Synthesis and properties of thienopyrrole based heteroacenes - indolodibenzothienopyrrole and dicarbazolodithienopyrrole

被引：10

作者：

Balaji, Ganapathy ^{[1
]}

Della Pelle, Andrea M. ^{[1
]}

Popere, Bhooshan C. ^{[1
]}

Chandrasekaran, A. ^{[1
]}

Thayumanavan, S. ^{[1
]}

机构：

[1] Univ Massachusetts, Dept Chem, Amherst, MA 01003 USA

来源：

ORGANIC & BIOMOLECULAR CHEMISTRY | 2012年 / 10卷 / 17期

关键词：

FIELD-EFFECT TRANSISTORS; ORGANIC SEMICONDUCTORS; TRANSPORT-PROPERTIES; CHARGE-TRANSPORT; HIGH-PERFORMANCE; DERIVATIVES; THIOPHENE; ACENES; ROUTE;

D O I：

10.1039/c2ob25087j

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

We report the syntheses and properties of thienopyrrole based unsymmetrical and extended heteroacenes, which are isoelectronic with heptacene (30 pi) and nonacene (38 pi), respectively. Optical and electrochemical properties of these seven and nine rings fused systems are studied. The optoelectronic properties of the syn and anti-isomers of the unsymmetrical heteroacenes are also compared. The influence of the position of the heteroatoms in the fused corona, upon the optical and electrochemical properties, is rationalized based on the contributions from the benzenoid vs. quinonoid-type structures of these molecules.

引用

页码：3455 / 3462

页数：8

共 49 条

[21]

Frisch M., 2004, GAUSSIAN 03 REVISION, DOI DOI 10.1016/J.MOLSTRUC.2017.03.014

[22] Pyrazine-containing acene-type molecular ribbons with up to 16 rectilinearly arranged fused aromatic rings [J].

Gao, Baoxiang ;

Wang, Ming ;

Cheng, Yanxiang ;

Wang, Lixiang ;

Jing, Xiabin ;

Wang, Fosong .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2008, 130 (26) :8297-8306

[23] High-performance field-effect transistor based on dibenzo[d,d′]thieno[3,2-b;4,5-b′]dithiophene, an easily synthesized semiconductor with high ionization potential [J].

Gao, Jianhua ;

Li, Rongjin ;

Li, Liqiang ;

Meng, Qing ;

Jiang, Hui ;

Li, Hongxiang ;

Hu, Wenping .

ADVANCED MATERIALS, 2007, 19 (19) :3008-+

[24] Dithieno[2,3-d;2′,3′-d′]benzo[1,2-b;4,5-b′]dithiophene (DTBDT) as Semiconductor for High-Performance, Solution-Processed Organic Field-Effect Transistors [J].

Gao, Peng ;

Beckmann, Dirk ;

Tsao, Hoi Nok ;

Feng, Xinliang ;

Enkelmann, Volker ;

Baumgarten, Martin ;

Pisula, Wojciech ;

Muellen, Klaus .

ADVANCED MATERIALS, 2009, 21 (02) :213-+

[25]

Gebhardt V, 1999, ADV MATER, V11, P119, DOI 10.1002/(SICI)1521-4095(199902)11:2<119::AID-ADMA119>3.0.CO

[26]

2-7

[27]

Hemi Q., 2010, CURR ORG CHEM, V14, P2070

[28]

Hush N. S., 1967, PROG INORG CHEM, V10, P247

[29] Design, Synthesis, and Characterization of a Persistent Nonacene Derivative [J].

Kaur, Irvinder ;

Jazdzyk, Mikael ;

Stein, Nathan N. ;

Prusevich, Polina ;

Miller, Glen P. .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2010, 132 (04) :1261-+

[30] Synthesis, structures, and properties of unsymmetrical heteroacenes containing both pyrrole and furan rings [J].

Kawaguchi, Keiko ;

Nakano, Koji ;

Nozaki, Kyoko .

ORGANIC LETTERS, 2008, 10 (06) :1199-1202

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