3,6-dithien-2-yl-2,5-bis[6-(1,1,1,3,5,5,5,-heptamethyltrisiloxan-3-yl)pentyl]pyrrolo[3,4-c]pyrrole-1,4-dione | 1443134-80-2

• 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-dithien-2-yl-2,5-bis[6-(1,1,1,3,5,5,5,-heptamethyltrisiloxan-3-yl)pentyl]pyrrolo[3,4-c]pyrrole-1,4-dione
• 英文别名: 2,5-Bis[5-[methyl-bis(trimethylsilyloxy)silyl]pentyl]-1,4-dithiophen-2-ylpyrrolo[3,4-c]pyrrole-3,6-dione
• CAS: 1443134-80-2
• 化学式: C₃₈H₆₈N₂O₆S₂Si₆
• 分子量: 881.613
• InChiKey: HORKSSNEOOLWDT-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  11.51
• 重原子数：
  54
• 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：
  134
• 氢给体数：
  0
• 氢受体数：
  8

反应信息

• 作为反应物：
  描述：

  3,6-dithien-2-yl-2,5-bis[6-(1,1,1,3,5,5,5,-heptamethyltrisiloxan-3-yl)pentyl]pyrrolo[3,4-c]pyrrole-1,4-dione 在 N-溴代丁二酰亚胺(NBS) 、 四(三苯基膦)钯 、 potassium carbonate 作用下， 以 四氢呋喃 、 氯仿 为溶剂， 反应 120.0h， 生成 5-[5-[2,5-Bis[5-[methyl-bis(trimethylsilyloxy)silyl]pentyl]-3,6-dioxo-1-thiophen-2-ylpyrrolo[3,4-c]pyrrol-4-yl]thiophen-2-yl]thiophene-2-carbaldehyde
  参考文献：
  名称：

  HETEROCYCLIC COMPOUND AND ORGANIC SOLAR CELL COMPRISING SAME

  摘要：

  本规范涉及一种杂环化合物和包括该化合物的有机太阳能电池。

  公开号：

  US20180057515A1
• 作为产物：
  描述：

  3,6-dithiophen-2-yl-2,5-dihydropyrrolo[3,4-c]pyrrole-1,4-dione 在 platinum⁽⁰⁾-1,3-divinyl-1,1,3,3-tetramethyldisiloxane 、 potassium carbonate 作用下， 以 5,5-dimethyl-1,3-cyclohexadiene 、 N,N-二甲基甲酰胺 、 甲苯 为溶剂， 生成 3,6-dithien-2-yl-2,5-bis[6-(1,1,1,3,5,5,5,-heptamethyltrisiloxan-3-yl)pentyl]pyrrolo[3,4-c]pyrrole-1,4-dione
  参考文献：
  名称：

  Boosting the Ambipolar Performance of Solution-Processable Polymer Semiconductors via Hybrid Side-Chain Engineering

  摘要：

  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.

  DOI：

  10.1021/ja403949g

文献信息

• Siloxane-Based Hybrid Semiconducting Polymers Prepared by Fluoride-Mediated Suzuki Polymerization
  作者：Junghoon Lee、A-Reum Han、Sang Myeon Lee、Dohyuk Yoo、Joon Hak Oh、Changduk Yang

  DOI：10.1002/anie.201411557

  日期：2015.4.7

  important class of organic‐inorganic hybrids. In this report, a practical variation of the Suzuki polymerization to generate semiconducting polymeric hybrids based on siloxane units, which proceeds under essentially nonbasic conditions, is presented. This method generates solution‐processable poly(diketopyrrolopyrrole‐alt‐benzothiadiazole) (PDPPBT‐Si) consisting of the hybrid siloxane substituents, which could

  含硅氧烷的材料是一类重要的有机-无机杂化材料。在该报告中，提出了一种实际的Suzuki聚合方法，以产生基于硅氧烷单元的半导体聚合物杂化体，该杂化体基本上在非碱性条件下进行。此方法生成溶液加工聚（diketopyrrolopyrrole- ALT -benzothiadiazole）（PDPPBT-Si）的组成混合的硅氧烷取代基，其不能使用常规的方法来制备的。PDPPBT-Si具有出色的双极性晶体管性能，且空穴和电子FET迁移率均衡。通过这种方法合成的含硅氧烷的DPP-噻吩聚合物类（PDPP3T-Si和PDPP4T-Si）具有高达1.29 cm 2  V -1的高空穴迁移率 s -1。通过使用各种芳基二卤化物和芳基二硼酸/酯，这种合成方法应可提供使用各种新颖的含硅氧烷共轭半导体种类的途径。