Influence of the heteroatom on the optoelectronic properties and transistor performance of soluble thiophene-, selenophene- and tellurophene-vinylene copolymers

被引:84
作者
Al-Hashimi, Mohammed [1 ,2 ,3 ]
Han, Yang [1 ,2 ,4 ]
Smith, Jeremy [2 ,4 ]
Bazzi, Hassan S. [3 ]
Alqaradawi, Siham Yousuf A. [5 ]
Watkins, Scott E. [6 ]
Anthopoulos, Thomas D. [2 ,4 ]
Heeney, Martin [1 ,2 ]
机构
[1] Univ London Imperial Coll Sci Technol & Med, Dept Chem, Exhibit Rd, London SW7 2AZ, England
[2] Univ London Imperial Coll Sci Technol & Med, Ctr Plast Elect, Exhibit Rd, London SW7 2AZ, England
[3] Texas A&M Univ Qatar, Dept Chem, POB 23874, Doha, Qatar
[4] Univ London Imperial Coll Sci Technol & Med, Dept Phys, Exhibit Rd, London SW7 2AZ, England
[5] Qatar Univ, Dept Chem & Earth Sci, POB 110003, Doha, Qatar
[6] CSIRO, Mol & Hlth Technol, Clayton, Vic 3169, Australia
基金
英国工程与自然科学研究理事会;
关键词
CONJUGATED POLYMER; SEMICONDUCTORS; REGIOREGULARITY;
D O I
10.1039/c5sc03501e
中图分类号
O6 [化学];
学科分类号
0703 ;
摘要
We report the first soluble poly(3-dodecyl tellurophenylene-vinylene) polymer (P3TeV) by Stille copolymerization and compare its properties to the analogous thiophene and selenophene containing polymers. The optical band gap of the polymers is shown to systematically decrease as the size of the heteroatom is increased, mainly as a result of a stabilization of the LUMO energy, resulting in a small band gap of 1.4 eV for P3TeV. Field effect transistors measurements in variety of architectures demonstrate that the selenophene polymer exhibits the highest mobility, highlighting that increasing the size of the heteroatom is not always beneficial for charge transport.
引用
收藏
页码:1093 / 1099
页数:7
相关论文
共 39 条
[1]   Synthesis, Characterization, and Field Effect Transistor Properties of Regioregular Poly(3-alkyl-2,5-selenylenevinylene) [J].
Al-Hashimi, Mohammed ;
Baklar, Mohammed A. ;
Colleaux, Florian ;
Watkins, Scott E. ;
Anthopoulos, Thomas D. ;
Stingelin, Natalie ;
Heeney, Martin .
MACROMOLECULES, 2011, 44 (13) :5194-5199
[2]   Chalcogenophene Comonomer Comparison in Small Band Gap Diketopyrrolopyrrole-Based Conjugated Polymers for High-Performing Field-Effect Transistors and Organic Solar Cells [J].
Ashraf, Raja Shahid ;
Meager, Iain ;
Nikolka, Mark ;
Kirkus, Mindaugas ;
Planells, Miquel ;
Schroeder, Bob C. ;
Holliday, Sarah ;
Hurhangee, Michael ;
Nielsen, Christian B. ;
Sirringhaus, Henning ;
McCulloch, Iain .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2015, 137 (03) :1314-1321
[3]   Aromaticity as a cornerstone of heterocyclic chemistry [J].
Balaban, AT ;
Oniciu, DC ;
Katritzky, AR .
CHEMICAL REVIEWS, 2004, 104 (05) :2777-2812
[4]   Semiconducting Polymers Containing Tellurium: Perspectives Toward Obtaining High-Performance Materials [J].
Carrera, Elisa I. ;
Seferos, Dwight S. .
MACROMOLECULES, 2015, 48 (02) :297-308
[5]   Thienothiophenes, Dithienothiophenes, and Thienoacenes: Syntheses, Oligomers, Polymers, and Properties [J].
Cinar, Mehmet Emin ;
Ozturk, Turan .
CHEMICAL REVIEWS, 2015, 115 (09) :3036-3140
[6]   Designing π-conjugated polymers for organic electronics [J].
Guo, Xin ;
Baumgarten, Martin ;
Muellen, Klaus .
PROGRESS IN POLYMER SCIENCE, 2013, 38 (12) :1832-1908
[7]   The Marriage of Metallacycle Transfer Chemistry with Suzuki-Miyaura Cross-Coupling To Give Main Group Element-Containing Conjugated Polymers [J].
He, Gang ;
Kang, Le ;
Delgado, William Torres ;
Shynkaruk, Olena ;
Ferguson, Michael J. ;
McDonald, Robert ;
Rivard, Eric .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2013, 135 (14) :5360-5363
[8]   Conjugated main-group polymers for optoelectronics [J].
He, Xiaoming ;
Baumgartner, Thomas .
RSC ADVANCES, 2013, 3 (29) :11334-11350
[9]   New building blocks for π-conjugated polymer semiconductors for organic thin film transistors and photovoltaics [J].
He, Yinghui ;
Hong, Wei ;
Li, Yuning .
JOURNAL OF MATERIALS CHEMISTRY C, 2014, 2 (41) :8651-8661
[10]  
Heeney M., 2007, CHEM COMMUN, V5061