3,6-dithien-2-yl-2,5-di(but-3-en-1-yl)pyrrolo[3,4-c]pyrrole-1,4-dione | 1443134-77-7

• 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(but-3-en-1-yl)pyrrolo[3,4-c]pyrrole-1,4-dione
• CAS: 1443134-77-7
• 化学式: C₂₂H₂₀N₂O₂S₂
• 分子量: 408.545
• InChiKey: ASXROAGUGZLSIH-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.77
• 重原子数：
  28.0
• 可旋转键数：
  8.0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.18
• 拓扑面积：
  40.62
• 氢给体数：
  0.0
• 氢受体数：
  4.0

反应信息

• 作为反应物：
  描述：

  3,6-dithien-2-yl-2,5-di(but-3-en-1-yl)pyrrolo[3,4-c]pyrrole-1,4-dione 在 N-溴代丁二酰亚胺(NBS) 、 platinum⁽⁰⁾-1,3-divinyl-1,1,3,3-tetramethyldisiloxane 作用下， 以 5,5-dimethyl-1,3-cyclohexadiene 、 氯仿 、 甲苯 为溶剂， 反应 48.0h， 生成 3,6-di(2-bromothien-5-yl)-2,5-bis[6-(1,1,1,3,5,5,5,-heptamethyltrisiloxan-3-yl)butyl]-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
• 作为产物：
  描述：

  3,6-dithiophen-2-yl-2,5-dihydropyrrolo[3,4-c]pyrrole-1,4-dione 、 4-溴-1-丁烯 在 potassium carbonate 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 以67%的产率得到3,6-dithien-2-yl-2,5-di(but-3-en-1-yl)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