Synthesis, Structures, and Properties of Thieno[3,2-b]thiophene and Dithiophene Bridged Isoindigo Derivatives and Their Organic Field-effect Transistors Performance

被引:28
作者
Wu, Ti [1 ,2 ]
Yu, Chunmeng [1 ,3 ]
Guo, Yunlong [1 ]
Liu, Hongtao [1 ,2 ]
Yu, Gui [1 ]
Fang, Yu [3 ]
Liu, Yunqi [1 ]
机构
[1] Chinese Acad Sci, Inst Chem, Beijing Natl Lab Mol Sci, Beijing 100190, Peoples R China
[2] Chinese Acad Sci, Grad Univ, Beijing 100049, Peoples R China
[3] Shanxi Normal Univ, MOE, Key Lab Appl Surface & Colloid Chem, Xian 710062, Peoples R China
基金
中国国家自然科学基金;
关键词
HIGH-MOBILITY; ANTITUMOR-ACTIVITY; SOLAR-CELLS; POLYMERS; SUBSTITUENTS; BANDGAP;
D O I
10.1021/jp304697r
中图分类号
O64 [物理化学(理论化学)、化学物理学];
学科分类号
070304 ; 081704 ;
摘要
Organic semiconductors (ITTI and IDTI) characterized of thieno[3,2-b]thiophene and dithiophene bridged isoindigo derivatives were designed and successfully synthesized. H-1-C-13 HMBC, (HH)-H-1-H-1 nuclear Overhauser enhancement spectroscopy (NOESY) spectra, and H-1 nuclear Overhauser enhancement (NOE) experiments were employed to determine the configurations of the synthesized molecules, indicating they belong to stable Z,Z configurations. Organic field-effect transistors based on ITTI and IDTI through a solution processed method have good air stabilities and exhibit hole mobilities of 0.045 and 0.075 cm(2) V-1 s(-1) after high-temperature annealing in air, respectively.
引用
收藏
页码:22655 / 22662
页数:8
相关论文
共 33 条
[21]   Synthesis of Isoindigo-Based Oligothiophenes for Molecular Bulk Heterojunction Solar Cells [J].
Mei, Jianguo ;
Graham, Kenneth R. ;
Stalder, Romain ;
Reynolds, John R. .
ORGANIC LETTERS, 2010, 12 (04) :660-663
[22]  
Moragas M., 1998, J ORG CHEM, V63, P8689
[23]   PROTOTYPES FOR THE POLARONIC FERROMAGNET - SYNTHESIS AND CHARACTERIZATION OF HIGH-SPIN ORGANIC POLYMERS [J].
MURRAY, MM ;
KASZYNSKI, P ;
KAISAKI, DA ;
CHANG, WH ;
DOUGHERTY, DA .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1994, 116 (18) :8152-8161
[24]   Isoindigo-Based Donor-Acceptor Conjugated Polymers [J].
Stalder, Romain ;
Mei, Jianguo ;
Reynolds, John R. .
MACROMOLECULES, 2010, 43 (20) :8348-8352
[25]   A low band gap, solution processable oligothiophene with a diketopyrrolopyrrole core for use in organic solar cells [J].
Tamayo, Arnold B. ;
Walker, Bright ;
Nguyen, Thuc-Quyen .
JOURNAL OF PHYSICAL CHEMISTRY C, 2008, 112 (30) :11545-11551
[26]   A low band gap, solution processable oligothiophene with a dialkylated diketopyrrolopyrrole chromophore for use in bulk heterojunction solar cells [J].
Tamayo, Arnold Bernarte ;
Dang, Xuan-Dang ;
Walker, Bright ;
Seo, Junghwa ;
Kent, Tyler ;
Nguyen, Thuc-Quyen .
APPLIED PHYSICS LETTERS, 2009, 94 (10)
[27]   Ultrahigh Mobility in Polymer Field-Effect Transistors by Design [J].
Tsao, Hoi Nok ;
Cho, Don M. ;
Park, Insun ;
Hansen, Michael Ryan ;
Mavrinskiy, Alexey ;
Yoon, Do Y. ;
Graf, Robert ;
Pisula, Wojciech ;
Spiess, Hans Wolfgang ;
Muellen, Klaus .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2011, 133 (08) :2605-2612
[28]   An isoindigo-based low band gap polymer for efficient polymer solar cells with high photo-voltage [J].
Wang, Ergang ;
Ma, Zaifei ;
Zhang, Zhen ;
Henriksson, Patrik ;
Inganas, Olle ;
Zhang, Fengling ;
Andersson, Mats R. .
CHEMICAL COMMUNICATIONS, 2011, 47 (17) :4908-4910
[29]   Narrow-bandgap diketo-pyrrolo-pyrrole polymer solar cells: The effect of processing on the performance [J].
Wienk, Martijn M. ;
Turbiez, Mathieu ;
Gilot, Jan ;
Janssen, Rene A. J. .
ADVANCED MATERIALS, 2008, 20 (13) :2556-+
[30]   A practical large-scale preparation of 5'-bromospiro(cyclohexane-1,3'-[3H]indol)-2'(1H)-one [J].
Wilk, BK ;
Rubezhov, A ;
Helom, JL ;
Routel, LR ;
Potoski, JR .
ORGANIC PREPARATIONS AND PROCEDURES INTERNATIONAL, 2005, 37 (03) :283-285