6,6'-dibromo-N,N'-(n-butyl)isoindigo | 1401727-33-0

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吲哚及其衍生物
• 英文名称: 6,6'-dibromo-N,N'-(n-butyl)isoindigo
• 英文别名: 6,6'-dibromo-N,N'-dibutylisoindigo；6,6-dibromo-N,N-dibutyl isoindigo
• CAS: 1401727-33-0
• 化学式: C₂₄H₂₄Br₂N₂O₂
• 分子量: 532.275
• InChiKey: UXJLIJKFKWYWAU-UHFFFAOYSA-N

物化性质

• 沸点：
  561.0±50.0 °C(Predicted)
• 密度：
  1.526±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  6.42
• 重原子数：
  30.0
• 可旋转键数：
  6.0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.33
• 拓扑面积：
  40.62
• 氢给体数：
  0.0
• 氢受体数：
  2.0

反应信息

• 作为反应物：
  描述：

  6,6'-dibromo-N,N'-(n-butyl)isoindigo 、 联硼酸频那醇酯 在 1,1'-双(二苯膦基)二茂铁二氯化钯(II)二氯甲烷复合物 、 potassium acetate 作用下， 以 1,4-二氧六环 为溶剂， 反应 40.0h， 以87%的产率得到dihexyl-6,6’-isoindigobis(pinacolborane)
  参考文献：
  名称：

  [EN] HIGHLY THERMALLY CONDUCTIVE, ULTRA-LOW-K TWO-DIMENSIONAL COVALENT ORGANIC FRAMEWORK DIELECTRIC LAYERS
  [FR] COUCHES DIÉLECTRIQUES À STRUCTURE ORGANIQUE COVALENTE BI-DIMENSIONNELLE À ULTRA-FAIBLE K, HAUTEMENT THERMOCONDUCTRICE

  摘要：

  Disclosed herein are low dielectric constant (low-k) two-dimensional covalent organic framework materials that have a dielectric constantkless than 2.4, optionally less than 1.9, and are comprised of regularly porous, covalently linked, layer structures.

  公开号：

  WO2022159668A1
• 作为产物：
  描述：

  6-溴靛红 在 盐酸 、 potassium carbonate 、 溶剂黄146 作用下， 以 水 、 N,N-二甲基甲酰胺 为溶剂， 反应 39.5h， 生成 6,6'-dibromo-N,N'-(n-butyl)isoindigo
  参考文献：
  名称：

  新型基于靛蓝的共轭聚电解质：水溶性聚对苯撑亚乙烯基的合成和荧光猝灭行为

  摘要：

  通过Heck偶联反应合成了两种新型的基于ID的水溶性共轭聚合物（+）-PIDPV和（-）-PIDPV。这两种聚电解质均由异靛蓝单元和亚苯基亚乙烯基单元组成。在紫外可见吸收光谱中，（+）-PIDPV和（-）-PIDPV均显示出宽吸收带，几乎覆盖了整个可见光区域。光物理研究表明，水溶性PPV的荧光可以通过以非常低的浓度带相反电荷的PIDPV来有效地猝灭。阳离子PPV示出了具有高效的淬灭效应Κ SV  = 1.01×10 6中号-1中的存在（ - ） - PIDPV而阴离子PPV给出与啤酒淬灭常数Κ SV  = 1.71×10 6在（+）-PIDPV存在的情况下M -1 此外，水溶性PPV和带相反电荷的PIDPV的共混膜也表现出出色的淬灭效果。这些性质表明，（+）-PIDPV和（-）-PIDPV是离子光敏层在有机太阳能电池中的应用前景广阔的材料。©2015 Wiley Periodicals，Inc

  DOI：

  10.1002/pola.27711

文献信息

• The effect of the length of alkyl side-chains on the molecular aggregation and photovoltaic performance of the isoindigo-based polymers
  作者：Xiai Sun、Zhiquan Zhang、Rongyan Hou、Meihua Huang、Bin Zhao、Songting Tan

  DOI：10.1016/j.dyepig.2016.12.036

  日期：2017.4

  To investigate the length of the alkyl side-chains on the photovoltaic performance, three isoindigo-based polymers with different-length side chains on the thiophene-benzene-thiophene (TBT) (electron-donating) moiety and isoindigo (electron-withdrawing) moiety have been designed and synthesized, in which the total carbon atom numbers of the side chains in a constitutional repeating unit are completely

  为了研究烷基侧链在光伏性能上的长度，在噻吩-苯-噻吩（TBT）（给电子）部分和isoindigo（吸电子）部分上具有不同长度侧链的三种基于靛蓝的聚合物设计并合成了其中结构重复单元中侧链的总碳原子数完全相同的化合物。结果表明，在TBT单元上具有较长支链侧链而在isoindigo单元上具有较短线性侧链的聚合物在1,2-二氯苯溶液和薄膜中表现出更强的链间相互作用和聚光能力，带隙较小，π更强-π堆积相互作用，与PC 71更合适的微相分离BM，更高的空穴迁移率和更好的光伏性能。结果，基于PTBTOD-IDB的本体异质结（BHJ）器件的TBT部分为2-辛基十二烷基，异靛蓝部分为正丁基，其功率转换效率（PCE）为5.29％，几乎是其的八倍。与PTBTEH-IDHD一样高，在TBT部分具有2-乙基己基侧链，在异靛蓝部分具有2-己基癸基侧链。
• ——
  作者：

  DOI：——

  日期：——
• Spectrally Switchable Photodetection with Near-Infrared-Absorbing Covalent Organic Frameworks
  作者：Derya Bessinger、Laura Ascherl、Florian Auras、Thomas Bein

  DOI：10.1021/jacs.7b06599

  日期：2017.8.30

  Most covalent organic frameworks (COFs) to date are made from relatively small aromatic subunits, which can only absorb the high-energy part of the visible spectrum. We have developed near-infrared-absorbing low bandgap COFs by incorporating donor acceptor-type isoindigo- and thienoisoindigo-based building blocks. The new materials are intensely colored solids with a high degree of long-range order and a pseudo-quadratic pore geometry. Growing the COF as a vertically oriented thin film allows for the construction of an ordered interdigitated heterojunction through infiltration with a complementary semiconductor. Applying a thienoisoindigo-COF:fullerene heterojunction as the photoactive component, we realized the first COF-based UV- to NIR-responsive photodetector. We found that the spectral response of the device is reversibly switchable between blue- and red-sensitive, and green- and NIR-responsive. To the best of our knowledge, this is the first time that such nearly complete inversion of spectral sensitivity of a photodetector has been achieved. This effect could lead to potential applications in information technology or spectral imaging.
• Poly[Bis-EDOT-Isoindigo]: An Electroactive Polymer Applied to Electrochemical Supercapacitors
  作者：Leandro A. Estrada、David Y. Liu、Danielle H. Salazar、Aubrey L. Dyer、John R. Reynolds

  DOI：10.1021/ma3016129

  日期：2012.10.23

  Poly[6,6'-bis(ethylene-3,4-dioxythien-2-yl)]-N,N'-dialkylisoindigo (PBEDOT-iI) was synthesized and incorporated as an electroactive material into electrochemical supercapacitors (ESCs) in type I and type III configurations. In type I ESCs, PBEDOT-iI provides a specific power of similar to 360 W/kg and specific energy of similar to 0.5 Wh/kg, while retaining about 80% of its electroactivity over 10 000 cycles. In addition, we report on the use of PBEDOT-iI in type III supercapacitors where operating voltages as high as 2.5 V were achieved with specific energies of ca. 15 Wh/kg, albeit with limited stability.