From Saddle-Shaped to Planar Cyclic Oligothienoacenes: Stepped-Cyclization and Their Applications in OFETs

被引：19
作者：
Li, Lu [1 ,3 ]
Zhao, Shuai [1 ]
Li, Bingbing [1 ]
Xu, Li [2 ]
Li, Chunli [1 ]
Shi, Jianwu [1 ]
Wang, Hua [1 ]
机构：
[1] Henan Univ, Engn Res Ctr Nanomat, Kaifeng 475004, Peoples R China
[2] Henan Univ, Coll Chem & Chem Engn, Kaifeng 475004, Peoples R China
[3] Shangqiu Normal Univ, Sch Chem & Chem Engn, Shangqiu 476000, Peoples R China
来源：
ORGANIC LETTERS | 2018年 / 20卷 / 08期
关键词：
FIELD-EFFECT TRANSISTORS; THIN-FILM TRANSISTORS; CROSS-CONJUGATED OLIGOTHIOPHENES; DENSITY-FUNCTIONAL THEORY; CARBON-SULFUR; ASYMMETRIC-SYNTHESIS; ANTIAROMATIC CYCLOOCTATETRAENES; NONCOVALENT INTERACTIONS; ORGANIC SEMICONDUCTORS; EXCITATION-ENERGIES;
D O I：
10.1021/acs.orglett.8b00482
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
A series of cyclic oligothienoacenes (1, 3, and 4) have been successfully synthesized through a stepped-cyclization synthetic strategy from tetra[3,4-thienylene] (2). Single-crystal X-ray diffraction analysis combined with theoretical calculations elucidated that the molecular configuration transforms from the saddle shape of 2 to the quasi-saddle shape (3b, 3c), then to the quasi-helical shape (4b), and at last to the quasi-plane shape (1, 3a, 4a). Organic field-effect transistors (OFETs) based on 1, 3a, and 4a were fabricated. The field-effect mobilities of 7.5 X 10(-4), 2.6 X 10(-3), and 6.8 X 10(-4) cm(2) V-1 s(-1) were obtained for 1, 3a, and 4a, respectively. Compounds 3a and 4a can act as air-stable p-type organic semiconductors, while 1 is sensitive to the air.
引用
收藏
页码：2181 / 2185
页数：5
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