Purification-Free and Protection-Free Synthesis of Regioregular Poly(3-hexylthiophene) and Poly(3-(6-hydroxyhexyl)thiophene) Using a Zincate Complex of tBu4ZnLi2

被引：41
作者：
Higashihara, Tomoya [1 ,2 ]
Goto, Eisuke [1 ]
Ueda, Mitsuru [1 ]
机构：
[1] Tokyo Inst Technol, Grad Sch Sci & Engn, Dept Organ & Polymer Mat, Meguro Ku, Tokyo 1528552, Japan
[2] Japan Sci & Technol Agcy JST, Kawaguchi, Saitama 3320012, Japan
来源：
ACS MACRO LETTERS | 2012年 / 1卷 / 01期
基金：
日本学术振兴会; 日本科学技术振兴机构;
关键词：
CHAIN-GROWTH POLYMERIZATION; ANIONIC-POLYMERIZATION; GRIGNARD METATHESIS; SOLAR-CELLS; POLY(3-ALKYLTHIOPHENES); DESIGN; MECHANISM;
D O I：
10.1021/mz200128d
中图分类号：
O63 [高分子化学（高聚物）];
学科分类号：
070305 ; 080501 ; 081704 ;
摘要：
The controlled synthesis of head-to-tail regioregular poly(3-hexylthiophene) (P3HT) using a dianion-type zincate complex, (Bu4ZnLi2)-Bu-t, is described. The molecular weights of P3HTs could be increased up to 30 kDa by increasing the feed ratio of the monomer to Ni catalyst while maintaining a low polydispersity (PDI < 1.2) and a high regioregularity (>97%, when M-n > 10 kDa). Surprisingly, this new system can be used in as-received THF as well as in THF containing protic impurities, such as isopropanol, methanol, and even 1000 ppm water. In addition, the direct synthesis of poly[3-(6-hydroxyhexyl)thiophene] (P3HHT) could be performed without protection based on the developed system.
引用
收藏
页码：167 / 170
页数：4
相关论文
共 20 条
  • [1] Development of Novel Conjugated Donor Polymers for High-Efficiency Bulk-Heterojunction Photovoltaic Devices
    Chen, Junwu
    Cao, Yong
    [J]. ACCOUNTS OF CHEMICAL RESEARCH, 2009, 42 (11) : 1709 - 1718
  • [2] REGIOCONTROLLED SYNTHESIS OF POLY(3-ALKYLTHIOPHENES) MEDIATED BY RIEKE ZINC - THEIR CHARACTERIZATION AND SOLID-STATE PROPERTIES
    CHEN, TA
    WU, XM
    RIEKE, RD
    [J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1995, 117 (01) : 233 - 244
  • [3] Synthesis of Conjugated Polymers for Organic Solar Cell Applications
    Cheng, Yen-Ju
    Yang, Sheng-Hsiung
    Hsu, Chain-Shu
    [J]. CHEMICAL REVIEWS, 2009, 109 (11) : 5868 - 5923
  • [4] High-performance organic field-effect transistors: Molecular design, device fabrication, and physical properties
    Di, Chong-an
    Yu, Gui
    Liu, Yunqi
    Zhu, Daoben
    [J]. JOURNAL OF PHYSICAL CHEMISTRY B, 2007, 111 (51) : 14083 - 14096
  • [5] Solar cell efficiency tables (version 35)
    Green, Martin A.
    Emery, Keith
    Hishikawa, Yoshihiro
    Warta, Wilhelm
    [J]. PROGRESS IN PHOTOVOLTAICS, 2010, 18 (02): : 144 - 150
  • [6] Synthesis of water-soluble polymethacrylates by living anionic polymerization of trialkylsilyl-protected oligo(ethylene glycol) methacrylates
    Ishizone, T
    Han, S
    Okuyama, S
    Nakahama, S
    [J]. MACROMOLECULES, 2003, 36 (01) : 42 - 49
  • [7] Efficient tandem polymer solar cells fabricated by all-solution processing
    Kim, Jin Young
    Lee, Kwanghee
    Coates, Nelson E.
    Moses, Daniel
    Nguyen, Thuc-Quyen
    Dante, Mark
    Heeger, Alan J.
    [J]. SCIENCE, 2007, 317 (5835) : 222 - 225
  • [8] A new chemoselective anionic polymerization method for poly(N-isopropylacrylamide) (PNIPAm) in aqueous media:: Design and application of bulky zincate possessing little basicity
    Kobayashi, M
    Matsumoto, Y
    Uchiyama, M
    Ohwada, T
    [J]. MACROMOLECULES, 2004, 37 (12) : 4339 - 4341
  • [9] Regioregular, head-to-tail coupled poly(3-alkylthiophenes) made easy by the GRIM method: Investigation of the reaction and the origin of regioselectivity
    Loewe, RS
    Ewbank, PC
    Liu, JS
    Zhai, L
    McCullough, RD
    [J]. MACROMOLECULES, 2001, 34 (13) : 4324 - 4333
  • [10] Loewe RS, 1999, ADV MATER, V11, P250, DOI 10.1002/(SICI)1521-4095(199903)11:3<250::AID-ADMA250>3.0.CO
12