2,6-dibromo-3,7-difluoro-4,8-bis(2-ethylhexyloxy)benzo[1,2-b:4,5-b']dithiophene | 1268280-00-7

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 苯并噻吩类
• 英文名称: 2,6-dibromo-3,7-difluoro-4,8-bis(2-ethylhexyloxy)benzo[1,2-b:4,5-b']dithiophene
• CAS: 1268280-00-7
• 化学式: C₂₆H₃₄Br₂F₂O₂S₂
• 分子量: 640.492
• InChiKey: PPMIRMZSPCYCMG-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  11.11
• 重原子数：
  34.0
• 可旋转键数：
  14.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.62
• 拓扑面积：
  18.46
• 氢给体数：
  0.0
• 氢受体数：
  4.0

反应信息

• 作为反应物：
  描述：

  2,6-dibromo-3,7-difluoro-4,8-bis(2-ethylhexyloxy)benzo[1,2-b:4,5-b']dithiophene 、 三甲基氯化锡 在 n-butyllithium 作用下， 以 not given 为溶剂， 生成 2,6-bis(trimethyltin)-3,7-difluoro-4,8-bis(2-ethylhexyloxy)benzo[1,2-b:4,5-b']dithiophene
  参考文献：
  名称：

  Synthesis of Fluorinated Polythienothiophene-co-benzodithiophenes and Effect of Fluorination on the Photovoltaic Properties

  摘要：

  Herein, we describe the synthesis of fluorinated polythienothiophene-co-benzodithiophenes (PTBFs) and the characterization of their physical properties, especially their performance in solar cells. Fluorination of the polymer backbone lowered both the HOMO and LUMO energy levels and simultaneously widened the energy bandgap of the polymer (0.1-0.2 eV). Incorporation of fluorine into the various positions of the polymer backbone significantly affected the solar cells' power conversion efficiency from 2.3% to 7.2%. Detailed studies revealed that the polymer containing mono-fluorinated thienothiophene gave the best solar cell performance. Perfluorination of the polymer backbone led to poor compatibility with PC71BM molecules, thus poor solar energy conversion efficiency. This is possibly due to the enhanced self-organization properties of the polymer chains and the fluorophobicity effect. Furthermore, it was found that perfluorination of the polymer backbone resulted in poor photochemical stability against singlet oxygen attack. Theoretical studies indicated that the internal polarization caused enhancement of the negative charge density on thienothiophene rings, which rendered them vulnerable to [2+4] cycloaddition reaction with singlet oxygen.

  DOI：

  10.1021/ja108601g
• 作为产物：
  描述：

  4,8-双(2-乙基己氧基)苯并 [1,2-b,4,5-b2]-二-噻吩 在 正丁基锂 、 溴 作用下， 以 四氢呋喃 、 正己烷 、 氯仿 为溶剂， 反应 31.33h， 生成 2,6-dibromo-3,7-difluoro-4,8-bis(2-ethylhexyloxy)benzo[1,2-b:4,5-b']dithiophene
  参考文献：
  名称：

  Synthesis of Fluorinated Polythienothiophene-co-benzodithiophenes and Effect of Fluorination on the Photovoltaic Properties

  摘要：

  Herein, we describe the synthesis of fluorinated polythienothiophene-co-benzodithiophenes (PTBFs) and the characterization of their physical properties, especially their performance in solar cells. Fluorination of the polymer backbone lowered both the HOMO and LUMO energy levels and simultaneously widened the energy bandgap of the polymer (0.1-0.2 eV). Incorporation of fluorine into the various positions of the polymer backbone significantly affected the solar cells' power conversion efficiency from 2.3% to 7.2%. Detailed studies revealed that the polymer containing mono-fluorinated thienothiophene gave the best solar cell performance. Perfluorination of the polymer backbone led to poor compatibility with PC71BM molecules, thus poor solar energy conversion efficiency. This is possibly due to the enhanced self-organization properties of the polymer chains and the fluorophobicity effect. Furthermore, it was found that perfluorination of the polymer backbone resulted in poor photochemical stability against singlet oxygen attack. Theoretical studies indicated that the internal polarization caused enhancement of the negative charge density on thienothiophene rings, which rendered them vulnerable to [2+4] cycloaddition reaction with singlet oxygen.

  DOI：

  10.1021/ja108601g