2,5-Dihexyl-3,6-bis-(4-methoxy-phenyl)-2,5-dihydro-pyrrolo[3,4-c]pyrrole-1,4-dione | 151426-36-7

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡咯啉
• 英文名称: 2,5-Dihexyl-3,6-bis-(4-methoxy-phenyl)-2,5-dihydro-pyrrolo[3,4-c]pyrrole-1,4-dione
• 英文别名: 2,5-Dihexyl-3,6-bis(4-methoxyphenyl)pyrrolo[3,4-c]pyrrole-1,4(2h,5h)-dione；2,5-dihexyl-1,4-bis(4-methoxyphenyl)pyrrolo[3,4-c]pyrrole-3,6-dione
• CAS: 151426-36-7
• 化学式: C₃₂H₄₀N₂O₄
• 分子量: 516.681
• InChiKey: JVDFJQWWVPCRCN-UHFFFAOYSA-N

物化性质

• 沸点：
  699.0±55.0 °C(Predicted)
• 密度：
  1.17±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  6.67
• 重原子数：
  38.0
• 可旋转键数：
  14.0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.44
• 拓扑面积：
  59.08
• 氢给体数：
  0.0
• 氢受体数：
  4.0

反应信息

• 作为反应物：
  描述：

  2,5-Dihexyl-3,6-bis-(4-methoxy-phenyl)-2,5-dihydro-pyrrolo[3,4-c]pyrrole-1,4-dione 在 三溴化硼 作用下， 以 二氯甲烷 为溶剂， 反应 24.0h， 以82%的产率得到2,5-Dihexyl-3,6-bis(4-hydroxyphenyl)pyrrolo[3,4-c]pyrrole-1,4(2h,5h)-dione
  参考文献：
  名称：

  Rational designs of multifunctional polymers

  摘要：

  To manifest photorefractive effects, a polymer must possess a photocharge generator, a charge transporter, a charge trapping center, and a nonlinear optical chromophore. We utilized the Stille coupling reaction to synthesize a novel type of multifunctional polymer that contains a conjugated backbone and a second-order NLO chromophore. The expectation that the polymers will possess photorefractivity is the design idea behind the structure of the polymers. Because the conjugated backbone absorbs photons in the visible region and is photoconductive, it is expected to play the triple role of charge generator, charge transporter, and backbone. Thus, the four functionalities necessary to manifest the PR effect will exist simultaneously in a single polymer. The second harmonic generation and the photoconductivity measurements revealed that the polymers are nonlinear-optically active and photoconductive. Two beam-coupling experiments clearly indicated asymmetric optical energy exchange, which is an unambiguous demonstration of photorefractivity.

  DOI：

  10.1021/ja00078a012
• 作为产物：
  描述：

  4-甲氧基苯甲腈 在 potassium tert-butylate 、 sodium hydride 作用下， 以 叔丁醇 为溶剂， 反应 5.0h， 生成 2,5-Dihexyl-3,6-bis-(4-methoxy-phenyl)-2,5-dihydro-pyrrolo[3,4-c]pyrrole-1,4-dione
  参考文献：
  名称：

  Rational designs of multifunctional polymers

  摘要：

  To manifest photorefractive effects, a polymer must possess a photocharge generator, a charge transporter, a charge trapping center, and a nonlinear optical chromophore. We utilized the Stille coupling reaction to synthesize a novel type of multifunctional polymer that contains a conjugated backbone and a second-order NLO chromophore. The expectation that the polymers will possess photorefractivity is the design idea behind the structure of the polymers. Because the conjugated backbone absorbs photons in the visible region and is photoconductive, it is expected to play the triple role of charge generator, charge transporter, and backbone. Thus, the four functionalities necessary to manifest the PR effect will exist simultaneously in a single polymer. The second harmonic generation and the photoconductivity measurements revealed that the polymers are nonlinear-optically active and photoconductive. Two beam-coupling experiments clearly indicated asymmetric optical energy exchange, which is an unambiguous demonstration of photorefractivity.

  DOI：

  10.1021/ja00078a012

文献信息

• Towards more sustainable synthesis of diketopyrrolopyrroles
  作者：Flavia Pop、Joshua Humphreys、Jesper Schwarz、Liam Brown、Ashmiani van den Berg、David B. Amabilino

  DOI：10.1039/c9nj01074b

  日期：——

  The alkylation of 1,4-diketo-3,6-arylpyrrolo[3,4-c]pyrroles (ArDPP) is one of the most important steps in the synthesis of soluble materials based on these molecules and the polymers derived from them (that are employed widely in putative organic solar cells). Here we report an improvement in their method of synthesis replacing habitual solvent and base. Compared with more usual conditions, we employed

  1,4-二酮-3,6-芳基吡咯并[3,4- c ]吡咯（ArDPP）的烷基化是基于这些分子和衍生自它们的聚合物合成可溶性材料的最重要步骤之一被广泛用于推定的有机太阳能电池中。在这里，我们报告了他们替代常规溶剂和碱的合成方法的改进。与更常用的条件相比，我们使用乙腈作为溶剂可提高产率或类似率，并且毒性和危险性废物更少，反应时间和温度更低，并且可以回收未反应的原料。与二甲基甲酰胺和N不同-甲基吡咯烷酮，是最常用的溶剂。我们的反应条件已在三种不同的ArDPP（Ar =噻吩，苯基和4-甲氧基苯基）上用各种直链和支链烷基试剂进行了测试。与已发表的报告相比，结果显示了相似且改进的结果，同时在许多情况下减少了反应的浪费和危害，并简化了产物的纯化。总体而言，该方法对环境的影响较小，具有更高的成本效益，并且不需要使用干燥溶剂或惰性气氛。