Conjugated Copolymers of Vinylene Flanked Naphthalene Diimide

被引:49
作者
Fei, Zhuping [1 ,2 ]
Han, Yang [1 ,2 ,3 ]
Martin, Jaime [2 ,4 ]
Scholes, Fiona H. [5 ]
Al-Hashimi, Mohammed [7 ]
AlQaradawi, Siham Y. [6 ]
Stingelin, Natalie [2 ,4 ]
Anthopoulos, Thomas D. [2 ,3 ]
Heeney, Martin [1 ,2 ]
机构
[1] Imperial Coll London, Dept Chem, London SW7 2AZ, England
[2] Imperial Coll London, Ctr Plast Elect, London SW7 2AZ, England
[3] Imperial Coll London, Dept Phys, London SW7 2AZ, England
[4] Imperial Coll London, Dept Mat, London SW7 2AZ, England
[5] CSIRO Mfg, Private Bag 10, Clayton, Vic 3169, Australia
[6] Qatar Univ, Dept Chem & Earth Sci, POB 2713, Doha, Qatar
[7] Texas A&M Univ Qatar, Dept Chem, POB 23874, Doha, Qatar
关键词
FIELD-EFFECT TRANSISTORS; CHANNEL ORGANIC TRANSISTORS; HIGH-ELECTRON-MOBILITY; POLYMER SOLAR-CELLS; N-CHANNEL; CHARGE-TRANSPORT; SEMICONDUCTING POLYMERS; HIGH-PERFORMANCE; DIRECT ARYLATION; HIGH HOLE;
D O I
10.1021/acs.macromol.6b01423
中图分类号
O63 [高分子化学(高聚物)];
学科分类号
070305 ; 080501 ; 081704 ;
摘要
We report the synthesis of a novel naphthalene diimide (NDI) monomer containing two (tributylstannyl)vinyl groups. The utility of this building block is demonstrated by its copolymerization with five different electron-rich comonomers under Stille conditions. The resulting high molecular weight polymers show red-shifted optical absorptions in comparison to the analogous polymers without the vinylene spacer and a significant increase in the intensity of the low-energy intramolecular charge transfer band. The polymers all exhibit ambipolar behavior in bottom-gate, top-contact organic thin-film transistors. The insertion of a solution-processed barium hydroxide layer between the polymer and the gold electrode led to unipolar behavior with improved electron mobilities.
引用
收藏
页码:6384 / 6393
页数:10
相关论文
共 52 条
  • [41] Tremel K., 2012, ACS NANO, V6, P10319
  • [42] High-Mobility Field-Effect Transistors Fabricated with Macroscopic Aligned Semiconducting Polymers
    Tseng, Hsin-Rong
    Phan, Hung
    Luo, Chan
    Wang, Ming
    Perez, Louis A.
    Patel, Shrayesh N.
    Ying, Lei
    Kramer, Edward J.
    Thuc-Quyen Nguyen
    Bazan, Guillermo C.
    Heeger, Alan J.
    [J]. ADVANCED MATERIALS, 2014, 26 (19) : 2993 - 2998
  • [43] Design, Synthesis, and Characterization of Ladder-Type Molecules and Polymers. Air-Stable, Solution-Processable n-Channel and Ambipolar Semiconductors for Thin-Film Transistors via Experiment and Theory
    Usta, Hakan
    Risko, Chad
    Wang, Zhiming
    Huang, Hui
    Deliomeroglu, Murat K.
    Zhukhovitskiy, Aleksandr
    Facchetti, Antonio
    Marks, Tobin J.
    [J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2009, 131 (15) : 5586 - 5608
  • [44] Improved Performance of Solution-Processed n-Type Organic Field-Effect Transistors by Regulating the Intermolecular Interactions and Crystalline Domains on Macroscopic Scale
    Vasimalla, Suresh
    Senanayak, Satyaprasad P.
    Sharma, Meenakshi
    Narayan, K. S.
    Iyer, Parameswar Krishnan
    [J]. CHEMISTRY OF MATERIALS, 2014, 26 (13) : 4030 - 4037
  • [45] A high-mobility electron-transporting polymer for printed transistors
    Yan, He
    Chen, Zhihua
    Zheng, Yan
    Newman, Christopher
    Quinn, Jordan R.
    Dotz, Florian
    Kastler, Marcel
    Facchetti, Antonio
    [J]. NATURE, 2009, 457 (7230) : 679 - U1
  • [46] Synthesis and characterization of fused-thiophene containing naphthalene diimide n-type copolymers for organic thin film transistor and all-polymer solar cell applications
    Yuan, Mingjian
    Durban, Matthew M.
    Kazarinoff, Peter D.
    Zeigler, David F.
    Rice, Andrew H.
    Segawa, Yukari
    Luscombe, Christine K.
    [J]. JOURNAL OF POLYMER SCIENCE PART A-POLYMER CHEMISTRY, 2013, 51 (19) : 4061 - 4069
  • [47] A high-mobility electron-transport polymer with broad absorption and its use in field-effect transistors and all-polymer solar cells
    Zhan, Xiaowei
    Tan, Zhan'ao
    Domercq, Benoit
    An, Zesheng
    Zhang, Xuan
    Barlow, Stephen
    Li, Yongfang
    Zhu, Daoben
    Kippelen, Bernard
    Marder, Seth R.
    [J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2007, 129 (23) : 7246 - +
  • [48] Rylene and Related Diimides for Organic Electronics
    Zhan, Xiaowei
    Facchetti, Antonio
    Barlow, Stephen
    Marks, Tobin J.
    Ratner, Mark A.
    Wasielewski, Michael R.
    Marder, Seth R.
    [J]. ADVANCED MATERIALS, 2011, 23 (02) : 268 - 284
  • [49] Copolymers of perylene diimide with dithienothiophene and dithienopyrrole as electron-transport materials for all-polymer solar cells and field-effect transistors
    Zhan, Xiaowei
    Tan, Zhan'ao
    Zhou, Erjun
    Li, Yongfang
    Misra, Rajneesh
    Grant, Adrian
    Domercq, Benoit
    Zhang, Xiao-Hong
    An, Zesheng
    Zhang, Xuan
    Barlow, Stephen
    Kippelen, Bernard
    Marder, Seth R.
    [J]. JOURNAL OF MATERIALS CHEMISTRY, 2009, 19 (32) : 5794 - 5803
  • [50] A Novel Alkylated Indacenodithieno[3,2-b]thiophene-Based Polymer for High-Performance Field-Effect Transistors
    Zhang, Weimin
    Han, Yang
    Zhu, Xiuxiu
    Fei, Zhuping
    Feng, Yu
    Treat, Neil D.
    Faber, Hendrik
    Stingelin, Natalie
    McCulloch, Iain
    Anthopoulos, Thomas D.
    Heeney, Martin
    [J]. ADVANCED MATERIALS, 2016, 28 (20) : 3922 - +