3-(5-bromothiophen-2-yl)-2-(2-ethylhexyl)-4-(2-ethylhexyloxy)-6-(thiophen-2-yl)pyrrolo[3,4-c]pyrrol-1(2H)-one | 1380497-24-4

• 分子结构分类: 有机化合物 - 有机杂环化合物
• 英文名称: 3-(5-bromothiophen-2-yl)-2-(2-ethylhexyl)-4-(2-ethylhexyloxy)-6-(thiophen-2-yl)pyrrolo[3,4-c]pyrrol-1(2H)-one
• CAS: 1380497-24-4
• 化学式: C₃₀H₃₉BrN₂O₂S₂
• 分子量: 603.688
• InChiKey: YPCJTVBTLSOYMO-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  9.4
• 重原子数：
  37.0
• 可旋转键数：
  14.0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.53
• 拓扑面积：
  41.9
• 氢给体数：
  0.0
• 氢受体数：
  5.0

反应信息

• 作为反应物：
  描述：

  9-(2-乙基己基)-2,7-双(4,4,5,5-四甲基-1,3,2-二噁硼烷-2-基)-9h-咔唑 、 3-(5-bromothiophen-2-yl)-2-(2-ethylhexyl)-4-(2-ethylhexyloxy)-6-(thiophen-2-yl)pyrrolo[3,4-c]pyrrol-1(2H)-one 在 四(三苯基膦)钯 、 potassium carbonate 作用下， 以 四氢呋喃 、 水 为溶剂， 反应 18.0h， 以27%的产率得到3,3'-(5,5'-(9-(2-ethylhexyl)-9H-carbazole-2,7-diyl)bis(thiophene-5,2-diyl))bis(2-(2-ethylhexyl)-4-(2-ethylhexyloxy)-6-(thiophen-2-yl)-pyrrolo[3,4-c]pyrrol-1(2H)-one)
  参考文献：
  名称：

  Family of Diazapentalene Chromophores and Narrow-Band-Gap Polymers: Synthesis, Halochromism, Halofluorism, and Visible–Near Infrared Photodetectivity

  摘要：

  A family of pyrrolo[3,4-c]pyrrol-1(2H)-one (PPO) and 2,5-diazapentalene (DAP) chromophores and DAP-containing polymers were synthesized, and their optical and electrochemical properties were studied. PPO and DAP chromophores are readily obtained by chemical transformation of the lactam unit in diketopyrrolopyrrole (DPP) dyes and can be used as versatile building blocks for construction of a variety of conjugated low-band-gap compounds and polymers. In comparison with the DPP chromophores, PPO and DAP chromophores have narrower energy gaps and low-lying HOMO levels in the order DPP > PPO > DAP. Interestingly, the PPO and DAP chromophores exhibit unique visible and near-infrared halochromic and halofluoric properties. The emission spectrum of DAP-containing polymer 6d covers the telecommunication window including the wavelength of 1310 nm. The photodetector with a device configuration of ITO/PEDOT:PSS (35 nm)/active layer (100 nm)/Al (100 nm) was fabricated using a blend of polymer 6d and [6,6]-phenyl-C-61-butyric acid methyl ester (PC61BM) in a weight ratio of 1:3 as the active layer and exhibited photocurrent spectral response from 400 to 1000 nm and the detectivity in an order of 10(11) Jones at 800 nm.

  DOI：

  10.1021/cm300938s
• 作为产物：
  描述：

  在 N-溴代丁二酰亚胺(NBS) 、 potassium carbonate 作用下， 以 氯仿 、 N,N-二甲基甲酰胺 为溶剂， 反应 6.0h， 生成 3-(5-bromothiophen-2-yl)-2-(2-ethylhexyl)-4-(2-ethylhexyloxy)-6-(thiophen-2-yl)pyrrolo[3,4-c]pyrrol-1(2H)-one
  参考文献：
  名称：

  Family of Diazapentalene Chromophores and Narrow-Band-Gap Polymers: Synthesis, Halochromism, Halofluorism, and Visible–Near Infrared Photodetectivity

  摘要：

  A family of pyrrolo[3,4-c]pyrrol-1(2H)-one (PPO) and 2,5-diazapentalene (DAP) chromophores and DAP-containing polymers were synthesized, and their optical and electrochemical properties were studied. PPO and DAP chromophores are readily obtained by chemical transformation of the lactam unit in diketopyrrolopyrrole (DPP) dyes and can be used as versatile building blocks for construction of a variety of conjugated low-band-gap compounds and polymers. In comparison with the DPP chromophores, PPO and DAP chromophores have narrower energy gaps and low-lying HOMO levels in the order DPP > PPO > DAP. Interestingly, the PPO and DAP chromophores exhibit unique visible and near-infrared halochromic and halofluoric properties. The emission spectrum of DAP-containing polymer 6d covers the telecommunication window including the wavelength of 1310 nm. The photodetector with a device configuration of ITO/PEDOT:PSS (35 nm)/active layer (100 nm)/Al (100 nm) was fabricated using a blend of polymer 6d and [6,6]-phenyl-C-61-butyric acid methyl ester (PC61BM) in a weight ratio of 1:3 as the active layer and exhibited photocurrent spectral response from 400 to 1000 nm and the detectivity in an order of 10(11) Jones at 800 nm.

  DOI：

  10.1021/cm300938s

文献信息

• Diketopyrrolopyrrole (DPP) functionalized tetrathienothiophene (TTA) small molecules for organic thin film transistors and photovoltaic cells
  作者：Nanjia Zhou、Sureshraju Vegiraju、Xinge Yu、Eric F. Manley、Melanie R. Butler、Matthew J. Leonardi、Peijun Guo、Wei Zhao、Yan Hu、Kumaresan Prabakaran、Robert P. H. Chang、Mark A. Ratner、Lin X. Chen、Antonio Facchetti、Ming-Chou Chen、Tobin J. Marks

  DOI：10.1039/c5tc01348h

  日期：——

  Diketopyrrolopyrrole (DPP) end capped tetrathienoacene (TTA) small molecules approaching the hole mobility 0.1 cm² V⁻¹ s⁻¹ in OFET and efficiency >4% in OPV.

  Diketopyrrolopyrrole（DPP）末端封端的四噻吩乙烯（TTA）小分子，在OFET中接近空穴迁移率0.1 cm² V⁻¹ s⁻¹，在OPV中的效率> 4％。