Linear organic π-conjugated systems featuring the heavy Group 14 and 15 elements

Coordination Chemistry Reviews

Volumn 244, Issue 1-2, 2003, Pages 1-44

  Hissler, Muriel ^a   Dyer, Philip W ^b   Réau, Régis ^a  

^a CNRS   (France)

^b UNIVERSITY OF LEICESTER   (United Kingdom)

Author keywords

Electronic structure; Heteroelements; Metalloles; Conjugated polymers

Indexed keywords

OLIGOMER; ORGANIC COMPOUND; PHOSPHOLE DERIVATIVE; POLYMER; SILICON DERIVATIVE;

CHEMICAL COMPOSITION; CONJUGATION; ELECTROCHEMISTRY; FLUORESCENCE SPECTROSCOPY; IONIZATION; POLYMERIZATION; REACTION ANALYSIS; REVIEW; SYNTHESIS; ULTRAVIOLET SPECTROSCOPY;

EID: 0242352408     PISSN: 00108545     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0010-8545(03)00098-5     Document Type: Review

References (240)

1. (a) H. Shirakawa, E.J. Lewis, A.G. MacDiarmid, C.K. Chiang, A.J. Heeger, J. Chem. Soc. Chem. Comm. (1977) 578;
2. (b) C.K. Chiang, C.R. Fincher, Y.W. Park, A.J. Heeger, A.J. Shirakawa, E.J. Louis, S.C. Gau, A.G. MacDiarmid, Phys. Rev. Lett. 39 (1977) 1098.
3. T.A. Skotheim, R.L. Elsenbaumer, J.R. Reynolds (Eds.), Handbook of Conducting Polymers, Marcel Dekker, New York, 1998.
4. H. Shirakawa, A. McDiarmid, A. Heeger, Chem. Commun. (2003) 1.
5. J.F. Lennard-Jones, Proc. R. Soc. London A 158 (1937) 280.
6. G. Natta, G. Mazzanti, P. Corrandini, Rend. Accad. Naz. Lincei CI Sc. Fis. Mat. e. Nat. 25 (1958) 3.
7. D.J. Berets, D.S. Smith, Trans. Faraday Soc. (1968) 823.
8. i is the carrier mobility.
9. (a) H. Shirakawa, S. Ikeda, Polym. J. 2 (1971) 231;
10. (b) H. Shirakawa, S. Ikeda, J. Polym. Sci. Polym. Chem. Ed. 12 (1973) 929;
11. (c) T. Ito, H. Shirakawa, S. Ikeda, J. Polym. Sci. Polym. Chem. Ed. 13 (1974) 11.
12. N. Basescu, Z. Liu, D. Moses, A.J. Heeger, H. Naarmann, N. Theophilou, Nature 327 (1987) 403.
13. N.C. Billingham, P.D. Calvert, Adv. Polym. Sci. 90 (1989) 1.
14. J.G. Verkade, J. Chem. Ed. 68 (1991) 739.
15. (a) J. Roncali, Chem. Rev. 97 (1997) 173;
16. (b) R.E. Martin, F. Diederich, Angew. Chem. Int. Ed. Engl. 38 (1999) 1350;
17. (c) K. Susumu, M.J. Therien, J. Am. Chem. Soc. 124 (2002) 8550.
18. E. Hückel, Z. Für. Phys. 70 (1931) 204.
19. O. Wennerström, Macromolecules 18 (1985) 1977.
20. D.O. Cowan, F.M. Wiygul, Chem. Eng. News 64 (1986) 28.
21. R.E. Peierls, Quantum Theory of Solids, OUP, London, 1956.
22. (a) A. Kraft, A.C. Grimsdale, A.B. Holmes, Angew. Chem. Int. Ed. Engl. 37 (1998) 403;
23. (b) U. Mitschke, P. Bäuerle, J. Mater. Chem. 10 (2000) 1471;
24. (c) U.H.F. Bunz, Chem. Rev. 110 (2000) 1605;
25. (d) J.M. Tour, Acc. Chem. Res. 33 (2000) 791.
26. (a) E.H. Bray, W. Hübel, Chem. Ind. (London) (1959) 1250.;
27. (b) E.H. Bray, W. Hübel, I. Caplier, J. Am. Chem. Soc. 83 (1961) 4406.
28. (a) F.C. Leavitt, T.A. Manuel, F. Johnson, J. Am. Chem. Soc. 81 (1959) 3163;
29. (b) F.C. Leavitt, T.A. Manuel, F. Johnson, L.U. Matternas, D.S. Lehman, J. Am. Chem. Soc. 82 (1960) 5099.
30. S. Yamaguchi, K. Tamao, J. Chem. Soc. Dalton Trans. (1998) 3693.
31. L. Nyulaszi, Chem. Rev. 101 (2001) 1229.
32. S. Yamaguchi, Y. Itami, K. Tamao, Organometallics 17 (1998) 4910.
33. (a) J. Dubac, A. Laporterie, G. Manuel, Chem. Rev. 90 (1990) 215;
34. (b) E. Colomer, R.J.P. Corriu, M. Lheureux, Chem. Rev. 90 (1990) 265.
35. F. Mathey, Chem. Rev. 88 (1988) 429.
36. L.D. Quin, in: A.R. Katritzky (Ed.), Comprehensive Heterocyclic Chemistry, Pergamon Press, Oxford, 1996, p. 757.
37. P. von Ragué Schleyer, P.K. Freeman, H. Jiao, B. Goldfuss, Angew. Chem. Int. Ed. Engl. 34 (1995) 337.
38. P. von Ragué Schleyer, C. Maerker, A. Dransfeld, H. Jiao, N.J.R. van Eikema Hommes, J. Am. Chem. Soc. 118 (1996) 6317.
39. W. Schäfer, A. Schweig, F. Mathey, J. Am. Chem. Soc. 28 (1975) 407.
40. E. Mattmann, F. Mathey, A. Sevin, G. Frison, J. Org. Chem. 67 (2002) 1208.
41. D. Delaere, A. Dransfeld, M.N. Nguyen, L.G. Vanquickenborne, J. Org. Chem. 65 (2000) 2631.
42. (a) G. Keglevitch, Z. Böcskei, G.M. Keseru, K. Ujszaszy, L.D. Quin, J. Am. Chem. Soc. 119 (1997) 5095;
43. (b) L. Nyulaszi, G. Keglevitch, L.D. Quin, J. Org. Chem. 61 (1996) 7808.
44. E. Mattmann, D. Simonutti, L. Ricard, F. Mercier, F. Mathey, J. Org. Chem. 66 (2001) 755.
45. C. Hay, M. Hissler, C. Fischmeister, J. Rault-Berthelot, L. Toupet, L. Nyulaszi, R. Réau, Chem. Eur. J. 7 (2001) 4222.
46. I. Albert, T. Marks, M. Ratner, J. Am. Chem. Soc. 119 (1997) 6575.
47. (a) P. Audebert, J.-M. Catel, G. Le Coustumer, V. Duchenet, P. Hapiot, J. Phys. Chem. B 102 (1998) 8661;
48. (b) P. Audebert, J.-M. Catel, V. Duchenet, L. Guyard, P. Hapiot, G. Le Coustumer, Synth. Met. 101 (1999) 642;
49. (c) Z. Zhou, T. Maruyama, T. Kanbara, T. Ikeda, K. Ichimura, T. Yamamoto, K. Tokuda, Chem. Commun. (1991) 1210;
50. (d) T. Yamamoto, Z.-H. Zhou, T. Kanbara, M. Shimura, K. Kizu, T. Maruyama, Y. Nakamura, T. Fukuda, B.L. Lee, N. Ooba, S. Tomura, T. Kurihara, T. Kaino, K. Kubota, S. Sasaki, J. Am. Chem. Soc. 118 (1996) 10389.
51. (a) J. Shinar, S. Ijadi-Maghsoodi, Q.-X. Ni, Y. Pang, T.J. Barton, Synth. Met. 28 (1989) C593;
52. (b) S. Grigoras, G.C. Lie, T.J. Barton, S. Ijadi-Maghsoodi, Y. Pang, J. Shinar, Z.V. Vardeny, K.S. Wong, S.G. Han, Synth. Met. 49-50 (1992) 293;
53. (c) S.Y. Hong, S.J. Kwon, S.C. Kim, D.S. Marynick, Synth. Met. 69 (1995) 701;
54. (d) S.Y. Hong, S.J. Kwon, S.C. Kim, J. Chem. Phys. 103 (1995) 1871.
55. U. Salzner, J.B. Lagowski, P.G. Pickup, R.A. Poirier, Synth. Met. 96 (1998) 177.
56. J. Ma, S. Li, Y. Jiang, Macromolecules 35 (2002) 1109.
57. D. Delaire, M.T. Nguyen, L.G. Vanquickenborne, J. Organomet. Chem. 643 (2002) 194.
58. D. Fichou (Ed.), Handbook of Oligo- and Poly-thiophene, Wiley-VCH, Weinheim, 1999.
59. M. Karelson, M.C. Zerner, Chem. Phys. Lett. 224 (1994) 213.
60. (a) M. Gouygou, O. Tissot, J.-C. Daran, G.G.A. Balavoine, Organometallics 16 (1997) 1008;
61. (b) O. Tissot, M. Gouygou, F. Dallemer, J.-C. Daran, G.G.A. Balavoine, Angew. Chem. Int. Ed. Engl. 40 (2001) 1076.
62. E. Deschamps, L. Ricard, F. Mathey, Angew. Chem. Int. Ed. Engl. 33 (1994) 1158.
63. (a) H.S. Nalwa, S. Miyata, Non-linear Optics of Organic Molecules and Polymers, CRC Press, Boca Raton, FL, 1997;
64. (b) G. Wagnière, Linear and Non-linear Optical Properties of Molecules, VCH, Weinheim, Germany, 1993.
65. A. Julg, P. François, Theoret. Chim. Acta 7 (1967) 249.
66. (a) R.D. Miller, J. Michl, Chem. Rev. 89 (1989) 1359;
67. (b) K. Tamao, S. Yamaguchi, J. Organomet. Chem. 611 (2000) 5.
68. V.N. Khabashesku, V. Balaji, S.E. Boganov, O.M. Nefedov, J. Michl, J. Am. Chem. Soc. 116 (1994) 320.
69. S. Yamaguchi, K. Tamao, Bull. Chem. Soc. Jpn. 69 (1996) 2327.
70. Y. Yamaguchi, Synth. Met. 82 (1996) 149.
71. S. Yamaguchi, K. Tamao, in: Z. Rappoport, Y. Apeloig (Eds.), The Chemistry of Organic Silicon Compounds, vol. 3, Wiley, New York, 2001, pp. 647-694.
72. J. Dubac, C. Guerin, P. Meunier, in: Z. Rappoport, Y. Apeloig (Eds.), The Chemistry of Organic Silicon Compounds, vol. 2 (Chapter 34), Wiley, New York, 1999, p. 34 (Chapter 34).
73. D.A. Armitage, in: A.R. Katritzky (Ed.), Comprehensive Heterocyclic Chemistry, Pergamon Press, Oxford, 1996, p. 903.
74. P. Jutzi, A. Karl, J. Organomet. Chem. 214 (1981) 289.
75. U. Losehund, N.W. Mitzel, J. Chem. Soc. Dalton Trans. (2000) 1049.
76. T.J. Barton, J. Organomet. Chem. 179 (1975) C17.
77. J. Dubac, Organometallics 5 (1986) 1742.
78. K. Tamao, S. Yamaguchi, M. Shiro, J. Am. Chem. Soc. 116 (1994) 11715.
79. N.E. Schore, in: B.M. Trost, I. Fleming (Eds.), Comprehensive Organic Synthesis, vol. 5, Pergamon Press, Oxford, 1991, p. 1129 See for example:
80. S. Yamaguchi, R.-Z. Jin, K. Tamao, M. Shiro, Organometallics 16 (1997) 2230.
81. T. Hiiro, N. Kambe, A. Ogawa, N. Miyoshi, S. Murai, N. Sonoda, Angew. Chem. Int. Ed. Engl. 26 (1987) 1187 (and references therein).
82. M. Katkevics, S. Yamaguchi, A. Toshimitsu, K. Tamao, Organometallics 17 (1998) 5796.
83. S. Yamaguchi, R.-Z. Jin, S. Ohno, K. Tamao, Organometallics 17 (1998) 5133.
84. S. Yamaguchi, R.-Z. Jin, K. Tamao, F. Sato, J. Org. Chem. 63 (1998) 10060.
85. See for examples: (a) A.J. Ashe, III, J.W. Kampf, S.M. Al-Taweel, J. Am. Chem. Soc., 114 (1992) 372;
86. (b) E. Negishi, S.J. Holmes, J.M. Tour, J.A. Miller, F.E. Cederbaum, D.R. Swanson, T. Takahashi, J. Am. Chem. Soc. 111 (1989) 3336 (and references therein).
87. K.-I. Kanno, M. Kira, Chem. Lett. (1999) 1127.
88. (a) P.J. Fagan, W.A. Nugent, J. Am. Chem. Soc. 110 (1988) 2310;
89. (b) P.J. Fagan, W.A. Nugent, J.C. Calabrese, J. Am. Chem. Soc. 116 (1994) 1880.
90. Y. Ura, Y. Li, Z. Xi, T. Takahashi, Tetrahedron Lett. 39 (1998) 2787.
91. B. Lucht, M. Buretea, T. Don Tilley, Organometallics 19 (2000) 3469.
92. W.P. Freeman, T.D. Tilley, L.M. Liable-Sands, A.L. Rheingold, J. Am. Chem. Soc. 118 (1996) 10457.
93. K. Tamao, S. Yamaguchi, M. Shiozaki, Y. Nakagawa, Y. Ito, J. Am. Chem. Soc. 114 (1992) 5867.
94. H. Sohn, R. Huddleston, D.R. Powell, R. West, J. Am. Chem. Soc. 121 (1999) 2935.
95. S. Yamaguchi, R.-Z. Jin, K. Tamao, M. Shiro, Organometallics 16 (1997) 2486.
96. K. Kanno, M. Ichinohe, C. Kabuto, M. Kira, Chem. Lett. (1998) 99.
97. J.H. Burroughs, D.D.C. Bradley, A.R. Brown, R.N. Marks, K. Mackay, P.L. Burns, A.B. Holmes, Nature 347 (1990) 539.
98. (a) J.-S. Yang, T.M. Swager, J. Am. Chem. Soc. 120 (1998) 5321;
99. (b) J.-S. Yang, T.M. Swager, J. Am. Chem. Soc. 120 (1998) 11864.
100. S. Content, W.C. Trogler, M.J. Sailor, Chem. Eur. J. 6 (2000) 2205.
101. H. Sohn, R. Calhoun, M.J. Sailor, W.C. Trogler, Angew. Chem. Int. Ed. 40 (2001) 2104.
102. W.P. Freeman, T. Don Tilley, G.P.A. Yap, A.L. Rheingold, Angew. Chem. Int. Ed. Engl. 35 (1996) 882.
103. J.-H. Hong, P. Boudjouk, S. Castellino, Organometallics 13 (1994) 3387.
104. J.-H. Hong, Y. Pan, P. Boudjouk, Angew. Chem. Int. Ed. Engl. 35 (1996) 186.
105. S. Yamaguchi, R.-Z. Jin, K. Tamao, J. Am. Chem. Soc. 121 (1999) 2937.
106. S. Yamaguchi, R.-Z. Jin, K. Tamao, ICR Annu. Rep. 4 (1997) 34.
107. S. Yamaguchi, R.-Z. Jin, Y. Itami, T. Goto, K. Tamao, J. Am. Chem. Soc. 121 (1999) 10420.
108. (a) K. Tamao, S. Yamaguchi, Pure Appl. Chem. 68 (1996) 139;
109. (b) S. Yamaguchi, K. Tamao, J. Syn. Org. Chem. Jpn. 56 (1998) 500.
110. R.J.P. Corriu, W.E. Douglas, Z.-X. Yang, J. Organomet. Chem. 456 (1993) 35 (and references therein).
111. E. Toyada, A. Kunai, M. Ishikawa, Organometallics 14 (1995) 1089.
112. T.J. Barton, S. Ijadi-Maghsoodi, Y. Pang, Macromolecules 24 (1991) 1257.
113. (a) B. Wrackmeyer, J. Chem. Soc. Chem. Comm. (1986) 397;
114. (b) B. Wrackmeyer, G. Kehr, J. Süß, Chem. Ber. 126 (1993) 2221.
115. S. Yamaguchi, K. Tamao, Tetrahedron Lett. 37 (1996) 2983.
116. J. Ferman, J.P. Kakareka, W.T. Kloster, J.L. Mullin, J. Quattrucci, J.S. Ricci, H.J. Tracy, W.J. Vining, S. Wallace, Inorg. Chem. 38 (1999) 2465.
117. K. Tamao, M. Asahara, A. Kawachi, J. Organomet. Chem. 521 (1996) 325.
118. L. Párkányi, J. Organomet. Chem. 216 (1981) 9.
119. H. Gilman, S.G. Cottis, W.H. Atwell, J. Am. Chem. Soc. 86 (1964) 1596.
120. B.Z. Tang, X. Zhan, G. Yu, P.P.S. Lee, Y. Liu, D. Zhu, J. Mater. Chem. 11 (2001) 2974.
121. A. Adachi, H. Yasuda, T. Sanji, H. Sakurai, H. Okita, J. Luminol. 87-89 (2000) 1174.
122. K. Tamao, M. Uchida, T. Izumizawa, K. Furukawa, S. Yamaguchi, J. Am. Chem. Soc. 118 (1996) 11974.
123. S. Yamaguchi, M. Endo, M. Uchida, T. Izumizawa, K. Furukawa, K. Tamao, Chem. Eur. J. 6 (2000) 1683.
124. J. Luo, Z. Xie, J.W.Y. Lam, L. Cheng, H. Chen, C. Qiu, H.S. Kwok, X. Zhan, Y. Liu, D. Zhu, B.Z. Tang, Chem. Commun. 18 (2001) 1740.
125. B.L. Lucht, M.A. Buretea, T. Don Tilley, Organometallics 19 (2000) 3469.
126. G. Froyer, Y. Pelous, G. Ollivier, Springer Ser. Solid State Sci. 76 (1988) 303.
127. For a review, see: R.H. Baughman, J.L. Bredas, R.R. Chance, R.L. Elsenbauer, L.W. Shacklette, Chem. Rev., 88 (1982) 209
128. K. Tamao, S. Yamaguchi, Y. Ito, Y. Matsuzaki, T. Yamabe, M. Fukushima, S. Mori, Macromolecules 28 (1995) 8668.
129. S. Yamaguchi, K. Tamao, J. Organomet. Chem. 653 (2002) 223.
130. S. Yamaguchi, T. Goto, K. Tamao, Angew. Chem. Int. Ed. 39 (2000) 1695.
131. For a review of cross-coupling reactions for the synthesis of π-conjugated polymers see: T. Yamamoto, J. Organomet. Chem., 653 (2002) 195
132. S.Y. Hong, J.M. Song, Synth. Met. 85 (1997) 1113.
133. S. Yamaguchi, K. Tamao, J. Organomet. Chem. 653 (2002) 223.
134. (a) J.W. Sease, L. Zechmeister, J. Am. Chem. Soc. 69 (1947) 3674;
135. (b) R.D. McCullough, R.D. Lowe, M. Jayaramam, D.L. Anderson, J. Org. Chem. 58 (1993) 904.
136. (a) Y. Lee, S. Sadki, B. Tsuie, P. Schottland, J.R. Reynolds, Synth. Met. 119 (2001) 77;
137. (b) Y. Lee, S. Sadki, B. Tsuie, J.R. Reynolds, Chem. Mater. 13 (2001) 2234.
138. K. Tamao, S. Ohno, S. Yamaguchi, Chem. Commun. (1996) 1873.
139. T. Kauffmann, L. Hexy, Chem. Ber. 114 (1981) 3674.
140. T. Yamamoto, K. Sugiyama, T. Kushida, T. Inoue, T. Kanbara, J. Am. Chem. Soc. 118 (1996) 3930.
141. (a) H. Murata, G.G. Malliaras, M. Uchida, Y. Shen, Z.H. Kafafi, Chem. Phys. Lett. 339 (2001) 161;
142. (b) M. Uchida, T. Izumizawa, T. Nakano, S. Yamaghushi, K. Tamao, K. Furukawa, Chem. Mater. 13 (2001) 2680;
143. (c) H. Murata, Z.H. Zakia, Z.H. Kafafi, M. Uchida, Appl. Phys. Lett. 80 (2002) 189.
144. S. Yamagushi, T. Endo, M. Uchida, T. Izumizawa, K. Furukawa, K. Tamao, Chem. Lett. (2001) 98.
145. S. Yamaguchi, K. Iimura, K. Tamao, Chem. Lett. (1998) 89.
146. W. Chen, S. Ijadi-Maghshoodi, T.J. Barton, Polym. Prepr. (Am. Chem. Soc. Div. Polym. Chem.) 38 (1997) 189.
147. M. Moroni, J.L. Moigne, T.A. Pham, J.-Y. Bigot, Macromolecules 30 (1997) 1964.
148. E. Toyada, A. Kunai, M. Ishikawa, Organometallics 14 (1995) 1089.
149. J. Oshita, T. Hamaguchi, E. Toyoda, A. Kunai, K. Komagushi, M. Shiotani, M. Ishikawa, A. Naka, Organometallics 18 (1999) 1717.
150. (a) R.J.P. Corriu, P. Gerbier, C. Guérin, B.J.L. Henner, A. Jean, P.H. Mutin, Organometallics 11 (1992) 2507;
151. (b) R.J.P. Corriu, W.E. Douglas, Z.-X. Yang, J. Organomet. Chem. 456 (1993) 35.
152. K.B. Dillon, F. Mathey, J.F. Nixon, Phosphorus: The Carbon Copy, Wiley, Chichester, UK, 1998.
153. (a) F. Mathey, F. Mercier, F. Nief, J. Fischer, A. Mitschler, J. Am. Chem. Soc. 104 (1982) 2077;
154. (b) F. Laporte, F. Mercier, L. Ricard, F. Mathey, J. Am. Chem. Soc. 116 (1994) 3306;
155. (c) M.O. Bevierre, F. Mercier, F. Mathey, A. Jutand, C. Amatore, New J. Chem. 15 (1991) 545.
156. (a) F. Mercier, F. Mathey, J. Fischer, J.H. Nelson, Inorg. Chem. 24 (1985) 4141;
157. (b) F. Mercier, F. Mathey, J. Fischer, J.H. Nelson, J. Am. Chem. Soc. 106 (1984) 425.
158. F. Mercier, S. Holand, F. Mathey, J. Organomet. Chem. 316 (1986) 271.
159. O. Tissot, J. Hydrio, M. Gouygou, F. Dallemer, J.-C. Daran, G.G.A. Balavoine, Tetrahedron 56 (2000) 85.
160. O. Tissot, M. Gouygou, J.-C. Daran, G.G.A. Balavoine, Chem. Commun (1996) 2287.
161. (a) O. Tissot, M. Gouygou, J.-C. Daran, G.G.A. Balavoine, Organometallics 17 (1998) 5927;
162. (b) O. Tissot, M. Gouygou, F. Dallemer, J.-C. Daran, G.G.A. Balavoine, Eur. J. Inorg. Chem. (2001) 2385.;
163. (c) T. Kojima, K. Saeki, K. Ono, Y. Matsuda, Bull. Chem. Soc. Jpn. 71 (1998) 2885.
164. O. Tissot, M. Gouygou, J.-C. Daran, G.G.A. Balavoine, Acta Crystallogr. Sect. C 54 (1998) 676.
165. E. Deschamps, F. Mathey, Bull. Soc. Chim. Fr. 129 (1992) 486.
166. (a) T.-A. Niemi, P.L. Coe, S.J. Till, J. Chem. Soc. Perkin Trans. 1 (2000) 1519;
167. (b) J. Hydrio, M. Gouygou, F. Dallemer, G.G.A. Balavoine, J.-C. Daran, Eur. J. Org. Chem. (2002) 675.
168. I.G.M. Campbell, R.C. Cookson, M.B. Hocking, A.N. Hughes, J. Chem. Soc. (1965) 2184.
169. Z. Raciszewski, E.H. Braye, Photochem. Photobiol. 12 (1970) 429.
170. W.P. Ozbirn, R.A. Jacobson, J.C. Clardy, J. Chem. Soc. Chem. Comm. (1971) 1062.
171. E. Deschamps, L. Ricard, F. Mathey, Heteroatom. Chem. 2 (1991) 377.
172. E. Deschamps, F. Mathey, J. Org. Chem. 55 (1990) 2494.
173. D. Le Vilain, C. Hay, V. Deborde, L. Toupet, R. Réau, Chem. Commun. (1999) 345.
174. C. Hay, C. Fischmeister, M. Hissler, L. Toupet, R. Réau, Angew. Chem. Int. Ed. Engl. 10 (2000) 1812.
175. Q.T. Zhang, J.T. Tour, J. Am. Chem. Soc. 120 (1998) 5355.
176. (a) A. Hucke, M.P. Cava, J. Org. Chem. 63 (1998) 7413;
177. (b) P.E. Niziurski, C.C. Scordilis-Kelley, T.L. Liu, M.P. Cava, R.T. Carlin, J.P. Ferraris, J. Am. Chem. Soc. 115 (1993) 887;
178. (c) J.P. Ferraris, R.G. Andrus, D.C. Hrncir, J. Chem. Soc. Chem. Commun. (1989) 1318.
179. M. Sauthier, B. Le Guennic, V. Deborde, L. Toupet, J.-F. Halet, R. Réau, Angew. Chem. Int. Ed. 40 (2001) 228.
180. M. Sauthier, F. Leca, L. Toupet, R. Réau, Organometallics 21 (2002) 1591.
181. (a) C. Hay, M. Sauthier, V. Deborde, M. Hissler, L. Toupet, R. Réau, J. Organomet. Chem. 643-644 (2002) 494;
182. (b) M. Sauthier, L. Toupet, R. Réau, J. Organomet. Chem. 643-644 (2002) 494.
183. (a) T. Pechmann, C.D. Brandt, H. Werner, Angew. Chem. Int. Ed. 39 (2000) 3909;
184. (b) P. Braunstein, N.M. Boag, Angew. Chem. Int. Ed. 40 (2001) 2427.
185. (a) V. Balzani, A. Juris, M. Venturi, S. Campagna, S. Serroni, Chem. Rev. 96 (1996) 759;
186. (b) R. Ziessel, M. Hissler, A. El-Ghayoury, A. Harriman, Coord. Chem. Rev. 178-180 (1998) 1251;
187. (c) J.M. Lehn, Supramolecular Chemistry, VCH, Weinheim, 1995;
188. (d) R. Dembinski, T. Bartik, B. Bartik, M. Jaeger, J.A. Gladysz, J. Am. Chem. Soc. 122 (2000) 810;
189. (e) F. Barigelletti, L. Flamigni, V. Balzani, J.-P. Colin, J.-P. Sauvage, A. Sour, E.C. Constable, A.M.W. Cargill-Thompson, J. Am. Chem. Soc. 104 (1994) 7692;
190. (f) F. Paul, C. Lapinte, Coord. Chem. Rev. 178-180 (1998) 431;
191. (g) C. Rovira, D. Ruiz-Molina, O. Elsner, J. Vidal-Gancedo, J. Bonvoisin, J.-P. Launay, J. Veciana, Chem. Eur. J. 7 (2001) 240;
192. (h) V. Wing-Wah Yam, Chem. Commun. (2001) 789.
193. C. Fave, M. Hissler, K. Sénéchal, I. Ledoux, J. Zyss, R. Réau, Chem. Commun. (2002) 1674.
194. M.O. Bevierre, F. Mercier, L. Ricard, F. Mathey, Angew. Chem. Int. Ed. 29 (1990) 655.
195. J.J. Apperloo, J.-M. Raimundo, P. Frère, J. Roncali, R.A.J. Janssen, Chem. Eur. J. 9 (2000) 1698.
196. S. Holand, F. Gandolfo, L. Ricard, F. Mathey, Bull. Soc. Chem. Fr. 33 (1996) 133.
197. (a) B.L. Lucht, S.S.H. Mao, T. Don Tilley, J. Am. Chem. Soc. 120 (1998) 4354;
198. (b) B.L. Lucht, T.D. Tilley, Chem. Commun (1998) 1645.
199. S.S.H. Mao, T. Don Tilley, Macromolecules 30 (1997) 5566.
200. (a) N. Matsumi, K. Naka, Y. Chujo, J. Am. Chem. Soc. 120 (1998) 10776;
201. (b) N. Matsumi, K. Naka, Y. Chujo, J. Am. Chem. Soc. 120 (1998) 5112.
202. (a) A.G. MacDiarmid, J.C. Chiang, A.J. Epstein, Synth. Met. 18 (1987) 285;
203. (b) F. Wudl, R.O. Angus, Jr., F.L. Lu, P.M. Allemand, D.F. Vachon, M. Novak, Z.X. Liu, A.J. Heeger, J. Am. Chem. Soc. 109 (1987) 3677;
204. (c) F. Lux, Polymer 14 (1994) 2915;
205. (d) A.G. MacDiarmid, A.J. Epstein, Faraday Discuss. Chem. Soc. 31 (1989) 31 and 317;
206. (e) T.A. Skotheim (Ed.), Handbook of Conducting Polymers, Vols. I and II, Marcel Dekker, New York, 1986.
207. (a) S.A. Hay, Adv. Polym. Sci. 4 (1967) 496;
208. (b) S.A. Hay, Polym. Eng. Sci. 16 (1967) 1;
209. (c) S.A. Hay, G.F. Endres, J. Polym. Sci. Polym. Lett. Ed. 3 (1965) 887;
210. (d) S.A. Hay, Macromolecules 2 (1969) 107;
211. (e) C.G. Overberger, Macromolecular Synthesis, vol. 1, Wiley, New York, 1963, p. 75 and 345;
212. (f) R.H. Baughman, J.L. Bredas, R.R. Chance, R.L. Elsenbaumer, L.W. Shacklette, Chem. Rev. 82 (1982) 209;
213. (g) E. Tsuchida, K. Yamamoto, H. Nishide, S. Yoshida, Macromolecules 20 (1987) 2030;
214. (h) L. Freund, W. Heitz, Makromol. Chem. 191 (1990) 815;
215. (i) E. Tsuchida, K. Yamamoto, M. Jikei, H. Nishide, Macromolecules 23 (1990) 930;
216. (j) K. Yamamoto, M. Jikei, H. Nishide, E. Tsuchida, J. Chem. Soc. Chem. Commun. (1991) 596;
217. (k) E. Tsuchida, M. Jikei, K. Miyatake, K. Yamamoto, H. Nishide, Macromolecules 26 (1993) 4732.
218. B.L. Lucht, N.O. St Onge, Chem. Commun. (2000) 2097.
219. (a) F.E. Goodson, T.I. Wallow, B.M. Novak, Macromolecules 31 (1998) 2047;
220. (b) F.E. Goodson, T.I. Wallow, B.M. Novak, J. Am. Chem. Soc. 119 (1997) 12441.
221. G. de la Torre, A. Gouloumis, P. Vazquez, T. Torres, Angew. Chem. Int. Ed. 40 (2001) 2895.
222. L.T. Scott, M. Unno, J. Am. Chem. Soc. 112 (1990) 7823.
223. G. Märkl, T. Zollitsch, P. Kreitmeier, M. Prinzhorn, S. Reithinger, E. Eibler, Chem. Eur. J. 6 (2000) 3806.
224. M.H. Chisholm, Acc. Chem. Res. 33 (2000) 53.
225. (a) P. Nguyen, P. Gomez-Elipe, I. Manners, Chem. Rev. 99 (1999) 1515;
226. (b) E.W. Neuse, J.G. Chris, J. Macromol. Sci. Chem. A 1 (1967) 371;
227. (c) C.U. Pittman, J. Polym. Sci. Al 5 (1967) 2927.
228. (a) E.W. Neuse, J.G. Chris, J. Macromol. Sci. Chem. A 1 (1967) 371;
229. (b) C.U. Pittman, J. Polym. Sci. A 5 (1967) 2927.
230. (a) H.P. Withers, D. Seyferth, Organometallics 1 (1982) 1275;
231. (b) H.P. Withers, D. Seyferth, J.D. Fellmann, P.E. Garrou, S. Martin, Organometallics 1 (1982) 1283.
232. J.D. Fellmann, P.E. Garrou, H.P. Withers, D. Seyferth, D. Traficante, Organometallics 2 (1983) 818.
233. C.H. Honeyman, T.J. Peckham, J.A. Massey, I. Manners, Chem. Commun. (1996) 2589.
234. (a) I. Manners, Adv. Organomet. Chem. 37 (1995) 131;
235. (b) T.J. Peckham, J.A. Massey, C.H. Honeyman, I. Manners, Macromolecules 32 (1999) 2830.
236. C.H. Honeyman, D.A. Foucher, F.Y. Dahmen, R. Rulkens, A.J. Lough, I. Manners, Organometallics 14 (1995) 5503.
237. R. Resendes, J.M. Nelson, A. Fischer, F. Jäkle, A. Bartole, A.J. Lough, I. Manners, J. Am. Chem. Soc. 123 (2001) 2116.
238. P. Nguyen, P. Gomez-Elipe, I. Manners, Chem. Rev. 99 (1999) 1515.
239. V.A. Wright, D.P. Gates, Angew. Chem. Int. Ed. 41 (2002) 2389.
240. S. Chung, D.W. Lee, D. Oh, C.E. Lee, J. Jin, Acta Polym. 50 (1999) 298.