3- and 3,4-substituted pyrroles and thiophenes and their corresponding polymers - A review

Current Organic Chemistry

Volumn 8, Issue 7, 2004, Pages 637-651

  Guernion, N J L ^a   Hayes, W ^a  

^a UNIVERSITY OF READING   (United Kingdom)

Author keywords

[No Author keywords available]

Indexed keywords

ALKENE DERIVATIVE; CARBOXYLIC ACID DERIVATIVE; ESTER DERIVATIVE; FUNCTIONAL GROUP; HETEROCYCLIC COMPOUND; POLYPYRROLE; PYRROLE DERIVATIVE; THIOPHENE DERIVATIVE;

BIOMOLECULAR ELECTRONICS; BIOSENSOR; CHEMICAL ANALYSIS; CHEMICAL MODIFICATION; CHEMICAL STRUCTURE; ELECTRODE; MATERIALS TESTING; METHODOLOGY; PATENT; PHYSICAL CHEMISTRY; POLYMERIZATION; REVIEW; STRUCTURE ANALYSIS; SYNTHESIS;

EID: 1942438642     PISSN: 13852728     EISSN: None     Source Type: Journal    
DOI: 10.2174/1385272043370771     Document Type: Review

References (150)

1. Chiang, C.K.; Park, Y.W.; Heeger, A.J.; Shirakawa, H.; Louis, E.J.; MacDiarmid, A.G. Phys. Rev. Lett., 1977, 39, 1098.
2. Sata, M., Tanaka, S.; Kaeriyama, K. J. Chem. Soc., Chem. Commun., 1986, 1346.
3. Borroughes, J.H.; Bradley, D.D.C.; Brown, A.R.; Marks, R.N.; MacKay, K.; Friend R.H.; Burn, P.L. Nature, 1990, 347, 539.
4. Ohmori, Y.; Uchida, M.; Muro, K.; Yoschino, K. Jpn. J. Appl. Phys., 1991, 30, L1938.
5. Kawai, T.; Kuwabara, T.; Wang, S.; Yoschino, K. Jpn. J. Appl. Phys., 29, (1990).
6. Bobacka, J.; Ivaska, A.; Grzeszcuk, P. Synth. Met., 1991, 44, 9.
7. Kim, S.R.; Choi, S.A.; Kim, J.D.; Kim, K.J.; Lee, C.; Rhee, S.B. Synth. Met., 1995, 71, 2027.
8. Chan, H.S.O.; Ng, C.S.; Scow, S. H. Synth. Met., 1994, 66, 177.
9. Chan, H.S.O.; Toh, C.S.; Gan, L. M. J. Mater. Chem., 1995, 5, 631.
10. Kobayashi, T. In Relax. Polym., T. Kobayashi, Ed.; World Scientific, Singapore, 1993, p. 1.
11. Roemer, M.; Kurzenknabe, T.; Oesterschulze, E.; Nicoloso, N. Anal. Bioanal. Chem., 2002, 373. 754.
12. Kraft, A.; Grimsdale, A.C.; Holmes, A.B. Angew. Chem., Int. Ed. Engl., 1998, 110, 416.
13. Roncali, J. J. Mater. Chem., 1999, 9, 1875.
14. Heeger, A.J. Synth. Met., 1993, 55-7, 3471.
15. Roncali, J. Annu. Rep. Prog. Chem. Soc. C, 1999, 95, 47.
16. Smela, E. Adv. Mater., 2003, 15, 481.
17. Oshawa, T.; Kaneto, K.; Yoshino, K. Jpn. J. Appl. Phys., 1984, L663.
18. Nishioka, Y.; Wang, S.; Yoshino, K. Synth. Met., 1991, 41-43, 815.
19. Alvarez-Ibarra, C.; Quiroga-Feijoo, M.L.; Toledano, E. J. Chem. Soc., Perkin Trans. 2, 1998, 679.
20. Frère, P.; Gallego-Planas, N.; Blanchard, P.; Mabon, G.; Rondeau, D. Tetrahedron Lett., 2002, 43, 1825.
21. Jenekhe, S.A. Nature, 1986, 322, 345.
22. Chen, T.A.; Rieke, R.D. J. Am. Chem. Soc., 1992, 114, 10087.
23. Leclerc, M.; Bergeron, J. Y. Synth. Met., 1993, 55-7, 287.
24. Eckhardt, H.; Shacklette, L. W.; Jen K. Y;. Elsenbaumer, R. L. J. Chem. Phys., 1989, 91, 1303.
25. Elsenbaumer, R. L.; Jen, K. Y.; Oboodi, R. Synth. Met., 1986, 15, 169.
26. Lemaire, M.; Roncali, J.; Garnier, F.; Garreau R.; Hannecart, French Patent No. 86.04744, 4th April, 1986.
27. Olserholm, J.E.; Laakso, J.; Nyholm, P.; Isotalo, H.; Stubb, H.; Inganäs, O.; Salaneck, W. R. Synth. Met., 1989, 28, C435.
28. Guernion, N.; Ewen, R.J.; Pihlainen, K.; Ratcliffe, N.M.; Teare, G.C. Synth. Met., 2002, 126, 301.
29. Miyasaki, Y.; Yamamoto, T. Synth. Met., 1994, 64, 69.
30. Groenendaal L. The Chemistry of Oligopyrroles, PhD Thesis, Technical University of Eindhoven, The Netherlands, 1996.
31. Faid, K.; Cloutier, R.; Leclerc, M. Macromolecules, 1993, 26, 2501.
32. Maior, R.M.S.; Hinckelmann, K.; Eckert, H.; Wudl, F. Macromolecules, 1990, 23, 1268.
33. Jones, R.A.; Bean, G.P; The Chemistry of Pyrroles, Academic Press, NYC, 1977.
34. Lue, P.; Greenhill, J.V. Adv. Heterocycl. Chem., 1996, 67, 207.
35. Gilchrist, T.L. J. Chem. Soc. Perkin Trans. 1, 1998, 615.
36. Gilchrist, T.L. J. Chem. Soc. Perkin Trans. 1, 1999, 2849.
37. Gilchrist, T.L. Contemp. Org. Synth., 1995, 2, 337.
38. Sundberg, R.J. Prog. Heterocycl. Chem., 1992, 4, 81.
39. Sundberg, R.J.; Nguyen, P.V. Prog. Heterocycl. Chem., 1994, 6, 110.
40. Ticler, M.; Kolar, M. Adv. Heterocycl. Chem., 1995, 64, 1.
41. Patterson, J.M.; Synthesis, 1976, 281.
42. Collins, I. J. Chem. Soc. Perkin Trans., 2000, 2845.
43. Bird, C. W.; Cheeseman, C.W.H. Comprehensive Heterocyclic Chemistry, A.R. Katrizki and C. W. Rees, Eds., Pergamon Press: Oxford, 1984, p.89.
44. Sundberg, R. J. Comprehensive Heterocyclic Chemistry II, A.R. Katrizki, C.W. Rees and E.F.V. Scriven, Eds.; Pergamon Press: Oxford, Vol. 2, 1996, p. 119.
45. Sundberg, R. J. Progress in Heterocyclic Chemistry, H. Suschitski and G.W. Griible, Eds.; Pergamon Press: Oxford, Vol. 8, 1996, p. 103.
46. Gilchrist, T.L. Heterocyclic Chemistry, 2nd ed., Longman Scientific & Technical, Harlow, UK, 1994, p. 189.
47. Kakushima, M.; Hamel, P.; Frenette, R.; Rokach, J. J. Org. Chem., 1983, 48, 3214.
48. Anderson, H. J.; Loader, H. J. Synthesis, 1985, 353.
49. Bray, B.L.; Mathies, P.H.; Naef, R.; Solas, D.R.; Tidwell, T.; Artis, D.R., Muchowski J.M. J. Org. Chem., 1990, 55, 6317.
50. Loader, C.E.; Anderson, H.J. Can. J. Chem. 1981, 59, 2673.
51. Joule, J.A.; Smith, G.F. Heterocyclic Chemistry, 2nd edition, Van Nostram Reynolds, NYC, 1978, p. 192.
52. Loader, C.E. Anderson, H. J.; Tetrahedron, 1969, 25, 3879.
53. Anderson, H.J. Can. J. Chem., 1957, 35, 21.
54. Xun Xu, R.; Anderson, H.J.; Gogan, N.J.; Loader, C.E.;McDonald, R. Tetrahedron Lett., 1981, 22, 4899.
55. Delabouglise D.; Garnier, F. Adv. Mater., 1990, 2, 91.
56. Hatfield, J.V.; Neaves, P.; Hicks, P.J.; Persaud, K.; Travers, P. Sensors and Actuators B-Chemical, 1994, 18 (1-3), 221.
57. Ho-Hoang, A.; Fache F.; Lemaire, M. Synth. Commun., 1996, 26, 1289.
58. Guernion, N.; de Lacy Costello, B.P.J.; Ratcliffe, N.M. Synth. Met., 2002, 128, 139.
59. Costantini, N.; Cagnolati, R.; Nucci, L.; Pergola, F.; Ruggieri, G. Synth. Met., 1998, 92, 139.
60. Delabouglise, D.; Lemaire, M.; Roncali, J.; Garnier, F. J. Chim. Phys., 1989, 86, 99.
61. Moussa, I.; Hedayatullah, M., Aaron, J. J. J. Chim. Phys., 1998, 95, 1551.
62. Tallman, D.E.; Spinks, G.; Dominis, A.; Wallace, G.G. J. Solid State Electrochem., 2002, 6, 73.
63. Gerard, M.; Chaubey, A.; Malhotra, B.D. Biosens, Bioelectron., 2002, 17, 345.
64. Ito, S.; Watanabe, H.; Uno, H.; Murashima, T.; Ono, N.; Chen Tsai, Y.; Crompton, R.G. Tetrahedron Lett., 2001, 42, 702.
65. Ito, S.; Murashima, T.; Ono, N. J. Chem. Soc., Perk. Trans. 1, 1997, 3161.
66. Settambolo, R.; Cazzaroni, R.; Misseri, T.; Mazzetti, M.; Salvadori, P. J. Org. Chem., 1993, 58, 7899.
67. Jones, R.A.; Marriott, M.T.P.; Rosenthal, W.P.; Arques, J.S. J. Org. Chem., 1980, 45, 4515.
68. Alvarez, A.; Guzman, A.; Ruiz, A.; Velarde, E.; Muchowski, J.M.J. Org. Chem., 1992, 57, 1653.
69. Sugihara, Y.; Miyatake, R.; Murata, I.; Inamura, A. J. Chem. Soc., Chem. Commun., 1995, 1249.
70. Liu, J.H.; Chan, H.W.; Wong, H.C. J. Org. Chem., 2001, 65, 3274.
71. Nicolaou, L; Demopoulos, V.J. J. Heter. Chem., 1998, 35, 1345.
72. Pavri, N.P.; Trudell, M.L. J. Org. Chem., 1997, 62, 2649.
73. Feldheim, D.L.; Hendricksen, S.M.; Krejcik, M.; Elliott, C.M. Chem. Mater., 1995, 7, 1124.
74. de Lacy Costello, B.P.J.; Evans, P.; Guernion, N.; Ratcliffe, N.M.; Sivannand, P.S.; Teare, G.C. Synth. Met., 2000, 114, 181.
75. Delabouglise, D.; Garnier, F. New J. Chem., 1991, 15, 233.
76. Waltman, R.J.; Bargon, J.; Diaz, A.F. J. Phys. Chem., 1983, 87, 1459.
77. Albey, W.J.; Fongbion, L.; Mount, A.R. J. Electroanal. Chem., 1991, 87, 239.
78. Ho-Hoang, A.; Schulz, E.S.; Fache, F.; Boiteux, G.; Lemaire, M. J. Mater. Chem., 1996, 6, 1107.
79. Ho-Hoang, A.; Fache, F.; Boiteux, G.; Lemaire, M. Synth. Met., 1994, 62, 277.
80. Delabouglise, D.; Garnier, F. Synt. Met., 1990, 39, 117.
81. Pleus, S.; Schwientek, M. Synt. Met., 1998, 95, 233.
82. Costello, B.P.J.; Ratcliffe, N.M.; Sivanand, P.S. Synth. Met., 2003, 139, 43.
83. Ryder, K.S.; Morris, D.G.; Cooper, J. M. Langmuir, 1996, 12, 5681.
84. Chen, Y.; Imrie, C.T.; Cooper, J.M.; Glidle, A.; Morris, D.G.; Ryder, K.S. Polym. Int., 1998, 47, 43.
85. Paganuzzi, V.; Guatteri, P.; Ricardo, P.; Sacchelli, T.; Barbera, J.; Costa, M.; Dalcanole, E. Eur. J. Org. Chem., 1999, 1527.
86. Delabouglise, D. Synth. Met., 1992, 51, 321.
87. Casas. R.; Dicko, A.; Ribo, J.M.; Valles, M.A.; Ferrer-Anglada, N.; Bonnett, R.; Hanly, N.; Bloor, D. Synth. Met., 1990, 39, 275.
88. Moon, D.K.; Padias, A.B.; Hall Jr, H.K.; Hantoon; T.; Calvert, P.P. Macromolecules, 1995, 28, 6205.
89. Zong, K.; Reynolds, J. R. J. Org. Chem., 2001, 66, 6873.
90. Pernaut, J.M.; Zong, K.; Reynolds, J.R. Synth. Met., 2002, 130, 1.
91. Korri-Youssoufi, H.; Makrouf, B.; Yassar, A. Mat. Sci. Eng. C, 2001, 15, 265.
92. Bartlett, P.N.; Chung, L.Y.; Moise, P. Electrochim. Acta, 1990, 35, 1273
93. Magnus, P.; Danikiewicz, W.; Katoh, T.; Huffman, J.C.; Folting, K. J. Am. Chem. Soc., 1990, 112, 2466.
94. Voigt, M.; Hallensleben, M. L.; Toppare, L. Synth. Met., 1993, 55-57, 1067.
95. Chen, J.; Too, C.O.; Wallace, G.C.; Swieger, G.F.; Skelton, B.W.; White, A.H. Electrochim. Acta, 2002, 47, 4227.
96. Nicolas, M.; Fabre, B.; Marchand, G.; Simonet, J. Eur. J. Org. Chem., 2000, 1703.
97. Nicolas, M.; Fabre, B.; Simonet, J. J. Chem. Soc., Chem. Commun., 1999, 1881.
98. Herbst; W.; Hunger, K. Industrial Organic Pigments, VCH, Weinheim, 1993.
99. Beyerlein, T.; Ticke, B.; Forero-Lenger, S.; Brutting, W. Synth. Met., 2002, 130, 115.
100. Hubler, K.; Hubler, U.; Roper, W.R.; Wright, L.J. J. Organometal. Chem., 1996, 526, 199.
101. Kon, A.B.; Foos, J.S.; Rose, T.L. Chem. Mater., 1992, 4, 416.
102. Langley, P.J.; Davis, F.J.; Mitchell, G.R. J. Chem. Soc., Perk. Trans. 2, 1997, 2229
103. Jego, C.; Agricole, B.; Vincentini, F.; Barrouillet, J.; Mauzac, M.; Mingotaud, C. J. Phys. Chem., 1994, 98, 13408.
104. Roncali, J. Chem. Rev., 1992, 92, 711
105. Chan, H.S.O.; Ng, S.C. Prog. Polym. Sci., 1998, 23, 1167.
106. Tourillon, G. In Handbook of Conducting Polymers, T. A. Skotheim, Ed.; Marcel Dekker, NYC, 1986, p.294.
107. Wallace, G.G.; Spinks, G.M.; Kane-Maguire, L.A.P.; Teasdale, P.R. In Conductive Electroactive Polymers: Intelligent Material Systems, CRC Press, New York, 2002, pp. 179-207.
108. Fichou, D. Handbook of oligo- and polythiophenes, Wiley-VCH, Berlin, 1998.
109. Patil, A.D.; Heeger, A.J.; Wudl, F. Chem, Rev., 1988, 88, 183.
110. Tamao, K.; Komada, S.; Nakujima, S.; Kumada, M. Tetrahedron Lett., 1982, 38, 3347.
111. Jen, K.Y.; Elsenbaumer, R.L. J. Chem. Soc., Chem. Commun., 1980, 1346.
112. Chen, T.A; Wu, X.; Rieke, R.D. J. Am. Chem. Soc., 1995, 117, 233.
113. Bao, Z.; Lovinger, A.J. Chem. Mater., 1999, 11, 2607.
114. McCullough, R.D. Adv. Mater., 1998, 10, 1.
115. Zhang, Z.B.; Fujiki, M.; Motonaga, M.; Nakashima, H.; Torimitsu, K.; Tang, H.Z. Macromolecules, 2002, 35, 941.
116. Tominaga, Y.; Lee, M.L.; Catee, R.N. J. Heter. Chem., 1981, 18, 967.
117. Kagan, J.; Liu, H. Synth. Met., 1996, 82, 75.
118. Smith, J.R.; Campbell, S.A.; Ratcliffe, N.M.; Dunleavy, M. Synth. Met., 1994, 63, 233.
119. Ye, Y.S.; Wong, H.N.C. J. Org. Chem., 1997, 62, 1940.
120. Naudin, E.; El Mehdi, N.; Saucy, C.; Breau, L.; Belanger, D. Chem. Mater., 2001, 13, 634.
121. Sato, M.; Tanaka, S.; Kaeriyama, K. J. Chem. Soc., Chem. Commun., 1987, 1725.
122. Sone, T.; Snowe, M.; Sato, K. Bull. Chem. Soc. Jpn., 1988, 661, 3779.
123. Wu, X.; Rieke, R.D. J. Org. Chem., 1995, 60, 6658.
124. Schiedel, M.S.; Briehn, C.A.; Bäuerle, P. J. Organomet. Chem., 2002, 653, 200.
125. Malenfant, P.R.L.; Fréchet, J. M. J. J. Chem. Soc., Chem. Commun., 1998, 2657.
126. Campaigne, E.; Lesuer, W.M. J. Org. Chem., 1948, 70, 1555.
127. Bauerle, P.; Wurthner, F.; Heid, S. Angew. Chem., Int. Ed. Engl., 1990, 29, 419.
128. Ballarin, B.; Seeber, R.; Tonelli, D.; Andreani, F.; Costa Bizzari, P.; Dellacasa, C.; Salatelli, E. Synth. Met., 1997, 88, 7.
129. Roncali, J. Chem. Rev., 1997, 97, 173.
130. Yoshino, K.; Yin, X.H.; Morita, S.; Zhakhidov, A.A. Solid State Commun., 1993, 85, 85.
131. Wang, C.; Schindler, J.L.; Kannewarf, C.R.; Kanatzilis, M.G. Chem. Mater., 1995, 7, 58.
132. Groenendaal, L.B.; Jonas, F.; Freitag, D.; Pielartzik, H.; Reynolds, J.R. Adv. Mater., 2000, 12, 48.
133. Kumar, A.; Welsh, D.M.; Morvant, M.C.; Piroux, F.; Abboud, K. A.; Reynolds, J.R. Chem. Mater., 1998, 10, 896.
134. Sankaran, B.; Reynolds, J.R. Macromolecules, 1997, 30, 2582.
135. Daoust, G.; Leclerc, M. Macromolecules, 1991, 24, 455.
136. Zhou, L.; Jin, S.; Yue, G. Synth. Commun., 1996, 26, 3725.
137. Fabre, B; Simonet, J. Coord. Chem. Rev., 1998, 178-80, 1211.
138. Chan, H.S.O.; Choon, N.G.S. Prog. Polym. Sci., 1998, 23, 1167.
139. Blatt, A.H.; Back, S.; Kresch, C.W. J. Org. Chem., 1957, 22, 1693.
140. Goldman, R.; Goldstein, L.; Katchalski, E. In Biochemical Aspects of Reaction on Solid Support, G. R. Starks, Ed.; Academic Press, New York., 1971, 1.
141. Welzel, H.; Kossmehl, G.; Engelmann, G.; Plieth, W. Eur. Polym. J., 1997, 33, 299.
142. Yassar, A.; Demanze, F.; Jaafari, A.; El Idrissi, M.; Coupry, C. Adv. Funct. Mater., 2002, 12, 699.
143. Barker, J.M.; Huddleston, P.R. In Thiophene and its derivatives, Part 3, S. Gronowitz, Ed.; John Wiley and Sons, New York, 1986.
144. Götz, G.; Scheib, S.; Klose, R.; Heinze, J.; Baüerle, P. Adv. Funct. Mater., 2002, 12, 723.
145. Blanchard, P.; Jousseline, B.; Frere, P.; Roncali, J. J. Org. Chem., 2002, 67, 3961.
146. Goldoni, F.; Janssen, R. A.; Meijer, E. W. J. Polym. Sci, Part A: Polym. Chem., 1999, 37, 4629.
147. Zotti, G.; Zecchin, S.; Schirvan, G.; Groenendaal, L. B. Macrom. Chem. Phys., 2002, 203, 1958.
148. Berthelot, M.; Marchand, G.; Huynh, H.T.; Pilard, J. F. Electrochem. Commun., 2001, 3, 557.
149. Miyasaka, M.; Yamasaki, T.; Tsuchida, E.; Hishida, H. Polyhedron, 2001, 20, 1157.
150. Hellberg, J.; Romonen, T.; Johansson, M.; Inganas, O.; Theander, M.; Engman, L.; Eriksson P. Synth. Met., 1997, 84, 251.