Synthesis of functional π-conjugated polymers from aromatic acetylenes

Polymer

Volumn 47, Issue 14, 2006, Pages 4867-4892

  Aoki, Toshiki ^a   Kaneko, Takashi ^a   Teraguchi, Masahiro ^a  

^a NIIGATA UNIVERSITY   (Japan)

Author keywords

poly(aryleneethynylene); Polyarylacetylene; conjugated polymers

Indexed keywords

ACETYLENE; AROMATIC COMPOUNDS; MAGNETIC SUSCEPTIBILITY; OXYGEN; SYNTHESIS (CHEMICAL);

POLY(ARYLENEETHYNYLENE); POLYARYLACETYLENE; Π-CONJUGATED POLYMERS;

ORGANIC POLYMERS;

CATALYST; MEMBRANE; ORGANIC POLYMER; PERFORMANCE ASSESSMENT; PERMEABILITY; POLYMERIZATION; SYNTHESIS;

EID: 33745383819     PISSN: 00323861     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.polymer.2006.04.047     Document Type: Review

References (179)

1. Ito T., Shirakawa H., and Ikeda T. J Polym Sci, Polym Chem Ed 12 (1974) 11
2. Shirakawa H., Louis E.J., MacDiarmid A.G., Chiang C.K., and Heeger A.J. J Chem Soc, Chem Commun (1977) 578
3. Masuda T., and Higashimura T. Acc Chem Res 17 (1984) 51
4. Masuda T., and Higashimura T. Adv Polym Sci 81 (1986) 121
5. Masuda T., Kaneshiro H., Hayano S., Misumi Y., and Bencze L. J Macromol Sci, Pure Appl Chem A34 (1997) 1977
6. Grubbs R.H., and Tumas W. Science 243 (1989) 907
7. Nguyen S.T., Grubbs R.H., and Ziller J.W. J Am Chem Soc 115 (1993) 9858
8. Feldman J., and Schrock R.R. Prog Inorg Chem 39 (1991) 1
9. Fox H.H., Wolf M.O., O'Dell R., Lin B.L., Schrock R.R., and Wrighton M.S. J Am Chem Soc 116 (1994) 2827
10. Schrock R.R., Luo S.-F., Lee Jr. J.C., Zanetti N.C., and Davis W.M. J Am Chem Soc 118 (1996) 3883
11. Odani H., and Masuda T. In: Toshima N. (Ed). Polymers for gas separations (1992), Wiley-VCH, New York 107
12. Nagai K., Masuda T., Nakagawa T., Freeman B.D., and Pinnau I. Prog Polym Sci 26 (2001) 721
13. Nishide H. Adv Mater 7 (1995) 937
14. Iwamura H., and Koga N. Acc Chem Res 26 (1993) 346
15. Nishide H., and Kaneko T. In: Lahti P.M. (Ed). Magnetic properties of organic materials (1999), Marcel Dekker, New York 285
16. Rajca A. Chem Eur J 8 (2002) 4834
17. Tabata M., Sone T., and Sadahiro Y. Macromol Chem Phys 200 (1999) 265
18. Tabata M., Kobayashi S., Sadahiro Y., Nozaki Y., Yokota K., and Yang W. J Macromol Sci, Pure Appl Chem A34 (1997) 641
19. Akagi K., Piao G., Kaneko S., Sakamaki K., Shirakawa H., and Kyotani M. Science 282 (1998) 1683
20. Akagi K., Piao G., Kaneko S., Higuchi I., Shirakawa H., and Kyotani M. Synth Met 102 (1999) 1406
21. Akagi K., Higuchi I., Piao G., Shirakawa H., and Kyotani M. Mol Cryst Liq Cryst Sci Technol, Sect A: Mol Cryst Liq Cryst 332 (1999) 2973
22. Yashima E., Maeda Y., and Okamoto Y. Chem Lett (1996) 955
23. Yashima E., Matsushima T., and Okamoto Y. J Am Chem Soc 117 (1995) 11596
24. Aoki T. Prog Polym Sci 24 (1999) 951
25. Aoki T., and Oikawa E. In: Salamone J.C. (Ed). Polymeric materials encyclopedia: synthesis, properties, and applications vol. 8 (1996), CRC Press, Boca Raton 6492
26. Kwak G., Aoki T., Toy L.G., Freeman B.D., and Masuda T. Polym Bull 45 (2000) 215
27. Teraguchi M., and Masuda T. J Polym Sci, Part A: Polym Chem 36 (1998) 2721
28. Teraguchi M., Masuda T., and Hachisuka H. J Macromol Sci, Pure Appl Chem A37 (2000) 1173
29. Toy L.G., Nagai K., Freeman B.D., Pinnau I., He Z., Masuda T., et al. Macromolecules 33 (2000) 2516
30. Nagai K., Toy L.G., Freeman B.D., Teraguchi M., Masuda T., and Pinnau I. J Polym Sci, Part B: Polym Phys 38 (2000) 1474
31. Fujita Y., Misumi Y., Tabata M., and Masuda T. J Polym Sci, Part A: Polym Chem 36 (1998) 3157
32. Teraguchi M., and Masuda T. J Polym Sci, Part A: Polym Chem 37 (1999) 4546
33. Yampolskii Y.P., Korikov A.P., Shantarovich V.P., Nagai K., Freeman B.D., Masuda T., et al. Macromolecules 34 (2001) 1788
34. Kanaya T., Tsukushi I., Kaji K., Sakaguchi T., Kwak G., and Masuda T. Macromolecules 35 (2002) 5559
35. Kanaya T., Teraguchi M., Masuda T., and Kaji K. Polymer 40 (1999) 7157
36. Yampolskii Y.P., Motyakin M.V., Wasserman A.M., Masuda T., Teraguchi M., Khotimskii V.S., et al. Polymer 40 (1999) 1745
37. Teraguchi M., and Masuda T. Macromolecules 35 (2002) 1149
38. Sakaguchi T., Yumoto K., Shiotsuki M., Sanda F., Yoshikawa M., and Masuda T. Macromolecules 38 (2005) 2704
39. Sakaguchi T., Shiotsuki M., and Masuda T. Macromolecules 37 (2004) 4104
40. Sakaguchi T., Shiotsuki M., Sanda F., Freeman B.D., and Masuda T. Macromolecules 38 (2005) 8327
41. Shida Y., Sakaguchi T., Shiotsuki M., Sanda F., Freeman B.D., and Masuda T. Macromolecules 38 (2005) 4096
42. Masuda T., Isobe E., and Higashimura T. J Am Chem Soc 105 (1983) 7473
43. Aoki T., Nakahara H., Hayakawa Y., Kokai M., and Oikawa E. J Polym Soc, Part A: Polym Chem 32 (1994) 849
44. Kwak G., Aoki T., and Kaneko T. Polymer 43 (2002) 1705
45. Aoki T., Nakahara H., and Oikawa E. Polym Prepr Jpn 41 (1992) 4036
46. Aoki T., Tada H., Kaneko T., and Oikawa E. Polym Prepr Jpn 46 (1997) 2159
47. Aoki T., Suzumura K., Kaneko T., and Oikawa E. Polym Prep Jpn 44 (1995) 1262
48. Hayakawa Y., Nishida M., Aoki T., and Muramatsu H. J Polym Sci, Part A: Polym Chem 30 (1992) 873
49. Aoki T., Kobayashi H., and Oikawa E. Polym Bull 34 (1995) 133
50. Inoue K. Prog Polym Sci 25 (2000) 453
51. Newkome G.R., Moorefield C.N., and Vögtle F. Dendrimers and dendrons-concepts, syntheses, applications (2001), Wiley-VCH, Weinheim
52. Tomalia D.A., and Fréchet J.M.J. J Polym Sci, Part A: Polym Chem 40 (2002) 2719
53. Fréchet J.M.J. J Polym Sci, Part A: Polym Chem 41 (2003) 3713
54. Aoki T., and Kaneko T. Polym J 37 (2005) 717
55. Schlüter A.D., and Rabe J. Angew Chem Int Ed Engl 39 (2000) 864
56. Zhang A., Shu L., Bo Z., and Schlüter A.D. Macromol Chem Phys 204 (2003) 328
57. Kaneko T., Horie T., Asano M., Aoki T., and Oikawa E. Macromolecules 30 (1997) 3118
58. Kaneko T., Horie T., Asano M., Matsumoto S., Yamamoto K., Aoki T., et al. Polym Adv 11 (2000) 685
59. Kaneko T., Asano M., Yamamoto K., and Aoki T. Polym J 33 (2001) 879
60. Kaneko T, Yamamoto K, Asano M, Teraguchi M, Aoki T. J Membr Sci; in press.
61. Itoh T., Jinbo Y., Hirai K., and Tomioka H. J Am Chem Soc 127 (2005) 1650
62. Kaneko T., Yamamoto T., Tatsumi H., Aoki T., and Oikawa E. Polymer 41 (2000) 4437
63. Aoki T., Shinohara K., Kaneko T., and Oikawa E. Macromolecules 29 (1996) 4192
64. Shinohara K., Aoki T., and Oikawa E. Polymer 36 (1995) 2403
65. Aoki T., Shinohara K., and Oikawa E. Makromol Chem Rapid Commun 13 (1992) 565
66. Aoki T., Kokai M., Shinohara K., and Oikawa E. Chem Lett 22 (1993) 2009
67. Shinohara K., Aoki T., and Kaneko T. J Poly Sci, Part A: Polym Chem 40 (2002) 1689
68. Aoki T., Shinohara K., Kokai M., and Oikawa E. Polym Prepr Jpn 43 (1994) 1884
69. Shinohara K., Aoki T., Fukuda T., Kaneko T., and Oikawa E. Polym Prepr Jpn 45 (1996) 1006
70. Aoki T., Fukuda T., Shinohara K., Kaneko T., Teraguchi M., and Yagi M. J Polym Sci, Part A: Polym Chem 42 (2004) 4502
71. Takeuchi M., Teraguchi M., Kaneko T., and Aoki T. Polym Prepr Jpn 50 (2001) 3094
72. Itagaki S., Kaneko T., and Aoki T. Polym Prepr Jpn 47 (1998) 2373
73. Aoki T., Kobayashi Y., Kaneko T., Oikawa E., Yamamura Y., Fujita Y., et al. Macromolecules 32 (1999) 79
74. Wagnière G., and Meire A. Chem Phys Lett 93 (1982) 78
75. Wagnière G. Chem Phys Lett 110 (1984) 546
76. Barron L.D., and Vrbancich J. Mol Phys 51 (1984) 715
77. Rikken G.L.J.A., and Raupach E. Nature 390 (1997) 493
78. Kaneko T., Yamamoto T., Aoki T., and Oikawa E. Chem Lett (1999) 623
79. Nishide H., Kaneko T., Igarashi M., Tsuchida E., Yoshioka N., and Lahti P.M. Macromolecules 27 (1994) 3082
80. Aoki T., Kaneko T., Maruyama N., Sumi A., Takahashi M., Sato T., et al. J Am Chem Soc 125 (2003) 6346
81. Sato T., Aoki T., Teraguchi M., Kaneko T., and Kim S.Y. Polymer 45 (2004) 8109
82. Teraguchi M., Tanioka D., Kaneko T., and Aoki T. Polym Prepr Jpn 52 (2003) 1591
83. Umeda Y., Kaneko T., Teraguchi M., and Aoki T. Chem Lett 34 (2005) 854
84. Kaneko T., Umeda Y., Yamamoto T., Teraguchi M., and Aoki T. Macromolecules 38 (2005) 9420
85. Teraguchi M., Suzuki J., Kaneko T., Aoki T., and Masuda T. Macromolecules 36 (2003) 9694
86. Teraguchi M., Mottate K., Kim S.Y., Aoki T., Kaneko T., Hadano S., et al. Macromolecules 38 (2005) 6367
87. Giesa R. J Macromol Sci, Rev Macromol Chem Phys C36 (1996) 631
88. Bunz U.H.F. Chem Rev 100 (2000) 1605
89. Jiang B., Yang S.-W., Barbini D.C., and Jones W.E.J. Chem Commun (1998) 213
90. Yamamoto T., Fukushima N., Nakajima H., Maruyama T., and Yamaguchi I. Macromolecules 33 (2000) 5988
91. Jégou G., and Jenekhe S.A. Macromolecules 34 (2001) 7926
92. Bangcuyo C.G., Evans U., Myrick M.L., and Bunz U.H.F. Macromolecules 34 (2001) 7592
93. Bangcuyo C.G., Ellsworth J.M., Evans U., Myrick M.L., and Bunz U.H.F. Macromolecules 36 (2003) 546
94. Yamamoto T., Fang Q., and Morikita T. Macromolecules 36 (2003) 4262
95. Bouchard J., Belletête M., Durocher G., and Leclerc M. Macromolecules 36 (2003) 4624
96. Leung A.C.W., Chong J.H., Patrick B.O., and MacLachlan M.J. Macromolecules 36 (2003) 5051
97. Morisaki Y., Aiki Y., and Chujo Y. Macromolecules 36 (2003) 2594
98. Zhang W., and Moore J.S. Macromolecules 37 (2004) 3973
99. Boydston A., Yin Y., and Pagenkopf B.L. J Am Chem Soc 126 (2004) 10350
100. Tomas S.W.I., and Swager T.M. Macromolecules 38 (2005) 2716
101. Kokil A., Yao P., and Weder C. Macromolecules 38 (2005) 3800
102. Ashraf R.S., and Klemm E. J Polym Sci, Part A: Polym Chem 43 (2005) 6445
103. Witzel S., Ott C., and Klemm E. Macromol Rapid Commun 26 (2005) 889
104. Takihana Y., Shiotsuki M., Sanda F., and Masuda T. Macromolecules 37 (2005) 7578
105. Yasuda T., Imase T., Nakamura Y., and Yamamoto T. Macromolecules 38 (2005) 4687
106. Pschirer N.G., Marshall A.R., Stanley C., Beckham H.W., and Bunz U.H.F. Macromol Rapid Commun 21 (2000) 493
107. Rodríguez J.G., and Tejedor J.L. J Org Chem 67 (2002) 7631
108. Toyota S., Goichi M., and Kotani M. Angew Chem Int Ed Engl 43 (2004) 2248
109. Nesterov E.E., Zhu Z., and Swager T.M. J Am Chem Soc 127 (2005) 10083
110. Hsieh B.R. Polym Bull 25 (1991) 177
111. Chmil K., and Scherf U. Makromol Chem 194 (1993) 1377
112. Sanechika K., Yamamoto T., and Yamamoto A. Bull Chem Soc Jpn 57 (1984) 752
113. Trumbo D.L., and Marvel C.S. J Polym Sci, Part A: Polym Chem 24 (1986) 2311
114. Giesa R., and Schulz R.C. Makromol Chem 191 (1990) 857
115. Bochmann M., and Kelly K. J Polym Sci, Part A: Polym Chem 30 (1992) 2503
116. Bochmann M., Kelly K., and Lu J. J Polym Sci, Part A: Polym Chem 30 (1992) 2511
117. Solomin V.A., and Heitz W. Macromol Chem Phys 195 (1994) 303
118. Häger H., and Heitz W. Macromol Chem Phys 199 (1998) 1821
119. Nishihara Y., Ando J., Kato T., Mori A., and Hiyama T. Macromolecules 33 (2000) 2779
120. Mori A., Kondo T., Kato T., and Nishihara Y. Chem Lett (2001) 286
121. Wilson J.N., Waybright S.M., McAlpine K., and Bunz U.H.F. Macromolecules 35 (2002) 3799
122. Pizzoferrato R., Berliocchi M., Carlo A.D., Lugli P., Venanzi M., Micozzi A., et al. Macromolecules 36 (2003) 2215
123. Kovalev A.I., Takeuchi K., Barzykin A.V., Asai M., Ueda M., and Rusanov A.L. Macromol Chem Phys 206 (2005) 2112
124. Tateishi M., Nishihara H., and Aramaki K. Chem Lett (1987) 1727
125. Weiss K., Michel A., Auth E.M., Bunz U.H.F., Mangel T., and Müllen K. Angew Chem Int Ed Engl 36 (1997) 506
126. Bunz U.H.F. Acc Chem Res 34 (2001) 998
127. Sonogashira K., Tohda Y., and Hagihara N. Tetrahedron Lett (1975) 4467
128. Moroni M., Le Moigne J., and Luzzati S. Macromolecules 27 (1994) 562
129. Jones L.I.I., Schumm J.S., and Tour J.M. J Org Chem 62 (1997) 1388
130. Cotts P.M., Swager T.M., and Zhou Q. Macromolecules 29 (1996) 7323
131. Ricks H.L., Choudry U.H., Marshall A.R., and Bunz U.H.F. Macromolecules 36 (2003) 1424
132. Zhao T., Beckham H.W., Ricks H.L., and Bunz U.H.F. Polymer 46 (2005) 4839
133. Pang Y., Li J., Hu B., and Karasz F.E. Macromolecules 31 (1998) 6730
134. Chu Q., Pang Y., Ding L., and Karasz F.E. Macromolecules 35 (2002) 7569
135. Nelson J.C., Saven J.G., Moore J.S., and Wolynes P.G. Science 277 (1997) 1793
136. Hill D.J., Mio M.J., Prince R.B., Hughes T.S., and Moore J.S. Chem Rev 101 (2001) 3893
137. Blatchly R.A., and Tew G.N. J Org Chem 68 (2003) 8780
138. Stone M.T., and Moore J.S. J Am Chem Soc 127 (2005) 5928
139. Jones T.V., Slutsky M.M., Laos R., de Greef T.F.A., and Tew G.N. J Am Chem Soc 127 (2005) 17235
140. Wagner M., and Nuyken O. Macromolecules 36 (2003) 6716
141. Prince R.B., Saven J.G., Wolynes P.G., and Moore J.S. J Am Chem Soc 121 (1999) 3114
142. Rajca A. Chem Rev 94 (1994) 871
143. Crayston J.A., Iraqui A., and Walton J.C. Chem Soc Rev 23 (1994) 147
144. In: Turnbull M.M., Sugimoto T., and Thompson L. (Eds). Molecule-based magnetic materials; theory, techniques, and applications. ACS Symposiun Series vol. 644 (1996), OUP USA, New York
145. In: Lahti P.M. (Ed). Magnetic properties of organic materials (1999), Marcel Dekker, Inc., New York
146. In: Itoh K., and Kinoshita M. (Eds). Molecular magnetism: new magnetic materials (2000), Kodansha and Gordon and Breach, Tokyo and Amsterdam
147. Crayston J.A., Devine J.N., and Walton J.C. Tetrahedron 56 (2000) 7829
148. Yoshizawa K., Chano A., Ito A., Tanaka K., and Yamabe T. Synth Met 52 (1992) 377
149. Maruta G., Yamaki D., Mori W., Yamaguchi K., and Nishide H. Mol Cryst Liq Cryst 279 (1996) 19
150. Kaneko T., Matsubara T., Aoki T., and Oikawa E. Mol Cryst Liq Cryst 334 (1999) 221
151. Longuet-Higgins H.C. J Chem Phys 18 (1950) 265
152. Borden W.T., and Davidson E.R. J Am Chem Soc 99 (1977) 4587
153. Itoh K. Pure Appl Chem 50 (1978) 1251
154. Mataga N. Theor Chim Acta 10 (1968) 372
155. Ovchinnikov A.A. Theor Chim Acta 47 (1978) 297
156. Klein D.J., Nelin C.J., Alexander S., and Matsen F.A. J Chem Phys 77 (1982) 3101
157. Tyutyulkov N.N., and Karabunarliev S.H. Chem Phys 112 (1987) 293
158. Yamaguchi K., Toyoda Y., and Fueno T. Synth Met 19 (1987) 81
159. Lahti P.M., and Ichimura A.S. J Org Chem 56 (1991) 3030
160. Nishide H., Maeda T., Oyaizu K., and Tsuchida E. J Org Chem 64 (1999) 7129
161. Nishide H., Takahashi M., Takashima J., and Tsuchida E. Polym J 31 (1999) 1171
162. Wautelet P., Philippe T., and Le Moigne J. Synthesis (2002) 1286
163. Miura Y., and Ushitani Y. Macromolecules 26 (1993) 7079
164. Miura Y., Issiki T., Ushitani Y., Teki Y., and Itoh K. J Mater Chem 6 (1996) 1745
165. Miura Y., Ushitani Y., Inui K., Teki Y., Takui T., and Itoh K. Macromolecules 26 (1993) 3698
166. Wautelet P., Le Moigne J., Videva V., and Philippe T. J Org Chem 68 (2003) 8025
167. van Meurs P.J., and Janssen R.A.J. J Org Chem 65 (2000) 5712
168. Sasaki S., and Iwamura H. Chem Lett (1992) 1759
169. Shultz D.A., and Hollomon M.G. Chem Mater 12 (2000) 580
170. Le Moigne J., Gallani J.L., Wautelet P., Moroni M., Oswald L., Cruz C., et al. Langmuir 14 (1998) 7484
171. Matsuda K., Stone M.T., and Moore J.S. J Am Chem Soc 124 (2002) 11836
172. Hayashi H., and Yamamoto T. Macromolecules 30 (1997) 330
173. Hayashi H., and Yamamoto T. Macromolecules 31 (1998) 6063
174. Li S., Ma J., and Jiang Y. J Phys Chem A 101 (1997) 5567
175. Kaneko T., Makino T., Sato G., and Aoki T. Polyhedron 20 (2001) 1291
176. Kaneko T., Matsubara T., and Aoki T. Chem Mater 14 (2002) 3898
177. Kaneko T., Makino T., Miyaji H., Teraguchi M., Aoki T., Miyasaka M., et al. J Am Chem Soc 125 (2003) 3554
178. Kaneko T., Onuma A., Ito H., Teraguchi M., and Aoki T. Polyhedron 24 (2005) 2544
179. Kaneko T., Makino T., Miyaji H., Onuma A., Teraguchi M., and Aoki T. Polyhedron 22 (2003) 1845