Antiaromatic planar cyclooctatetraene: a strategy for developing ambipolar semiconductors for field effect transistors

被引:87
作者
Nishinaga, Tohru [1 ]
Ohmae, Takeshi [1 ]
Aita, Kazunari [1 ]
Takase, Masayoshi [1 ]
Iyoda, Masahiko [1 ]
Arai, Tatsuya [2 ]
Kunugi, Yoshihito [2 ]
机构
[1] Tokyo Metropolitan Univ, Grad Sch Sci & Engn, Dept Chem, Hachioji, Tokyo 1920397, Japan
[2] Tokai Univ, Dept Appl Chem, Hiratsuka, Kanagawa 2591292, Japan
关键词
INDEPENDENT CHEMICAL-SHIFTS; THIN-FILM TRANSISTORS; AROMATICITY; DERIVATIVES; ELECTRON; UNITS; CORE;
D O I
10.1039/c3cc41764f
中图分类号
O6 [化学];
学科分类号
0703 ;
摘要
Tetra[2,3-thienylene] planarised by sulphur bridges and radially pi-extended with (triisopropylsilyl)ethynyl groups had a narrow HOMO-LUMO gap due to the antiaromatic cyclooctatetraene core, and its single crystal FET device exhibited ambipolar characteristics with hole and electron mobilities of up to 0.40 and 0.18 cm(2) V-1 s(-1), respectively.
引用
收藏
页码:5354 / 5356
页数:3
相关论文
共 40 条
[1]   Electron-Donating Tetrathienyl-Substituted Borole [J].
Araki, Takafumi ;
Fukazawa, Aiko ;
Yamaguchi, Shigehiro .
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2012, 51 (22) :5484-5487
[2]   Recent advances in high mobility donor-acceptor semiconducting polymers [J].
Biniek, Laure ;
Schroeder, Bob C. ;
Nielsen, Christian B. ;
McCulloch, Iain .
JOURNAL OF MATERIALS CHEMISTRY, 2012, 22 (30) :14803-14813
[3]   Recent developments in the chemistry of antiaromatic boroles [J].
Braunschweig, Holger ;
Kupfer, Thomas .
CHEMICAL COMMUNICATIONS, 2011, 47 (39) :10903-10914
[4]   ANTIAROMATICITY [J].
BRESLOW, R .
ACCOUNTS OF CHEMICAL RESEARCH, 1973, 6 (12) :393-398
[5]   6,12-Diarylindeno[1,2-b]fluorenes: Syntheses, Photophysics, and Ambipolar OFETs [J].
Chase, Daniel T. ;
Fix, Aaron G. ;
Kang, Seok Ju ;
Rose, Bradley D. ;
Weber, Christopher D. ;
Zhong, Yu ;
Zakharov, Lev N. ;
Lonergan, Mark C. ;
Nuckolls, Colin ;
Haley, Michael M. .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2012, 134 (25) :10349-10352
[6]   Indeno[1,2-b]fluorenes: Fully Conjugated Antiaromatic Analogues of Acenes [J].
Chase, Daniel T. ;
Rose, Bradley D. ;
McClintock, Sean P. ;
Zakharov, Lev N. ;
Haley, Michael M. .
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2011, 50 (05) :1127-1130
[7]   Nucleus-independent chemical shifts (NICS) as an aromaticity criterion [J].
Chen, ZF ;
Wannere, CS ;
Corminboeuf, C ;
Puchta, R ;
Schleyer, PV .
CHEMICAL REVIEWS, 2005, 105 (10) :3842-3888
[8]  
Gleiter R., 2012, AROMATICITY OTHER CO, P1
[9]   CASSCF CALCULATIONS FIND THAT A D(8H) GEOMETRY IS THE TRANSITION-STATE FOR DOUBLE-BOND SHIFTING IN CYCLOOCTATETRAENE [J].
HROVAT, DA ;
BORDEN, WT .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1992, 114 (14) :5879-5881
[10]   Thiophene-Fused Ladder Boroles with High Antiaromaticity [J].
Iida, Azusa ;
Yamaguchi, Shigehiro .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2011, 133 (18) :6952-6955