N-(4-bromothiophen-3-yl)-3-ethylheptanamide | 1346523-38-3

• 分子结构分类: 有机化合物 - 有机氮化合物
• 英文名称: N-(4-bromothiophen-3-yl)-3-ethylheptanamide
• CAS: 1346523-38-3
• 化学式: C₁₃H₂₀BrNOS
• 分子量: 318.278
• InChiKey: VHCGKUBZCNPPDA-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.9
• 重原子数：
  17
• 可旋转键数：
  7
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.62
• 拓扑面积：
  57.3
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  N-(4-bromothiophen-3-yl)-3-ethylheptanamide 在 劳森试剂 、 copper(l) iodide 、 新铜试剂 、 potassium carbonate 作用下， 以 四氢呋喃 为溶剂， 生成 2-(2-ethylhexyl)thieno[3,4-d]thiazole
  参考文献：
  名称：

  Improved Synthesis of Thienothiazole and Its Utility in Developing Polymers for Photovoltaics

  摘要：

  In response to the structural and electronic limitations of the popular benzo[1,2-b:4,5-b']dithiophene-thieno[3,4-b]thiophene (PBnDT-TT) polymer series, this study explores the design and synthesis of a thienothiazole (TTz) moiety. The synthesis of TTz was streamlined down to four high-yielding steps, resulting in the new polymer PBnDT-TTz for organic solar cells. By incorporating TTz, a nitrogen is directly introduced into the polymer backbone which tunes the HOMO level and eliminates the reliance on external substituents. Compared to its TT analogue, PBnDT-TTz exhibits the same HOMO level of -5.06 eV and the same V-oc of 0.69 eV, yet a higher power conversion efficiency of 2.5%. These promising results demonstrate the benefits of backbone modification and the great potential of TTz in the design of new polymers for organic photovoltaics.

  DOI：

  10.1021/ma201835h
• 作为产物：
  描述：

  3-乙基庚酸 、 3-azido-4-bromothiophene 在 三甲基膦 作用下， 以 甲苯 为溶剂， 以65%的产率得到N-(4-bromothiophen-3-yl)-3-ethylheptanamide
  参考文献：
  名称：

  Improved Synthesis of Thienothiazole and Its Utility in Developing Polymers for Photovoltaics

  摘要：

  In response to the structural and electronic limitations of the popular benzo[1,2-b:4,5-b']dithiophene-thieno[3,4-b]thiophene (PBnDT-TT) polymer series, this study explores the design and synthesis of a thienothiazole (TTz) moiety. The synthesis of TTz was streamlined down to four high-yielding steps, resulting in the new polymer PBnDT-TTz for organic solar cells. By incorporating TTz, a nitrogen is directly introduced into the polymer backbone which tunes the HOMO level and eliminates the reliance on external substituents. Compared to its TT analogue, PBnDT-TTz exhibits the same HOMO level of -5.06 eV and the same V-oc of 0.69 eV, yet a higher power conversion efficiency of 2.5%. These promising results demonstrate the benefits of backbone modification and the great potential of TTz in the design of new polymers for organic photovoltaics.

  DOI：

  10.1021/ma201835h

文献信息

• Improved Synthesis of Thienothiazole and Its Utility in Developing Polymers for Photovoltaics
  作者：Rycel Uy、Liqiang Yang、Huaxing Zhou、Samuel C. Price、Wei You

  DOI：10.1021/ma201835h

  日期：2011.12.13

  In response to the structural and electronic limitations of the popular benzo[1,2-b:4,5-b']dithiophene-thieno[3,4-b]thiophene (PBnDT-TT) polymer series, this study explores the design and synthesis of a thienothiazole (TTz) moiety. The synthesis of TTz was streamlined down to four high-yielding steps, resulting in the new polymer PBnDT-TTz for organic solar cells. By incorporating TTz, a nitrogen is directly introduced into the polymer backbone which tunes the HOMO level and eliminates the reliance on external substituents. Compared to its TT analogue, PBnDT-TTz exhibits the same HOMO level of -5.06 eV and the same V-oc of 0.69 eV, yet a higher power conversion efficiency of 2.5%. These promising results demonstrate the benefits of backbone modification and the great potential of TTz in the design of new polymers for organic photovoltaics.