2,5-bis(2-thienyl)terephthaloyl chloride | 1209012-29-2

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: 2,5-bis(2-thienyl)terephthaloyl chloride
• 英文别名: 2,5-dithien-2-ylterephthalic acid chloride；2,5-dithiophen-2-ylbenzene-1,4-dicarbonyl chloride
• CAS: 1209012-29-2
• 化学式: C₁₆H₈Cl₂O₂S₂
• 分子量: 367.276
• InChiKey: UWIWDCXUSBTSCX-UHFFFAOYSA-N

物化性质

• 沸点：
  559.8±50.0 °C(Predicted)
• 密度：
  1.458±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  5.6
• 重原子数：
  22
• 可旋转键数：
  4
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  90.6
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  2,5-bis(2-thienyl)terephthaloyl chloride 在 aluminum (III) chloride 、 一水合肼 、 potassium hydroxide 作用下， 以 二氯甲烷 、 二乙二醇 为溶剂， 反应 24.0h， 生成 4,9-二氢--S-苯并二茚并[1,2-B:5,6-B']二噻吩(PM146)
  参考文献：
  名称：

  4,9-Dihydro-4,4,9,9-tetrahexyl-s-indaceno[1,2-b:5,6-b′]dithiophene as a π-Spacer of Donor−π–Acceptor Dye and Its Photovoltaic Performance with Liquid and Solid-State Dye-Sensitized Solar Cells

  摘要：

  A new D-pi-A organic dye, LC-5, containing 4,9-dihydro-4,4,9,9-tetrahexyl-s-indaceno[1,2-b:5,6-b']-dithiophene as a novel pi-conjugated spacer has been synthesized and tested as a sensitizer in dye-sensitized solar cells (DSC). Volatile and ionic liquid electrolytes have been used in conjunction with the synthesized dye, and the electrolyte influence on the photovoltaic performance of DSCs was investigated. A detailed investigation, including transient photocurrent/photovoltage decay measurements and electrochemical impedance spectroscopy data, provide important conclusions about the influence of electrolytes on the photovoltaic parameters.

  DOI：

  10.1021/ol402749s
• 作为产物：
  描述：

  2,5-二溴对苯二甲酸 在 bis-triphenylphosphine-palladium(II) chloride 、 草酰氯 、 2,6-二叔丁基苯酚 、 硫酸 、 potassium hydroxide 作用下， 以 乙醇 、 二氯甲烷 、 水 、 N,N-二甲基甲酰胺 、 甲苯 为溶剂， 反应 108.25h， 生成 2,5-bis(2-thienyl)terephthaloyl chloride
  参考文献：
  名称：

  4,9-Dihydro-4,4,9,9-tetrahexyl-s-indaceno[1,2-b:5,6-b′]dithiophene as a π-Spacer of Donor−π–Acceptor Dye and Its Photovoltaic Performance with Liquid and Solid-State Dye-Sensitized Solar Cells

  摘要：

  A new D-pi-A organic dye, LC-5, containing 4,9-dihydro-4,4,9,9-tetrahexyl-s-indaceno[1,2-b:5,6-b']-dithiophene as a novel pi-conjugated spacer has been synthesized and tested as a sensitizer in dye-sensitized solar cells (DSC). Volatile and ionic liquid electrolytes have been used in conjunction with the synthesized dye, and the electrolyte influence on the photovoltaic performance of DSCs was investigated. A detailed investigation, including transient photocurrent/photovoltage decay measurements and electrochemical impedance spectroscopy data, provide important conclusions about the influence of electrolytes on the photovoltaic parameters.

  DOI：

  10.1021/ol402749s

文献信息

• Narrow band gap D-A copolymer of indacenodithiophene and diketopyrrolopyrrole with deep HOMO level: Synthesis and application in field-effect transistors and polymer solar cells
  作者：Xiaochen Wang、Hao Luo、Yeping Sun、Maojie Zhang、Xiaoyu Li、Gui Yu、Yunqi Liu、Yongfang Li、Haiqiao Wang

  DOI：10.1002/pola.25042

  日期：2012.1.15

  This mobility is one of the highest values for narrow band gap conjugated polymers. The power conversion efficiency of the polymer solar cell based on the polymer as donor was 1.76% with a high open circuit voltage of 0.88 V. To the best of our knowledge, this is the first report on the photovoltaic properties of alkyl substituted IDT‐based polymers. © 2011 Wiley Periodicals, Inc. J Polym Sci Part

  通过钯催化的斯蒂勒偶联法设计合成了一种新型的梯形交替D-A共聚物PIDT-DPP，其中烷基取代的茚并二噻吩（IDT）为供体单元，二酮吡咯并吡咯（DPP）为受体单元。该共聚物具有良好的溶解性和成膜能力，并具有良好的热稳定性。PIDT–DPP表现出从350到900 nm的宽吸收带，吸收峰集中在735 nm。由聚合物膜的吸收开始确定的光学带隙为1.37eV。聚合物的最高占据分子轨道能级高达-5.32 eV。经过溶液处理的有机场效应晶体管（OFET）具有底部栅极/顶部触点几何形状。PIDT–DPP的最大FET空穴迁移率达到0.065 cm 2 V -1s -1的开/关比为4.6×10 5。该迁移率是窄带隙共轭聚合物的最高值之​​一。以聚合物为施主的聚合物太阳能电池的功率转换效率为1.76％，开路电压为0.88V。据我们所知，这是有关烷基取代IDT的光伏性能的第一份报告。聚合物。©2011 Wiley
• Indacenodithiophene and Indacenodiselenophene Polymers and their Use as Organic Semiconductors
  申请人：Tierney Steven

  公开号：US20110226999A1

  公开（公告）日：2011-09-22

  The invention relates to conjugated polymers comprising indacenodithiophene or indacenoselenophene units or derivatives thereof, to methods of their preparation, to novel monomer units used therein, to the use of the polymers in organic electronic (OE) devices, and to OE devices comprising the polymers.

  这项发明涉及包含吲哚并噻吩或吲哚硒吩单元或其衍生物的共轭聚合物，涉及其制备方法，其中使用的新型单体单元，以及在有机电子（OE）器件中使用这些聚合物和包含这些聚合物的OE器件。
• Indacenodithiophene and indacenodiselenophene polymers and their use as organic semiconductors
  申请人：Tierney Steven

  公开号：US09017577B2

  公开（公告）日：2015-04-28

  The invention relates to conjugated polymers comprising indacenodithiophene or indacenoselenophene units or derivatives thereof, to methods of their preparation, to novel monomer units used therein, to the use of the polymers in organic electronic (OE) devices, and to OE devices comprising the polymers.

  本发明涉及包含吲哚并二噻吩或吲哚并硒吡嗪单元或其衍生物的共轭聚合物，其制备方法，其中使用的新型单体单元，以及在有机电子（OE）器件中使用聚合物和包含聚合物的OE器件。
• Indacenodithiophene Semiconducting Polymers for High-Performance, Air-Stable Transistors
  作者：Weimin Zhang、Jeremy Smith、Scott E. Watkins、Roman Gysel、Michael McGehee、Alberto Salleo、James Kirkpatrick、Shahid Ashraf、Thomas Anthopoulos、Martin Heeney、Iain McCulloch

  DOI：10.1021/ja1049324

  日期：2010.8.25

  High-performance, solution-processed transistors fabricated from semiconducting polymers containing indacenodithiohene repeat units are described. The bridging functions on the backbone contribute to suppressing large-scale crystallization in thin films. However, charge carrier mobilities of up to 1 cm(2)/(V s) for a benzothiadiazole copolymer were reported and, coupled with both ambient stability and long-wavelength absorption, make this family of polymers particularly attractive for application in next-generation organic optoelectronics.
• Synthesis and Characterization of Planar Five-Ring-Fused Dithiophene-dione
  作者：Jing Wang、Weijing Zeng、Huan Xu、Bin Li、Xiaoping Cao、Haoli Zhang

  DOI：10.1002/cjoc.201100141

  日期：2012.3

  AbstractA series of new organic semiconductors based on s‐indaceno[1,2‐b:5,6‐b′]dithiophene‐4,9‐dione was successfully synthesized and characterized. The electron withdrawing carbonyl group lowers the LUMO energy levels, leading to increased electronegativities, which is beneficial for high photo‐stability in air. The n‐alkyl substituted compounds, 1c and 1d, crystallize with the rigid coplanar systems packed into slipped face‐to‐face π‐stacks. Interestingly, 1c and 1d also show liquid crystalline behaviors, which give highly ordered molecular packing over large area.