Synthesis and Characterization of New Thieno[3,2-b]thiophene Derivatives

被引：15

作者：

Ahmed, Moawia O. ^{[1
]}

Pisula, Wojciech ^{[2
]}

Mhaisalkar, Subodh G. ^{[3
]}

机构：

[1] Taibah Univ, Dept Chem, Fac Sci, Medina Munawarah 41477, Saudi Arabia

[2] Max Planck Inst Polymer Res, D-55128 Mainz, Germany

[3] Nanyang Technol Univ, Sch Mat Sci & Engn, Singapore 639798, Singapore

来源：

MOLECULES | 2012年 / 17卷 / 10期

关键词：

Thieno[3,2-b]thiophene; 2,5-dibromothieno[3,2-b]thiophene; 4-dodecyl-phenylboronic acid; 4-(trifluoromethyl)phenylboronic acid; SEMICONDUCTORS; PHENYLENE; EMISSION;

D O I：

10.3390/molecules171012163

中图分类号：

Q5 [生物化学]; Q7 [分子生物学];

学科分类号：

071010 ; 081704 ;

摘要：

Three derivatives of thieno[3,2-b]thiophene end-capped with phenyl units have been synthesized and characterized by MALDI TOF mass spectroscopy, elemental analysis, UV-vis absorption spectroscopy and thermogravimetric analysis (TGA). All compounds were prepared using Pd-catalyzed Stille or Suzuki coupling reactions. Optical measurements and thermal analysis revealed that these compounds are promising candidates for p-type organic semiconductor applications.

引用

页码：12163 / 12171

页数：9

共 21 条

[1] Thieno[3,2-b]thiophene oligomers and their applications as p-type organic semiconductors [J].

Ahmed, Moawia O. ;

Wang, Chunmei ;

Keg, Peisi ;

Pisula, Wojciech ;

Lam, Yeng-Meng ;

Ong, Beng S. ;

Ng, Siu-Choon ;

Chen, Zhi-Kuan ;

Mhaisalkar, Subodh G. .

JOURNAL OF MATERIALS CHEMISTRY, 2009, 19 (21) :3449-3456

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

Anthony, John E. .

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

[3]

Frisch M.J., 1998, GAUSSIAN 98

[4] Thienothiophenes .2. Synthesis, metallation and bromine->lithium exchange reactions of thieno[3,2-b]thiophene and its polybromo derivatives [J].

Fuller, LS ;

Iddon, B ;

Smith, KA .

JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 1997, (22) :3465-3470

[5] An alignable fluorene thienothiophene copolymer with deep-blue electroluminescent emission at 410 nm [J].

Gather, Malte C. ;

Heeney, Martin ;

Zhang, Weimin ;

Whitehead, Katherine S. ;

Bradley, Donal D. C. ;

McCulloch, Iain ;

Campbell, Alasdair J. .

CHEMICAL COMMUNICATIONS, 2008, (09) :1079-1081

[6] Alkylsubstituted Thienothiophene Semiconducting Materials: Structure-Property Relationships [J].

He, Mingqian ;

Li, Jianfeng ;

Sorensen, Michael L. ;

Zhang, Feixia ;

Hancock, Robert R. ;

Fong, Hon Hang ;

Pozdin, Vladimir A. ;

Smilgies, Detlef-M. ;

Malliaras, George G. .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2009, 131 (33) :11930-11938

[7] Stable polythiophene semiconductors incorporating thieno[2,3-b]thiophene [J].

Heeney, M ;

Bailey, C ;

Genevicius, K ;

Shkunov, M ;

Sparrowe, D ;

Tierney, S ;

McCulloch, I .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2005, 127 (04) :1078-1079

[8] Thiophene-phenylene and thiophene-thiazole oligomeric semiconductors with high field-effect transistor on/off ratios [J].

Hong, XM ;

Katz, HE ;

Lovinger, AJ ;

Wang, BC ;

Raghavachari, K .

CHEMISTRY OF MATERIALS, 2001, 13 (12) :4686-4691

[9] Synthesis and studies on 2-hexylthieno[3,2-b]thiophene end-capped oligomers for OTFTs [J].

Kim, Hyung-Sun ;

Kim, Yun-Hi ;

Kim, Tae-Hoon ;

Noh, Yong-Young ;

Pyo, Seungmoon ;

Yi, Mi Hye ;

Kim, Dong-You ;

Kwon, Soon-Ki .

CHEMISTRY OF MATERIALS, 2007, 19 (14) :3561-3567

[10] Solution-processable field-effect transistor using a fluorene- and selenophene-based copolymer as an active layer [J].

Kim, Young Mi ;

Lim, Eunhee ;

Kang, In-Nam ;

Jung, Byung-Jun ;

Lee, Jaemin ;

Koo, Bon Won ;

Do, Lee-Mi ;

Shim, Hong-Ku .

MACROMOLECULES, 2006, 39 (12) :4081-4085

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