3-(4-bromo-5-methyl-thien-2-yl)-2-cyanoacrylic acid | 1315330-93-8

• 分子结构分类: 有机化合物 - 有机杂环化合物
• 英文名称: 3-(4-bromo-5-methyl-thien-2-yl)-2-cyanoacrylic acid
• 英文别名: 3-(4-bromo-5-methylthiophen-2-yl)-2-cyanoprop-2-enoic acid
• CAS: 1315330-93-8
• 化学式: C₉H₆BrNO₂S
• 分子量: 272.122
• InChiKey: VNAAZAMSPSCLNR-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.81
• 重原子数：
  14.0
• 可旋转键数：
  2.0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.11
• 拓扑面积：
  61.09
• 氢给体数：
  1.0
• 氢受体数：
  3.0

反应信息

• 作为反应物：
  描述：

  3-(4-bromo-5-methyl-thien-2-yl)-2-cyanoacrylic acid 在 三叔丁基膦 、 potassium carbonate 、 sodium fluoride 、 三乙胺 、 bis(dibenzylideneacetone)-palladium⁽⁰⁾ 、 tri tert-butylphosphoniumtetrafluoroborate 作用下， 以 四氢呋喃 、 甲苯 为溶剂， 反应 9.0h， 生成 3-[4-(4-aminophenyl)-5-methyl-thien-2-yl]-2-cyanoacrylic acid
  参考文献：
  名称：

  Effect of side chain substituents on the electron injection abilities of unsymmetrical perylene diimide dyes

  摘要：

  Three near-infrared (NIR) absorbing unsymmetrical perylene diimide D A D type dyes containing 6-undecanoxy as donor group were utilized in dye-sensitized nanocrystalline TiO(2) solar cells. Structure of the acceptor side of the molecules were improved by adding 4-[2-methyl-5-(cyanoacrylic acid)-3-thienyl]-phenyl (V), 3-carboxy-2-pyridil (VI) and 3-carboxy-2-pyrazyl (VII) moieties attached to one of the N-side of the dye. The relationship between the molecular structure of the acceptor sites of the dyes and the photovoltaic performances were discussed. Electrochemical measurements indicated that band gaps of the dyes were energetically favorable for electron injection from the excited state of the dyes to the conduction band of TiO(2) nanoparticles. However, three dyes gave lower conversion efficiency on DSSC applications. Strong electron-withdrawing nature of perylene core might not permit to transfer the photo-generated electrons to the carboxyl groups anchoring to TiO(2) surface, and then solar-to-electricity conversion efficiencies of the dyes were reduced. (C) 2011 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.dyepig.2011.03.022
• 作为产物：
  描述：

  5-甲基-2-噻吩甲醛 在 哌啶 、 N-溴代丁二酰亚胺(NBS) 、 溶剂黄146 、 过氧化苯甲酰 作用下， 以 乙腈 为溶剂， 反应 17.0h， 生成 3-(4-bromo-5-methyl-thien-2-yl)-2-cyanoacrylic acid
  参考文献：
  名称：

  Effect of side chain substituents on the electron injection abilities of unsymmetrical perylene diimide dyes

  摘要：

  Three near-infrared (NIR) absorbing unsymmetrical perylene diimide D A D type dyes containing 6-undecanoxy as donor group were utilized in dye-sensitized nanocrystalline TiO(2) solar cells. Structure of the acceptor side of the molecules were improved by adding 4-[2-methyl-5-(cyanoacrylic acid)-3-thienyl]-phenyl (V), 3-carboxy-2-pyridil (VI) and 3-carboxy-2-pyrazyl (VII) moieties attached to one of the N-side of the dye. The relationship between the molecular structure of the acceptor sites of the dyes and the photovoltaic performances were discussed. Electrochemical measurements indicated that band gaps of the dyes were energetically favorable for electron injection from the excited state of the dyes to the conduction band of TiO(2) nanoparticles. However, three dyes gave lower conversion efficiency on DSSC applications. Strong electron-withdrawing nature of perylene core might not permit to transfer the photo-generated electrons to the carboxyl groups anchoring to TiO(2) surface, and then solar-to-electricity conversion efficiencies of the dyes were reduced. (C) 2011 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.dyepig.2011.03.022