Toward Low-Band Gap Dithienophosphole Copolymers for an Application in Organic Solar Cells

被引:30
作者
Durben, Stefan [1 ]
Nickel, Debby [1 ]
Krueger, Robin A. [1 ]
Sutherland, Todd C. [1 ]
Baumgartner, Thomas [1 ]
机构
[1] Univ Calgary, Dept Chem, Calgary, AB T2N 1N4, Canada
基金
加拿大自然科学与工程研究理事会;
关键词
conjugated polymers; copolymerization; heteroatom-containing polymers; polyaromatics; structure-property relations;
D O I
10.1002/pola.23115
中图分类号
O63 [高分子化学(高聚物)];
学科分类号
070305 ; 080501 ; 081704 ;
摘要
Two functionalized dithieno[3,2-b:2',3'-d]phospholes with solubilizing groups have been synthesized that allow for the generation of a series of pi-conjugated AB- and ABC-copolymers. The polymers obtained show notable optoelectronic properties with red-shifted absorption and emission in the orange to red section of the optical solar spectrum. Although combination of dithienophosphole units with fluorene building blocks gives access to processable polymers with band gaps between 2.2 and 2.3 eV in solution and 2.0 eV in the solid state, an ABC copolymer based on dithienophosphole, fluorene, and bis(thienyl)benzothiadiazole units was found to not only exhibit a suitable band gap for solar cell applications (solution: 2.0 eV; solid state: 1.7 eV) but also showed good solubility as well as good electron transfer properties in the presence of fullerene (C-60). (C) 2008 Wiley Periodicals, Inc. J Polym Sci Part A: Polym Chem 46: 8179-8190, 2008
引用
收藏
页码:8179 / 8190
页数:12
相关论文
共 49 条
[1]   Organic semiconductors for solution-processable field-effect transistors (OFETs) [J].
Allard, Sybille ;
Forster, Michael ;
Souharce, Benjamin ;
Thiem, Heiko ;
Scherf, Ullrich .
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2008, 47 (22) :4070-4098
[2]  
[Anonymous], 1998, ELECT MAT OLIGOMER A
[3]   The larger acenes: Versatile organic semiconductors [J].
Anthony, John E. .
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2008, 47 (03) :452-483
[4]   Photochemical conversion of solar energy [J].
Balzani, Vincenzo ;
Credi, Alberto ;
Venturi, Margherita .
CHEMSUSCHEM, 2008, 1 (1-2) :26-58
[5]   From model compounds to extended π-conjugated systems:: Synthesis and properties of dithieno[3,2-b:2′,3′-d]phospholes [J].
Baumgartner, T ;
Bergmans, W ;
Kárpáti, T ;
Neumann, T ;
Nieger, M ;
Nyulászi, L .
CHEMISTRY-A EUROPEAN JOURNAL, 2005, 11 (16) :4687-4699
[6]   The dithieno[3,2-b:2′,3′-d]phosphole system:: A novel building block for highly luminescent π-conjugated materials [J].
Baumgartner, T ;
Neumann, T ;
Wirges, B .
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2004, 43 (45) :6197-6201
[7]  
Baumgartner T, 2005, J INORG ORGANOMET P, V15, P389, DOI 10.1007/s10904-006-9013-3
[8]   Toward a rational design of poly(2,7-carbazole) derivatives for solar cells [J].
Blouin, Nicolas ;
Michaud, Alexandre ;
Gendron, David ;
Wakim, Salem ;
Blair, Emily ;
Neagu-Plesu, Rodica ;
Belletete, Michel ;
Durocher, Gilles ;
Tao, Ye ;
Leclerc, Mario .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2008, 130 (02) :732-742
[9]   A low-bandgap poly(2,7-carbazole) derivative for use in high-performance solar cells [J].
Blouin, Nicolas ;
Michaud, Alexandre ;
Leclerc, Mario .
ADVANCED MATERIALS, 2007, 19 (17) :2295-+
[10]   KNOWLEDGE OF ORGANOPHOSPHORUS COMPOUNDS .23. ALKENYL SUBSTITUTED AMINOPHOSPHANES AND HALOGENOPHOSPHANES AND EXPERIMENTS ON INTRAMOLECULAR PHOSPHINIDENE OBSERVATION [J].
DIEMERT, K ;
KOTTWITZ, B ;
KUCHEN, W .
PHOSPHORUS SULFUR AND SILICON AND THE RELATED ELEMENTS, 1986, 26 (03) :307-320