A New, General Approach to Tuning the Properties of Functionalized Polythiophenes: The Oxidative Polymerization of Monosubstituted Bithiophenes

Chemistry of Materials

Volumn 10, Issue 7, 1998, Pages 1990-1999

  Rasmussen, Seth C ^a   Pickens, Jason C ^a   Hutchison, James E ^a  

^a UNIVERSITY OF OREGON   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 0000618596     PISSN: 08974756     EISSN: None     Source Type: Journal    
DOI: 10.1021/cm980150x     Document Type: Article

References (83)

1. Kaner, R. B.; MacDiarmid, A. G. Sci. Am. 1988, 258 (2), 106.
2. Yam, P. Sci. Am. 1995, 273 (1), 82.
3. Tourillon, G. In Handbook of Conducting Polymers; Skothem, T. A., Ed.; Marcel Dekker: New York, 1986; p 350.
4. (a) Waltman, R. J.; Diaz, A. F.; Bargon, J., J. Electrochem. Soc. 1984, 131, 1452.
5. (b) Waltman, R. J.; Bargon, J. Can. J. Chem. 1986, 64, 76.
6. Nguyen, M. T.; Leclerc, M.; Diaz, A. F. Trends Polym. Sci. 1995, 3, 186.
7. Roncali, J. Chem. Rev. 1992, 92, 711.
8. Schopf, G.; Kossmehl, G. Adv. Polym. Sci. 1997, 129, 1.
9. Garnier, F. Angew. Chem., Int. Ed. Engl. 1989, 28, 513.
10. Roncali, J.; Garreau, R.; Delabouglise, D.; Garnier, F.; Lemaire, M. Synth. Met. 1989, 28, C341.
11. Chen, T A., Wu, X.; Rieke, R. D. J. Am. Chem. Soc. 1995, 117, 233.
12. McCullough, R. D.; Lowe, R. D.; Jayaraman, M.; Anderson, D. L. J. Org. Chem. 1993, 58, 904.
13. McCullough, R. D.; Jayaraman, M. J. Chem. Soc., Chem. Commun. 1995, 135.
14. McCullough, R. D.; Ewbank, P. C.; Loewe, R. S. J. Am. Chem. Soc. 1997, 119, 633.
15. Swager, T M.; Marsella, M. J. Mater Res. Soc. Symp. Proc. 1994, 328, 263.
16. Andersson, M.; Ekeblad, P. O.; Hjettberg, T.; Wennerström, O.; Inganäs. O. Polym. Commun. 1991, 32, 546.
17. Bäuerle, P.; Gaudl, K. U.; Wurthner, F.; Sariciftei, N. S.; Neugebauer, H.; Mehring, M.; Zhong, C.; Doblhofer, K. Adv. Mater 1990, 2, 490
18. (a) Patil, A. O.; Ikenoue, Y.; Basecu, N.; Colaneri, N.; chen, J.; Wudl, F.; Heeger, A. J. Synth. Met. 1987, 20, 151.
19. (b) Patil. A. O.; Ikenoue, Y.; Wudl, F.; Heeger, A. J. J. Am. Chem. Soc. 1987, 109, 1858,
20. (c) Ikenoue, Y.; Saida, Y.; Kira, M.; Tomozawa, H.; Yashima, H.; Kobayashi, M. J. Chem Soc., Chem. Commun. 1990, 1694
21. Aldissi, M. Mol. Cryst. Liq. Cryst. 1988, 160, 121.
22. Casa, C. D.; Bertinelli, F.; Bizzarri, P. C.; Salatelli, E. Adv. Mater. 1995, 7, 1005.
23. Pohjakallio, M.; Sundholm, G. Synth. Met. 1993, 55-57, 1590.
24. Welzel, H.-P.; Kossmehl, G.; Schneider, J.; Plieth, W. Macromolecules 1995, 28, 5575.
25. Rasmussen, S. C.; Pickens, J. C.; Hutchison, J. E. Macromolecules 1998, 31, 933.
26. Bartlett, P. N.; Dawson, D. H. J. Mater. Chem. 1994, 4, 1805.
27. Demanze, F.; Yassar, A.; Garnier. F Adv: Mater. 1995, 7, 907.
28. Demanze, F.; Yassar, A.; Garnier, F. Macromolecules 1996, 29, 4267.
29. Curtis, M. D.; McClain, M. D. Chem. Mater. 1996, 8, 936.
30. (a) Masuda, H.; Kaeriyama, K. Makromol. Chem., Rapid Commun. 1992, 13, 46.
31. (b) Masuda, H., Kaeriyama, K. Synth. Met. 1995, 69, 513.
32. Pomerantz, M.; Yang, H.; Cheng, Y. Macromolecules 1995, 28, 5706.
33. Souto Maior, R. M.; Hinkelmann, K.; Eckert, H.; Wudl, F. Macromolecules 1990, 23, 1268.
34. Zagórska, M.; Kulszewicz-Bajer, I. Synth. Met. 1991, 45, 385.
35. Lapkowski, M.; Zagórska, M.; Kulszewicz-Bajer, I.; Koziel, K.; Pron, A. J. Electroanal. Chem. 1991, 310, 57.
36. Zagórska, M.; Krische, B Polymer 1990, 31, 1379.
37. Wang, C.; Benz, M.; LeGoff, E.; Schindler, J. L.; Allbritton-Thomas, J.; Kannewurf, C. R.; Kanatzidis, G. Chem. Mater. 1994, 6, 401.
38. (a) Andereson, M. R.; Pei, Q: Hjertberg, T., Inganäs, O.; Wennerström, O.; Österholm, J. E. Synth. Met. 1993, 55-57, 1227.
39. (b) Pei, Q.; Inganäs, O.; Gustafsson, G.; Granström, M.; Andersson, M.; Hjertberg, T.; Wennerström, O.; Österholm, J. E.; Laakso, J.; Järvinen, H. Synth. Met. 1993, 55-57, 1221
40. Masuda, H.; Kaeriyama, K.; Suezawa, H.; Hirota, M. J. Polym. Sci. A: Polym. Chem. 1992, 30, 945.
41. Rasmussen, S. C.; Straw, B.; Hutchison, J. E. Palym. Prep. 1998, 39, 87.
42. Rasmussen, S. C.; Pickens, J. C. Hutchison, J. E. J. Heterocycl. Chem. 1997, 34, 285.
43. Oberg, K. A.; Palleros, D. R. J. Chem. Educ. 1995, 72, 857.
44. Crisp, G. T. Synth. Commun. 1989, 19, 307.
45. Sugimoto, R.; Takeda, S.; Gu, H. B.; Yoshino, K. Chem. Express 1986, 1, 635.
46. 3OH competely removed all Fe impurities as indicated by XPS.
47. Krische, B.; Zagórska, M. Synth. Met. 1989, 28, C257.
48. 43c the actual molecular weight of the polymer.
49. (b) Pomerantz, M.; Tseng, J. J.; Zhu, H.; Sproull, S. J.; Reynolds, JR.; Uitz, R.; Arnott, H. J. Synth. Met. 1991, 41-43, 825.
50. (c) Yue, S.; Berry, G. C.; McCullough, R. D. Macromolecules 1996, 29, 933.
51. Sanechika, K.; Yamamoto, T.; Yamamoto, A. J. Polym. Sci.; Potym. Lett. 1982, 20, 365.
52. Zerbi, G.; Chierichetti, B.; Inganäs, O. J. Chem. Phys. 1991, 94, 4646.
53. Winokur, M. J.; Spiegel, D.; Kim, Y.; Hotta, S.; Heeger, A. J. Synth. Met. 1989, 28, C419.
54. This exception is most likely due to the fact that the only soluble portion of this polymer is oligomeric in nature.
55. Rughooputh, S D. D. V.; Hotta, S.; Heeger, A. J.; Wudl, F. J. Polym Sci. B: Polym. Phys. 1987, 25, 1071.
56. Chen, S.-A.; Ni, J.-M. Marcomolecules 1992, 25, 6081.
57. Inganäs, O.; Salaneck, W. R.; Osterholm, J. E.; Laakso, J. Synth. Met. 1988, 22, 395.
58. Audebert, P.; Hapiot, P. Synth. Met. 1996, 75, 95.
59. Zuman, P. Substituent Effects in Organic Polarography; Plenum Press: New York, 1967.
60. Wagner, P.; Hegner, M.; Güntherodt, H.-J.; Semenza, G. Langmuir 1995, 11, 3867.
61. Roncali, J.; Garnier, F., Lemaire, M., Garreau, R. Synth. Met. 1986, 15, 323.
62. Ruckenstein, E.; Park, J. S. Synth. Met. 1991, 44, 293.
63. Zotti, G.; Schiavon, G. Synth. Met. 1990, 39, 183.
64. 57c to allow comparison.
65. (b) Larson, R. C.; Iwanoto, R. T.; Adams, R. N. Anal. Chim. Acta 1961, 25, 371.
66. Bard, A. J.; Falkner, L. R. Electrochemical Methods, Fundamentals and Applications: John Wiley & Sons: New York, 1980.
67. Mayeda, E. A.; Miller, L. L.; Wolf, J. F. J. Am. Chem. Soc. 1972, 94, 6812.
68. The resulting potential is very dependent on the casting conditions of the film. Thin, highly uniform Alms gave the best results. Other films resulted in higher oxidation potentials.
69. Faid, K.; Cloutier, R.; Leclerc, M. Macromolecules 1993, 26, 2501.
70. Leclerc, M.; Diaz, F. M.; Wegner, G. Makromol. Chem. 1989, 90, 3105.
71. Mao, H.; Xu, B.; Holdcroa, S. Macromolecules 1993, 26, 1163.
72. Modeling was accomplished using SPARTAN version 4.1.2 Wavefunction, Inc.). Intial structures were calculated using molecular mechanics (SYBYL force field) followed by geometry optimization and spin population analysis using DFT.
73. Rasmussen, S. C.; Hutchison, J. E. (manuscript in preparation).
74. Pomerantz, M.; Tseng, J. J.; Zhu, H.; Sproull, S. J.; Reynolds, J. R.; Uitz, R.; Arnott, H. J. Synth. Met. 1991, 41-43, 825.
75. (a) Lee, C.; Kim, K. J.; Rhee, S. B. Synth. Met. 1995, 69, 295.
76. (b) Lee, C.; Kim, K. J.; Rhee, S. B. Mol. Cryst. Liq. Cryst. 1994, 247, 31.
77. Kang, T. J.; Kim, J. Y.; Kim, K. J.; Lee, C.; Rhee, S. B. Synth. Met. 1995, 69, 377.
78. Casa, C. D.; Andreani, F.; Bizzarri, P. C.; Salatelli, E. J. Mater. Chem. 1994, 4, 1035.
79. Daoust, G.; Leclerc, M. Macromolecules 1991, 24, 455.
80. Thémans, B.; Salaneck, W. R.; Bredas, J. L. Synth. Met. 1989, 28, C359.
81. 45,46
82. Roncali, J.; Garreau, R.; Yassar, A.; Marque, P.; Garnier, F.; Lemaire, M. J. Phys. Chem. 1987, 91, 6706.
83. Ciprelli, J. L.; Clarisse, C.; Delabouglise, D. Synth. Met. 1995, 74, 217.