3,6-bis{5-[(ethylfuran-2-carboxylate)-2-yl]thiophene-2-yl}-2,5-bis(2-ethylhexyl)pyrrolo[3,4-c]pyrrole-1,4-dione | 1597492-86-8

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 呋喃
• 英文名称: 3,6-bis{5-[(ethylfuran-2-carboxylate)-2-yl]thiophene-2-yl}-2,5-bis(2-ethylhexyl)pyrrolo[3,4-c]pyrrole-1,4-dione
• 英文别名: Ethyl 5-[5-[4-[5-(5-ethoxycarbonylfuran-2-yl)thiophen-2-yl]-2,5-bis(2-ethylhexyl)-3,6-dioxopyrrolo[3,4-c]pyrrol-1-yl]thiophen-2-yl]furan-2-carboxylate；ethyl 5-[5-[4-[5-(5-ethoxycarbonylfuran-2-yl)thiophen-2-yl]-2,5-bis(2-ethylhexyl)-3,6-dioxopyrrolo[3,4-c]pyrrol-1-yl]thiophen-2-yl]furan-2-carboxylate
• CAS: 1597492-86-8
• 化学式: C₄₄H₅₂N₂O₈S₂
• 分子量: 801.037
• InChiKey: UYKQPUMHGRHWMX-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  10.5
• 重原子数：
  56
• 可旋转键数：
  22
• 环数：
  6.0
• sp3杂化的碳原子比例：
  0.45
• 拓扑面积：
  176
• 氢给体数：
  0
• 氢受体数：
  10

反应信息

• 作为产物：
  描述：

  5-溴-2-糠酸 在 四(三苯基膦)钯 、 三甲基氯硅烷 作用下， 以 甲苯 为溶剂， 反应 73.0h， 生成 3,6-bis{5-[(ethylfuran-2-carboxylate)-2-yl]thiophene-2-yl}-2,5-bis(2-ethylhexyl)pyrrolo[3,4-c]pyrrole-1,4-dione
  参考文献：
  名称：

  A diketopyrrolopyrrole molecule end-capped with a furan-2-carboxylate moiety: the planarity of molecular geometry and photovoltaic properties

  摘要：

  我们设计并合成了一种具有全平面分子几何结构的二吡咯并吡咯（DPP）分子，即3,6-双{5-[(乙基呋喃-2-羧酸酯)-2-基]噻吩-2-基}-2,5-双(2-乙基己基)吡咯并[3,4-c]吡咯-1,4-二酮（DPP(CF)2），用于溶液加工有机太阳能电池（OSC）。根据理论计算，两个呋喃-2-羧酸酯端基与DPP核心之间的二面角仅为0.56°。由于这种可忽略的位错畸变，DPP(CF)2的分子构象可视为完全共面，从而提高了DPP(CF)2薄膜的结晶度。因此，DPP(CF)2的空穴迁移率比以噻吩-2-羧酸酯为端基的DPP衍生物（DPP(CT)2）高一个数量级。DPP(CF)2具有1.60 eV的低光带隙（Eg）和-5.33 eV的低能级最高占分子轨道（HOMO），这意味着DPP(CF)2是OSC的有前景的电子给体。我们制造了以DPP(CF)

  DOI：

  10.1039/c3ta13534a

文献信息

• A diketopyrrolopyrrole molecule end-capped with a furan-2-carboxylate moiety: the planarity of molecular geometry and photovoltaic properties
  作者：Lei Fu、Weifei Fu、Pei Cheng、Zhixin Xie、Congcheng Fan、Minmin Shi、Jun Ling、Jianhui Hou、Xiaowei Zhan、Hongzheng Chen

  DOI：10.1039/c3ta13534a

  日期：——

  We designed and synthesized a diketopyrrolopyrrole (DPP) molecule with a fully-planar molecular geometry, 3,6-bis5-[(ethylfuran-2-carboxylate)-2-yl]thiophene-2-yl}-2,5-bis(2-ethylhexyl)pyrrolo[3,4-c]pyrrole-1,4-dione (DPP(CF)2), for solution-processable organic solar cells (OSCs). It is theoretically calculated that the dihedral angles between the two furan-2-carboxylate end-groups and the DPP core are both only 0.56°. Due to this negligible steric distortion, the molecular conformation of DPP(CF)2 can be considered fully coplanar, leading to a higher crystallinity for the DPP(CF)2 film. As a result, the hole mobility of DPP(CF)2 is one order of magnitude higher than that of the DPP derivative with thiophene-2-carboxylate as the end-group (DPP(CT)2). DPP(CF)2 exhibits both a low optical band gap (Eg) of 1.60 eV and a low-lying highest occupied molecular orbital (HOMO) energy level of −5.33 eV, implying that DPP(CF)2 is a promising electron donor for OSCs. OSCs with DPP(CF)2 or DPP(CT)2 as the electron donor and [6,6]-phenyl-C71-butyric acid methyl ester (PC71BM) as the electron acceptor were fabricated. It is found that the DPP(CF)2-based devices exhibit much better photovoltaic performance than the DPP(CT)2-based devices, with the highest power conversion efficiency of 5.37% and a short-circuit current density of 11.4 mA cm−2. This phenomenon can be ascribed to the superior charge-transporting ability of DPP(CF)2 due to its fully-planar molecular geometry.

  我们设计并合成了一种具有全平面分子几何结构的二吡咯并吡咯（DPP）分子，即3,6-双5-[(乙基呋喃-2-羧酸酯)-2-基]噻吩-2-基}-2,5-双(2-乙基己基)吡咯并[3,4-c]吡咯-1,4-二酮（DPP(CF)2），用于溶液加工有机太阳能电池（OSC）。根据理论计算，两个呋喃-2-羧酸酯端基与DPP核心之间的二面角仅为0.56°。由于这种可忽略的位错畸变，DPP(CF)2的分子构象可视为完全共面，从而提高了DPP(CF)2薄膜的结晶度。因此，DPP(CF)2的空穴迁移率比以噻吩-2-羧酸酯为端基的DPP衍生物（DPP(CT)2）高一个数量级。DPP(CF)2具有1.60 eV的低光带隙（Eg）和-5.33 eV的低能级最高占分子轨道（HOMO），这意味着DPP(CF)2是OSC的有前景的电子给体。我们制造了以DPP(CF)