Low band gap poly-thienopyrazines for solar cells—Introducing the 11-thia-9,13-diaza-cyclopenta[b]triphenylenes
Low band gap poly-thienopyrazines for solar cells—Introducing the 11-thia-9,13-diaza-cyclopenta[b]triphenylenes
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DOI：
10.1016/j.solmat.2007.02.022
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发表时间：
2007-07
影响因子：
6.9
通讯作者：
M. H. Petersen;O. Hagemann;K. T. Nielsen;M. Jørgensen;F. Krebs
中科院分区：
文献类型：
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作者：
M. H. Petersen;O. Hagemann;K. T. Nielsen;M. Jørgensen;F. Krebs
噻吩并吡嗪类化合物的化学性质已被探索，目的是生产新的低带隙聚合物。合成并表征了吡嗪环上被烷基、芳基和稠合芳环取代的5，7-二（噻吩-2-基）噻吩并[3，4-B]吡嗪。电子光谱表明，作为这种替代的结果，在最长波长的吸收带的变化很大。一个特殊的例子是通过3′，4 ′-二氨基-[2，2 ′，5 ′，2 ″]三噻吩与菲-9，10-醌缩合制备的11-硫杂-9，13-二氮杂-环戊二烯并[B]苯并菲。使用Kumada偶联进行最有前途的单体的烷基取代，并且这些单体与2，5-双（三甲基甲锡烷基）噻吩或3-（3，7，11-三甲基-十二烷基）-2，5-双-三甲基甲锡烷基-噻吩共聚以形成六种新的低带隙聚合物：RISO-GREEN 1-3和RISO-BROWN 1-3。从紫外-可见吸收光谱估算了这些聚合物的带隙，发现它们的带隙约为0.001。1.3eV.用六种聚合物与[60]PCBM或[70]PCBM的混合物制造光伏器件的初步结果显示，开路电压Vocof 0.3V和短路电流Jsc（1000 Wm −2AM1.5）在2 mAcm −2范围内时，最大效率为0.2%。
The chemistry of the thienopyrazines has been explored with the aim of producing new low band gap polymers. 5,7-Di-(thiophen-2-yl)-thieno[3,4-b]pyrazines substituted in the pyrazine ring with alkyl groups, aryl groups and fused aromatic rings have been prepared and characterized. The electronic spectra show a great variation in the longest wavelength absorption band as a consequence of this substitution. A special case is the 11-thia-9,13-diaza-cyclopenta[b]triphenylene prepared by condensation of 3′,4′-diamino-[2,2′,5′,2″]terthiophene with phenanthrene-9,10-quinone. Alkyl substitution of the most promising monomers were carried out using the Kumada coupling and these were copolymerized with either 2,5-bis(trimethylstannyl)thiophene or 3-(3,7,11-trimethyl-dodecyl)-2,5-bis-trimethylstannyl-thiophene to form six new low band gap polymers: RISO-GREEN 1–3 and RISO-BROWN 1–3. The band gaps of these polymers were estimated from the UV–visible absorption spectra and found to be ca. 1.3eV. Preliminary results from photovoltaic device fabrication with mixtures of the six polymers with either [60]PCBM or [70]PCBM gave modest efficiencies of max 0.2% with open circuit voltages Vocof 0.3V and short circuit currents Jsc(1000Wm−2AM1.5) in the range of 2mAcm−2.