Synthesis and Characterization of Optical and Redox Properties of Bithiophene-Functionalized Diketopyrrolopyrrole Chromophores

被引:171
作者
Buerckstuemmer, Hannah [1 ]
Weissenstein, Annike [1 ]
Bialas, David [1 ]
Wuerthner, Frank [1 ]
机构
[1] Univ Wurzburg, Inst Organ Chem, D-97074 Wurzburg, Germany
关键词
OLIGOTHIOPHENE DERIVATIVES; SOLAR-CELLS; PIGMENTS; DYES; BANDGAP; COLOR; LASER; CORE;
D O I
10.1021/jo2003117
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
A series of six new 2,2'-bithiophene-functionalized diketopyrrolopyrrole (DPP) dyes 7a-f bearing different electron-donating and electron-withdrawing substituents at the terminal thiophene units was synthesized by palladium-catalyzed cross-coupling reactions. The to date unknown diiodinated DPP 2 and the corresponding boronic ester derivative 3 could be prepared in high yields, and these are shown to be versatile building blocks for the synthesis of DPP-based molecular materials by Negishi, Stile, and Suzuki coupling. The influence of the peripheral substituents on the optical and electrochemical properties of the present series of DPP dyes 7a-f were investigated by UV/vis and steady-state fluorescence spectroscopy and cyclic voltammetry, revealing an appreciable effect on the electronic nature of these dyes. The diamino-substituted DPP derivative 7e exhibits a strong absorption band reaching in the near-infrared (NIR) region, which is a highly desirable feature for application in organic photovoltaics.
引用
收藏
页码:2426 / 2432
页数:7
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