聚噻吩的合成方法

舒昕, 李兆祥, 夏江滨

doi:10.7536/PC141029

化学进展 ›› 2015, Vol. 27 ›› Issue (4) :385-394 DOI: 10.7536/PC141029

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聚噻吩的合成方法

舒昕, 李兆祥, 夏江滨

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Synthetic Methods for Poly(thiophene)s

Shu Xin, Li Zhaoxiang, Xia Jiangbin*

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文章历史 +

摘要

自从1977年白川英树等发现聚乙炔这种导电聚合物以来,打破了高分子材料长期以来被认为是绝缘体的观点。随后聚苯胺、聚吡咯、聚噻吩等的出现使导电聚合物的种类不断出新,其用途也扩展到如导电材料、电极材料、催化材料以及太阳能电池等应用中,且已有部分产品实现了商品化。其中,聚噻吩因其良好的稳定性、易于制备、掺杂后具有良好的光电化学性能等特点而受到广泛关注。本文总结了几种合成聚噻吩及其衍生物的常见方法,包括化学氧化聚合法、电化学聚合法、金属催化偶联法、光致合成法、光电化学沉积法,以及近年来新发现的固相聚合法和酸催化聚合法,并简要介绍了各自的合成机理及优缺点。

Abstract

Since Shirakawa et al discovered that polyacetylene can reach extremely high conductivities, the polymer material has no longer been regarded as electrical insulators. Subsequently, the discovery of polyaniline, polypyrrole, poly(thiophene) expanded the type of conductive polymer. In addition, the conductive polymer has promising application in the fields such as electrode material, solar cell, and other applications, and some of them have achieved the commercialization. Among them, poly(thiophene)s has been widely concerned because of their good stability, easy preparation and good characteristics of photoelectrochemical performance after doping. Thus, in this review, several synthetic methods for poly(thiophene)s and their derivatives are reviewed, including chemical oxidation polymerization, electrochemical synthesis, and so on, especially the newly developed solid state polymerization and acid-assisted polymerization. Their synthesis mechanism, the advantages and disadvantages are also discussed.

Contents
1 Introduction
2 Synthetic methods
2.1 Chemical oxidation polymerization and electrochemical polymerization
2.2 Metal-catalysed polymerization
2.3 Photo-induced polymerization
2.4 Photo-electrochemically polymerization
2.5 Solid state polymerization
2.6 Acid-assisted polymerization
3 Conclusion and outlook

Graphical abstract

关键词

共轭聚噻吩 / 导电聚合物 / 聚合方法

Key words

conjugated poly(thiophene)s / conducting polymers / synthetic methods

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舒昕, 李兆祥, 夏江滨. 聚噻吩的合成方法[J]. 化学进展, 2015, 27(4): 385-394 DOI:10.7536/PC141029

Synthetic Methods for Poly(thiophene)s[J]. Progress in Chemistry, 2015, 27(4): 385-394 DOI:10.7536/PC141029

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参考文献

原文顺序 | 出版日期 | 本文引用

[1] (a)Shirakawa H, Louis E J, Macdiarmid A G, Chiang C K, Heeger A J. Chem. Commun., 1997, 16: 578.; (b) Handbook of Conducting Polymers. 2nd ed. Marcel Dekker: New York, 1998.; (c)Nalwa H S. Handbook of Organic Conductive Molecules and Polymer. Chichester, 1997, 1.
[2] Diaz A F, Kanazawa K K, Gardini G P. Chem. Commun., 1979, 14: 635.
[3] Diaz A F. Chem. Scr., 1981, 17: 145.
[4] Tourillon G, Garnier F J. J. Electroanal. Chem., 1982, 135(1): 173.
[5] Joachim B, Shamsher M, Robert J. IBM J. Res. Develop., 1983, 27(4): 330.
[6] Sharma P S, Pietrzyk-Le A, Souza F D, Kutner W. Anal. Bioanal. Chem., 2012, 402(10): 3177.
[7] Joelle R B, Jacques S. J. Electroanal. Chem., 1985, 182(1): 187.
[8] Naarmann H. Polymers, Electrically Conduction in Ullmann’s Encyclopedia of Industrial Chemistry, Wiley-VCH, Weinheim, 2002.
[9] Pei Q B, Yang Y G, Zhang C, Heeger A J. J. Am. Chem. Soc., 1996, 118(16): 3922.
[10] Wang H L, Huang F, MacDiarmid A G, Wang Y Z, Gebler D D, Epstein A J. Synth. Met., 1996, 80(2): 97.
[11] Xia J B, Masaki N, Jiang K, Yanagida S. J. Mater. Chem., 2007, 17(27): 2845.
[12] Xia Y J, Sun K, Ouyang J Y. Adv. Mater., 2012, 24(18): 2436.
[13] Yoshino K, Hayashi S, Sugimoto R.Japanese Journal of Applied Physics, Part2:Letters, 1984, 23(12): 899.
[14] Tourillon G, Garnier F. J. Electroanal. Chem., 1982, 135(1): 173
[15] Xu Z G, Gilles H, Francis G. J. Electroanal. Chem., 1988, 246(2): 467.
[16] Genies E M, Bidan G, Diaz A F. J. Electroanal. Chem., 1983, 149(1/2): 101.
[17] Abdulla H S. Int. J. Electrochem. Sci., 2013, 8(10): 11782.
[18] Hillman A R, Elizabeth F J. Electroanal. Chem., 1988, 243(2): 403.
[19] Tourillon G, Garnier F. J. Phys. Chem., 1983, 87(13): 2289.
[20] Waltman R J, Joachim B, Diaz A F. J. Phys. Chem., 1983, 87(8): 1459.
[21] Roncali J, Yaaaar A, Garnier F Z. Chem. Commun., 1988, 9: 581.
[22] Yaaaar A, Roncali J, Garnier F. Macromolecules, 1989, 22: 804.
[23] Hotta S, Hosaka T, Shimotsuma W. Synth. Met., 1983, 6: 317.
[24] Tanaka S, Sato M, Kaeriyama K. Makromol. Chem., 1984, 185: 1295.
[25] Sato M, Tanaka S, Kaeriyama K. J. Chem. Soc. Chem. Commun., 1985, 713.
[26] (a) Shi G Q, Jin S, Xue G, Li C. Science, 1995, 267: 994.; (b) Shi G Q, Shi G Q, Chun L, Liang Y Q. Adv. Mater., 1999, 11: 131145.;(c) Fu M X, Zhu Y F, Tan R Q, Shi G Q. Adv. Mater., 2001, 13: 1874.; (d) Li C, Bai H, Shi G Q. Chem. Soc. Rev., 2009, 38: 2397.
[27] Kochi J K, Tamura Masuhiko.J.Am.Chem.Soc., 1971, 93(6): 1483.
[28] Masuhiko T, Kochi J K. J. Am. Chem. Soc., 1971, 93(6): l487.
[29] Yamamoto T, Sanechika K, Yamamoto A. J. Polym. Sci. C: Polym. Lett., 1980, 18(1): 9.
[30] Lin J W P, Dudek L P. J. Polym. Sci. A: Polym. Chem., 1980, 18(9): 2869.
[31] Pei J, Ni J, Zhou X H, Cao X Y, Lai Y H. J. Org. Chem. 2002, 67: 4924.
[32] Chen T A, Wu X M, Rieke R D. J. Am. Chem. Soc. 1995, 117(1): 233.
[33] Chen T A, Rieke R D. J. Am. Chem. Soc., 1992, 114(25): 10087.
[34] McCullough R D, Lowe R D. J. Chem. Soc. Chem. Commun., 1992, 1: 70.
[35] McCullough R D, Williams S P, Tristram-Nagle S, Jayaraman M. Synth. Met., 1995, 69(1/3): 279.
[36] Loewe R S, Khersonsky S M, McCullough R D. Adv. Mater., 1999, 11(3): 250.
[37] Ullmann F, Bielecki J. Berichte der Deuts-chen Chemischen Gesellschaft, 1901, 34: 2174.
[38] Pomerantz M, Yang H, Cheng Y. Macromolecules, 1995, 28(17): 5706.
[39] Pomerantz M, Cheng Y, Kasim R K, Elsenbaumer R L. J. Mater. Chem., 1999, 9(9): 2155.
[40] Castro C E, Stephenes R D. J. Org. Chem., 1963, 28(8): 2163.
[41] Stephens R D, Castro C E. J. Org. Chem., 1963, 28(12): 3313.
[42] Cassar L. J. Organomet. Chem., 1975, 93(2): 253.
[43] Sonogashira K, Tohda Y, Hagihara N. Tetrahedron. Lett., 1975, 50: 4467.
[44] Coombs B A, Rutter S R, Goeta A E, Sparkes H A, Batsanov A S, Beeby A. RSC. Adv., 2012, 2: 1870.
[45] (a) Mizoroki T, Mori K, Ozaki A. Bull. Chem. Soc. Jpn., 1971, 44(2): 581.; (b) Heck R F, Nolley J P. J. Org. Chem., 1972, 37(14): 2320.
[46] Hassan J, Schulz E, Gozzi C, Lemaire M. J. Mol. Cataly. A: Chem., 2003, 195: 125.
[47] Guillerez S, Bidan G. Synth. Met., 1998, 93: 123.
[48] Rehahn M, Schlüter A D, Wegner G Feast W J. Polymer, 1989, 30: 1060
[49] Kosugi M, Shimizu Y, Migita T. Chem. Lett., 1977, 12: 1423.
[50] Milstein D, Stille J K. J. Am. Chem. Soc., 1978, 100(11):3636.
[51] Bochmann M, Kelly K. J. Chem. Soc. Chem. Commum., 1989, 9: 532.
[52] Giesa R, Schulz R C. Makromol. Chem., 1990, 191(4): 857.
[53] Galarini R, Musco A, Pontellini R, Bolognesi A, Destri S, Cataellani M, Mascherpa M, Zhuo G. J. Chem. Soc. Chem. Commum., 1991, 6: 364.
[54] Carsten B, He F, Son H J, Xu T, Yu L P. Chem. Rev., 2011, 111: 1493.
[55] Mak C S K, Cheung W K, Leung Q Y, Chan W K. Macromol. Rapid Commum., 2010, 31(9/10): 875.
[56] Sévignon M, Papillon J, Schulz E, Lemaire M. Tetrahedron Lett., 1999, 49: 5873.
[57] Wang Q F, Takita R, Kikuzaki Y, Ozawa F. J. Am. Chem. Soc., 2010, 132: 11420.
[58] Crivello J V. Adv. Polym. Sci., 1984, 62: 1.
[59] Rabeck J F, Lucki J, Zuber M. Polymer, 1992, 33(22): 4838.
[60] Iyoda T, Kitano M, Shimidzu T. J. Chem. Soc. Chem. Commun., 1991, 22: 1618.
[61] Yagci Y, Kornowski A, Schnabel W. J. Polym. Sci. Part A: Polym. Chem., 1992, 30(9): 1987.
[62] Yagci Y, Yilmaz F, Kiralp S, Toppare L. Macromol. Chem. Phys., 2005, 206(12): 1178.
[63] Aydogan B, Gunbas G E, Durmus A, Toppare L, Yagci Y. Macromolecules, 2010, 43(1): 101.
[64] Tabei H, Fujiki M, Imamura S. Jpn. J. Appl. Phys., 1985, 24(9): 685.
[65] Okano M, Itoh K, Kikuchi E, Akira F. J. App. Phys., 1987, 62(5): 1.
[66] Murakoshi K, Kogure R, Wada Y, Yanagida S. Chem. Lett., 1997, 5: 471.
[67] Saito Y, Fukuri N, Senadeera R, Kitamura T, Wada Y, Yanagida S. Electrochem. Commun., 2004, 6: 71.
[68] Xia J B, Masaki N, Lira-Cantu M, Kim Y, Jiang K J, Yanagida S. J. Am. Chem. Soc., 2008, 130: 1258.
[69] De Leeuw D M, Kraakman P, Bongaert P F G, Mutsaers C M J, Klaassen D B M. Synth. Metal., 1994, 66: 263.
[70] (a) Magat M. Polymer, 1962, 3(3): 449.;(b)Baughman R H. J. Polym. Sci.: Polym. Phys. Ed., 1974, 12: 1511.
[71] (a) Wenger G Z. Naturforsch, 1969, 24b: 824.;(b) Wegner G. Makromol. Chem., 1971, 145: 85.;(c) Enkelmann V, Schleier G, Wegner G, Eichelf H, Schwoerer M. Chem. Phys. Lett., 1977, 52(2): 314.;(d) Yee K C, Chance R R. J. Polym. Sci.: Polym. Phys. Ed., 1978, 16: 431.
[72] (a) Walatka V V, Labes M M, Perlstein J H. Phys. Rev. Lett., 1973, 31(18): 1139.; (b) Cohen M J, Garito A F, Heeger A J, MacDiarmid A G, Mikulski C M, Saran M S, Kleppinger J. J. Am. Chem. Soc., 1976, 98: 3844.
[73] Meng H, Perepichka D F, Wudl F. Angew. Chem. Int. Ed., 2003, 42: 658.
[74] Meng H, Perepichka D F, Bendikov M, Pan G Z, Yu W J, Dong W J, Brown S, Wudl F. J. Am. Chem. Soc., 2003, 125: 15151.
[75] Spencer H J, Berridge R, Crouch D J, Wrigh S P, Giles M, McCulloch I, Coles S J, Hursthouse M B, Skabara P J. J. Mater. Chem., 2003, 13: 2075.
[76] Patra A, Wijsboom Y H, Zade S S, Li M, Sheynin Y, Leitus G, Bendikov M. J. Am. Chem. Soc., 2008, 130: 6734.
[77] Chen S A, Xu J K, Lu B Y, Duan X M, Kong F F. Adv. Mater. Res., 2011, 239/242: 924.
[78] Chen S, Luo B Y, Duan X M, Xu J K. Polym. Chem., 2012, 50: 1967.
[79] Tusy C, Huang L L, Jin J P, Xia J B. RSC Adv., 2014, 4: 8011.
[80] Tusy C, Huang L L, Peng K, Xia J B. RSC Adv., 2014, 4: 29032.
[81] Walczak R M, Leonard J K, Reynolds J R. Macromolecules, 2008, 41: 691.
[82] Koh J K, Kim J, Kim B, Kim J H, Kim E. Adv. Mater., 2011, 23: 1641.
[83] Chen L, Jin J P, Shu X, Xia J B. J. Power Sources, 2014, 248: 1234.
[84] Yin X, Wu F, Fu N Q, Han J, Chen D L, Xu P, He M, Lin Y. Appl. Mater. Interfaces., 2013, 5: 8423.
[85] Wagner P, Jolley K W, Officer D L. Aust. J. Chem., 2011, 64: 335.
[86] (a) Yin Y H. Bachelor’s Thesis of Wuhan University, 2012. (b)Yin Y H, Li Z X, Jin J P, Tusy C, Xia J B. Synth. Met., 2013, 175: 97.
[87] Bonillo B, Swager T M. J. Am.Chem. Soc., 2012, 134: 18916.
[88] Balasubramanian A, Ku T C, Shih H P, Suman A, Lin H J, Shih T W, Han C C. Polym. Chem., 2014, 5: 5928
[89] Heeger A J. Chem. Soc. Rev., 2010, 39, 2354.