Thiophene-fused bowl-shaped polycyclic aromatics with a dibenzo[a,g] corannulene core for organic field-effect transistors

被引：71

作者：

Lu, Ru-Qiang ^{[1
]}

Zhou, Yi-Nyu ^{[1
]}

Yan, Xiao-Yun ^{[1
]}

Shi, Ke ^{[2
]}

Zheng, Yu-Qing ^{[2
]}

Luo, Ming ^{[1
]}

Wang, Xin-Chang ^{[1
]}

Pei, Jian ^{[2
]}

Xia, Haiping ^{[1
]}

Zoppi, Laura ^{[3
]}

Baldridge, Kim K. ^{[3
]}

Siegel, Jay S. ^{[4
]}

Cao, Xiao-Yu ^{[1
]}

机构：

[1] Xiamen Univ, Coll Chem & Chem Engn, State Key Lab Phys Chem Solid Surfaces, Xiamen 361005, Peoples R China

[2] Peking Univ, Coll Chem & Mol Engn, Minist Educ, Key Lab Bioorgan Chem & Mol Engn,Beijing Natl Lab, Beijing 100871, Peoples R China

[3] Univ Zurich, Inst Organ Chem, CH-8057 Zurich, Switzerland

[4] Tianjin Univ, Sch Pharmaceut Sci & Technol, Tianjin 300072, Peoples R China

来源：

CHEMICAL COMMUNICATIONS | 2015年 / 51卷 / 09期

关键词：

OPTOELECTRONIC PROPERTIES; SCHOLL REACTION; CRYSTAL; HETEROARENES; ACCEPTOR; POLYMER; STRATEGY; DDQ;

D O I：

10.1039/c4cc08451a

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

For the first time, electron-rich thiophene units were fused into the skeleton of corannulene to extend pi-surfaces and tune arrangement in single crystals. Two isomeric butterfly-like thiophene-fused dibenzo[a, g]corannulenes (3 and 5) were synthesized. Isomer 3 showed p-type transport properties, with a hole mobility of 0.06 cm(2) V-1 s(-1).

引用

页码：1681 / 1684

页数：4

共 51 条

[1] Functionalized acenes and heteroacenes for organic electronics [J].

Anthony, John E. .

CHEMICAL REVIEWS, 2006, 106 (12) :5028-5048

[2] Oligoacenes: Theoretical prediction of open-shell singlet diradical ground states [J].

Bendikov, M ;

Duong, HM ;

Starkey, K ;

Houk, KN ;

Carter, EA ;

Wudl, F .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2004, 126 (24) :7416-7417

[3] Two-dimensional structural motif in thienoacene semiconductors: Synthesis, structure, and properties of tetrathienoanthracene isomers [J].

Brusso, Jaclyn L. ;

Hirst, Oliver D. ;

Dadvand, Afshin ;

Ganesan, Srinivasan ;

Cicoira, Fabio ;

Robertson, Craig M. ;

Oakley, Richard T. ;

Rosei, Federico ;

Perepichkat, Dmitrii F. .

CHEMISTRY OF MATERIALS, 2008, 20 (07) :2484-2494

[4] Kilogram-Scale Production of Corannulene [J].

Butterfield, Anna M. ;

Gilomen, Bruno ;

Siegel, Jay S. .

ORGANIC PROCESS RESEARCH & DEVELOPMENT, 2012, 16 (04) :664-676

[5] Iron(III) Chloride Promoted Cyclization: A Facile Approach to Polycyclic Aromatics for Functional Materials [J].

Cao, Yue ;

Wang, Xiao-Ye ;

Wang, Jie-Yu ;

Pei, Jian .

SYNLETT, 2014, 25 (03) :313-323

[6] 25th Anniversary Article: Key Points for High-Mobility Organic Field-Effect Transistors [J].

Dong, Huanli ;

Fu, Xiaolong ;

Liu, Jie ;

Wang, Zongrui ;

Hu, Wenping .

ADVANCED MATERIALS, 2013, 25 (43) :6158-6182

[7] CRYSTAL AND MOLECULAR-STRUCTURE OF CORANNULENE, C-20H-10 [J].

HANSON, JC ;

NORDMAN, CE .

ACTA CRYSTALLOGRAPHICA SECTION B-STRUCTURAL SCIENCE, 1976, 32 (APR15) :1147-1153

[8] Organic single-crystal light-emitting field-effect transistors [J].

Hotta, Shu ;

Yamao, Takeshi ;

Bisri, Satria Zulkarnaen ;

Takenobu, Taishi ;

Iwasa, Yoshihiro .

JOURNAL OF MATERIALS CHEMISTRY C, 2014, 2 (06) :965-980

[9] Polyacene and cyclacene geometries and electronic structures: Bond equalization, vanishing band gaps, and triplet ground states contrast with polyacetylene [J].

Houk, KN ;

Lee, PS ;

Nendel, M .

JOURNAL OF ORGANIC CHEMISTRY, 2001, 66 (16) :5517-5521

[10] Heteroarenes as high performance organic semiconductors [J].

Jiang, Wei ;

Li, Yan ;

Wang, Zhaohui .

CHEMICAL SOCIETY REVIEWS, 2013, 42 (14) :6113-6127

← 1 2 3 4 5 6 →