π-Conjugated polymers bearing electronic and optical functionalities. Preparation, properties and their applications

Reactive and Functional Polymers

Volumn 37, Issue 1-3, 1998, Pages 1-17

  Yamamoto, Takakazu ^a   Hayashida, Naoki ^a  

^a TOKYO INSTITUTE OF TECHNOLOGY   (Japan)

Author keywords

Electrochromism; Electroluminescence; Nonlinear optics; Organometallic polycondensation; Polymer battery; Conjugated polymer

Indexed keywords

DIODES; ELECTRIC BATTERIES; ELECTROCHROMISM; ELECTROLUMINESCENCE; ELECTRONIC PROPERTIES; LUMINESCENT DEVICES; NONLINEAR OPTICS; OPTICAL DEVICES; OPTICAL PROPERTIES; POLYCONDENSATION; TRANSITION METAL COMPOUNDS;

POLYMERIC BATTERIES;

METALLORGANIC POLYMERS;

EID: 0032094822     PISSN: 13815148     EISSN: None     Source Type: Journal    
DOI: 10.1016/S1381-5148(97)00140-5     Document Type: Review

References (144)

1. (a) T. Yamamoto, A, Yamamoto, S. Ikeda, J. Am. Chem. Soc. 93 (1980) 3350 and (1971) 3360;
2. (b) T. Kohara, T. Yamamoto, A. Yamamoto, J. Organomet. Chem. 192 (1980) 265;
3. (c) K. Tatsumi, A. Nakamura, S. Komiya, T. Yamamoto, A, Yamamoto, J. Am. Chem. Soc. 106 (1984) 8181;
4. (d) S. Komiya, Y. Abe, A. Yamamoto, T. Yamamoto, Organometallics 2 (1983) 1466;
5. (e) B. Åkermark, A. Ljungovist, J. Organomet. Chem. 149 (1978) 97;
6. (f) B. Åkermark, H. Johnasen, B. Ross, U. Wahlgren, J. Am. Chem. Soc. 101 (1979) 5876;
7. (g) Y.-J. Kim, R. Sato, T. Maruyama, K. Osakada, T. Yamamoto, J. Chem. Soc., Dalton (1994) 943.
8. (a) M.F. Semmelhack, L.S. Ryono, J. Am. Chem. Soc. 97 (1975) 3873;
9. (b) Z.-H. Zhou, T. Yamamoto, J. Organomet. Chem. 414 (1991) 119;
10. (c) T. Yamamoto, S. Wakabayashi, K. Osakada, J. Organomet. Chem. 428 (1992) 223.
11. (a) T. Yamamoto, A. Yamamoto, Chem. Lett. (1977) 353;
12. (b) T. Yamamoto, Y. Hayashi, A. Yamamoto, Bull. Chem. Soc. Jpn. 51 (1978) 2091;
13. (c) T. Yamamoto, A. Yamamoto, Polym. Prepr. Jpn. 25 (1976) G2B07;
14. (d) T. Yamamoto, T. Kanbara, C. Mori, Synth. Met. 38 (1990) 399, J. Phys. Chem. 100 (1996) 12,631.
15. (d) T. Yamamoto, T. Kanbara, C. Mori, Synth. Met. 38 (1990) 399, J. Phys. Chem. 100 (1996) 12,631.
16. (a) T. Yamamoto, T. Ito, K. Kubota, Chem. Lett. (1988) 153;
17. (b) T. Yamamoto, A. Monta, Y. Miyazaki, T. Maruyama, H. Wakayama, Z.-H. Zhou, Y. Nakamura, T. Kanbara, S. Sasaki, K. Kubota, Macromolecules 25 (1992) 1214;
18. (c) T. Yamamoto, T. Maruyama, Z.-H. Zhou, T. Ito, T. Fukuda, Y. Yoneda, F. Begum, T. Ikeda, S. Sasaki, H. Takezoe, A. Fukuda, K. Kubota, J. Am. Chem. Soc. 116 (1994) 4832;
19. (d) T. Miyamae, D. Yoshimura, H. Ishii, Y. Ouchi, K. Seki, T. Miyazaki, T. Koike, T. Yamamoto, J. Chem. Phys. 103 (1995) 2738.
20. (a) N. Saito, T. Kanbara, T. Sato, T. Yamamoto, Polym. Bull. 30 (1993) 285;
21. (b) N. Saito, T. Kanbara, Y. Nakamura, T. Yamamoto, K. Kubota, Macromolecules 27 (1994) 756.
22. (a) T. Yamamoto, K. Osakada, T. Wakabayashi, A. Yamamoto, Makromol. Chem., Rapid Commun. 6 (1985) 671;
23. (b) T. Yamamoto, Japan Kokai Patent, 233014, 1986;
24. (c) T. Yamamoto, A. Kashiwazaki, K. Kato, Makromol. Chem. 190 (1989) 1649.
25. (a) N. Saito, T. Yamamoto, Macromolecules 28 (1995) 4260;
26. (b) T. Yamamoto, N. Saito, Maclomol. Chem. Phys. 197 (1996) 165.
27. (a) T. Yamamoto, N. Hayashida, T. Maruyama, Macromol. Chem. Phys. 198 (1997) 341;
28. (b) K. Kitada, S. Ozaki, Polym. J. 27 (1995) 1161.
29. (a) A. Tamao, K. Sumitani, Y. Kiso, M. Zembayashi, A. Fujioka, K. Kodama, I. Nakajima, A. Minato, M. Kumada, Bull. Chem. Soc. Jpn. 49 (1976) 1958;
30. (b) A.S. Kende, L.S. Liebsking, D. Braitsch, Tetrahedron Lett. (1977) 3375;
31. (c) M. Iyoda, M. Sakitani, H. Otsuka, M. Oda, Chem. Lett. (1985) 127;
32. (d) M. Zembayashi, K. Tamao, J. Yoshida, M. Kumada, Tetrahedron Lett (1977) 4089.
33. (a) J.K. Stille, Angew. Chem., Int. Ed. Engl. 25 (1986) 508;
34. (b) A. Suzuki, Acc. Chem. Res. 15 (1982) 178;
35. (c) A. Suzuki, Pure Appl. Chem. 57 (1985) 1749.
36. (a) M. Remmers, M. Schize, G. Wegner, Macromol. Rapid Commun. 17 (1996) 239;
37. (b) Q.-S. Hu, D. Vitharana, G. Liu, V. Jain, L. Pu, Macromolecules 29 (1996) 5075.
38. (a) M. Bochmann, J. Lu, J. Polym. Sci., Part A: Polym. Chem. 32 (1994) 2493;
39. (b) T. Kanbara, Y. Miyazaki, T. Yamamoto, J. Polym. Sci., Part A: Polym. Chem. 33 (1995) 999;
40. (c) T. Yamamoto et al., J. Am. Chem. Soc. 118 (1996) 10,389;
41. (d) K. Tamao, S. Yamaguchi, Y. Ito, Y. Matsuzaki, T. Yamabe, M. Fukushima, S. Mori, Macromolecules 28 (1995) 8668.
42. (a) T. Yamamoto, K. Sanechika, A. Yamamoto, Japan Kokai Patent, 47,421, 1981; Jpn. Patent, 120,926, 1984; 1,236,581, 1984;
43. (a) T. Yamamoto, K. Sanechika, A. Yamamoto, Japan Kokai Patent, 47,421, 1981; Jpn. Patent, 120,926, 1984; 1,236,581, 1984;
44. (a) T. Yamamoto, K. Sanechika, A. Yamamoto, Japan Kokai Patent, 47,421, 1981; Jpn. Patent, 120,926, 1984; 1,236,581, 1984;
45. (b) T. Yamamoto, K. Sanechika, A. Yamamoto, Japan Kokai Patent, 147,426, 1983 (applied: 26 February 1981; Japan, 1,258,016, 1985 and 1,262,404, 1985;
46. (b) T. Yamamoto, K. Sanechika, A. Yamamoto, Japan Kokai Patent, 147,426, 1983 (applied: 26 February 1981; Japan, 1,258,016, 1985 and 1,262,404, 1985;
47. (c) U.S. Patent, 4,521,589, 1985.
48. (a) T. Yamamoto, K. Sanechika, A Yamamoto, J. Polym. Sci., Polym. Lett. Ed. 18 (1980) 9;
49. (b) K. Sanechika, T. Yamamoto, A. Yamamoto, Polym. Prepr. Jpn. 27 (1979) 966;
50. (c) T. Yamamoto, K. Sanechika, A. Yamamoto, Bull. Chem. Soc. Jpn. 56 (1983) 1497, 1503;
51. (d) T. Yamamoto, A. Morita, Y. Miyazaki, T. Maruyama, H. Wakayama, Z.-H. Zhou, Y. Nakamura, T. Kanbara, S. Sasaki, K. Kubota, Macromolecules 25 (1992) 1214.
52. (a) T. Yamamoto, K. Sanechika, Chem. Ind. (London) (1982) 301;
53. (b) Y. Miyazaki, T. Yamamoto, Synth. Met. 64 (1994) 69.
54. (a) R.D. McCullough, R.D. Lowe, M. Jayaraman, D.L. Anderson, J. Org. Chem. 58 (1993) 904;
55. (b) T. Chen, X. Wu, R.D. Rieke, J. Am. Chem. Soc. 117 (1995) 233.
56. (a) T. Mizoroki, K. Mori, A. Ozaki, Bull. Chem. Soc. Jpn. 44 (1971) 581;
57. (b) R.F. Heck, J.P. Nolley, Jr., J. Org. Chem. 37 (1972) 2320;
58. (c) H.A. Dieck, R.F. Heck, J. Organomet. Chem. 93 (1975) 259.
59. K. Sonogashira, Y. Tohda, N. Hagihara, Tetrahedron Lett. 16 (1975) 4467.
60. (a) A. Greiner, B. Bolle, P. Hesemann, J.M. Oberski, R. Sander, Macromol. Chem. Phys. 197 (1996) 113;
61. (b) W.-K. Chan, L. Yu, Macromolecules 28 (1995) 6410;
62. (c) H. Nishide, T. Kaneko, S. Toriu, Y. Kuzumaki, E. Tsuchida, Bull. Chem. Soc. Jpn. 69 (1996) 499.
63. (a) K. Sanechika, T. Yamamoto, A. Yamamoto, Bull. Chem. Soc. Jpn. 57 (1984) 752;
64. (b) T. Yamamoto, M. Takagi, K. Kizu, T. Maruyama, K. Kubota, H. Kanbara, T. Kurihara, T. Kaino, J. Chem. Soc., Chem. Commun. (1993) 797;
65. (c) K. Sanechika, T. Yamamoto, A. Yamamoto, Polym. Prepr. Jpn. 30 (1981) 160;
66. (d) T. Yamamoto, W. Yamada, M. Takagi, K. Kizu, T. Maruyama, N. Ooba, S. Tomaru, T. Kurihara, T. Kaino, K. Kubota, Macromolecules 27 (1994) 6620.
67. T. Yamamoto, H. Suganuma, T. Maruyama, K. Kubota, J. Chem. Soc., Chem. Commun. (1995) 1613.
68. (a) Z.-H. Zhou, T. Maruyama, T. Kanbara, T. Ikeda, K. Ichimura, T. Yamamoto, K. Tokuda, J. Chem. Soc., Chem. Commun. (1991) 1210;
69. (b) T. Kurihara, T. Kaino, Z.-H. Zhou, T. Kanbara, T. Yamamoto, Electronics Lett. 28 (1992) 681;
70. (c) K. Kizu, T. Maruyama, T. Yamamoto, Polym. J. 27 (1995) 205.
71. (a) T. Yamamoto, M. Shimura, K. Osakada, K. Kubota, Chem. Lett. (1992) 1003;
72. (b) T. Yamamoto, Z.-H. Zhou, T. Kanbara, M. Shimura, K. Kizu, T. Maruyama, Y. Nakamura, T. Fukuda, B.-L. Lee, N. Ooba, S. Tomaru, T. Kurihara, T. Kaino, K. Kubota, S. Sasaki, J. Am. Chem. Soc. 118 (1996) 10,389.
73. (a) T. Yamamoto, Prog. Polym. Sci. 17 (1992) 1153; J. PoIm. Sci., Part A: Polym. Chem. 34 (1996) 997;
74. (a) T. Yamamoto, Prog. Polym. Sci. 17 (1992) 1153; J. PoIm. Sci., Part A: Polym. Chem. 34 (1996) 997;
75. (b) Y. Wang, R.P. Quirk, Macromolecules 28 (1995) 3495;
76. (c) K. Erdmann, W. Czerwinski, B.C. Grestein, M. Pruski, J. Polym. Sci., Part B: Polym. Phys. 32 (1994) 1961.
77. (a) N. Saito, T. Kanbara. T. Kushida, K. Kubota, T. Yamamoto, Chem. Lett. (1993) 1775;
78. (b) N. Saito, T. Kanbara, Y. Nakamura, T. Yamamoto, K. Kubota, Macromolecules 27 (1994) 419.
79. N. Saito, T. Yamamoto, Macromolecules 28 (1995) 4260.
80. Y. Saitoh, T. Yamamoto, Chem. Lett. (1995) 785.
81. T. Yamamoto, Y. Yoneda, K. Kizu, Makromol. Rapid Commun. 16 (1995) 549.
82. T. Kanbara, Y. Miyazaki, T. Yamamoto, J. Polym. Sci., Part A, Polym. Chem. 33 (1995) 999.
83. (a) N. Ooba, S. Tomaru, T. Kurihara, T. Kaino, W. Yamada, M. Takagi, T. Yamamoto, Jpn. J. Appl. Phys. 34 (1995) 3139;
84. (b) N. Ooba, M. Asobe, S. Tomaru, T. Kaino, W. Yamada, M. Takagi, T. Yamamoto, Nonlinear Optics 15 (1996) 481.
85. K. Suruga, T. Fukuda, K. Ishikawa, H. Takezoe, A. Fukuda, T. Kanbara, T. Yamamoto, Synth. Met. 79 (1996) 149.
86. (a) H. Etori, T. Kanbara, T. Yamamoto, Chem. Lett. (1994) 461;
87. (b) T. Yamamoto, H. Etori, Macromolecules 28 (1995) 3371.
88. Y. Muramatsu, T. Yamamoto, Chem. Lett. (1997) 581.
89. T.A. Skotheim, Handbook of Conducting Polymers, Vols. I and II, Marcel Dekker, New York, NY, 1986.
90. T. Yamamoto, K. Sanechika, A. Yamamoto, M. Katada, I. Motoyama, H. Sano, Inorg. Chim. Acta 73f (1983) 75.
91. (a) T. Yamamoto, Chem. Lett. (1996) 703;
92. (b) T. Yamamoto, T. Maruyama, H. Suganuma, M. Arai, D. Komarudin, S. Sasaki, Chem. Lett. (1997) 139;
93. (c) T. Yamamoto, H. Suganuma, T. Maruyama, T. Inoue, Y. Muramatsu, M. Arai, D. Komarudin, N. Ooba, S. Tomaru, S. Sasaki, K. Kubota, Chem. Mat. 9 (1997) 1217;
94. (d) L. Gonzalez Londa, D.C. Martin, Macromolecules 30 (1997) 1524.
95. T. Yamamoto, B.-L. Lee, Chem. Lett. (1996) 65.
96. (a) T. Yamamoto, Z.-H. Zhou, T. Maruyama, T. Kanbara, Chem. Lett. (1990) 223;
97. (b) M.O. Wolf, M.S. Wrighton, Chem. Mat. 6 (1994) 1526.
98. (a) S.I. Yaniger, D.J. Rose, W.P. Mckenna, E.M. Eyring, Macromolecules 17 (1984) 2579;
99. (b) J. Matsuda, K. Aramaki, H. Nishihara, J. Chem. Soc., Faraday 91 (1995) 1477;
100. (c) H. Funaki, K. Aramaki, H. Nishihara, Synth. Met. 74 (1995) 59.
101. (a) T. Kanbara, T. Yamamoto, Macromolecules 26 (1993) 1975;
102. (b) T. Yamamoto, T. Kanbara, U.S. Patent, 5,310,829, 1994.
103. (a) T. Yamamoto, N. Saito, Chem. Lett. (1996) 127;
104. (b) T. Yamamoto, B.-L. Lee, H. Hayashi, N. Saito, T. Maruyama, Polymer 38 (1997) 4233.
105. T. Maruyama, T. Yamamoto, J. Phys. Chem. B 101 (1997) 3806.
106. T. Yamamoto, H. Hayashi, Kino Zairyo 15 (1995) 39.
107. (a) M. Wakabayashi, Y. Miyazaki, T. Kanbara, K. Osakada, T. Yamamoto, A. Ishibashi, Synth. Met. 55/57 (1993) 3632;
108. (b) T. Yamamoto, M. Wakabayashi, Eur. Pat. Appl. EP 597, 234 (1994);
109. (c) T. Yamamoto, M. Inami, T. Kanbara, Chem. Mat. 6 (1994) 44;
110. (d) T. Kanbara, M. Inami, T. Yamamoto, J. Power Sources 36 (1991) 87.
111. (a) T. Kanbara, T. Yamamoto, Chem. Lett. (1993) 1459;
112. (b) T. Yamamoto, T. Inoue, T. Kanbara, Jpn. J. Appl. Phys. 33 (1994) L250.
113. (a) T. Yamamoto, J. Chem. Soc., Chem. Commun. (1981) 187;
114. (b) D. Maclnnes Jr., M.A. Dury, P.J. Nigrey, D.P. Nairns, A.G. MacDiarmid, A.J. Heeger, J. Chem. Soc., Chem. Commun. (1981) 317;
115. (c) L.W. Schacklette, R.L. Elsenbaumer, R.R. Chance, J.M. Sowa, D.M. Ivory, G.G. Miller, R.H. Baughmann, J. Chem. Soc., Chem. Commun. (1982) 361;
116. (d) T. Yamamoto, M. Zama, M. Hishinuma, A. Yamamoto, J. Appl. Electrochem. 17 (1987) 607;
117. (e) T. Yamamoto, M. Zama, A. Yamamoto, Chem. Lett. (1985) 563;
118. (f) T. Yamamoto, Chem. Lett. (1984) 1576.
119. (a) A.G. MacDiarmid, L.S. Yang, W.S. Haung, B.D. Humphry, Synth. Met. 18 (1987) 393;
120. (b) Chem. Eng. News, 10 September 1984, p. 38;
121. c. J.C. Chiang, A.G. MacDiarmid, Synth. Met. 13 (1986) 193;
122. d. E. Daifuku, Kino Zairyo 8 (1988) 17;
123. e T. Yamamoto, T. Matsunaga, Polymer Battery, Kyoritsu, Tokyo, 1990.
124. (a) J.H. Burroughes, D.D.C. Bradley, A.R. Brown, R.N. Marks, K. Mackay, R.H. Friend, P.L. Burn, A.B. Holmes, Nature 347 (1990) 539;
125. (b) D. Brown, A.J. Heeger, H. Kroemer, J. Electron Mat. 20 (1991) 945;
126. (c) D.D.C. Bradley, Synth. Met. 54 (1993) 401;
127. (d) M. Ueda, Y. Ohmori, T. Noguchi, T. Ohnishi, Jpn. J. Appl. Phys. 32 (1993) L921;
128. (e) C. Adachi, T. Tsutsui, S. Saito, Appl. Phys. Lett. 57 (1990) 531.
129. (a) T. Yamamoto, K. Sugiyama, T. Kushida, T. Inoue, T. Kanbara, J. Am. Chem. Soc. 118 (1996) 3930;
130. (b) Eur. Pat. Appl., EP 643118, 1995.
131. T. Yamamoto, H. Wakayama, T. Fukuda, T. Kanbara, J. Phys. Chem. 96 (1992) 8677.
132. (a) A. Tsumura, H. Koezuka, T. Ando, Synth. Met. 25 (1988) 11;
133. (b) A. Tsumura, H. Fuchigami, H. Koezuka, Synth. Met. 41/4 (1991) 1181;
134. (c) F. Gamier, G. Horowitz, X.Z. Peng, D. Fichou, Synth. Met. 45 (1991) 163.
135. T. Yamamoto, H. Wakayama, T. Kanbara, K. Sasaki, K. Tsutsui, J. Furukawa, Denki Kagaku 62 (1994) 84.
136. (a) D.-K. Moon, T. Maruyama, K. Osakada, Chem. Lett. (1991) 1633;
137. (b) D.-K. Moon, K. Osakada, T. Maruyama, T. Yamamoto, Makromol. Chem. 193 (1992) 1723;
138. (c) D.-K. Moon, M. Ezuka, T. Maruyama, K. Osakada, T. Yamamoto, Macromolecules 26 (1993) 364;
139. (d) T. Yamamoto, Chem. Lett. (1993) 1211;
140. (e) T. Yamamoto, D.-K. Moon, Makromol. Chem. Rapid Commun. 14 (1993) 495;
141. (f) D.-K. Moon, M. Ezuka, T. Maruyama, K. Osakada, T. Yamamoto, Makromol. Chem. 194 (1993) 3149;
142. (g) D.-K. Moon, K. Osakada, T. Maruyama, K. Kubota, T. Yamamoto, Macromolecules 26 (1993) 6992.
143. (a) C.-F. Liu, T. Maruyama, T. Yamamoto, Polym. J. 25 (1993) 363;
144. (b) C.-F. Liu, D.-K. Moon, T. Maruyama, T. Yamamoto, Polym. J. 25 (1993) 775.