3,6-bis(5-bromofuran-2-yl)-2,5-di-(2-butyloctyl)pyrrolo[3,4-c]pyrrole-1,4(2H,5H)-dione | 1350611-52-7

• 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-di-(2-butyloctyl)pyrrolo[3,4-c]pyrrole-1,4(2H,5H)-dione
• 英文别名: 1,4-Bis(5-bromofuran-2-yl)-2,5-bis(2-butyloctyl)pyrrolo[3,4-c]pyrrole-3,6-dione
• CAS: 1350611-52-7
• 化学式: C₃₈H₅₄Br₂N₂O₄
• 分子量: 762.666
• InChiKey: KOQCDKLLKYCCCL-UHFFFAOYSA-N

物化性质

• 沸点：
  770.0±60.0 °C(Predicted)
• 密度：
  1.31±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  13
• 重原子数：
  46
• 可旋转键数：
  22
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.63
• 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-di-(2-butyloctyl)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

• [EN] DITHIENOBENZOFURAN POLYMERS AND SMALL MOLECULES FOR ELECTRONIC APPLICATION<br/>[FR] POLYMÈRES DE DITHIÉNOBENZOFURANE ET PETITES MOLÉCULES POUR APPLICATION ÉLECTRONIQUE
  申请人：BASF SE

  公开号：WO2014016219A1

  公开（公告）日：2014-01-30

  The present invention relates to polymers comprising a repeating unit of the formula (I), and compounds of formula (VIII), or (IX), wherein Y, Y15, Y16 and Y17 are independently of each other a group of formula (I), and their use as organic semiconductor in organic electronic devices, especially in organic photovoltaics and photodiodes, or in a device containing a diode and/or an organic field effect transistor. The polymers and compounds according to the invention can have excellent solubility in organic solvents and excellent film-forming properties. In addition, high efficiency of energy conversion, excellent field-effect mobility, good on/off current ratios and/or excellent stability can be observed, when the polymers and compounds according to the invention are used in organic field effect transistors, organic photovoltaics (solar ells) and photodiodes.

  本发明涉及具有重复单元式(I)的聚合物以及式(VIII)或(IX)的化合物，其中Y、Y15、Y16和Y17各自独立地是式(I)的基团，并且它们在有机电子器件中的用途，特别是在有机光伏和光电二极管中作为有机半导体，或在包含二极管和/或有机场效应晶体管的器件中。本发明中的聚合物和化合物可以在有机溶剂中具有优异的溶解性和优异的成膜性能。此外，当本发明中的聚合物和化合物用于有机场效应晶体管、有机光伏（太阳电池）和光电二极管时，可以观察到高效率的能量转换、优异的场效应迁移率、良好的开/关电流比和/或优异的稳定性。
• CONJUGATED POLYMERS FOR ELECTRONIC DEVICES
  申请人：The Regents of the University of California

  公开号：US20150028265A1

  公开（公告）日：2015-01-29

  A conjugated polymer for electronic devices can include a repeated unit having the structure of formula (I)

  一种用于电子设备的共轭聚合物可以包括具有公式（I）结构的重复单元。
• 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。
• DIKETOPYRROLOPYRROLE POLYMERS FOR USE IN ORGANIC SEMICONDUCTOR DEVICES
  申请人：BASF SE

  公开号：EP2571919B1

  公开（公告）日：2018-07-11
• FUNCTIONALIZED BENZODITHIOPHENE POLYMERS FOR ELECTRONIC APPLICATION
  申请人：CLAP Co., Ltd.

  公开号：EP2928940B1

  公开（公告）日：2021-03-03