Rapid Synthesis of D-A′-π-A Dyes through a One-Pot Three-Component Suzuki-Miyaura Coupling and an Evaluation of their Photovoltaic Properties for Use in Dye-Sensitized Solar Cells

被引:20
作者
Irie, Shunsuke [1 ]
Fuse, Shinichiro [1 ,2 ]
Maitani, Masato M. [1 ]
Wada, Yuji [1 ]
Ogomi, Yuhei [3 ]
Hayase, Shuzi [3 ]
Kaiho, Tatsuo [4 ]
Masui, Hisashi [5 ]
Tanaka, Hiroshi [1 ]
Takahashi, Takashi [5 ]
机构
[1] Tokyo Inst Technol, Dept Appl Chem, Meguro Ku, Tokyo 1528552, Japan
[2] Tokyo Inst Technol, Chem Resources Lab, Midori Ku, Yokohama, Kanagawa 2268503, Japan
[3] Kyushu Inst Technol, Grad Sch Life Sci & Syst Engn, Fukuoka 8080196, Japan
[4] Kanto Nat Gas Dev Co Ltd, Brine Resources Res & Dev Div, Chiba 2978550, Japan
[5] Yokohama Univ Pharm, Totsuka Ku, Yokohama, Kanagawa 2450066, Japan
关键词
combinatorial chemistry; cross-coupling; dyes; pigments; solar cells; one-pot reactions; UNSYMMETRICAL SQUARAINE DYES; NANOCRYSTALLINE TIO2 FILMS; ORGANIC-DYES; MOLECULAR DESIGN; EFFICIENCY; ABSORPTION; HALIDES; ARYL; CONVERSION; CATALYSTS;
D O I
10.1002/chem.201504277
中图分类号
O6 [化学];
学科分类号
0703 ;
摘要
Twenty-four D-A--A dyes were rapidly synthesized through a one-pot three-component Suzuki-Miyaura coupling reaction, which was assisted by microwave irradiation. We measured the absorption spectra, electrochemical properties, and solar-cell performance of all the synthesized dyes. The D5A4 dye contained our originally designed rigid and nonplanar donor and exerted the highest efficiency at 5.4%. The short-circuit current (J(sc)) was the most important parameter for the conversion efficiency () in the case of the organic D-A--A dyes. Optimal ranges for the D-A--A dyes were observed for high values of J(sc)/(max) at =560-620nm, an optical-absorption edge of =690-790nm, and E-HOMO and E-LUMO values of <1.14 and -0.56 to -0.76V, respectively.
引用
收藏
页码:2507 / 2514
页数:8
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