1,4-bis(2-ethylhexylthio)-3,6-di(thiophen-2-yl)pyrrolo[3,4-c]-pyrrole | 1370507-71-3

• 分子结构分类: 有机化合物 - 有机硫化合物 - 亚氨硫酯类
• 英文名称: 1,4-bis(2-ethylhexylthio)-3,6-di(thiophen-2-yl)pyrrolo[3,4-c]-pyrrole
• 英文别名: 1,4-Bis(2-ethylhexylsulfanyl)-3,6-dithiophen-2-ylpyrrolo[3,4-c]pyrrole；1,4-bis(2-ethylhexylsulfanyl)-3,6-dithiophen-2-ylpyrrolo[3,4-c]pyrrole
• CAS: 1370507-71-3
• 化学式: C₃₀H₄₀N₂S₄
• 分子量: 556.925
• InChiKey: DXYHIEUNDKGMLY-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  10.8
• 重原子数：
  36
• 可旋转键数：
  16
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.53
• 拓扑面积：
  132
• 氢给体数：
  0
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  1,4-bis(2-ethylhexylthio)-3,6-di(thiophen-2-yl)pyrrolo[3,4-c]-pyrrole 在 N-溴代丁二酰亚胺(NBS) 作用下， 以 氯仿 为溶剂， 以63%的产率得到1,4-bis(5-bromothiophen-2-yl)-3,6-bis(2-ethylhexylthio)pyrrolo-[3,4-c]pyrrole
  参考文献：
  名称：

  近红外热致变色二氮杂戊烯染料

  摘要：

  可见一系列具有可调能隙的含2,5-二氮杂戊烯的染料，对各种酸的近红外卤代变色，其质子化的对应物代表一类新的热致变色材料，其近红外吸收在室温下开启，在高于室温时关闭50°C。

  DOI：

  10.1002/adma.201104711
• 作为产物：
  描述：

  在 劳森试剂 、 potassium carbonate 作用下， 以 丙酮 为溶剂， 反应 12.0h， 生成 1,4-bis(2-ethylhexylthio)-3,6-di(thiophen-2-yl)pyrrolo[3,4-c]-pyrrole
  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

• Dithioalkylpyrrolopyrroles and the use thereof as dyes
  申请人：Merck Patent GmbH

  公开号：US10868257B2

  公开（公告）日：2020-12-15

  Novel dithiopyrrolopyrrole derivatives having dichroic properties which have very high photostability in solution in a liquid-crystalline host are proposed.

  本研究提出了具有二向色特性的新型二硫吡咯衍生物，它们在液晶主溶液中具有极高的光稳定性。
• DITHIOALKYLPYRROLOPYRROLE UND IHRE VERWENDUNG ALS FARBSTOFFE
  申请人：Merck Patent GmbH

  公开号：EP3319964B1

  公开（公告）日：2020-07-22
• [DE] DITHIOALKYLPYRROLOPYRROLE UND IHRE VERWENDUNG ALS FARBSTOFFE<br/>[EN] DITHIO-ALKYL-PYRROLO-PYRROLES AND USE THEREOF AS DYES<br/>[FR] DITHIOALKYLPYRROLOPYRROLES ET LEUR UTILISATION EN TANT QUE COLORANTS
  申请人：MERCK PATENT GMBH

  公开号：WO2017008880A1

  公开（公告）日：2017-01-19

  Vorgeschlagen werden neue Dithiopyrrolopyrrol-Derivate mit dichroitischen Eigenschaften, die in Lösung in einem flüssigkristallinen Host eine sehr hohe Lichtechtheit aufweisen.
• Family of Diazapentalene Chromophores and Narrow-Band-Gap Polymers: Synthesis, Halochromism, Halofluorism, and Visible–Near Infrared Photodetectivity
  作者：Gang Qian、Ji Qi、James A. Davey、James S. Wright、Zhi Yuan Wang

  DOI：10.1021/cm300938s

  日期：2012.6.26

  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.
• Near-Infrared Thermochromic Diazapentalene Dyes
  作者：Gang Qian、Zhi Yuan Wang

  DOI：10.1002/adma.201104711

  日期：2012.3.22

  A series of 2,5‐diazapentalene containing dyes with tunable energy gaps are visible and near‐infrared halochromic towards various acids and their protonated counterparts represent a new class of thermochromic materials with the near‐infrared absorption being switched on at room temperature and off above 50 °C.

  可见一系列具有可调能隙的含2,5-二氮杂戊烯的染料，对各种酸的近红外卤代变色，其质子化的对应物代表一类新的热致变色材料，其近红外吸收在室温下开启，在高于室温时关闭50°C。