Synthesizing optoelectronic heteroaromatic conjugated polymers by cross-coupling reactions

Journal of Organometallic Chemistry

Volumn 689, Issue 24 SPEC. ISS., 2004, Pages 4137-4148

  Cheng, Yen Ju ^a   Luh, Tien Yau ^a  

^a NONE

Author keywords

[No Author keywords available]

Indexed keywords

OPTOELECTRONIC DEVICES; ORGANIC POLYMERS; REACTION KINETICS; SYNTHESIS (CHEMICAL);

CROSS-COUPLING REACTIONS; HETEROAROMATICS; ORGANOMETALLIC CROSS-COUPLING;

ORGANOMETALLICS;

AROMATIC COMPOUND; POLYMER;

CHEMICAL ANALYSIS; CHEMICAL STRUCTURE; CROSS COUPLING REACTION; ELECTROCHEMISTRY; OPTICS; REVIEW; STRUCTURE ANALYSIS; SYNTHESIS;

EID: 10044282926     PISSN: 0022328X     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.jorganchem.2004.08.011     Document Type: Review

References (110)

1. H.S. Nalwa Handbook of Organic Conductive Molecules and Polymers vol. 1-4 1997 Wiley Chechester, UK
2. R.D. McCullogh, S. Tristram-Nagel, S.P. Williams, R.D. Lowe, and M. Jayaraman J. Am. Chem. Soc. 115 1993 4910
3. T. Chen, and R.D. Rieke J. Am. Chem. Soc. 114 1992 10087
4. R.J. Waltman, and J. Bargon Can. J. Chem. 46 1986 76
5. G.B. Street, T.C. Clarke, R.H. Geiss, V.Y. Lee, P. Pfluger, and J.C. Scott J. Phys. Colloq. C3 1985 599
6. S. Naitoh, K. Sanui, and N. Ogata J. Chem. Soc., Chem. Commun. 1986 1348
7. R. Lazzaroni, J. Riga, J.J. Verbist, L. Chrisiaens, and M. Rensen J. Chem. Soc., Chem. Commun. 1985 999
8. T. Shimidsu, A. Ohtani, T. Iyoda, and K. Honda J. Chem. Soc., Chem. Commun. 1986 1414
9. P. Kovacic, and A. Kyriakis J. Am. Chem. Soc. 85 1963 454
10. J.G. Speight, P. Kovacic, and F.W. Koch J. Macromol. Sci. C5 1971 295
11. G.K. Noren, and J.K. Stille Macromol. Rev. 5 1971 385
12. J.G. Speight, and F.W. Koch J. Macromol. Sci., Rev. Macromol. Chem. 6 1971 295
13. G. Goldfinger J. Polym. Sci. 4 1949 93
14. H.O. Wirth, R. Muller, and W. Kern Makromol. Chem. 77 1964 90
15. L.S. Hegedus Transition Metals in the Synthesis of Complex Organic Molecules second ed. 1999 University Science Books Sausalito, CA
16. F. Diederich P. Stang Metal-Catalyzed Cross-Coupling Reactions 1998 Wiley-VCH Weinheim
17. N. Miyaura Cross-Coupling Reactions: A Pratical Guide 2002 Springer Berlin
18. K. Tamao, T. Hiyama, and E.-i. Negishi J. Organomet. Chem. 653 2002
19. For reviews, see: T.-Y. Luh, M.-K. Leung, and K.-T. Wong Chem. Rev. 100 2000 3187
20. D.J. Cárdenas Angew. Chem. Int. Ed. 42 2003 384
21. M. Eckhardt, and G.C. Fu J. Am. Chem. Soc. 125 2003 13642 and references cited therein
22. K.-Y. Jen, G.G. Miller, and R.L. Elsenbaumer J. Chem. Soc., Chem. Commun. 1986 1346
23. J.P. Ruiz, K. Nayak, D.S. Marynick, and J.R. Reynolds Macromolecules 22 1989 1231
24. R.D. McCullough, and R.D. Lowe J. Chem. Soc., Chem. Commun. 1992 70
25. R.D. McCullough, R.D. Lowe, M. Jayaraman, and D.L. Anderson J. Org. Chem. 58 1993 904
26. M. Sato, and H. Morii Polym. Commun. 32 1991 42
27. M. Sato, and H. Morii Macromolecules 24 1991 1196
28. R. Suginoto, S. Takeda, H.B. Gu, and K. Yoshino Chem. Express 1 1986 635
29. G. Dauust, and M. LeClerc Macromolecules 24 1991 455
30. R.D. McCullough, and S.P. Williams J. Am. Chem. Soc. 115 1993 11608
31. R.D. McCullough, S.P. Williams, S. Tristram-Nagle, M. Jayaraman, P.C. Ewbank, and L. Miller Synth. Methods 69 1995 279
32. R.D. McCullough, and M. Jayaraman J. Chem. Soc., Chem. Commun. 1995 135
33. A. Iraqi, J.A. Crayston, and J.C. Walton J. Mater. Chem. 8 1998 31
34. L. Zhai, D.W. Laird, and R.D. McCullough Langmuir 19 2003 6492
35. M.M. Bouman, and E.W. Meijer Adv. Mater. 7 1995 385
36. B.M.W. Langeveld-Voss, R.J.M. Waterval, R.A.J. Janssen, and E.W. Meijer Macromolecules 32 1999 227
37. R.S. Loewe, S.M. Khersonsky, and R.D. McCullough Adv. Mater. 11 1999 250
38. R.S. Loewe, P.C. Ewbank, J. Liu, L. Zhai, and R.D. McCullough Macromolecules 34 2001 4324
39. L. Zhu, R.M. Wehmeyer, and R.D. Rieke J. Org. Chem. 56 1991 1445
40. T.-A. Chen, and R.D. Rieke J. Am. Chem. Soc. 114 1992 10087
41. T.-A. Chen, R.A. O'Brien, and R.D. Rieke Macromolecules 26 1993 3462
42. X. Wu, T.-A. Chen, and R.D. Rieke Macromolecules 28 1995 2101
43. T.-A. Chen, X. Wu, and R.D. Rieke J. Am. Chem. Soc. 117 1995 233
44. J. Liu, and R.D. McCullough Macromolecules 35 2002 9882
45. A. Iraqi, and I. Wataru Synth. Methods 119 2001 159
46. M.D. McClain, D.A. Whittington, D.J. Mitchell, and M.D. Curtis J. Am. Chem. Soc. 117 1995 3887
47. M.D. Curtis, and M.D. McClain Chem. Mater. 8 1996 936 945
48. A. Gandini, and M.N. Belgacem Prog. Polym. Sci. 22 1997 1203
49. H. Saadeh, T. Goodson III, and L. Yu Macromolecules 30 1997 4608
50. L.-Z. Zhang, C.-W. Chen, C.-F. Lee, C.-C. Wu, and T.-Y. Luh Chem. Commun. 2002 2336
51. A. Pelter, M. Rowlands, and I.H. Jenkins Tetrahedron Lett. 28 1987 5213
52. A. Pelter, J.M. Maud, I. Jenkins, C. Sadeka, and G. Coles Tetrahedron Lett. 30 1989 3461
53. T. Yamamoto J. Organomet. Chem. 653 2002 195
54. T. Yamamoto, T. Ito, and K. Kubota Chem. Lett. 1988 153
55. T. Yamamoto, T. Maruyama, Z.-h. Zhou, T. Ito, T. Fukuda, Y. Yoneda, F. Begum, T. Ikeda, S. Sasaki, H. Takezoe, A. Fukuda, and K. Kubota J. Am. Chem. Soc. 116 1994 4832
56. B.-K. Choi, and T. Yamamoto Electrochem. Commun. 5 2003 566
57. T. Yamamoto, A. Morita, Y. Miyazaki, T. Maruyama, H. Wakayama, Z.-H. Zhou, Y. Nakamura, T. Kanbara, S. Sasaki, and K. Kubota Macromolecules 25 1992 1214
58. L. Tan., M.D. Curtis, and A.H. Francis Macromolecules 35 2002 4628
59. J.I. Nanos, J.W. Dampf, and M.D. Curtis Chem. Mater. 7 1995 2232
60. M.D. Curtis, H. Cheng, J.I. Nanos, and G.-A. Nazri Macromolecules 31 1998 205
61. J.K. Politis, M.D. Curtis, L. González-Ronda, and D.C. Martin Chem. Mater. 12 2000 2798
62. T. Yamamoto, T. Uemura, A. Tanimoto, and S. Sasaki Macromolecules 36 2003 1047
63. J.K. Politis, J.C. Nemes, and M.D. Curtis J. Am. Chem. Soc. 123 2001 2537
64. T. Yamamoto, and B.-L. Lee Macromolecules 35 2002 2993
65. T. Yamamoto, Y. Fuiwara, H. Fukumoto, Y. Nakamura, S.-y. Koshihara, and T. Ishikawa Polymer 44 2003 4487
66. Z.-B. Zhang, M. Fujiki, H.-Z. Tang, M. Motonaga, and K. Torimitsu Macromolecules 35 2002 1988
67. J.K. Stille Angew. Chem., Int. Ed. Engl. 25 1986 508
68. R. Galarini, A. Musco, R. Pontellini, A. Bolognesi, S. Destri, M. Catellani, M. Mascherpa, and G. Zhuo J. Chem. Soc., Chem. Commun. 1991 364
69. R.S. Loewe, and R.D. McCullough Chem. Mater. 12 2000 3214
70. K. Tamao, S. Yamaguchi, M. Shiozaki, Y. Nakagawa, and Y. Ito J. Am. Chem. Soc. 114 1992 5867
71. J. Roncali Chem. Rev. 92 1992 711
72. G. Heywang, and F. Jonas Adv. Mater. 4 1992 116
73. R.D. McCullogh, S. Tristram-Nagle, S.D. Williams, R.D. Lowe, and M. Jayaraman J. Am. Chem. Soc. 115 1993 4910
74. M.J. Marsella, and T.M. Swager J. Am. Chem. Soc. 115 1993 12214
75. T. Bjørnholm, D.R. Greve, N. Reitzel, T. Hassenkam, K. Kjaer, P.B. Howes, N.B. Larsen, J. Bøgelund, M. Jayaraman, P.C. Ewbank, and R.D. McCullough J. Am. Chem. Soc. 120 1998 7643
76. R.D. McCullough, P.C. Ewbank, and R.S. Loewe J. Am. Chem. Soc. 119 1997 633
77. K.K. Stokes, K. Heuzé, and R.D. McCullough Macromolecules 36 2003 7114
78. A. Iraqi, and G.W. Barker J. Mater. Chem. 8 1998 25
79. Z. Bao, W. Chan, and L. Yu Chem. Mater. 5 1993 2
80. W.-K. Chan, Y. Chen, Z. Peng, and L. Yu J. Am. Chem. Soc. 115 1993 11735
81. Z. Bao, W.K. Chan, and L. Yu J. Am. Chem. Soc. 117 1995 12426
82. Y. Yao, J.J.S. Lamba, and J.M. Tour J. Am. Chem. Soc. 120 1998 2805
83. T. Yamamoto, M. Arai, H. Kokubo, and S. Sasaki Macromolecules 36 2003 7986
84. A. Suzuki, and H.C. Brown Organic Syntheses via Boranes Suzuki Coupling vol. 3 2003 Milwaukee Aldrich
85. N. Miyaura, T. Ishiyama, H. Sasaki, M. Ishikawa, M. Satoh, and A. Suzuki J. Am. Chem. Soc. 111 1989 314
86. S. Martina, and A.-D. Schlüter Macromolecules 25 1992 3607
87. J.-F. Morin, and M. Lecleric Macromolecules 34 2001 4680
88. B. Liu, W.-L. Yu, Y.-H. Lai, and W. Huang Chem. Mater. 13 2001 1984
89. T. Yasuda, and T. Yamamoto Macromolecules 36 2003 7513
90. S. Guillerez, and G. Bidan Synth. Methods 93 1998 123
91. B. Liu, and G.C. Bazan J. Am. Chem. Soc. 126 2004 1942
92. S. Yamaguchi, T. Goto, and K. Tamao Angew. Chem., Int. Ed. 39 2000 1695
93. S. Yamaguchi, and K. Tamao J. Organomet. Chem. 653 2002 223
94. K. Sonogashira, Y. Tohda, and N. Hagihara Tetrahedron Lett. 50 1975 4467
95. T. Yamamoto, W. Yamaada, M. Takagi, K. Kizu, T. Maruyama, N. Ooba, S. Tomaru, T. Kurihara, T. Kaino, and K. Kubota Macromolecule 27 1994 6620
96. T. Yamamoto, Q. Fang, and T. Morikita Macromolecules 36 2003 4262
97. Z. Zhu, and J.S. Moore Macromolecules 33 2000 801
98. X. Zhen, Y. Liu, G. Yu, X. Wu, D. Zhu, R. Sun, D. Wang, and A.J. Epstein J. Mater. Chem. 11 2001 1606
99. J.H. Burroughes, D.D.C. Bradley, A.R. Brown, R.N. Marks, K. MacKay, R.H. Friend, B.L. Burn, and A.B. Holmes Nature 147 1991 539
100. W. Heitz, W. Brugging, L. Freund, M. Gaillberger, A. Greiner, H. Jung, U. Kampsulte, N. Niener, and F. Oscan Makromol. Chem. 189 1988 119
101. H. Martelock, A. Greiner, and W. Heitz Makromol. Chem. 192 1991 967
102. M. Suzuki, J.C. Lim, and T. Saegusa Macromolecules 23 1990 1574
103. H.P. Weitzel, and K. Müllen Makromol. Chem. 191 1990 2837
104. N.C. Greeham, S.C. Moratti, D.C.C. Bradley, R.H. Friend, and A.B. Holmes Nature 1993 628
105. M.J. Marsella, D.-K. Fu, and T.M. Swager Adv. Mater. 7 1995 145
106. Z. Bao, Y. Chen, and L. Yu Macromolecules 27 1994 4629
107. Z. Peng, and L. Yu J. Am. Chem. Soc. 118 1996 3777
108. S. Maruyama, X.-T. Tao, H. Hokari, T. Noh, Y. Zhang, T. Wada, H. Sasabe, H. Suzuki, T. Watanabe, and S. Miyata J. Mater. Chem. 9 1999 893
109. D.W. Polis, C.L. Young, M.R. MeLean, and L.R. Dalton Macromolecules 23 1990 3231
110. C.L. Young, D.W. Polis, A.N. Bain, L.S. Sapochak, and L.R. Dalton Macromolecules 23 1990 3236