3,6-di(thiophen-2-yl)pyrrolo[3,4-c]pyrrole-1,4(2H,5H)-dithione | 952146-92-8

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑烷类
• 英文名称: 3,6-di(thiophen-2-yl)pyrrolo[3,4-c]pyrrole-1,4(2H,5H)-dithione
• 英文别名: 1,4-dithiophen-2-yl-2,5-dihydropyrrolo[3,4-c]pyrrole-3,6-dithione
• CAS: 952146-92-8
• 化学式: C₁₄H₈N₂S₄
• 分子量: 332.495
• InChiKey: JNBDVGXUMTZIIA-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.79
• 重原子数：
  20.0
• 可旋转键数：
  2.0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  24.06
• 氢给体数：
  2.0
• 氢受体数：
  4.0

反应信息

• 作为反应物：
  描述：

  3,6-di(thiophen-2-yl)pyrrolo[3,4-c]pyrrole-1,4(2H,5H)-dithione 在 N-溴代丁二酰亚胺(NBS) 、 potassium carbonate 作用下， 以 氯仿 、 丙酮 为溶剂， 反应 12.0h， 生成 1,4-bis(5-bromothiophen-2-yl)-3,6-bis(2-ethylhexylthio)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
• 作为产物：
  描述：

  在 劳森试剂 作用下， 生成 3,6-di(thiophen-2-yl)pyrrolo[3,4-c]pyrrole-1,4(2H,5H)-dithione
  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

• An A‐D‐A′‐D‐A Conjugated Molecule Entailing Diazapentalene Unit for an n‐Type Organic Semiconductor
  作者：Gaobo Lin、Lingna Wang、Yizhou Yang、Zitong Liu、Guanxin Zhang、Deqing Zhang

  DOI：10.1002/asia.201801691

  日期：2019.5.15

  Conjugated molecules with low lying LUMO levels are demanding for the development of air stable n‐type organic semiconductors. In this paper, we report a new A‐D‐A′‐D‐A conjugated molecule (DAPDCV) entailing diazapentalene (DAP) and dicyanovinylene groups as electron accepting units. Both theoretical and electrochemical studies manifest that the incorporation of DAP unit in the conjugated molecule

  LUMO含量低的共轭分子对开发空气稳定的n型有机半导体提出了要求。在本文中，我们报道了一种新的A‐D‐A′‐D‐A共轭分子（DAPDCV），其中以重氮杂戊烯（DAP）和二氰基亚乙烯基为电子接受单元。理论和电化学研究均表明，在共轭分子中掺入DAP单元可有效降低LUMO能级。因此，薄膜的DAPDCV显示n型半导体与电子迁移率高达行为0.16厘米2个⋅V -1 ⋅s -1氮气氛下热处理后2气氛。另外，DAPDCV的薄膜还示出了在空气中的迁移率达到0.078厘米稳定n型传输性质2个⋅V -1 ⋅s -1。
• 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
• DITHIOALKYLPYRROLOPYRROLES AND THE USE THEREOF AS DYES
  申请人：Merck Patent GmbH

  公开号：US20180375030A1

  公开（公告）日：2018-12-27

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