Synthesis and Structural Analysis of Thiophene-Pyrrole-Based S,N-Heteroacenes

被引：61

作者：

Wetzel, Christoph ^{[1
]}

Mishra, Amaresh ^{[1
]}

Mena-Osteritz, Elena ^{[1
]}

Liess, Andreas ^{[2
,3
]}

Stolte, Matthias ^{[2
,3
]}

Wuerthner, Frank ^{[2
,3
]}

Baeuerle, Peter ^{[1
]}

机构：

[1] Univ Ulm, Inst Organ Chem & Neue Mat 2, D-89081 Ulm, Germany

[2] Univ Wurzburg, Inst Organ Chem, D-97074 Wurzburg, Germany

[3] Univ Wurzburg, Ctr Nanosyst Chem, D-97074 Wurzburg, Germany

来源：

ORGANIC LETTERS | 2014年 / 16卷 / 02期

关键词：

ORGANIC SEMICONDUCTORS; ACENES; HETEROACENES;

D O I：

10.1021/ol403153z

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Fused S,N-heterohexacene 4 was synthesized by applying Pd-catalyzed tandem Buchwald-Hartwig coupling and further functionalized to corresponding acceptor-capped derivatives 5 and 6 showing bond length equalization in the pi-conjugated backbone and intense optical transitions. Organic thin film transistors (OTFTs) based on a vacuum-deposited film of 6 exhibit p-channel charge-carrier mobilities as high as 0.021 cm(2)V(-1) s(-1) and current on/off ratios of 10(5).

引用

页码：362 / 365

页数：4

共 24 条

[11] Synthesis of Nitrogen-Bridged Terthiophenes by Tandem Buchwald-Hartwig Coupling and Their Properties [J].

Mitsudo, Koichi ;

Shimohara, Shuichi ;

Mizoguchi, Jun ;

Mandai, Hiroki ;

Suga, Seiji .

ORGANIC LETTERS, 2012, 14 (11) :2702-2705

[12] A simple and efficient route to N-functionalized dithieno[3,2-b:2′,3′-d]pyrroles:: Fused-ring building blocks for new conjugated polymeric systems [J].

Ogawa, K ;

Rasmussen, SC .

JOURNAL OF ORGANIC CHEMISTRY, 2003, 68 (07) :2921-2928

[13] Dithieno[3,2-b:2′,3′-d]pyrrole-based materials: Synthesis and application to organic electronics [J].

Rasmussen, Seth C. ;

Evenson, Sean J. .

PROGRESS IN POLYMER SCIENCE, 2013, 38 (12) :1773-1804

[14] Comparative Study of Microscopic Charge Dynamics in Crystalline Acceptor-Substituted Oligothiophenes [J].

Schrader, Manuel ;

Fitzner, Roland ;

Hein, Moritz ;

Elschner, Chris ;

Baumeier, Bjoern ;

Leo, Karl ;

Riede, Moritz ;

Baeuerle, Peter ;

Andrienko, Denis .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2012, 134 (13) :6052-6056

[15]

Skabara P.J, 2009, HDB THIOPHENE BASED, P219

[16] Thienoacene-Based Organic Semiconductors [J].

Takimiya, Kazuo ;

Shinamura, Shoji ;

Osaka, Itaru ;

Miyazaki, Eigo .

ADVANCED MATERIALS, 2011, 23 (38) :4347-4370

[17]

Tolbert L. M., 1991, J AM CHEM SOC, V113, P3253

[18]

Watanabe M, 2012, NAT CHEM, V4, P574, DOI [10.1038/NCHEM.1381, 10.1038/nchem.1381]

[19] Electronic and crystal engineering of acenes for solution-processible self-assembling organic semiconductors [J].

Würthner, F ;

Schmidt, R .

CHEMPHYSCHEM, 2006, 7 (04) :793-797

[20] Merocyanine dyes in the cyanine limit:: A new class of chromophores for photorefractive materials [J].

Würthner, F ;

Wortmann, R ;

Matschiner, R ;

Lukaszuk, K ;

Meerholz, K ;

DeNardin, Y ;

Bittner, R ;

Bräuchle, C ;

Sens, R .

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 1997, 36 (24) :2765-2768

← 1 2 3 →