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

被引:777
作者
Yamamoto, Tatsuya
Takimiya, Kazuo [1 ]
机构
[1] Hiroshima Univ, Grad Sch Engn, Dept Appl Chem, Higashihiroshima 7398527, Japan
[2] Hiroshima Univ, Inst Adv Mat Res, Higashihiroshima 7398530, Japan
关键词
D O I
10.1021/ja068429z
中图分类号
O6 [化学];
学科分类号
0703 ;
摘要
A facile three-step synthetic procedure for highly pi-extended heteroarenes, dinaphtho[2,3-b:2',3'-f]thieno[3,2-b]thiophene (DNTT) and dinaphtho[2,3-b:2',3'-f]selenopheno[3,2-b]selenophene (DNSS), was established. Solution UV-vis spectra and electrochemistry indicated that they have relatively low-lying HOMO levels and large HOMO-LUMO energy gaps. OFET devices fabricated with evaporated thin-films of DNTT and DNSS showed excellent FET characteristics in air, and the highest field-effect mobility of DNTT- and DNSS-based OFETs is 2.9 and 1.9 cm(2) V-1 s(-1), respectively.
引用
收藏
页码:2224 / +
页数:3
相关论文
共 15 条
[1]   Circuit resonance energy: A key quantity that links energetic and magnetic criteria of aromaticity [J].
Aihara, J .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2006, 128 (09) :2873-2879
[2]   CHAIN-LENGTH DEPENDENCE OF ELECTRONIC AND ELECTROCHEMICAL PROPERTIES OF CONJUGATED SYSTEMS - POLYACETYLENE, POLYPHENYLENE, POLYTHIOPHENE, AND POLYPYRROLE [J].
BREDAS, JL ;
SILBEY, R ;
BOUDREAUX, DS ;
CHANCE, RR .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1983, 105 (22) :6555-6559
[3]  
Clar E., 1972, The Aromatic Sextet
[4]   ORTHO METALATION DIRECTED BY ALPHA-AMINO ALKOXIDES [J].
COMINS, DL ;
BROWN, JD .
JOURNAL OF ORGANIC CHEMISTRY, 1984, 49 (06) :1078-1083
[5]   Thin-film transistors based on well-ordered thermally evaporated naphthacene films [J].
Gundlach, DJ ;
Nichols, JA ;
Zhou, L ;
Jackson, TN .
APPLIED PHYSICS LETTERS, 2002, 80 (16) :2925-2927
[6]   The special issue on organic electronics [J].
Jenekhe, SA .
CHEMISTRY OF MATERIALS, 2004, 16 (23) :4381-4382
[7]   High-performance OTFTs using surface-modified alumina dielectrics [J].
Kelley, TW ;
Boardman, LD ;
Dunbar, TD ;
Muyres, DV ;
Pellerite, MJ ;
Smith, TYP .
JOURNAL OF PHYSICAL CHEMISTRY B, 2003, 107 (24) :5877-5881
[8]   Stacked pentacene layer organic thin-film transistors with improved characteristics [J].
Lin, YY ;
Gundlach, DJ ;
Nelson, SF ;
Jackson, TN .
IEEE ELECTRON DEVICE LETTERS, 1997, 18 (12) :606-608
[9]   CARBONYL-COUPLING REACTIONS USING LOW-VALENT TITANIUM [J].
MCMURRY, JE .
CHEMICAL REVIEWS, 1989, 89 (07) :1513-1524
[10]   REDUCTIVE COUPLING OF CARBONYL-COMPOUNDS TO PINACOLS AND OLEFINS BY USING TICL4 AND ZN [J].
MUKAIYAMA, T ;
SATO, T ;
HANNA, J .
CHEMISTRY LETTERS, 1973, (10) :1041-1044