Hexathienocoronenes: Synthesis and Self-Organization

被引:86
作者
Chen, Long [1 ]
Puniredd, Sreenivasa R. [1 ]
Tan, Yuan-Zhi [1 ]
Baumgarten, Martin [1 ]
Zschieschang, Ute [2 ]
Enkelmann, Volker [1 ]
Pisula, Wojciech [1 ]
Feng, Xinliang [1 ]
Klauk, Hagen [2 ]
Muellen, Klaus [1 ]
机构
[1] Max Planck Inst Polymer Res, D-55128 Mainz, Germany
[2] Max Planck Inst Solid State Res, D-70569 Stuttgart, Germany
关键词
DISCOTIC LIQUID-CRYSTALS; FIELD-EFFECT TRANSISTORS; ISOMERICALLY PURE; HIGH-PERFORMANCE; ORGANIC TRANSISTORS; EFFECT MOBILITY; MOLECULE; EFFICIENCY; AMBIPOLAR; KETONES;
D O I
10.1021/ja3082395
中图分类号
O6 [化学];
学科分类号
0703 ;
摘要
Here we report hexathienocoronenes (HTCs), fully thiophene-annelated coronenes in which six double bonds in the periphery are thieno-fused. The derivatives tetrasubstituted with hexyl and dodecyl chains show a phase formation that strongly depends on the chain length. HTCs are remarkably stronger donors than the known thiophene-annelated coronenes but do not readily assemble into well-ordered films when deposited from the vapor phase. Thus, thin-film transistors fabricated by vacuum deposition have only modest field-effect mobilities of 0.002 cm(2) V-1 s(-1).
引用
收藏
页码:17869 / 17872
页数:4
相关论文
共 62 条
[51]   Synthesis of Isomerically Pure anti-Anthradithiophene Derivatives [J].
Tylleman, Benoit ;
Vande Velde, Christophe M. L. ;
Balandier, Jean-Yves ;
Stas, Sara ;
Sergeyev, Sergey ;
Geerts, Yves Henri .
ORGANIC LETTERS, 2011, 13 (19) :5208-5211
[52]   Self-assembly of positively charged discotic PAHs:: From nanofibers to nanotubes [J].
Wu, Dongqing ;
Zhi, Linjie ;
Bodwell, Graham J. ;
Cui, Guanglei ;
Tsao, Nok ;
Muellen, Klaus .
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2007, 46 (28) :5417-5420
[53]   Oxygen- and Sulfur-Containing Positively Charged Polycyclic Aromatic Hydrocarbons [J].
Wu, Dongqing ;
Pisula, Wojciech ;
Haberecht, Monika C. ;
Feng, Xinliang ;
Muellen, Klaus .
ORGANIC LETTERS, 2009, 11 (24) :5686-5689
[54]   Transferring self-assembled, nanoscale cables into electrical devices [J].
Xiao, Shengxiong ;
Tang, Jinyao ;
Beetz, Tobias ;
Guo, Xuefeng ;
Tremblay, Noah ;
Siegrist, Theo ;
Zhu, Yimei ;
Steigerwald, Michael ;
Nuckolls, Colin .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2006, 128 (33) :10700-10701
[55]   Molecular wires from contorted aromatic compounds [J].
Xiao, SX ;
Myers, M ;
Miao, Q ;
Sanaur, S ;
Pang, KL ;
Steigerwald, ML ;
Nuckolls, C .
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2005, 44 (45) :7390-7394
[56]   Facile synthesis of highly π-extended heteroarenes, dinaphtho[2,3-b:2′,3′-f]chalcogenopheno[3,2-b]chalcogenophenes, and their application to field-effect transistors [J].
Yamamoto, Tatsuya ;
Takimiya, Kazuo .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2007, 129 (08) :2224-+
[57]   Thin film structure of tetraceno[2,3-b]thiophene characterized by grazing incidence X-ray scattering and near-edge X-ray absorption fine structure analysis [J].
Yuan, Quan ;
Mannsfeld, Stefan C. B. ;
Tang, Ming L. ;
Toney, Michael F. ;
Luening, Jan ;
Bao, Zhenan .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2008, 130 (11) :3502-3508
[58]   Synthesis, Self-Assembly, and Charge Transporting Property of Contorted Tetrabenzocoronenes [J].
Zhang, Xiaojie ;
Jiang, Xiaoxia ;
Zhang, Kai ;
Mao, Lu ;
Luo, Jing ;
Chi, Chunyan ;
Chan, Hardy Sze On ;
Wu, Jishan .
JOURNAL OF ORGANIC CHEMISTRY, 2010, 75 (23) :8069-8077
[59]   CONTROLLING INTERMOLECULAR INTERACTIONS BETWEEN METALLOMESOGENS - SIDE-CHAIN EFFECTS IN DISCOTIC COPPER, PALLADIUM, AND VANADYL BIS(BETA-DIKETONATES) [J].
ZHENG, HX ;
LAI, CK ;
SWAGER, TM .
CHEMISTRY OF MATERIALS, 1995, 7 (11) :2067-2077
[60]   Saddle Shaped Hexaaryl[a,c,fg,j,l,op]tetracenes from 4,5,9,10-Tetrafunctionalized Pyrenes [J].
Zoephel, Lukas ;
Enkelmann, Volker ;
Rieger, Ralph ;
Muellen, Klaus .
ORGANIC LETTERS, 2011, 13 (17) :4506-4509