Abstract
An extensive review of the synthesis of π-conjugated polymers is presented using a tutorial approach to provide an introduction to the field intended for the undergraduate student and the experienced chemist alike. The many synthetic methodologies that have been used for the synthesis of conjugated polymers are outlined for each class of polymers with a focus on research from the 1990s. The effect of structure on electrical properties is detailed. Specific systems reviewed include the polyacetylenes, polyanilines, polypyrroles, polythiophenes, poly(arylene vinylenes), and polyphenylenes.
Access this chapter
Tax calculation will be finalised at checkout
Purchases are for personal use only
Preview
Unable to display preview. Download preview PDF.
References
Kovacic P, Jones MB (1987) Chem Rev 87: 357
Patil AO, Heeger AJ, Wudl F (1988) Chem Rev 88: 183
Reynolds JR (1988) Chemtech 18: 440
Billingham NC, Calvert PD (1989) Adv Poly Sci 90: 1
Kanatzidis MG (1990) Chem Eng News 68:(49)36
MacDiarmid AG, Epstein AJ (1991) Makromol Chem Makromol Symp 51: 11
Baughman RH (1991) Makromol Chem Makromol Symp 51: 193
Syed AA, Dinesan MK (1991) Talanta 38: 815
Reynolds JR, Pomeranz M (1991) Electroresponsive Molecular and Polymeric Systems 2: 187
Yamamoto T (1992) Prog Polym Sci 17: 1153
Roncali J (1992) Chem Rev 92: 711
Schlüter AD, Wegner G (1993) Acta Polym 44: 59
Naarmann HJ (1993) Polym Sci: Polym Symp 75: 53
Lux F (1994) Polymer 35: 2915
Tour JM (1994) Adv Mater 6: 190
Toshima N, Hara S (1995) Prog Polym Sci 20: 155
Feast W J, Tsibouklis J, Pouwer KL, Groenendaal L, Meijer EW (1996) Polymer 37: 5017
Pelter A, Jenkins I, Jones DE (1997) Tetrahedron 53: 10357
Roncali J (1997) Chem Rev 97: 173
Miller JS (1993) Adv Mater 5: 587
Miller JS (1993) Adv Mater 5: 671
Peierls RE (1955) In Quantum Theory of Solids. Oxford University Press, Oxford
Shimamura K, Karasz FE, Hirsch JA, Chien JCW (1981) Makromol Chem Rapid Commun 2: 473
Hill MG, Penneau JF, Zinger B, Mann KR, Miller LL (1992) Chem Mater 4: 1106
Bäuerle P, Segelbacher U, Maier A, Mehring M (1993) J Am Chem Soc 115: 10217
Furukawa Y (1996) J Phys Chem 100: 15644
Grubbs RH (1982) In: Wilkinson G, Stone FGA, Abel EW (eds) Comprehensive Organometallic Chemistry. Pergamon, New York, p. 502
Yamamoto A (1986) In: Organotransition Metal Chemistry. Wiley, New York
Dragutan V, Balaban AT, Dimonie M (1986) In: Olefin Metathesis and Ring Opening Polymerization of Cycloolefins. Wiley, New York
Collman JP, Hegedus LS, Norton JR, Finke RG (1987) In: Principles and Applications of Organotransition Metal Chemistry. University Science Books, Mill Valley
Stille JK (1986) Angew Chem, Intl Ed Engl 25: 508
Yamamoto T, Hayashi Y, Yamamoto Y (1978) Bull Chem Soc Japan 51: 2091
Miyaura N, Suzuki A (1995) Chem Rev 95: 2457
Shirakawa H, Louis EJ, MacDiarmid AG, Chiang CK, Heeger AJ (1977) J Chem Soc, Chem Commun: 578
Chiang CK, Fincher CR Jr, Park YW, Heeger AJ, Shirakawa H, Louis EJ, Gau SC, Mac Diarmid AG (1977) Phys Rev Lett 39: 1098
MacDiarmind AG, Heeger AJ (1979) Synth Met 1: 101
Wegner G (1981) Angew Chem, Int Ed Engl 20: 361
Wynne KJ, Street GB (1982) I&EC Product Research and Development 21: 23
Baughman RH (1984) In: Vandenberg EJ (ed) Contemporary Topics in Polymer Science Vol 5. Plenum Publishing
Greene RL, Street GB (1984) Science 226: 651
Chien JCW (1984) In: Polyacetylene:Chemistry, Physics and Materials Science. Academic Press, Orlando FL
Krivoshei IV, Skorobogatov VM (1991) In Polyacetylene and Polyarylenes, Polymer Monographs Vol 10. Gordon and Breach
Gibson HW (1986) In: Skotheim TA (ed) Handbook of Conducting Polymers Vol 1. Marcel Dekker Inc, New York, pp. 405–439
Chien JCW, Wnek GE, Karasz FE, Hirsch JA (1981) Macromolecules 14: 479
Masuda T, Higashimura T (1984) Accts Chem Res 17: 51
Jin SH, Choi SJ, Ahn W, Cho HN, Choi SK (1993) Macromolecules 26: 1487
Choi SJ, Jin SH, Park JW, Cho HN, Choi SK (1994) Macromolecules 27: 309
Simionescu CI, Dumitrescu S, Grigoras M, Percec V (1979) J Polym Sci, Polym Lett Ed 17: 287
Gibson HW, Bailey FC, Epstein AJ, Rommelman H, Kaplan S, Harbour J, Yang XQ, Tanner DB, Pochan JM (1983) J Am Chem Soc 105: 4417
Gal YS, Choi SK (1988) J Polym Sci, Polym Lett C 26: 115
Yakhimovich RI, Shilov EA, Dvorko GF (1966) Dokl Akad Nauk SSSR 166: 388
Kang KL, Kim SH, Cho HN, Choi KY, Choi SK (1993) Macromolecules 26: 4539
Kim SH, Choi SJ, Park JW, Cho HN, Choi SK (1994) Macromolecules 27: 2339
Subramanyam S, Blumstein A (1991) Makromol Chem Rapid Commun 12: 23
Subramanyam S, Blumstein A (1991) Macromolecules 24: 2668
Subramanyam S, Li KP, Blumstein A (1992) Macromolecules 25: 2065
Subramanyam S, Blumstein A (1992) Macromolecules 25: 4058
Subramanyam S, Chetan MS, Blumstein A (1993) Macromolecules 26: 3212
Edwards JH, Feast WJ (1980) Polymer 21: 595
Edwards JH, Feast WJ, Buff DC (1984) Polymer 25: 395
Swager TM, Dougherty DA, Grubbs RH (1988) J Am Chem Soc 110: 2973
Swager TM, Grubbs RH (1989) J Am Chem Soc 111: 4413
Ginsburg EJ, Gorman CB, Marder SR, Grubbs RH (1989) J Am Chem Soc 111: 7621
Klavetter FL, Grubbs RH (1989) J Am Chem Soc 111: 7807
Gorman CB, Ginsburg EJ, Sailor MJ, Moore JC, Jozefiak TH, Lewis NS, Grubbs RH, Marder SR, Perry JW (1991) Synth Met 41: 1033
Sailor MJ, Ginsburg EJ, Gorman CB, Kumar A, Grubbs RH, Lewis NS (1990) Science 249: 1146
Moore JS, Gorman CB, Grubbs RH (1991) J Am Chem Soc 113: 1704
Jozefiak TH, Ginsburg EJ, Gorman CB, Grubbs RH, Lewis NS (1992) J Am Chem Soc 115: 4705
Noren GK, Stille JK (1971) Makromol Rev 5: 385
Ried W, Freitag D (1966) Naturwiss 53: 305
Stille JK, Gilliams Y (1971) Macromolecules 4: 515
Stille JK (1972) Makromol Chem 154: 49
Krigbaum WR, Krause KJ (1978) J Polym Sci, Polym Chem Ed 16: 3151
Dineen JM, Howell EE, Volpe AA (1982) Polym Sci, Polym Chem Ed 23: 282
Claesson S, Gehm R, Kern W (1949) Makromol Chem 7: 46
Goldfinger G (1949) J Polym Sci 4: 93
Edwards A, Goldfinger G (1955) J Polym Sci 16: 589
Speight JG, Kovacic P, Koch FW (1971) J Macromol Sci, Rev Macromol Chem 5: 275
Kocacic P, Kyriakis A (1963) J Am Chem Soc 85: 454
Kovacic P, Wu C (1960) J Polym Sci 47: 448
Kovacic P, Hsu LC (1966) J Polym Sci 4: 5
Yamamoto T, Yamamoto A (1977) Chem Lett 356
Yamamoto T, Hayashi Y, Yamamoto Y (1978) Bull Chem Soc Jpn 51: 2091
Elsenbaumer RL, Schacklette LW (1986) In: Handbook of Conducting Polymers. Marcel Dekker Inc, New York
Rehahn M, Schlüter AD, Wegner G, Feast WJ (1989) Polymer 30: 1054
Rehahn M, Schlüter AD, Wegner G, Feast WJ (1989) Polymer 30: 1060
Rehahn M, Schlüter AD, Wegner G (1990) Makromol Chem 191: 1991
Rulkens R, Schulze M, Wegner G (1994) Macromol Rapid Commun 15: 669
Vahlenkamp T,W egner G (1994) Macromol Chem Phys 195: 1933
Remmers M, Schulze M, Wegner G (1996) Macromol Rapid Commun 17: 239
Vanhee S, Rulkens R, Lehmann U, Rosenauer C, Schulze M, Köhler W, Wegner G (1996) Macromolecules 29: 5136
Lauter U, Meyer WH, Wegner G (1997) Macromolecules 30: 2092
Percec V, Okita S, Weiss R (1992) Macromolecules 25: 1816
Percec V, Okita S, Bae J (1992) Polym Bull 29: 271
Percée V, Pugh C, Cramer E, Okita S, Weiss R (1992) Makromol Chem Macromol Symp: 54/55: 113
Qian X, Pena M (1995) Macromolecules 28: 4415
Percec V, Bae JY, Zhao M, Hill DH (1995) J Org Chem 60: 176
Percec V, Bae JY, Zhao M, Hill DH (1995) J Org Chem 60: 1066
Percec V, Zhao M, Bae JY, Hill DH (1996) Macromolecules 29: 3727
Grob MC, Feiring AE, Auman BC, Percec V, Zhao M, Hill DH (1996) Macromolecules 29: 7284
Colon I, Kelsey DR (1986) J Org Chem 51: 2627
Ueda M, Ichikawa F (1990) Macromolecules 23: 926
Ueda M, Seino Y, Sugiyama J (1993) Polym J 25: 1319
Phillips RW, Sheares VV, Samulski ET, DeSimone JM (1994) Macromolecules 27: 2354
Wang Y, Quirk RP (1995) Macromolecules 28: 3495
Reddinger JL, Reynolds JR (1997) Macromolecles 30: 479
Tour JM, Stephens EB (1991) J Am Chem Soc 113: 2309
Stephens EB, Kinsey KE, Davis JP, Tour JM (1993) Macromolecules 26: 3519
Kim YH, Webster OW (1990) J Am Chem Soc 112: 4592
Kim YH, Webster OW (1992) Macromolecules 25: 5561
Cassidy PE, Marvel CS (1972) Macromol Synth 4: 7
Frey DA, Hasegawa M, Marvel CS (1963) J Polym Sci, Part A 1: 2057
Gin DL, Avlyanov JK, MacDiarmid AG (1994) Synth Met 66: 169
Ballard DGH, Courtis A, Shirley IM, Taylor SC (1983) J Chem Soc, Chem Commun: 954
Ballard DGH, Courtis A, Shirley IM, Taylor SC (1988) Macromolecules 21: 294
McKean DR; Stille JK (1987) Macromolecules 20: 1787
Gin DL; Conticello VP, Grubbs RH (1992) J Am Chem Soc 114: 3167
Lockhardt TP, Comita PB, Bergman RG (1981) J Am Chem Soc 103: 4082
Lockhardt TP, Bergman RG (1981) J Am Chem Soc 103: 4091
John JA, Tour JM (1994) J Am Chem Soc 116: 5011
Wallow TI, Novak BM (1991) J Am Chem Soc 113: 7411
Child AD, Reynolds JR (1994) Macromolecules 27: 1975
Scherf U, Müllen K (1991) Makromol Chem, Rapid Commun 12: 489
Scherf U, Müllen K (1992) Polymer 33: 2443
Scherf U, Müllen K (1992) Macromolecules 25: 3546
Scherf U, Bohnen A, Müllen K (1992) Makromol Chem 193: 1127
Scherf U (1993) Synth Met 55: 767
Chmil K, Scherf U (1993) Makromol Chem, Rapid Commun 14: 217
Tour JM, Lamba JJS (1993) J Am Chem Soc 115: 4935
Lamba JJS, Tour JM (1994) J Am Chem Soc 116: 11723
Hörhold HH, Helbig M, Raabe D, Opfermann J, Scherf U, Stockmann R, Weib DZ (1987) Chem 27: 126
Bradley DDC (1987) J Phys D, Appl Phys 20: 1389
Prasad PN (1991) Polymer 32: 1746
Bradley DDC (1992) Adv Mater 4: 756
Murase I, Ohnishi T, Noguchi T, Hirooka M (1984) Polym Commun 25: 327
Antoun S, Gagnon DR, Karasz FE, Lenz RW (1986) J Polym Sci, Polym Lett 24: 503
Kaino T, Kobayashi H, Kubodera T, Kurihara T, Saito S, Tsutsui T, Tokito S (1989) Appl Phys Lett 54: 1619
Wung CJ, Pang Y, Prasad PN, Karasz FE (1991) Polymer 32: 605
Shim HK, Hwang DH, Lee KS (1993) Makromol Chem 194: 1115
Shim HK, Lee KS, Jin JI (1996) Macromol Chem Phys 197: 3501
Burroughes JH, Bradley DDC, Brown AR, Marks RN, Mackay K, Friend RH, Burn PL, Holmes AB (1990) Nature 347: 539
Braun D, Heeger AJ (1991) Appl Phys Lett 58: 1982
Burn PL, Holmes AB, Kraft A, Bradley DDC, Brown AR, Friend RH, Gymer RW (1992) Nature 356: 47
Gustafsson G, Cao Y, Treacy GM, Klavetter F, Colaneri N, Heeger AJ (1992) Nature 357: 477
Greenham NC, Moratti SC, Bradley DDC, Friend RH, Holmes AB (1993) Nature 365: 628
Holmes AB, Bradley DDC, Brown AR, Burn PL, Burroughes JH, Friend RH, Greenham NC, Gymer RW, Halliday DA, Jackson RW, Kraft A, Martens JHF, Pichler K, Samuel IDW (1993) Synth Met 55-57: 4031
Yu G (1996) Synth Met 80: 143
Cornil J, Beljonne D, dos Santos DA, Shuai Z, Brédas JL (1996) Synth Met 78: 209
Yang Y, Pei Q, Heeger AJ (1996) J Appl Phys 79: 934
Lee CH, Yu G, Moses D, Sariciftci NS, Heeger AJ, Wudl F (1993) Phys Rev B 48: 15425
Martelock H, Griener A, Heitz W (1991) Makromol Chem 192: 967
Yu L, Bao Z (1994) Adv. Mater 4: 156
McDonald RN, Campbell TW (1960) J Am Chem Soc 82: 4669
Hörhold HH, Opfermann J (1969) Makromol Chem 129: 105
Manecke VG, Zerpner D (1969) Makromol Chem 129: 183
Kossmehl VG, Härtel M, Manecke G (1970) Makromol Chem 131: 37
Gourley KD, Lillya CP, Reynolds JR, Chien JCW (1984) Macromolecules 17: 1025
Huang WS, Jen KY, Angelopoulos AG, MacDiarmid AG, Cava MP (1990) Mol Cryst Liq Cryst 189: 237
Lenz RW, Handlovits CE (1960) J Org Chem 25: 813
Funke VW, Schütze EC (1963) Makromol Chem 74: 71
Debord D, Golé J (1971) Bull Chem Soc 4: 1401
Hörhold HHZ (1972) Chem 12: 41
Lahti PM, Sarker A, Garay RO, Lenz RW, Karasz FE (1994) Polymer 35: 1312
Moratti SC (1995) Synth Met 71: 2117
Baigent DR, Hamer PJ, Friend RH, Moratti SC, Holmes AB (1995) Synth Met 71: 2175
Hoeg DF, Lusk DI, Goldberg EP (1964) J Polym Sci Part B, Polym Lett 2: 697
Gilch HG, Wheelwright WL (1966) J Polym Sci Part A, Polym Chem 4: 1337
Hörhold HH, Opfermann J (1970) Makromol Chem 131: 105
Rajaraman L, Balasubramanian M, Nanjan MJ (1980) Curr Sci 49: 101
Cataldo F (1991) Polym Commun 32: 354
Rehahn M, Schlüter AD (1990) Macromol Chem, Rapid Commun 11: 375
Kumar A, Eichenger BE (1992) Macromol Chem, Rapid Commun 13: 311
Thorn-Csányi E, Pflug KP (1993) Macromol Chem, Rapid Commun 14: 619
Thorn-Csányi E, Kraxner P (1995) Macromol Chem, Rapid Commun 16: 147
Wessling RA, Zimmerman RG (1985) J Polym Sci, Polym Symp 72: 55
Lenz RW, Han CC, Stenger-Smith JD, Karasz FE (1988) J PolymSCi, Polym Chem Ed 26: 3241
Stenger-Smith JD, Lenz RW, Wegner G (1989) Polymer 30: 1048
Burn PL, Bradley DDC, Brown AR, Friend RH, Holmes AB (1991) Synth Met 41–43: 261
Schlenoff JB, Wang LJ (1991) Macromolecules 24: 6653
Berdeen A, Vanderzande D, Gelan J (1992) Synth Met 52: 387
Garay RO, Baier U, Bubeck C, Müllen K (1993) Adv Mater 5: 561
Murase I, Ohnishi T, Noguchi T, Hirooka M (1985) Polym Commun 26: 362
Antoun S, Karasz FE, Lenz RW (1988) J Polym Sci A, Polym Sci 26: 1809
Lenz RW, Han CC, Lux M (1989) Polymer 30: 1041
Jen KY, Shacklette LW, Elsenbaumer RL (1987) Synth Met 22: 179
Jin JI, Park CK, Shim HK (1993) Macromolecules 26: 1799
Shi S, Wudl F (1990) Macromolecules 23: 2119
Louwet F, Vanderzande D, Gelan J (1995) Synth Met 69: 509
Louwet F, Vanderzande D, Gelan J, Mullens J (1995) Macromolecules 28: 1330
Conticello VP, Gin DL, Grubbs RH (1992) J Am Chem Soc 114: 9708
Pu L, Wagaman MW, Grubbs RH (1996) Macromolecules 29: 1138
Wagaman MW, Grubbs RH (1997) Macromolecules 30: 3978
Heck RF (1968) J Am Chem Soc 90: 5518
Heck RF (1979) Acc Chem Res 12: 146
Heck RF. (1982) Org React 27: 345
de Meijere A, Meyer FE (1994) Angew Chem, Int Ed Engl 33: 2379
Greiner A, Heitz A (1988) Makromol Chem, Rapid Commun 9: 581
Heitz W (1988) Makromol Chem 189: 119
Brenda M, Greiner A, Heitz W (1990) Makromol Chem 191: 1083
Nishide H, Kaneko T, Nii T, Katoh K, Tsuchida E, Yamaguchi K (1995) J Am Chem Soc 117: 548.
Nishide H, Kaneko T, Nii T, Katoh K, Tsuchida E, Lahti P (1996) J Am Chem Soc 118: 9695
Nishide H, Hozumi Y, Nii T, Tsuchida E (1997) Macromolecules 30: 3986
Bäuerle P (1993) Adv Mater 5: 879
Kovacic P, McFarland KN (1979) J Poly Sci, Polym Chem Ed 17: 1963
Yamamoto T, Sanechika K, Yamamoto A (1980) J Polym Sci, Polym Lett Ed 18: 9
Lin J, Dudek LP (1980) J Polym Sci, Polym Chem Ed 18: 2869
Kossmehl G, Chatzitheodorou G (1981) Makromol Chem Rapid Commun 2: 551
Diaz AF (1981) Chem Scripta 17: 142
Tourillon G, Garnier F (1982) J Electroanal Chem 135: 173
Sugimoto R, Takeda S, Gu HB, Yoshino K (1986) Chem Express 1: 635
Yoshino K, Nakajima S, Fuji M, Sugimoto R (1987) Polym Commun 28: 309
Waltman RJ, Bargon J, Diaz AF (1983) Phys Chem 87: 1458
Roncali J, Lemaire M, Garreau R, Garnier F (1987) Synth Met 18: 139
Corradi R, Armes SP (1997) Synth Met 84: 453
Bao Z, Chan WK, Yu L (1995) J Am Chem Soc 117: 12426
Fanta PE (1964) Chem Rev 64: 613
Fanta PE (1974) Synthesis 9
Pomerantz M, Yang H, Cheng Y (1995) Macromolecules 28: 5706
Yamamoto T, Morita A, Miyazaki Y, Maruyama T, Wakayama H, Zhou Z, Nakamura Y, Kanbara T, Sasaki S, Kubota K (1992) Macromolecules 25: 1214
Yamamoto T, Wakabayashi S, Osakada K (1992) J Organomet Chem 428: 223
Miyazaki Y, Kanbara T, Osakada K, Yamamoto T (1993) Chem. Lett: 415
Masuda H; Kaeriyama K (1992) Makromol Chem, Rapid Commun 13: 461
Ueda M, Miyaji Y, Ito T, Oba Y, Sone T (1991) Macromolecules 24: 2694
Lemaire M, Delabouglise D, Garreau R, Guy A, Roncali J (1988) J Chem Soc, Chem Commun: 658
Sato M, Tanaka S, Kaeriyama K (1986) J Chem Soc, Chem Commun: 873
Jen KY, Miller GG, Elsenbaumer RL (1986) J Chem Soc, Chem Commun: 1346
Hotta S, Rughooputh SDV, Heeger AJ, Wudl F (1987) Macromolecules 20: 212
Tamao K, Sumitani K, Kumada M (1972) J Am Chem Soc 94: 4374
Gronowitz S (1985) The Chemistry of Heterocyclic Compounds:Thiophene and Its Derivatives. Wiley, New York
Roncali J, Garreau R, Yassar A, Marque P, Garnier F (1987) J Phys Chem 91: 6706
Roncali J, Marque P, Garreau R, Garnier F, Lemaire M (1990) Macromolecules 23: 1347
Roncali J, Garreau R, Delabouglise D, Garnier F, Lemaire M (1989) J Chem Soc, Chem Commun: 679
Heywang G, Jonas F (1992) Adv Mater 4: 116
Li HS, Garnier F, Roncali J (1992) Macromolecules 25: 6425
McCullough RD, Williams SP (1993) J Am Chem Soc 115: 11608
Kang TJ; Kim JY, Kim KY, Lee C, Rhee SB (1995) Synth Met 69: 377
Lee C, Kim KY, Rhee SB (1995) Synth Met 69: 295
Middlecoff JS, Collard DM (1997) Synth Met 84: 221
Büchner W, Garreau R, Lemaire M, Roncali J (1990) J Electroanal Chem 277: 355
El Kassmi A, Büchner W, Fache F, Lemaire M (1992) J Electroanal Chem 326: 357
Ritter SK, Noftle RE, Ward AE (1993) Chem Mater 5: 752
Robitaille L, Leclerc M (1994) Chem Mater. 27: 1847
Kotkar D, Joshi V, Gosh K (1988) J Chem Soc, Chem Commun: 917
Sato M, Tanaka S, Kaeriyama K (1989) Makromol Chem: 1233
Lemaire M, Garreau R, Delabouglise D, Korri Youssoufi H, Garnier F (1990) New J Chem 14: 359
Patil AO, Ikenoue Y, Wudl F, Heeger AJ (1987) J Am Chem Soc 109: 1858
Ikenoue Y, Saida Y, Kira M, Tomozowa H, Yashima H, Kobayashi M (1990) J Chem Soc, Chem Commun: 1694
Chen SA, Hua MY (1993) Macromolecules 26: 7108
Arroyo-Villan MI, Diaz-Quijada GA, Abdou MSA, Holdcroft S (1995) Macromolecules 28: 975
Leclerc M, Diaz FM, Wegner G (1989) Makromol Chem 190: 3105
Sato M, Morii H (1991) Polym Commun 32: 42
Mao H, Holdcroft S (1992) Macromolecules 25: 554
Souto Maior RM, Hinkelmann K, Eckert H, Wudl F (1990) Macromolecules 23: 1268
Mao, H.; Xu, B.; Holdcroft, S. Macromolecules 1993, 26, 1163
Anderson MR, Selse D, Berggren M, Jarvinen H, Hjertberg T, Inganäs O, Wennerström O, Österholm JE (1994) Macromolecules 27: 6503
Sato M, Morii H (1991) Macromolecules 24: 1196
McCullough RD, Lowe RD (1992) J Chem Soc Chem Commun: 70
Gallazzi MC, Castellani L, Zerbi G, Sozzani P (1991) Synth Met 41–43: 495
McCullough RD, Lowe RD, Jayaraman M, Anderson DL (1993) J Org Chem 58: 904
Chen TA, Rieke RD (1992) J Am Chem Soc 114: 10087
Chen TA, O'Brien RA, Rieke RD (1993) Macromolecules 26: 3462
Chen TA, Rieke RD (1995) J Am Chem Soc 117: 233
Wu X, Chen TA, Rieke RD (1995,) Macromolecules 28: 2101
Jonas F, Heywang G, Schidtberg W (1989) Ger Offen DE 3, 813: 589
Jonas F, Heywang G, Schidtberg W, Heinze J, Dietrich M (1989) Eur Pat App EP 339: 340
Jonas F, Heywang G, Schidtberg W, Heinze J, Dietrich M (1991) U.S. Patent No. 5,035: 926
Heywang G, Jonas F (1992) Adv Mater 4: 116
Pei Q, Zuccarello G, Ahlskog M, Inganäs O (1994) Polymer 35: 1347
Gustafsson JC, Liedberg B, Inganäs O (1994) Solid State Ionics 69: 145
Dietrich M, Heize J, Heywang G, Jonas F (1994) J Electroanal Chem 369: 87
Kumar A, Reynolds JR (1996) Macromolecules 29: 8551
Stéphan O, Schottland P, Le Gall PY, Chevrot C, Mariet C, Carrier M (1998) J Electroanal Chem 443: 217
Sankaran B, Reynolds JR (1997) Macromolecules 30: 2582
Havinga EE, Mutsaers CMJ, Jenneskens LW (1996) Chem Mater 8: 769
Kumar A, Welsh DM, Morvant MC, Piroux F, Abboud KA, Reynolds JR (1998) Chem Mater 10: 896
Sotzing GA, Reynolds JR (1995) J Chem Soc, Chem Commun: 703
Sotzing GA, Reynolds JR, Steel PJ (1996) Chem Mater 8: 882
Reddinger JL, Sotzing GA, Reynolds JR (1996) J Chem Soc, Chem Commun: 1777
Sotzing GA, Reddinger JL, Katritzky AR, Soloducho J, Musgrave R, Steel PJ, Reynolds JR (1997) Chem Mater 9: 1578
Sapp SA, Sotzing GA, Reddinger JL, Reynolds JR (1996) Adv Mater 8: 808
Sotzing GA, Thomas CA, Reynolds JR, Steel PJ (1998) Macromolecules 31: 3750
Dall'Olio A, Dascola G, Varacca V, Bocchi V (1968) R Acad Sci C267: 433
Diaz AF, Kanazwa KK, Gardini GP (1979) J Chem Soc, Chem Commun: 635
Kanazawa KK, Diaz AF, Geiss RH, Gill WD, Kwak JF, Logan JA, Rabolt JF, Street GB (1979) J Chem Soc, Chem Commun: 854
Wynne KJ, Street GB (1985) Macromolecules 18: 2361
Diaz AF, Bargon J (1986) Handbook of Conducting Polymers. Skotheim TA (ed) Marcel Dekker Inc, New York, p. 81
Street, G. B. Handbook of Conducting Polymers T.A. Skotheim, Ed.; Marcel Dekker Inc.: New York, 1986, p. 265
Malhotra BD, Kumar N, Chandra S (1986) Progr Polym Sci 12: 179
Saunders BR, Fleming RJ, Murray KS (1995) Chem Mater 7: 1082
Novak P (1992) Electrochim Acta 37: 1227
Bartlett PN, Birkin PR (1993) Synth Met 61: 15
Salmon M, Kanazwa KK, Diaz AF, Krounbi M (1982) J Polym Sci, Polym Lett 20: 187
Chan HSO, Munro HS, Davies C, Kang ET (1988) Synth Met 22: 365
Mermilliod N, Tanguy J, Petiot F (1986) J Electrochem Soc 133: 6
Myers RE (1986) J Electron Mater 2: 61
Armes SP (1987) Synth Met 20: 365
Nishio K, Fujimoto M, Ando O, Ono H, Murayama T (1996) J Appl Electrochem 26: 425
Thiéblemont JC, Gabelle JL, Planche MF (1994) Synth Met 66: 243
Curran D, Gromshaw J, Perera SD (1991) Chem Soc Rev 20: 391
Deronzier A, Moutet JC (1996) Coord Chem Rev 147: 339
Havinga EE, van Horssen LW, ten Hoeve W, Wynberg H, Meijer EW (1987) Polym Bull 18: 277
Inagaki T, Hunter M, Yang XQ, Skotheim TA, Okaoto Y (1988) J Chem Soc, Chem Commun: 126
Rühe J, Ezquerra TA, Wegner G (1989) Synth Met 28: C177
Andrieux CP, Audebert P (1989) J Electroanal Chem 261: 443
Zotti G, Shiavon G, Berlin A, Pagani G (1989) Synth Met 28: C183
Martina S, Enkelmann V, Wegner G, Schlüter AD (1991) Synthesis: 613
Martina S, Enkelmann V, Wegner G, Schlüter AD (1992) Synth Met 51: 299
Groenendaal L, Peerlings HWI, van Dongen JLJ, Havinga EE, Vekemans JAJM, Meijer EW (1995) Macromolecules 28: 116
Brockmann TW, Tour JM (1994) J Am Chem Soc 116: 7435
Letheby H (1862) J Chem Soc 15: 161
Mohilner DM, Adams RN, Argersinger Jr WJ (1962) J Am Chem Soc 84: 3618
Jozefewicz M, Yu LT, Belorgey G, Buvet R (1967) J Polym Sci, Part C 16: 2931
Honzl J, Tlustakova M (1968) J Polym Sci, Part C 22: 451
Jozefewicz M, Yu LT, Perichon J, Buvet R (1969) J Polym Sci, Part C 22: 1187
MacDiarmid AG, Epstein AJ (1989) Faraday Discuss Chem Soc 88: 317
Epstein AJ (1991) Makromol Chem, Macromol Symp 51: 217
MacDiarmid AG (1997) Synth Met 84: 27
Green AG, Woodhead AE (1910) J Chem Soc Trans 97: 2388
Green AG, Woodhead AE (1912) J Chem Soc Trans 101: 1117
Chiang JC, MacDiarmid AG (1986) Synth Met 13: 193
Lu FL, Wudl F, Nowak M, Heeger AJ (1986) J Am Chem Soc 108: 8311
Lu FL, Allemand PM, Vachon DJ, Nowak M, Liu ZX, Heeger AJ (1987) J Am Chem Soc 109: 3677
Wang L, Jing X, Wang F (1986) Synth Met 13: 329
Scherr EM, MacDiarmid AG, Manohar SK, Masters JG. Sun Y, Tang X, Druy MA, Glatkowski PJ, Cajipe VB, Fisher JE, Cromack KR, Jozefowitcz ME, Ginder JM, McCall RP, Epstein AJ (1991) Synth Met 41–43: 735
Epstein AJ, Ginder JM, Zuo F, Bigelow RW, Tanner DB, Richter AF, Huang WS. MacDiarmid AG (1987) Synth Met 18: 303
Wang L, Jing X, Wang F (1991) Synth Met 41–43: 739
MacInnes D, Funt BL (1988) Synth Met 25: 235
Leclerc M, Guay J, Dao LH (1989) Macromolecules 22: 649
Pelter A, Jenkins I, Jones DE (1997) Tetrahedron 53: 10357
Gooding R, Lillya CP, Chien CW (1983) J Chem Soc, Chem Commun: 151
Jen KY, Maxfield M, Shacklette LW, Elsenbaumer RL (1987) J Chem Soc, Chem Commun: 309
Yamada S, Tokito S, Tsutsui T, Saito S (1987) J Chem Soc, Chem Commun: 1448.
Sarker A, Lahti PM, Karasz FE (1994) J Polym Sci, Part A 32: 65
Zhou Z, Maruyama T, Kanbara T, Iveda T, Ichimura K, Yamamoto T, Tokuda K (1991) J Chem Soc, Chem Commun: 1210
Reynolds JR, Ruiz JP, Child AD, Nayak K, Marynick DS (1991) Macromolecules 24: 678
Ruiz JP, Dharia JR, Reynolds JR (1992) Macromolecules 25: 849
Bao Z, Chan W, Yu L (1993) Chem Mater 5: 2
Niziurski-Mann R, Cava MP (1993) Adv Mater 5: 547
Parakka JP, Chacko AP, Nickles DE, Wang P, Hasegawa S, Maruyama Y, Metzger RM, Cava MP (1996) Macromolecules 29: 1928
Tour JM (1996) Chem Rev 96: 537
Bohnen A, Heitz W, Müllen K, Räder HJ, Schenk R (1991) Makromol Chem 192: 1679
Zotti G, Martina S, Wegner G, Schlüter AD (1992) Adv Mater 4: 798
Zerbi G, Veronelli M, Martina S, Schlüter AD, Wegner G (1994) Adv Mater 6: 385
Rohde N, Eh M, Geibler U, Hallensleben ML, Voigt B, Voigt M (1995) Adv Mater 7: 401
Nakayama J, Konishi T, Hoshino M (1988) Heterocycles 27: 1731
Tour JM, Wu R (1992) Macromolecules 25: 1901
Barbarella G, Zambianchi M, Di Toro R, Colonna Jr M, Iarossi D, Goldoni F, Bongini A (1996) J Org Chem 61: 8285
Emge A, Bäuerle P (1997) Synth Met 84: 213
Dodabalapur A, Katz HE, Torsi L, Haddon RC (1995) Science 269: 1560
Dodabalapur A, Torsi L, Katz HE (1995) Science 268: 270
Havinga EE, Rotte I, Meijer EW, ten Hoeve W, Wynberg H (1991) Synth Met 41–43: 473
Yasser A, Delabouglise D, Hmyene M, Nessak B, Horowitz G, Garnier F (1992) Adv Mater 4: 490
Garnier F (1994) Science 179: 1684
Reisch J, Schulte KE (1961) Angew Chem 7: 241
Schulte KE, Reisch J, Hörner L (1962) Chem Ber 7: 241
Stetter H, Schreckenberg S (1974) Chem Ber 107: 2453
Stetter H, Kuhlmann H (1991) Org React 40: 407
Scheeren J W, Oomes PHJ, Nivard RJF (1973) Synthesis: 149
Bracke W (1972) J Polym Sci, Part A-1 10: 975
Pouwer KL, Vries TR, Havinga EE, Meijer EW, Wynberg HJ (1988) Chem Soc, Chem Commun: 1432
ten Hoeve W; Wynberg H, Havinga EE, Meijer EW (1991) J Am Chem Soc 113: 5887
Tamao K, Yamaguchi S, Shiozaki M, Nakagawa Y, Ito Y (1992) J Am Chem Soc 114: 5867
Tamao K, Yamaguchi S, Shiro M (1994) J Am Chem Soc 116: 11715
Tamao K, Yamaguchi S, Ito Y, Matsuzaki Y, Yamabe T, Fukushima M, Mori S (1995) Macromolecules 28: 8668
Tamao K, Yamaguchi S (1996) Pure & Appl Chem 68: 139
Okinoshima H, Yamamoto K, Kumada M (1972) J Am Chem Soc 94: 9263
Deronzier A, Moutet JC (989) Acc Chem Res 122: 255
Wolf MO, Wrighton MS (1994) Chem Mater 6: 1526
Yamamoto T, Maruyama T, Zhou ZH, Ito T, Fukuda T, Yoneda Y, Begum F, Ikeda T, Sasaki S, Takezoe H, Fukuda A, Kubota K (1994) J Am Chem Soc 116: 4832
Peng Z, Yu L (1996) J Am Chem Soc 118: 3777
Sauvage JP (1990) Acc Chem Res 23: 321
Zhu S, Swager TM (1996) Adv Mater 8: 497
Zhu S, Swager TM (1996) J Am Chem Soc 118: 8713
Wang B,W asielewski MR (1997) J Am Chem Soc 119: 12
Reddinger JL, Reynolds JR (1997) Macromolecules 30: 673
Reddinger JL, Reynolds JR (1998) Chem Mater 10: 1236
Reddinger JL, Reynolds JR (1998) Chem Mater 10: 3
Author information
Authors and Affiliations
Editor information
Rights and permissions
Copyright information
© 1999 Springer-Verlag Berlin Heidelberg
About this chapter
Cite this chapter
Reddinger, J.L., Reynolds, J.R. (1999). Molecular Engineering of π-Conjugated Polymers. In: Capek, I., Hernfández-Barajas, J., Hunkeler, D., Reddinger, J.L., Reynolds, J.R., Wandrey, C. (eds) Radical Polymerisation Polyelectrolytes. Advances in Polymer Science, vol 145. Springer, Berlin, Heidelberg. https://doi.org/10.1007/3-540-70733-6_2
Download citation
DOI: https://doi.org/10.1007/3-540-70733-6_2
Received:
Published:
Publisher Name: Springer, Berlin, Heidelberg
Print ISBN: 978-3-540-65210-6
Online ISBN: 978-3-540-70733-2
eBook Packages: Springer Book Archive