English
往期目录
新闻公告
More
化学进展 2013, Vol. 25 Issue (07): 1166-1176 DOI: 10.7536/PC121111 前一篇   后一篇

• 综述与评论 •

聚(3-烷基噻吩)合成方法研究

陈周群1,2,3, 马昌期1*   

  1. 1. 中国科学院苏州纳米技术与纳米仿生研究所 印刷电子技术研究中心 苏州 215123;
    2. 中国科学院化学研究所 北京 100190;
    3. 中国科学院大学 北京 100049
  • 收稿日期:2012-11-01 修回日期:2013-01-01 出版日期:2013-07-25 发布日期:2013-04-16
  • 通讯作者: 马昌期 E-mail:cqma2011@sinano.ac.cn
  • 基金资助:

    国家自然科学基金项目(No.91123034)资助

下载PDF ( 900 ) 引用
导出 被引次数 ( 3 )

Synthesis of Poly(3-Alkylthiophene)s

Chen Zhouqun1,2,3, Ma Chang-Qi1*   

  1. 1. Printable Electronics Research Center, Suzhou Institute of Nano-Tech and Nano-Bionics, Chinese Academy of Sciences, Suzhou 215123, China;
    2. Institute of Chemistry, Chinese Academy of Sciences, Beijing 100190, China;
    3. University of Chinese Academy of Sciences, Beijing 100049, China
  • Received:2012-11-01 Revised:2013-01-01 Online:2013-07-25 Published:2013-04-16

作为导电共轭聚合物中的一个典型代表,聚(3-烷基噻吩) (poly(3-alkylthiophene), P3AT) 因其良好的光电性能,已广泛应用于有机光电子领域,如有机场效应晶体管、有机发光二极管和有机聚合物太阳能电池等。P3AT的合成制备方法也成为导电共轭聚合物合成方法的方向标,其发展的历史进程代表了共轭聚合物合成方法的共同历程。本文简要介绍了P3AT的发展历史、分子构效关系及其在有机光电器件上的应用,并按合成方法的不同分类,详细介绍了P3AT的各类合成方法,包括:McCullough 法、Rieke法、格氏置换合成法、Suzuki反应、Still反应、C-H活化直接偶联等,总结比较了各种方法的反应机理及其优缺点,以期为读者展示出导电共轭聚合物合成方法发展变化的整体过程,并对其发展方向提出了展望。

关键词： 共轭高分子, 聚(3-烷基噻吩), 结构规整性, 金属催化C-C偶联, C-H活化聚合

Owing to their excellent optoelectronic properties, poly(3-alkylthiophene)s (P3AT) has been considered as one of the best conjugated polymers for use in organic electronics devices, such as, organic field-effect transistors (OFET), organic light-emitting diodes (OLED), and organic photovoltaics (OPV). Because of the asymmetrical structure of 3-alkylthiophene, there are three possible linkages between two neighboring thiophene units, which leads to the regioregularity issues for P3AT. In comparison with regiorandom P3AT, the regioregular P3ATs exhibit better optoelectronic performance, and have attracted much attention. Synthesis of the regioregular P3AT is, however, more challenging for synthetic polymer scientists. Over the past three decades, various metal-catalyzed C-C coupling reaction have been utilized for synthesis of regioregular P3AT, including McCullough method, Rieke method, Grignard methathesis (GRIM), Suzuki-coupling, Stille-coupling, and C-H activated polymerization. In this mini-review paper, the above mentioned synthetic methods are summarized. The mechanism and advantages of these methods are compared and discussed. The current review paper gives an general overview on the research development on the synthesis of P3AT. In the end, we would like point out that direct C-H activated polymerization is the most promising synthetic method for conjugated polymers due to its high atom economy efficiency. Contents
1 Introduction
2 Regioregularity and applications of poly(3-alkylthiophene)s
2.1 Regioregularity of poly(3-alkylthiophene)s
2.2 Application of poly(3-alkylthiophene)s in the organic electronic devices
3 Methods for the synthesis of poly(3-alkyl-thiophene)s
3.1 Chemical and electrochemical polymerization
3.2 Chemical coupling methods to regiorandom poly(3-alkylthiophene)s
3.3 Synthesis of regioregular poly(3-alkylthiophene) by metal-catalyzed C-C coupling reaction
4 Summary and outlook

Key words: conjugated polymer, poly(3-alkylthiophene), structural regularity, metal-catalyzed C-C coupling, C-H activated polymerization

中图分类号: 

()

[1] Shirakawa H, Louis E J, MacDiarmid A G, Chiang C K, Heeger A J. J. Chem. Soc., Chem. Commun., 1977, 578-580
[2] Diza A F, Kanazawa K K, Gardini G P. J. Chem. Soc., Chem. Commun., 1979, 645-636
[3] Yamamoto T, Sanechika K, Yamamoto A. J. Polym. Sci. Polym. Lett. Ed., 1980, 18: 9-12
[4] MacDiarmid A G, Chiang J C, Richter A F. Synth. Met., 1987, 18: 285-290
[5] Burroughes J H, Bradley D D C, Brown A R, Marks R N, Mackay K, Friend R H, Burns P L, Holmes A B. Nature, 1990, 347: 539-541
[6] Dang M T, Hirsch L, Wantz G. Adv. Mater., 2011, 23: 3597-3602
[7] Perepichka I F, Perepichka D F, Meng H, Wudl F. Adv. Mater., 2005, 17: 2281-2305
[8] Facchetti A. Chem. Mater., 2011, 23: 733-758
[9] Lin J W P, Dudek L P. J. Polym. Sci. Polym. Chem. Ed., 1980, 18: 2869-2873
[10] Yamamoto T, Sanechika K, Yamamoto A. Bull. Chem. Soc. Jpn., 1983, 56: 1497-1502
[11] Jen K Y, Miller G G, Elsenbaumer R L. J. Chem. Soc., Chem. Commun., 1986, 1346-1347
[12] Elsenbaumer R L, Jen K Y, Oboodi R. Synth. Met., 1986, 15: 169-174
[13] Sato M A, Tanaka S, Kaeriyama K. J. Chem. Soc., Chem. Commun., 1986, 873-874
[14] Hotta S, Rughooputh S D D V, Heeger A J, Wudl F. Macromolecules, 1987, 20: 212-215
[15] Wei Y, Chan C C, Tian J, Jang G W, Hsueh K F. Chem. Mater., 1991, 3: 888-897
[16] McCullough R D. Adv. Mater., 1998, 10: 93-116
[17] Osaka I, McCullough R D. Acc. Chem. Res., 2008, 41: 1202-1214
[18] Sato M, Morii H. Macromolecules, 1991, 24: 1196-1200
[19] Barbarella G, Bongini A, Zambianchi M. Macromolecules, 1994, 27: 3039-3045
[20] McCullough R D, Tristram-Nagle S, Williams S P, Lowe R D, Jayaraman M. J. Am. Chem. Soc., 1993, 115: 4910-4911
[21] McCullogh R D, Wiliams S P, Tristam-Nagle S, Jayaraman M, Ewbank P C, Miller L. Synth. Met., 1995, 69: 279-282
[22] Prosa T J, Winokur M J, McCullough R D. Macromolecules, 1996, 29: 3654-3656
[23] Daoud W A, Xin J H. J. Appl. Polym. Sci., 93: 2131-2135
[24] McCullough R D, Lowe R D, Jayaraman M, Anderson D L. J. Org. Chem., 1993, 58: 904-912
[25] Chen T A, Rieke R D. J. Am. Chem. Soc., 1992, 114: 10087-10088
[26] McCullough R D, Lowe R D. J. Chem. Soc., Chem. Commun., 1992, 70-72
[27] Chen T A, Rieke R D. Synth. Met., 1993, 2: 175-177
[28] Ong B S, Wu Y, Li Y, Liu P, Pan H. Chem. Eur. J., 2008, 14: 4766-4778
[29] Dennler G, Scharber M C, Brabec C J. Adv. Mater., 2009, 21: 1323-1338
[30] Brabec C J, Gowrisanker S, Halls J J M, Laird D, Jia S, Williams S P. Adv. Mater., 2010, 22: 3839-3856
[31] Tsumura A, Koezuka H, Ando T. Appl. Phys. Lett., 1986, 49: 1210-1212
[32] Assadi A, Svensson C, Willander M, Inganäs O. Appl. Phys. Lett., 1988, 53: 195-197
[33] Sirringhaus H, Tessler N, Friend R H. Science, 1998, 280: 1741-1744
[34] Sirringhaus H, Brown P J, Friend R H, Nielsen M M, Bechgaard K, Langeveld-Voss B M W, Spiering A J H, Janssen R A J, Meijer E W, Herwig P, Leeuw D M. Nature, 1999, 401: 685-688
[35] Allard S, Forster M, Souharce B, Thiem H, Scherf U. Angew. Chem. Int. Ed., 2008, 47: 4070-4098
[36] Ohmori Y, Uchida M, Muro K, Yoshino K. Jpn. J. Appl. Phys., 51: L1938-L1940
[37] Braun D, Gustafsson G, McBranch D, Heeger A J. J. Appl. Phys., 1992, 72: 564-568
[38] Xu B, Holdcroft S. Macromolecules, 1993, 26: 4457-4460
[39] Chen F, Mehta P G, Takiff L, McCullough R D. J. Mater. Chem., 1996, 6: 1763-1766
[40] Wilson G, Hulstrom R. Research Cell Efficiency Records (2012-5-28). http: //www. nrel. gov/ncpv/images/efficiency_chart. jpg
[41] Yu G, Gao J, Hummelen J C, Wudl F, Heeger A J. Science, 1995, 270: 1789-1791
[42] Wienk M M, Kroon J M, Verhees W J H, Knol J, Hummelen J C, van Hal P A, Janssen R A. Angew. Chem. Int. Ed., 2003, 42: 3371-3375
[43] Schilinsky P, Waldaul C, Brabec C J. Appl. Phys. Lett., 2002, 81: 3885-3887
[44] Yang X, Joachim L, Sjoerd C V, Wiljan J H V, Martijn M W, Jan M K, Matthias A J M, René A J J. Nano Lett., 2005, 5: 579-583
[45] Peet J, Kim J Y, Coates N E, Ma W L, Moses D, Heeger A J, Bazan G C. Nat. Mater., 2007, 6: 497-500
[46] Irwin M D, Buchholz D B, Hains A W, Chang R P H, Marks T J. Proc. Natl. Acad. Sci. U. S. A., 2008, 105: 2783-2787
[47] Liao S H, Li Y L, Jen T H, Cheng Y S, Chen S A. J. Am. Chem. Soc., 2012, 134: 14271-14274
[48] Roncali J. Chem. Rev., 1992, 92: 711-738
[49] Roncali J, Garreau R, Yassar A, Marque P, Garnier F, Lemaire M. J. Phys. Chem., 1987, 91: 6706-6714
[50] Niemi V M, Knuuttila P, Österholm J E. Polymer, 1992, 33: 1559-1562
[51] Amou S, Haba O, Shirato K, Hayakawa T, Ueda M, Takeuchi K, Asai M. J. Polym. Sci. Part A: Polym. Chem., 1999, 37: 1943-1948
[52] Andersson M R, Selse D, Berggren M, Järvinen H, Hjertberg T, Inganäs O, Wennerström O, Österholm J E. Macromolecules, 1994, 27: 6503-6506
[53] Lévesque I, Leclerc M. J. Chem. Soc., Chem. Commun., 1995, 22: 2293-2294
[54] Yamaoto T, Morita A, Miyazaki Y, Maruyama T, Wakayama H, Zhou Z H, Nakamura Y, Kanbara T, Sasaki S, Kubota K. Macromolecules, 1992, 25: 1214-1223
[55] Chen S A, Tsai C C. Macromolecules, 1993, 26: 2234-2239
[56] Chen T A, Wu X, Rieke R D. J. Am. Chem. Soc., 1995, 117: 233-244
[57] Mao H, Xu B, Holdcroft S. Macromolecules, 1993, 26: 1163-1169
[58] Loewe R S, Khersonsky S M, McCullough R D. Adv. Mater., 1999, 11: 250-253
[59] Loewe R S, Ewbank P C, Liu J, Zhai L, McCullough R D. Macromolecules, 2001, 34: 4324-4333
[60] Yokoyama A, Miyakoshi R, Yokozawa T. Macromolecules, 2004, 37: 1169-1171
[61] Miyakoshi R, Yokoyama A, Yokozawa T. J. Am. Chem. Soc., 2005, 127: 17542-17547
[62] Lovu M C, Sheina E E, Gil R R, McCullough R D. Macromolecules, 2005, 38: 8649-8656
[63] Adachi I, Miyakoshi R, Yokoyama A, Yokozawa T. Macromolecules, 2006, 39: 7793-7795
[64] Jeffries-EI M, Sauvé G, McCullough R D. Macromolecules, 2005, 38: 10346-10352
[65] Jeffries-EI M, Sauvé G, McCullough R D. Adv. Mater., 2004, 16: 1017-1019
[66] Stefan M C, Bhatt M P, Sista P, Magurudeniva H D. Poly. Chem., 2012, 3: 1693-1701
[67] Magurudeniva H D, Sista P, Westbrook J K, Ourso T E, Nguyen K, Maher M C, Alemseghed M G, Biewer M C, Stefan M C. Macromol. Rapid Commun. 2011, 32: 1748-1752
[68] Lin Y H, Smith K A, Kempf C N, Verduzco R. Polym. Chem., 2013, 4: 229-232
[69] Tamba S, Tanaka S, Okubo Y. Chem. Lett., 2011, 40: 398-399
[70] Tanaka S, Tamba S, Tanaka D, Sugie A, Mori A. J. Am. Chem. Soc., 2011, 133: 16734-16737
[71] Tanaka S, Tanaka D, Tatsuta G, Murakami K, Tamba S, Sugie A, Mori A. Chem. Eur. J., 2013, 19: 1658-1665
[72] Tamba S, Shono K, Sugie A, Mori A. J. Am. Chem. Soc., 2011, 133: 9700-9703
[73] Guillerez S, Bidan G. Synth. Met., 1998, 93: 123-126
[74] Jayakannan M, Lou X, Van Dongen J L J, Janssen R A J. J. Polym. Sci. Part A: Polym. Chem., 2005, 43: 1454-1462
[75] Yokozawa T, Suzuki R, Nojima M, Ohta Y, Yokoyama A. Macromol. Rapid Commun., 2011, 32: 801-806
[76] Li W, Han Y, Li B, Liu C, Bo Z. J. Polym. Sci., Part A: Polym. Chem., 2008, 46: 4556-4563
[77] Liversedge I A, Higgins S J, Giles M, Heeney M, McCulloch I. Tetrahedron Lett., 2006, 47: 5143-5146
[78] McCullough R D, Ewbank P C, Loewe R S. J. Am. Chem. Soc., 1997, 119: 633-634
[79] Iraqi A, Barker G W. J. Mater. Chem., 1998, 8: 25-29
[80] Lère-Porte J P, Moreau J J E, Torreilles C. Eur. J. Org. Chem., 2001, 7: 1249-1258
[81] Chen X, Engle K M, Wang D H, Yu J Q. Angew. Chem. Int. Ed., 2009, 48: 5094-5115
[82] Davies H M L, Bois J D, Yu J Q. Chem. Soc. Rev., 2011, 40: 1855-1856
[83] Gozzi C, Lavenot L, Ilg K, Penalva V, Lemaire M. Tetrahedron Lett., 1997, 38: 8867-8870
[84] Yanagisawa S, Sudo T, Noyori R, Itami K. J. Am. Chem. Soc., 2006, 128: 11748-11749
[85] Join B, Yamamoto T, Itami K. Angew. Chem. Int. Ed., 2009, 48: 3644-3647
[86] Ackermann L, Vicente R, Kapdi A R. Angew. Chem. Int. Ed., 2009, 48: 9792-9826
[87] Facchetti A, Vaccaro L, Marrocchi A. Angew. Chem. Int. Ed., 2012, 51: 3520-3523
[88] Sévignon M, Papillon J, Schulz E, Lemaire M. Tetrahedron Lett., 1999, 40: 5873-5876
[89] Hassan J, Schulz E, Gozzi C, Lemaire M. J. Mol. Catal. A: Chem., 2003, 195: 125-131
[90] 张杰(Zhang J), 李坚(Li J), 孙明慧(Sun M H). 化工学报(CIESC Journal), 2010, 61(6): 1587-1591
[91] Wang Q, Takita R, Kikuzaki Y, Ozawa F. J. Am. Chem. Soc., 2010, 132: 11420-11421
[92] Lu W, Kuwabara J, Kanbara T. Macromolecules, 2011, 44: 1252-1255
[93] Berrouard P, Najari A, Pron A, Gendron D, Morin P O, Pouliot J R, Veilleux J, Leclerc M. Angew. Chem. Int. Ed., 2012, 51: 2068-2071
[94] Chang S W, Waters H, Kettle J, Kuo Z R, Li C H, Yu C Y, Horie M. Macromol. Rapid. Commun., 2012, 33: 1927-1932
[95] Pouliot J R, Mercier L G, Caron S, Leclerc M. Macromol. Chem. Phys., 2013, 214: 453-457
[1] 陈云, 邵亚, 范丽娟. 共轭高分子材料荧光颜色的调节机理及方法[J]. 化学进展, 2014, 26(11): 1801-1810.
[2] 刘兴奋,王丽华,宋世平,樊春海,黄维. 基于共轭高分子材料的光学生物传感器*[J]. 化学进展, 2008, 20(09): 1375-1384.
阅读次数
全文


摘要

聚(3-烷基噻吩)合成方法研究