Tetracene Dicarboxylic Imide and Its Disulfide: Synthesis of Ambipolar Organic Semiconductors for Organic Photovoltaic Cells

被引：42

作者：

Okamoto, Toshihiro ^{[2
]}

Suzuki, Tsuyoshi ^{[2
]}

Tanaka, Hideyuki ^{[2
]}

Hashizume, Daisuke ^{[1
]}

Matsuo, Yutaka ^{[2
]}

机构：

[1] RIKEN, Adv Technol Support Div, Wako, Saitama 3510198, Japan

[2] Univ Tokyo, Dept Chem, Bunkyo Ku, Tokyo 1130033, Japan

来源：

CHEMISTRY-AN ASIAN JOURNAL | 2012年 / 7卷 / 01期

基金：

日本科学技术振兴机构;

关键词：

ambipolar compounds; disulfides; organic photovoltaic cells; semiconductors; tetracene; THIN-FILM TRANSISTORS; FIELD-EFFECT TRANSISTORS; HIGH-ELECTRON-MOBILITY; HIGH-PERFORMANCE; COMPLEMENTARY CIRCUITS; DIIMIDE DERIVATIVES; TRANSPORT; ACENES; PENTACENE; STABILITY;

D O I：

10.1002/asia.201100590

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

We have designed and synthesized a new donor/acceptor-type tetracene derivative by the introduction of dicarboxylic imide and disulfide groups as electron-withdrawing and -donating units, respectively. The prepared compounds, tetracene dicarboxylic imide (TI) and its disulfide (TIDS) have high chemical and electrochemical stability as well as long-wavelength absorptions of up to 886 nm in the thin films. The crystal packing structure of TIDS molecules features face-to-face p-stacking, derived from dipoledipole interactions. Notably, TIDS exhibited ambipolar properties of both electron-donating and -accepting natures in pn and pin heterojunction organic thin-film photovoltaic devices. Accordingly, TI and TIDS are expected to be promising compounds for designing new organic semiconductors.

引用

页码：105 / 111

页数：7

共 44 条

[41] Ambipolar Hexa-peri-hexabenzocoronene-Fullerene Hybrid Materials [J].

Wong, Wallace W. H. ;

Vak, Doojin ;

Singh, Th. Birendra ;

Ren, Shijie ;

Yan, Chao ;

Jones, David J. ;

Liaw, Irving I. ;

Lamb, Robert N. ;

Holmes, Andrew B. .

ORGANIC LETTERS, 2010, 12 (21) :5000-5003

[42] High-performance solution-deposited n-channel organic transistors and their complementary circuits [J].

Yoo, Byungwook ;

Jones, Brooks A. ;

Basu, Debarshi ;

Fine, Daniel ;

Jung, Taeho ;

Mohapatra, Siddharth ;

Facchetti, Antonio ;

Dimmler, Klaus ;

Wasielewski, Michael R. ;

Marks, Tobin J. ;

Dodabalapur, Ananth .

ADVANCED MATERIALS, 2007, 19 (22) :4028-+

[43] Electron and ambipolar transport in organic field-effect transistors [J].

Zaumseil, Jana ;

Sirringhaus, Henning .

CHEMICAL REVIEWS, 2007, 107 (04) :1296-1323

[44] Synthesis and structure of fused α-oligothiophenes with up to seven rings [J].

Zhang, XN ;

Côté, AP ;

Matzger, AJ .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2005, 127 (30) :10502-10503

← 1 2 3 4 5 →