3,6-di(2-bromothien-5-yl)-2,5-bis[6-(1,1,1,3,5,5,5,-heptamethyltrisiloxan-3-yl)hexyl]-pyrrolo[3,4-c]pyrrole-1,4-dione | 1415649-62-5

• 分子结构分类: 有机化合物 - 有机金属化合物 - 有机类金属化合物
• 英文名称: 3,6-di(2-bromothien-5-yl)-2,5-bis[6-(1,1,1,3,5,5,5,-heptamethyltrisiloxan-3-yl)hexyl]-pyrrolo[3,4-c]pyrrole-1,4-dione
• 英文别名: 1,4-Bis(5-bromothiophen-2-yl)-2,5-bis[6-[methyl-bis(trimethylsilyloxy)silyl]hexyl]pyrrolo[3,4-c]pyrrole-3,6-dione；1,4-bis(5-bromothiophen-2-yl)-2,5-bis[6-[methyl-bis(trimethylsilyloxy)silyl]hexyl]pyrrolo[3,4-c]pyrrole-3,6-dione
• CAS: 1415649-62-5
• 化学式: C₄₀H₇₀Br₂N₂O₆S₂Si₆
• 分子量: 1067.46
• InChiKey: XKTYHRVKYNAZHV-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  13.81
• 重原子数：
  58
• 可旋转键数：
  24
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.65
• 拓扑面积：
  134
• 氢给体数：
  0
• 氢受体数：
  8

反应信息

• 作为产物：
  描述：

  6-溴-1-己烯 在 铂(0)-1,3-二乙烯-1,1,3,3-四甲基二硅氧烷 、 N-溴代丁二酰亚胺(NBS) 、 potassium carbonate 作用下， 以 5,5-dimethyl-1,3-cyclohexadiene 、 氯仿 、 N,N-二甲基甲酰胺 、 甲苯 为溶剂， 反应 53.0h， 生成 3,6-di(2-bromothien-5-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

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-Based Low-Bandgap Conjugated Polymers with Siloxane Side Chains for Electrochromic Applications
  作者：Zugui Shi、Wei Teng Neo、Hui Zhou、Jianwei Xu

  DOI：10.1071/ch15738

  日期：——

  A series of conjugated copolymers P1–P3 were synthesized from 3,6-bis(5-bromothiophen-2-yl)-2,5-bis(6-(1,1,1,3,5,5,5-heptamethyltrisiloxan-3-yl)hexyl)-2,5-dihydropyrrolo[3,4-c]pyrrole-1,4-dione and 2,5-bis(trimethylstannyl)-3,4-dialkoxythiophene or its analogue via Stille coupling reactions, with molecular weights in the range of 13000–18000 g mol–1 and polydispersity indexes of 1.4–1.7. This new type

  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。