3,6-bis(5-bromofuran-2-yl)-2,5-ditetradecyl-pyrrolo[3,4-c]pyrrole-1,4(2H,5H)-dione | 1356822-43-9

• 分子结构分类: 有机化合物 - 有机卤素化合物 - 芳基卤化物
• 英文名称: 3,6-bis(5-bromofuran-2-yl)-2,5-ditetradecyl-pyrrolo[3,4-c]pyrrole-1,4(2H,5H)-dione
• 英文别名: 1,4-Bis(5-bromofuran-2-yl)-2,5-di(tetradecyl)pyrrolo[3,4-c]pyrrole-3,6-dione
• CAS: 1356822-43-9
• 化学式: C₄₂H₆₂Br₂N₂O₄
• 分子量: 818.773
• InChiKey: BOCJGYBHUDMXDV-UHFFFAOYSA-N

物化性质

• 沸点：
  809.1±65.0 °C(Predicted)
• 密度：
  1.26±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  15.8
• 重原子数：
  50
• 可旋转键数：
  28
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.67
• 拓扑面积：
  66.9
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  2-氰基呋喃 在 N-溴代丁二酰亚胺(NBS) 、 2-甲基-2-丁醇 、 sodium 作用下， 以 氯仿 、 N,N-二甲基甲酰胺 为溶剂， 反应 5.33h， 生成 3,6-bis(5-bromofuran-2-yl)-2,5-ditetradecyl-pyrrolo[3,4-c]pyrrole-1,4(2H,5H)-dione
  参考文献：
  名称：

  Side-Chain Tunability of Furan-Containing Low-Band-Gap Polymers Provides Control of Structural Order in Efficient Solar Cells

  摘要：

  The solution-processability of conjugated polymers in organic solvents has classically been achieved by modulating the size and branching of alkyl substituents appended to the backbone. However, these substituents impact structural order and charge transport properties in thin-film devices. As a result, a trade-off must be found between material solubility and insulating alkyl content. It was recently shown that the substitution of furan for thiophene in the backbone of the polymer PDPP2FT significantly improves polymer solubility, allowing for the use of shorter branched side chains while maintaining high device efficiency. In this report, we use PDPP2FT to demonstrate that linear alkyl side chains can be used to promote thin-film nanostructural order. In particular, linear side chains are shown to shorten pi-pi stacking distances between backbones and increase the correlation lengths of both pi-pi stacking and lamellar spacing, leading to a substantial increase in the efficiency of bulk heterojunction solar cells.

  DOI：

  10.1021/ja2089662

文献信息

• Furan Conjugated Polymers Useful for Photovoltaic Applications
  申请人：Beaujuge Pierre M.

  公开号：US20120085992A1

  公开（公告）日：2012-04-12

  The present invention provides for a polymer comprising a π-conjugated backbone comprising a furan. The polymer has a narrow or low band gap and/or is solution processable. In some embodiments, the polymer is PDPP2FT or PDPP3F. The present invention also provides for a device comprising the polymer, such as a light-emitting diode, thin-film transistor, chemical biosensor, non-emissive electrochromic, memory device, photovoltaic cells, or the like.

  本发明提供了一种聚合物，其包括一个π-共轭骨架，其中包括呋喃。该聚合物具有窄或低带隙和/或可溶解性。在某些实施例中，该聚合物是PDPP2FT或PDPP3F。本发明还提供了一种包括该聚合物的器件，例如发光二极管、薄膜晶体管、化学生物传感器、非发光电致变色、记忆器件、光伏电池等。
• Side-Chain Tunability of Furan-Containing Low-Band-Gap Polymers Provides Control of Structural Order in Efficient Solar Cells
  作者：Alan T. Yiu、Pierre M. Beaujuge、Olivia P. Lee、Claire H. Woo、Michael F. Toney、Jean M. J. Fréchet

  DOI：10.1021/ja2089662

  日期：2012.2.1

  The solution-processability of conjugated polymers in organic solvents has classically been achieved by modulating the size and branching of alkyl substituents appended to the backbone. However, these substituents impact structural order and charge transport properties in thin-film devices. As a result, a trade-off must be found between material solubility and insulating alkyl content. It was recently shown that the substitution of furan for thiophene in the backbone of the polymer PDPP2FT significantly improves polymer solubility, allowing for the use of shorter branched side chains while maintaining high device efficiency. In this report, we use PDPP2FT to demonstrate that linear alkyl side chains can be used to promote thin-film nanostructural order. In particular, linear side chains are shown to shorten pi-pi stacking distances between backbones and increase the correlation lengths of both pi-pi stacking and lamellar spacing, leading to a substantial increase in the efficiency of bulk heterojunction solar cells.