3,6-双(5-(苯并呋喃-2-基)噻吩-2-基)-2,5-双(2-乙基己基)吡咯[3,4-c]吡咯-1,4(2H,5H)-二酮 | 1241836-03-2

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 苯并呋喃
• 中文名称: 3,6-双(5-(苯并呋喃-2-基)噻吩-2-基)-2,5-双(2-乙基己基)吡咯[3,4-c]吡咯-1,4(2H,5H)-二酮
• 中文别名: （5-（苯并呋喃-2-基）噻吩-2-基）-2,5-双（2-乙基己基）吡咯并[3,4-c]吡咯-1,4（2H，5H）-二酮
• 英文名称: (3,6-bis[5-(benzofuran-2-yl)-thiophen-2-yl]-2,5-bis(2-ethylhexyl)pyrrolo[3,4-c]pyrrole-1,4-dione)
• 英文别名: pyrrolo[3,4-c]pyrrole-1,4(2H,5H)-dione；1,4-bis[5-(1-benzofuran-2-yl)thiophen-2-yl]-2,5-bis(2-ethylhexyl)pyrrolo[3,4-c]pyrrole-3,6-dione
• CAS: 1241836-03-2
• 化学式: C₄₆H₄₈N₂O₄S₂
• 分子量: 757.03
• InChiKey: AHUQRGHAKJSUKU-UHFFFAOYSA-N

物化性质

• 沸点：
  897.1±65.0 °C(Predicted)
• 密度：
  1.28±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  12.1
• 重原子数：
  54
• 可旋转键数：
  16
• 环数：
  8.0
• sp3杂化的碳原子比例：
  0.35
• 拓扑面积：
  123
• 氢给体数：
  0
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  3,6-双(5-(苯并呋喃-2-基)噻吩-2-基)-2,5-双(2-乙基己基)吡咯[3,4-c]吡咯-1,4(2H,5H)-二酮 在 劳森试剂 作用下， 以 甲苯 为溶剂， 以20%的产率得到2,5-diethylhexyl-3,6-bis(5-(benzofuran-2-yl)thiophen-2-yl)pyrrolo[3,4-c]pyrrole-1,4-dionothione
  参考文献：
  名称：

  Structure–properties relationships in conjugated molecules based on diketopyrrolopyrrole for organic photovoltaics

  摘要：

  Conjugated systems built by connecting two electron-donor side-chains to a diketopyrrolopyrrole (DPP) core have been synthesized and evaluated as donor material in heterojunction organic solar cells. The effects of composition of the side-chain on the electronic properties of the conjugated system have been analyzed on first series of compounds containing various combinations of benzofuran, benzothiophene, thiophene and furan units. In a second series of compounds, the keto groups of DPP have been replaced by one or two thioketo groups. Results of UV-vis absorption spectroscopy, fluorescence emission spectroscopy and cyclic voltammetry show that the composition of the side-chain has little effect on the HOMO and LUMO levels of the system, but strongly affects the sensitivity of the material toward thermal treatment and thus indirectly the performances of the resulting solar cells. On the other hand, replacement of the keto groups of DPP by thioketo ones leads at the same time to significant reduction of the band gap due to a decrease of the LUMO level, to a quenching of fluorescence and to dramatic decrease of the photovoltaic activity of the molecule. (C) 2012 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.dyepig.2012.03.021
• 作为产物：
  描述：

  2-氰基噻吩 在 iron(III) chloride 、 N-溴代丁二酰亚胺(NBS) 、 四(三苯基膦)钯 、 sodium 、 potassium carbonate 作用下， 以 氯仿 、 N,N-二甲基甲酰胺 、 甲苯 为溶剂， 反应 34.0h， 生成 3,6-双(5-(苯并呋喃-2-基)噻吩-2-基)-2,5-双(2-乙基己基)吡咯[3,4-c]吡咯-1,4(2H,5H)-二酮
  参考文献：
  名称：

  Structure–properties relationships in conjugated molecules based on diketopyrrolopyrrole for organic photovoltaics

  摘要：

  Conjugated systems built by connecting two electron-donor side-chains to a diketopyrrolopyrrole (DPP) core have been synthesized and evaluated as donor material in heterojunction organic solar cells. The effects of composition of the side-chain on the electronic properties of the conjugated system have been analyzed on first series of compounds containing various combinations of benzofuran, benzothiophene, thiophene and furan units. In a second series of compounds, the keto groups of DPP have been replaced by one or two thioketo groups. Results of UV-vis absorption spectroscopy, fluorescence emission spectroscopy and cyclic voltammetry show that the composition of the side-chain has little effect on the HOMO and LUMO levels of the system, but strongly affects the sensitivity of the material toward thermal treatment and thus indirectly the performances of the resulting solar cells. On the other hand, replacement of the keto groups of DPP by thioketo ones leads at the same time to significant reduction of the band gap due to a decrease of the LUMO level, to a quenching of fluorescence and to dramatic decrease of the photovoltaic activity of the molecule. (C) 2012 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.dyepig.2012.03.021

文献信息

• Solvatochromism in Diketopyrrolopyrrole Derivatives: Experimental and Computational Studies
  作者：Rebecca S. Szabadai、Jesse Roth-Barton、Kenneth P. Ghiggino、Jonathan M. White、David J. D. Wilson

  DOI：10.1071/ch14057

  日期：——

  synthesised and their solution absorption spectra characterised in a range of solvents of varying polarity. The absorption spectra of these diketopyrrolopyrrole derivatives exhibited significant negative solvatochromism. The behaviour is consistent with results of time-dependent density-functional theory calculations of excitation energies. Calculated electronic structures suggest that there is significant

  合成了一系列七个噻吩取代的二酮吡咯并吡咯衍生物，其溶液吸收光谱在一系列极性不同的溶剂中表征。这些二酮吡咯并吡咯衍生物的吸收光谱显示出显着的负溶剂变色现象。该行为与激励能量的时变密度泛函理论计算结果一致。计算的电子结构表明，在给电子体的噻吩取代基与二酮吡咯并吡咯核之间存在明显的电荷转移，但与基态相比，在激发态该电荷位移的幅度减小了。激发态的极性降低导致观察到的负溶剂溶变色。
• SEMICONDUCTING MIXTURES
  申请人：Merck Patent GmbH

  公开号：EP3173435A1

  公开（公告）日：2017-05-31

  The invention relates to novel semiconducting mixtures comprising a p-type organic semiconductor and a poly(pyrrolidinofullerene), to their use in organic photovoltaic (OPV) devices and organic photodetectors (OPD), and to OPV and OPD devices comprising these mixtures.

  本发明涉及由 p 型有机半导体和聚（吡咯烷富勒烯）组成的新型半导体混合物、它们在有机光伏器件（OPV）和有机光电探测器（OPD）中的应用，以及包含这些混合物的 OPV 和 OPD 器件。
• EP3173435B1
  申请人：——

  公开号：EP3173435B1

  公开（公告）日：2020-11-25
• [EN] PHOTOACTIVE OPTOELECTRONIC AND TRANSISTOR DEVICES<br/>[FR] DISPOSITIFS OPTOÉLECTRONIQUES PHOTOACTIFS ET À TRANSISTORS
  申请人：COMMW SCIENT IND RES ORG

  公开号：WO2014026244A1

  公开（公告）日：2014-02-20

  The present invention relates to photoactive optoelectronic devices, such as organic photovoltaic devices, and transistor devices, and to organic compounds for use in the optoelectronic and transistor devices. The present invention also relates to processes for preparing photoactive optoelectronic and transistor devices. The photoactive optoelectronic devices comprise a first and second electrode, and at least one organic light-absorbing electroactive layer in electrical connection with the first and second electrodes that generates an electrical current in response to electromagnetic radiation. The light-absorbing electroactive layer comprises an electron donor material and an electron acceptor material, the electron acceptor material comprising a compound as described herein.
• Structure–properties relationships in conjugated molecules based on diketopyrrolopyrrole for organic photovoltaics
  作者：Emilie Ripaud、Dora Demeter、Théodulf Rousseau、Emmanuel Boucard-Cétol、Magali Allain、Riccardo Po、Philippe Leriche、Jean Roncali

  DOI：10.1016/j.dyepig.2012.03.021

  日期：2012.10

  Conjugated systems built by connecting two electron-donor side-chains to a diketopyrrolopyrrole (DPP) core have been synthesized and evaluated as donor material in heterojunction organic solar cells. The effects of composition of the side-chain on the electronic properties of the conjugated system have been analyzed on first series of compounds containing various combinations of benzofuran, benzothiophene, thiophene and furan units. In a second series of compounds, the keto groups of DPP have been replaced by one or two thioketo groups. Results of UV-vis absorption spectroscopy, fluorescence emission spectroscopy and cyclic voltammetry show that the composition of the side-chain has little effect on the HOMO and LUMO levels of the system, but strongly affects the sensitivity of the material toward thermal treatment and thus indirectly the performances of the resulting solar cells. On the other hand, replacement of the keto groups of DPP by thioketo ones leads at the same time to significant reduction of the band gap due to a decrease of the LUMO level, to a quenching of fluorescence and to dramatic decrease of the photovoltaic activity of the molecule. (C) 2012 Elsevier Ltd. All rights reserved.