A new poly(3-alkylthiophene) synthesis via Pd-catalyzed coupling of thienyl mercuric chlorides

Chemistry of Materials

Volumn 8, Issue 4, 1996, Pages 936-944

  Curtis, M David ^a   McClain, Mark D ^a  

^a UNIVERSITY OF MICHIGAN   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 0000720949     PISSN: 08974756     EISSN: None     Source Type: Journal    
DOI: 10.1021/cm9505308     Document Type: Article

References (102)

1. (a) Roncali, J. Chem. Rev. 1992, 92, 711-738 and references therein.
2. (b) Sato, M.; Tanaka, S.; Kaeriyama, K. J. Chem. Soc., Chem. Commun. 1986, 873-874.
3. Waltman, R. J.; Bargon, J. Can. J. Chem. 1986, 64, 76-95.
4. Krische, B., Zagorska, M. Synth. Met. 1989, 28, C263-C268.
5. Logsdon, P. B.; Pfleger, J.; Prasad, P. N. Synth. Met. 1988, 26, 369-381.
6. Ruiz, J. P.; Nayak, K.; Marynick, D. S.; Reynolds, J. R. Macromolecules 1989, 22, 1231-1238.
7. (a) Bryce, M. R.; Chissel, A.; Kathirgamanathan, P.; Parker, D.; Smith, N. R. M. J. Chem. Soc., Chem. Commun. 1987, 466-467.
8. (b) Bryce, M. R.; Chissel, A.; Smith, N. R. M.; Parker, D.; Kathirgamanathan, P. Synth. Met. 1988, 26, 153-168.
9. Li, F.; Albery, W. J. J. Electroanal. Chem. 1991, 302, 279-284.
10. Zinger, B.; Greenwald, Y.; Rubinstein, I. Synth. Met. 1991, 41-43, 583-592.
11. Roncali, J.; Garreau, R.; Delabouglise, D.; Garnier, F.; Lemaire, M. Synth. Met. 1989, 28, C341-C348.
12. Báuerle, P.; Gaudl, K. U. Synth. Met. 1991, 41-43, 3037-3042.
13. (a) Büchner, W.; Garreau, R.; Lemaire, M.; Roncali, J. J. Electroanal. Chem. 1990, 277, 355.
14. (b) Ritter, S. K.; Noftle, R. E.; Ward, A. E. Chem. Mater. 1993, 5, 752-754.
15. Patil, A O.; Ikenoue, Y.; Wudl, F.; Heeger, A. J. J. Am. Chem. Soc. 1987, 109, 1858-1859.
16. Mirrazaei, R.; Parker, D.; Munro, H. S. Synth. Met. 1989, 30, 265.
17. Grimshaw, J.; Perera, S. D. J. Electroanal. Chem. 1990, 278, 287.
18. Bryce, M. R.; Chissel, A. D.; Gopal, J.; Kathirgamanathan, P.; Parker, D. Synth. Met. 1991, 39, 397.
19. Sugimoto, R.; Takeda, S.; Gu, H. B.; Yoshino, K. Chem. Express 1986, 1, 635-638.
20. Inoue, M. B.; Velazquez, E. F.; Inoue, M. Synth. Met. 1988, 24, 223-229.
21. (a) Kovacic, P.; McFarland, K. N. J. Polym. Sci., Polym. Lett. Ed. 1979, 17, 1963-1976
22. (b) Hotta, S.; Soga, M.; Sonoda, N. Synth. Met. 1988, 26, 267-279.
23. Yoshino, K.; Nakajima, S.; Sugimoto, R. Jpn. J. Appl Phys. 1987, 26, L1038-1039.
24. Murray, D. P.; Kispert, L. D.; Petrovic, S.; Frommer, J. E. Synth. Met 1989, 28, C269-C274.
25. Souto Maior, R. M.; Hinkelmann, K.; Eckert, H.; Wudl, F. Macromolecules 1990, 23, 1268-1279.
26. Abdou, M. S. A.; Holdcroft, S. Macromoleeules 1993, 26, 2954-2962.
27. Della Casa, C.; Salatelli, E.; Andreani, F.; Costa Bizzarri, P. Makromol. Chem., Macromol. Symp. 1992, 59, 233-246.
28. Chen, S.-A.; Tsai, C.-C. Macromolecules 1993, 26, 2234-2239.
29. Roux, C.; Bergeron, J.-Y.; Leclerc, M. Makromol. Chem. 1993, 194, 869.
30. Berggren, M.; Gustafsson, G.; Inganäs, O.; Andersson, M. R.; Wennerström, O.; Hjertberg, T. Appl. Phys. Lett. 1994, 65, 1489.
31. (a) Lemaire, M.; Buchner, W.; Garreau, R.; Hoa, H. A.; Guy, A.; Roncali, J. J. Electroanal. Chem. 1990, 281, 293-298.
32. (b) Roncali, J.; Guy, A.; Lemaire, M.; Garreau, R.; Hoa, H. A. J. Electroanal. Chem. 1991, 312, 277-283.
33. Masuda, H.; Taniki, Y.; Kaeriyama, K. Synth. Met. 1993, 55-57, 1246-1250.
34. Amer, A.; Zimmer, H.; Mulligan, K. J.; Mark, H. B.; Pons, S.; McAleer, J. F. J. Polym. Sci., Polym. Lett. Ed. 1984, 22, 77-82.
35. Berlin, A.; Pagani, G. A.; Sannicolo, F. J. Chem. Soc., Chem. Commun. 1986, 1663-1664.
36. Bao, Z.; Chan, W.; Yu, L. Chem Mater. 1993, 5, 2-3.
37. Lin, J. W. P.; Dudek, L. P. J. Polym. Sci., Polym. Chem. Ed. 1980, 18, 2869-2873.
38. Yamamoto, T.; Sanechika, K.; Yamamoto, A. J. Polym. Sci., Polym. Lett. Ed. 1980, 18, 9-12.
39. (a) Jen, K. Y.; Miller, G. G.; Elsenbaumer, R. L. J. Chem Soc., Chem. Commun. 1986, 1346-1347.
40. (b) Elsenbaumer, R. L.; Jen, K. Y.; Oboodi, R. Synth. Met. 1986, 15, 169-174.
41. (a) McCullough, R. D.; Lowe, R. D. J. Chem. Soc., Chem. Commun. 1992, 70-72.
42. (b) McCullough, Lowe, R D.; Jayaraman, M.; Anderson, D. L. J. Org. Chem. 1993, 58, 904-912.
43. (c) McCullough, R. D.; Williams, S. P. J. Am. Chem. Soc. 1993, 115, 11608.
44. (a) Chen, T. A.; Rieke, R. D. J. Am. Chem. Soc. 1992, 114, 10087-10088; 1995, 117, 233-244.
45. (a) Chen, T. A.; Rieke, R. D. J. Am. Chem. Soc. 1992, 114, 10087-10088; 1995, 117, 233-244.
46. (b) Faid, K.; Frechette, M.; Ranger, M.; Mazerolle, L.; Levesque, I.; Leclerc, M.; Chen, T.; Rieke, R. D. Chem. Mater. 1995, 7, 1390.
47. (c) Sandstedt, C. A.; Rieke, R. D.; Eckhardt, C. J. Chem. Mater 1995, 7, 1057-1059.
48. McCullough, R. D.; Tristram-Nagle, S.; Williams, S. P.; Lowe, R. D.; Jayaraman, M. J. Am. Chem. Soc. 1993, 115, 4910-4911.
49. (a) Yamamoto, T.; Morita, A.; Miyazaki, Y.; Maruyama, T ; Wakayama, H.; Zhou, Z.; Nakmura, Y.; Kanbara, T.; Sasaki, S.; Kubota, K. Macromolecules 1992, 25, 1214-1223.
50. (b) Miyazaki, Y.; Kanbara, T.; Osakada, K.; Yamamoto, T. Chem. Lett. 1993, 415-418.
51. Yamamoto, T.; Wakabayashi, S.; Osakada, K. J. Organomet. Chem. 1992, 428, 223-237.
52. Colon, I.; Kwiatkowski, G. T. J. Polym. Sci., Polym. Chem. 1990, 28, 367-383.
53. Masuda, H.; Kaeriyama, K. Makromol. Chem., Rapid Commun 1992, 13, 461-465.
54. Volhard, J. Ann. Chem. 1892, 267, 172-185.
55. (a) Razuvaev, G. A.; Koton, M. M. J. Gen. Chem. USSR 1931, 1, 864.
56. (b) Razuvaev, G. A.; Koton, M M. J. Gen. Chem. USSR 1934, 4, 647.
57. (c) Razuvaev, G. A.; Koton, M. M. J. Gen. Chem. USSR 1935, 5, 361.
58. Razuvaev, G. A.; Koton, M. M. Chem. Ber. 1933, 66B, 854.
59. (e) Razuvaev, G. A.; Koton, M. M. Chem. Ber. 1933, 66B, 1210
60. (a) Nesmeyanova, O. A.; Perevalova, E. G. Dokl. Akad. Nauk SSSR 1959, 126, 1007.
61. (b) Rausch, M D. Inorg. Chem. 1962, 1, 414-417.
62. Rausch, M. D. J Org. Chem. 1963, 28, 3337-3341.
63. McClain, M. D.; Whittington, D. A.; Mitchell, D. J.; Curtis, M. D J. Am. Chem. Soc. 1995, 117, 3887.
64. Kretchmer, R. A.; Glowinski, R. J. Org. Chem. 1976, 41, 2661-2662.
65. Larock, R. C. Organomercury Compounds in Organic Synthesis; Springer-Verlag: Berlin, 1985.
66. Curtis, M. D.; McClain, M. D. Chem Mater. 1996, 8, 945.
67. Valdes, L. Proc. I. R. E. 1954, 42, 420.
68. Tamao, K.; Kodama, S.; Nakajima, I.; Kumada, M.; Minato, A.; Suzuki, K. Tetrahedron 1982, 38, 3347-3354.
69. Steinkopf, W.; Bauermeister, M. Ann. Chem. 1914, 403, 50-72.
70. Nefedov, V. A. J. Gen. Chem. USSR 1969, 39, 630.
71. Bulman, M. J. Tetahedron 1969, 25, 1433-1439.
72. Makarova, L. G. In Organometallic Reactions; Becker, E I., Tsutsui, M., Eds.; Wiley-Interscience: New York, 1971; Vol. 2, pp 335-423.
73. Hanus, V.; Cermak, V. Coll. Czech. Chem. Commun. 1959, 24, 1602-1607.
74. (a) Neugebauer, H.; Nauer, G ; Neckel, A.; Tourillon, G.; Garnier, F.; Lang, P. J. Phys. Chem. 1984, 88, 652-654.
75. (b) Hotta, S.; Rughooputh, S. D. D. V.; Heeger, A. J.; Wudl, F. Macromolecules 1987, 20, 212-215.
76. Barbarella, G.; Bongini, A.; Zambianchi, M. Macromolecules 1994, 27, 3039-3045.
77. Heffner, G. W.; Pearson, D. S. Macromolecules 1991, 24, 6295-6299.
78. Gustafsson, G.; Inganas, O.; Salaneck, W. R.; Laakso, J.; Loponen, M.; Taka, T.; Österholm, J. E., Stubb, H.; Hjertberg, T. In Conjugated Polymers; Bredas, J. L., Silbey, R., Eds.; Kluwer: Copenhagen, 1991; pp 315-362.
79. (a) Cunningham, D. D.; Laguren-Davidson, L.; Mark, H. B.; Pham, C. V.; Zimmer, H. J. Chem. Soc., Chem. Commun. 1987, 1021-1023.
80. (b) Laguren-Davidson, L.; Pham, C. V.; Zimmer, H.; Mark, H. B. J. Electrochem. Soc., Chem. Commun. 1988, 135, 1406-1414.
81. Guay, J.; Kasai, P.; Diaz, A.; Wu, R.; Tour, J. M., Dao, L. H Chem. Mater. 1992, 4, 1097-1105.
82. Havinga, E. E.; Rotte, I.; Meijer, E. W.; Ten Hoeve, W ; Wynberg, H. Synth. Met. 1991, 41-43, 473-478.
83. Gallazzi, M. C.; Castellani, L.; Zerbi, G.; Sozzani, P. Synth. Met. 1991, 41-43, 495-498.
84. Wang, C.; Benz, M. E.; LeGoff, E.; Schindler, J. L.; Allbritton-Thomas, J.; Kannewurf, C. R ; Kanatzidis, M. G Chem. Mater. 1994, 6, 401-411.
85. (a) Horowitz, G.; Bachet, B.; Yassar, A.; Lang, P.; Demanze, F.; Fave, J.; Garnier, F. Chem. Mater. 1995, 7, 1337.
86. (b) Barbarella, G.; Zambianchi, M., Bongini, A.; Antolini, L. Adv. Mater. 1993, 5, 834
87. Cotts, D. B. ; Reyes, Z. Electrically Conductive Organic Polymers for Advanced Applications; Noves Data Corp.: Park Ridge, NJ, 1986; pp 75-99.
88. Assadi, A.; Svensson, C.; Willander, M.; Inganäs, O. Appl. Phys. Lett. 1988, 53, 195-197
89. Garnier, F.; Yassar, A.; Hajlaoui, R.; Horowitz, G.; Deloffre, F . Servet, B.; Ries, S.; Alnot, P. J. Am. Chem. Soc. 1993, 115, 8716-8721.
90. Hein, F.; Wagler, K. Chem. Ber. 1925, 58, 1499-1509.
91. Unger, M. O.; Fouty, R. A. J. Org Chem. 1969, 34, 18-21.
92. (a) Heck, R. F. J. Am. Chem. Soc. 1968, 90, 5518-5526.
93. (b) Heck, R. F. J. Am. Chem. Soc. 1968, 90, 5526-5531.
94. (c) Heck, R. F. J. Am. Chem. Soc. 1968, 90, 5531-5535.
95. (d) Heck, R. F. J. Am. Chem. Soc. 1968, 90, 5535-5538.
96. (e) Heck, R. F. J. Am. Chem. Soc. 1968, 90, 5538-5542.
97. (f) Heck, R. F. J. Am. Chem. Soc. 1968, 90, 5542-5546.
98. (g) Heck, R. F. J. Am. Chem. Soc. 1968, 90, 5546-5548.
99. Sokolov, V. I.; Bashilov, V. V.; Anishichenko, L. M.; Reutov, O. A. J. Organomet. Chem. 1974, 77, C41-C42.
100. Larock, R. C. J. Org. Chem. 1976, 41, 2241-2245.
101. Heck, R. F. Acc. Chem. Res. 1979, 12, 146-151.
102. Giordano, T. J.; Rasmussen, P G Inorg. Chem. 1975, 14, 1628.