2,5-bis(2-ethylhexyl)-3,6-bis(5-(4-methoxyphenyl)thiophen-2-yl)pyrrolo[3,4-c]pyrrole-1,4(2H,5H)-dione | 1401967-47-2

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯酚醚
• 英文名称: 2,5-bis(2-ethylhexyl)-3,6-bis(5-(4-methoxyphenyl)thiophen-2-yl)pyrrolo[3,4-c]pyrrole-1,4(2H,5H)-dione
• 英文别名: 2,5-Bis(2-ethylhexyl)-1,4-bis[5-(4-methoxyphenyl)thiophen-2-yl]pyrrolo[3,4-c]pyrrole-3,6-dione
• CAS: 1401967-47-2
• 化学式: C₄₄H₅₂N₂O₄S₂
• 分子量: 737.04
• InChiKey: XRGKKECHBQRLHK-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  11.1
• 重原子数：
  52
• 可旋转键数：
  18
• 环数：
  6.0
• sp3杂化的碳原子比例：
  0.41
• 拓扑面积：
  116
• 氢给体数：
  0
• 氢受体数：
  6

反应信息

• 作为产物：
  描述：

  2,5-双(2-乙基己基)-3,6-二(噻吩-2-基)吡咯并[3,4-c]吡咯-1,4(2H,5h)-二酮 、 4-碘苯甲醚 在 tris-(dibenzylideneacetone)dipalladium(0) 、 三(2-甲氧基苯基)膦 、 caesium carbonate 、 三甲基乙酸 作用下， 以 neat (no solvent) 为溶剂， 反应 15.0h， 以51%的产率得到2,5-bis(2-ethylhexyl)-3,6-bis(5-(4-methoxyphenyl)thiophen-2-yl)pyrrolo[3,4-c]pyrrole-1,4(2H,5H)-dione
  参考文献：
  名称：

  通过C–H键活化的无溶剂Pd催化杂芳基-芳基偶联，用于合成扩展的杂芳族共轭分子。

  摘要：

  在无溶剂和非无水条件下，噻吩并吡咯烷二酮，二酮并吡咯并吡咯，苯并二噻吩衍生物和氟化杂芳基与官能化的芳基碘化物直接芳基化已得到证明。该反应在空气存在下进行，并且在两个偶联配偶体上都具有多个官能团，从而可以方便地合成扩展的杂芳族共轭分子。

  DOI：

  10.1021/acs.joc.8b01284

文献信息

• Transition metal-catalyzed C–H activation as a route to structurally diverse di(arylthiophenyl)-diketopyrrolopyrroles
  作者：Junxiang Zhang、Dun-Yen Kang、Stephen Barlow、Seth R. Marder

  DOI：10.1039/c2jm35398a

  日期：——

  Dithiophenyldiketopyrrolopyrroles can be directly (hetero)arylated in moderate to excellent yields by Pd-catalyzed coupling to the CH position of a fluoro(hetero)arene (in the presence of Ag2CO3) or the CBr position of a bromo(hetero)arene.

  在 Ag2CO3 的存在下，通过 Pd 催化与氟代（杂）炔的 CH 位或溴代（杂）炔的 CBr 位偶联，二硫苯基二酮吡咯并可直接（杂）芳基化，产率从中等到极好。
• “N-alkyl diketopyrrolopyrrole-based fluorophores for luminescent solar concentrators: Effect of the alkyl chain on dye efficiency”
  作者：Jonathan Lucarelli、Marco Lessi、Chiara Manzini、Pierpaolo Minei、Fabio Bellina、Andrea Pucci

  DOI：10.1016/j.dyepig.2016.03.036

  日期：2016.12

  We report on the preparation of luminescent solar concentrators (LSCs) made of poly(methyl methacrylate) (PMMA) thin films doped with six new diketopyrrolopyrrole (DPP) fluorophores obtained in good yields by using simple N-alkylation and direct C-H arylation synthetic strategies. Spectroscopic investigations in solution and in PMMA thin films combined with photocurrent measurements revealed that the branched alkyl chains were efficient in preventing DPP segregation from the PMMA matrix thanks to their higher steric hindrance. The aromatic substituent was found to expand DPP conjugation but favoured DPP adverse aggregation, thus affecting fluorescence emission and photocurrents of PMMA films. The worthwhile combination of the appropriate alkyl chain and aromatic moieties assured to achieve optical efficiency of 6.8% that was comparable to that of PMMA LSCs of the state-of-the art (7.2%). (C) 2016 Elsevier Ltd. All rights reserved.