3,6-dithien-2-yl-2,5-di(hex-5-en-1-yl)-pyrrolo[3,4-c]pyrrole-1,4-dione | 1415649-60-3

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 杂芳族化合物
• 英文名称: 3,6-dithien-2-yl-2,5-di(hex-5-en-1-yl)-pyrrolo[3,4-c]pyrrole-1,4-dione
• 英文别名: 2,5-di(hex-5-en-1-yl)-3,6-di(thiophen-2-yl)-2,5-dihydropyrrolo[3,4-c]pyrrole-1,4-dione；2,5-Bis(hex-5-enyl)-1,4-dithiophen-2-ylpyrrolo[3,4-c]pyrrole-3,6-dione；2,5-bis(hex-5-enyl)-1,4-dithiophen-2-ylpyrrolo[3,4-c]pyrrole-3,6-dione
• CAS: 1415649-60-3
• 化学式: C₂₆H₂₈N₂O₂S₂
• 分子量: 464.653
• InChiKey: PAYNEAJLWVFEMK-UHFFFAOYSA-N

物化性质

• 熔点：
  159 °C
• 沸点：
  691.2±55.0 °C(Predicted)
• 密度：
  1.25±0.1 g/cm3(Temp: 20 °C; Press: 760 Torr)(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  5.3
• 重原子数：
  32
• 可旋转键数：
  12
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.31
• 拓扑面积：
  97.1
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  双三甲基硅氧基甲基硅烷 、 3,6-dithien-2-yl-2,5-di(hex-5-en-1-yl)-pyrrolo[3,4-c]pyrrole-1,4-dione 在 铂(0)-1,3-二乙烯-1,1,3,3-四甲基二硅氧烷 作用下， 以 5,5-dimethyl-1,3-cyclohexadiene 、 甲苯 为溶剂， 以78%的产率得到3,6-dithien-2-yl-2,5-bis[6-(1,1,1,3,5,5,5,-heptamethyltrisiloxan-3-yl)hexyl]-pyrrolo[3,4-c]pyrrole-1,4-dione
  参考文献：
  名称：

  用于电致变色应用的基于二酮吡咯并吡咯的低带隙共轭聚合物和硅氧烷侧链

  摘要：

  由3,6-双（5-溴噻吩-2-基）-2,5-双（6-（1,1,1,3,5,5,5,5-七庚甲基三硅氧烷）合成一系列共轭共聚物P1 - P3 -3-基）己基）-2,5-二氢吡咯并[3,4- c ]吡咯-1,4-二酮和2,5-双（三甲基锡烷基）-3,4-二烷氧基噻吩或其类似物，通过Stille偶联反应，分子量范围为13000–18000 g mol –1和多分散指数为1.4-1.7。这种新型的供体-受体聚合物表现出合理的转换速度，有希望的氧化还原稳定性，高的光学对比度和着色效率。尽管在当前阶段，杂化的硅氧烷封端的侧链并未显着改善所得聚合物的整体性能，但硅氧烷基团的独特化学性质将为经过适当的聚合后处理提供交联的可能性，从而为将来微调电致变色膜形态的方法。

  DOI：

  10.1071/ch15738
• 作为产物：
  描述：

  2-氰基噻吩 在 potassium carbonate 、 sodium t-butanolate 作用下， 以 2-甲基-2-丁醇 、 N,N-二甲基甲酰胺 为溶剂， 反应 25.0h， 生成 3,6-dithien-2-yl-2,5-di(hex-5-en-1-yl)-pyrrolo[3,4-c]pyrrole-1,4-dione
  参考文献：
  名称：

  通过操纵烷基链间隔物上的偶极锚定端子，增强二酮吡咯并吡咯太阳能电池的光电流。

  摘要：

  我们选择DPP-BDT-DPP {DPP = diketopyrrolopyrrole，BDT = 4,8-di- [2-（2-乙基己基）-噻吩基]苯并[1,2- b：4,5- b ']二噻吩}作为模型骨架和改变锚定基团[  ç 5 ħ 11， COOCH 3，和 SICH 3（OSICH 3）2 ]终止于DPP单元的N-取代烷基链间隔来研究锚定终端的效果混合膜的形态以及块状异质结太阳能电池的器件性能 通过更换非极性 Ç 5 ħ 11锚定终端与极性 COOCH 3锚固端子引线在短路电流密度的增强（Ĵ SC）（4.62对9.32毫安厘米-2），而值Ĵ SC急剧下降到0.45毫安厘米-2如果 ç 5 ħ 11锚固终端由替换 SICH 3（OSICH 3）2基团。J sc的变化与在π-π堆积的距离（3.39→3.34埃与3.39→3.45埃）和相位尺寸变化有关（50→20纳米与50→>

  DOI：

  10.1002/asia.201301416

文献信息

• Solution-Processable Ambipolar Diketopyrrolopyrrole–Selenophene Polymer with Unprecedentedly High Hole and Electron Mobilities
  作者：Junghoon Lee、A-Reum Han、Jonggi Kim、Yiho Kim、Joon Hak Oh、Changduk Yang

  DOI：10.1021/ja308927g

  日期：2012.12.26

  There is a fast-growing demand for polymer-based ambipolar thin-film transistors (TFTs), in which both n-type and p-type transistor operations are realized in a single layer, while maintaining simplicity in processing. Research progress toward this end is essentially fueled by molecular engineering of the conjugated backbones of the polymers and the development of process architectures for device fabrication, which has recently led to hole and electron mobilities of more than 1.0 cm(2) V-1 s(-1). However, ambipolar polymers with even higher performance are still required. By taking into account both the conjugated backbone and side chains of the polymer component, we have developed a dithienyi-diketopyrrolo-pyrrole (TDPP) and selenophene containing polymer with hybrid silmane-solubilizing groups (PTDPPSe-Si). A synergistic combination of rational polymer backbone design, side-chain dynamics, and solution processing affords an enormous boost in ambipolar TFT performance, resulting in unprecedentedly high hole and electron mobilities of 3.97 and 2.20 cm(2) V-1 s(-1), respectively.
• Boosting the Ambipolar Performance of Solution-Processable Polymer Semiconductors via Hybrid Side-Chain Engineering
  作者：Junghoon Lee、A-Reum Han、Hojeong Yu、Tae Joo Shin、Changduk Yang、Joon Hak Oh

  DOI：10.1021/ja403949g

  日期：2013.6.26

  Ambipolar polymer semiconductors are highly suited for use in flexible, printable, and large-area electronics as they exhibit both n-type (electron-transporting) and p-type (hole-transporting) operations within a single layer. This allows for cost-effective fabrication of complementary circuits with high noise immunity and operational stability. Currently, the performance of ambipolar polymer semiconductors lags behind that of their unipolar counterparts. Here, we report on the side-chain engineering of conjugated, alternating electron donoracceptor (D-A) polymers using diketopyrrolopyrrole-selenophene copolymers with hybrid siloxane-solubilizing groups (PTDPPSe-Si) to enhance ambipolar performance. The alkyl spacer length of the hybrid side chains was systematically tuned to boost ambipolar performance. The optimized three-dimensional (3-D) charge transport of PTDPPSe-Si with pentyl spacers yielded unprecedentedly high hole and electron mobilities of 8.84 and 4.34 cm(2) V-1 s(-1), respectively. These results provide guidelines for the molecular design of semiconducting polymers with hybrid side chains.
• DIKETOPYRROLOPYRROLE POLYMERS AND SMALL MOLECULES
  申请人：BASF SE

  公开号：EP2834286B1

  公开（公告）日：2019-01-23
• US9293718B2
  申请人：——

  公开号：US9293718B2

  公开（公告）日：2016-03-22
• [EN] DIKETOPYRROLOPYRROLE POLYMERS AND SMALL MOLECULES<br/>[FR] POLYMÈRES DE DICÉTOPYRROLOPYRROLE ET PETITES MOLÉCULES
  申请人：BASF SE

  公开号：WO2013150005A1

  公开（公告）日：2013-10-10

  The present invention relates to polymers,comprising a repeating unit of the formula (I), and compounds of formula (II), wherein Y, Y15, Y16 and Y17 are independently of each other a group of formula (a) characterized in that the polymers and compounds comprise silicon-containing solubilizing side chains and their use as organic semiconductor in organic 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 and photodiodes.