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
[1]   Dimers of Anthrathiophene and Anthradithiophene Derivatives: Synthesis and Characterization [J].
Balandier, Jean-Yves ;
Quist, Florence ;
Stas, Sara ;
Tylleman, Benoit ;
Ragoen, Celine ;
Mayence, Arnaud ;
Bouzakraoui, Said ;
Cornil, Jerome ;
Geerts, Yves Henri .
ORGANIC LETTERS, 2011, 13 (04) :548-551
[2]   Tetrathiafulvalenes, oligoacenenes, and their buckminsterfullerene derivatives: The brick and mortar of organic electronics [J].
Bendikov, M ;
Wudl, F ;
Perepichka, DF .
CHEMICAL REVIEWS, 2004, 104 (11) :4891-4945
[3]   N-Heteroacenes [J].
Bunz, Uwe H. F. .
CHEMISTRY-A EUROPEAN JOURNAL, 2009, 15 (28) :6780-6789
[4]   Sulflower: A new form of carbon sulfide [J].
Chernichenko, Konstantin Yu. ;
Sumerin, Viktor V. ;
Shpanchenko, Roman V. ;
Balenkova, Elizabeth S. ;
Nenajdenko, Valentine G. .
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2006, 45 (44) :7367-7370
[5]   Shape-shifting in contorted dibenzotetrathienocoronenes [J].
Chiu, Chien-Yang ;
Kim, Bumjung ;
Gorodetsky, Alon A. ;
Sattler, Wesley ;
Wei, Sujun ;
Sattler, Aaron ;
Steigerwald, Michael ;
Nuckolls, Colin .
CHEMICAL SCIENCE, 2011, 2 (08) :1480-1486
[6]  
Cornil J, 2001, ADV MATER, V13, P1053, DOI 10.1002/1521-4095(200107)13:14<1053::AID-ADMA1053>3.0.CO
[7]  
2-7
[8]   DISC-LIKE MESOGEN POLYMORPHISM [J].
DESTRADE, C ;
FOUCHER, P ;
GASPAROUX, H ;
TINH, NH ;
LEVELUT, AM ;
MALTHETE, J .
MOLECULAR CRYSTALS AND LIQUID CRYSTALS, 1984, 106 (1-2) :121-146
[9]   Elaboration of diaryl ketones into naphthalenes fused on two or four sides: A naphthoannulation procedure [J].
Donovan, PM ;
Scott, LT .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2004, 126 (10) :3108-3112
[10]   Heterosuperbenzenes: A new family of nitrogen-functionalized, graphitic molecules [J].
Draper, SM ;
Gregg, DJ ;
Madathil, R .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2002, 124 (14) :3486-3487