Type: Article

References (37)

1. For recent reviews, see: (a) Patil, A. O.; Heeger, A. J.; Wudl, F. Chem. Rev. 1988, 88, 183–200. (b) Roncali, J. Chem. Rev. 1992, 92, 711–738. (c) Kaner, R. B.; MacDiarmid, A. G. Sci. Am. 1988 (Feb), 106–111. (d) Kanatzidis, M. G. Chem. Eng. News 1990 (Dec 3), 36–54. (e) Kovacic, P.; Jones, M. B. Chem. Rev. 1987, 87, 357–379. (f) Baughman, R. H.; Brédas, J. L.; Chance, R. R.; Elsenbaumer, R. L.; Shacklette, L. W. Chem. Rev. 1982, 82, 209–222. (g) Brédas, J. L.; Street, G. B. Acc. Chem. Res. 1985, 18, 309–315. (h) Skotheim, T. A. Handbook of Conducting Polymers; Marcel Dekker: New York, 1986. (i) Sandman, D. J. Trends Polym. Sci. 1994, 2, 44–55. (j) Clery, D. Science 1994, 263, 1700–1702.
2. Scrosati, B. Applications of Electroactive Polymers; Chapman & Hall: London, 1994. (b) Greenham, N. C.; Moratt, S. C.; Bradley, D. D. C.; Friend, R. H.; Holmes, A. B. Nature 1993, 365, 628–630. (c) Gustafsson, G.; Cao, Y.; Treacy, G. M.; Klavetter, F.; Colaneri, N.; Heeger, A. J. Nature 1992, 357, 477–479. (d) McCoy, C. H.; Wrighton, M. S. Chem. Mater. 1993, 5, 914–916. (e) Gamier, F.; Yassar, A.; Hajlaoui, R.; Horowitz, G.; Deloffre, F.; Servet, B.; Ries, S.; Alnot, P. J. Am. Chem. Soc. 1993, 115, 8716–8721. (f) Prasad, P. N.; Williams, D. J. Introduction to Nonlinear Optical Effects in Molecules & Polymers; John Wiley: New York, 1991. (g) Robitaille, L.; Leclerc, M.; Callender, C. L. Chem. Mater. 1993, 5, 1755–1761. (h) Chittibabu, K. G.; Li, L.; Kamath, M.; Kumar, J.; Tripathy, S. K. Chem. Mater. 1994, 6, 475–480.
3. Yamamoto, T.; Sanechika, K.; Yamamoto, A. J. Polym. Sci., Polym. Lett. Ed. 1980, 18, 9–12. (b) Lin, J. W.-P.; Dudek, L. P. J. Polym. Sci., Polym. Chem. Ed. 1980, 18, 2869–2873.
4. Jen, K.-Y.; Miller, G. G.; Elsenbaumer, R. L. J. Chem. Soc., Chem. Commun. 1986, 1346-1347. (b) Elsenbaumer, R. L.; Jen, K.-Y.; Oboodi, R. Synth. Met. 1986, 15, 169–174.
5. Sato, M.; Tanaka, S.; Kaeriyama, K. J. Chem. Soc., Chem. Commun. 1986, 873–874. (b) Lemaire, M.; Roncali, J.; Gamier, F.; Garreau, R.; Hannecart, E. French Patent 86.04744, April 4, 1986.
6. Yoshino, K.; Nakajima, S.; Onoda, M.; Sugimoto, R. Synth. Met. 1989, 28, C349—C357. (b) Österholm, J. E.; Laakso, J.; Nyholm, P.; Isotalo, H.; Stubb, H.; Inganäs, O.; Salaneck, W. R. Synth. Met. 1989, 28, C435-C444.
7. Yamamoto, T.; Morita, A.; Miyazaki, Y.; Maruyama, T.; Wakayama, H.; Zhou, Z.-h.; Nakamura, Y.; Kanbara, T.; Sasaki, S.; Kubota, K. Macromolecules 1992, 25, 1214-1223.
8. Ito, T.; Shirakawa, H.; Ikeda, S. J. Polym. Sci., Polym. Chem. Ed. 1974, 12, 11-20. (b) Ito, T.; Shirakawa, H.; Ikeda, S. J. Polym. Sci., Polym. Chem. Ed. 1975, 13, 1943–1950. (c) Shirakawa, H.; Louis, B. J.; MacDiarmid, A. G.; Chiang, C. K.; Heeger, A. J. J. Chem. Soc., Chem. Commun. 1977, 578–580. (d) Shirakawa, H.; Zhang, Y.-X.; Akagi, K. Polym. Prepr. 1994, 35, 189.
9. Basescu, N.; Liu, Z.-X.; Moses, D.; Heeger, A. J.; Naarmann, H.; Theophilou, N. Nature, 1987, 327, 403-405.
10. Roncali, J.; Carreau, R.; Yassar, A.; Marque, P.; Gamier, F.; Lemaire, M. J. Phys. Chem. 1987, 91, 6706-6714. (b) Roncali, J.; Marque, P.; Garreau, R.; Gamier, F.; Lemaire, M. Macromolecules 1990, 23, 1347-1352.
11. Souto Maior, R. M.; Hinkelmann, K.; Eckert, H.; Wudl, F. Macromolecules 1990, 23, 1268-1279.
12. Wei, Y.; Chan, C.-C.; Tian, J.; Jang, G.-W.; Hsueh, K. F. Chem. Mater. 1991, 3, 888–897.
13. Mao, H.; Holdcroft, S. Macromolecules 1992, 25, 554-558. (b) Mao, H.; Xu, B.; Holdcroft, S. Macromolecules 1993, 26, 1163-1169, 4457–4460.
14. Tour, J. M.; Wu, R.; Schumm, J. S. J. Am. Chem. Soc. 1991, 113, 7064–7066. (b) Pearson, D. L.; Schumm, J. S.; Tour, J. M. Macromolecules 1994, 27, 2348-2350. (c) Tour, J. M.; Wu, R. Macromolecules 1992, 25, 1901-1907.
15. McCullough, R. D.; Lowe, R. D. J. Chem. Soc., Chem. Commun. 1992, 70-72. (b) McCullough, R. D.; Lowe, R. D. Jayaraman, M.; Anderson, D. L. J. Org. Chem. 1993, 58, 904-912. (c) McCullough, R. D.; Tristram-Nagle, S.; Williams, S. P.; Lowe, R. D.; Jayarman, M. J. Am. Chem. Soc. 1993, 115, 4910-4911. (d) McCullough, R. D.; Williams, S. P. J. Am. Chem. Soc. 1993, 115, 11 608–11 609.
16. Chen, T.-A.; Rieke, R. D. J. Am. Chem. Soc. 1992, 114, 10087–10088. (b) Chen, T.-A.; Rieke, R. D. Synth. Met. 1993, 60, 175–177. (c) Chen, T.-A.; O'Brien, R. A.; Rieke, R. D. Macromolecules 1993, 26, 3462-3463. (d) Sell, M. S.; Hanson, M. V.; Rieke, R. D. Synth. Commun., in press.
17. Zhu, L.; Wehmeyer, R. M.; Rieke, R. D. J. Org. Chem. 1991, 56, 1445-1453. (b) Zhu, L.; Rieke, R. D. Tetrahedron Lett. 1991, 32, 2865–2866.
18. For a review of catalyzed cross-coupling reactions of organozinc compounds, see: (a) Negishi, E.; King, A. O.; Okukado, N. J. Org. Chem. 1977, 42, 1821-1823. (b) Negishi, E.; Organometallics in Organic Synthesis; Wiley: New York, 1980; Vol. 1. (c) Negishi, E. Acc. Chem. Res. 1982, 15, 340–348.
19. Kellogg, R. M.; Schaap, A. P.; Harper, E. T.; Wynberg, H. J. Org. Chem. 1968, 33, 2902-2909. (b) Fournari, P.; Guilard, R.; Person, M. Bull. Soc. Chim. Fr. 1967, 11, 4115–4120.
20. Barker, J. M.; Huddleston, P. R.; Wood, M. L. Synth. Commun. 1975, 5, 59–64.
21. Tamao, K.; Kodama, S.; Nakajima, I.; Kumada, M.; Minato, A.; Suzuki, K. Tetrahedron 1982, 38, 3347–3354. (b) Pham, C. V.; Mark, H. B., Jr.; Zimmer, H. Synth. Commun. 1986, 16, 689-696.
22. For a general review of the subject, see: Bumagin, N. A.; Beletskaya, I. P. Russ. Chem. Rev. 1990, 59, 1174-1184 (translated from Uspekhi Khimii 1990, 59, 2003-2020) and references cited therein.
23. Yamamoto, A.; Yamamoto, T.; Ozawa, F. Pure Appl. Chem. 1985, 57, 1799–1808. (b) Ozawa, F.; Hidaka, T.; Yamamoto, T.; Yamamoto, A. J. Organomet. Chem. 1987, 330, 253-263. (c) Yamamoto, T.; Wakabayashi, S.; Osakada, K. J. Organomet. Chem. 1992, 428, 223-237.
24. Sato, M.-a.; Morii, H. Macromolecules 1991, 24, 1196-1200. (b) Sato, M.-a.; Morii, H. Polym. Commun. 1991, 32, 42-44.
25. Barbarella, G.; Bongini, A.; Zambianchi, M. Macromolecules 1994, 27, 3039–3045.
26. Ekeblad, P. O.; Inganäs, O. Polym. Commun. 1991, 32, 436-438.
27. Hotta, S.; Rughooputh, S. D. D. V.; Heeger, A. J.; Wudl, F. Macromolecules 1987, 20, 212-215.
28. Furukawa, Y.; Akimoto, M.; Harad, I. Synth. Met. 1987, 18, 151 — 156.
29. Rughooputh, S. D. D. V.; Hotta, S.; Heeger, A. J.; Wudl, F. J. Polym. Sci., Part B: Polym. Phys. 1987, 25, 1071–1078.
30. Winokur, M. J.; Prosa, T. J.; Moulton, J.; Smith, P.; Heeger, A. J. Macromolecules 1992, 25, 4364-4372.
31. Chen, S.-A.; Ni, J.-M. Macromolecules 1992, 25, 6081–6089.
32. Mårdalen, J.; Samuelsen, E. J.; Gautun, O. R.; Carlsen, P. H. Synth. Met. 1992, 48, 363–380.
33. Yassar, A.; Roncali, J.; Gamier, F. Macromolecules 1989, 22, 804-809. (b) Tourillon, G. In Handbook of Conducting Polymers: Skotheim, T. A., Ed.; Marcel Dekker: New York, 1986; pp 293–350.
34. Jenekhe, S. A. Nature 1986, 322, 345–347. (b) Chung, T. C.; Haufman, J. H.; Heeger, A. J.; Wudl, F. Phys. Rev. B, 1984, 30, 702–710.
35. Theémans, B.; Andre, J. M.; Brédas, J. L. Synth. Met. 1987, 21, 149–156.
36. A manuscript on the systematic study of the conductivity of the regiospecific poly(3-alkylthiophenes) is in preparation by Reghu, M.; Yoon, C. O.; Moses, D.; Heeger, A. J.; Chen, T.-A.; Wu, X., and Rieke, R. D.
37. Coulson, D. R.; Satek, L. C.; Grim, S. O. Inorg. Synth. 1972, 13, 121–123.