1-(2-thienyl)butan-2-one ethylene acetal | 1252668-59-9

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 1-(2-thienyl)butan-2-one ethylene acetal
• CAS: 1252668-59-9
• 化学式: C₁₀H₁₄O₂S
• 分子量: 198.286
• InChiKey: JSLDWGIFSMJDAA-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.44
• 重原子数：
  13.0
• 可旋转键数：
  3.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.6
• 拓扑面积：
  18.46
• 氢给体数：
  0.0
• 氢受体数：
  3.0

反应信息

• 作为反应物：
  描述：

  1-(2-thienyl)butan-2-one ethylene acetal 在 N-溴代丁二酰亚胺(NBS) 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 以88%的产率得到1-(5-bromo-2-thienyl)butan-2-one ethylene acetal
  参考文献：
  名称：

  Quinoidal Oligothiophenes with (Acyl)cyanomethylene Termini: Synthesis, Characterization, Properties, and Solution Processed n-Channel Organic Field-Effect Transistors

  摘要：

  A new class of oligothienoquinoidal derivatives with newly employed (acyl)cyanomethylene termini are reported. For the synthesis of (acyl)cyanomethylene-substituted thienoquinoidals, similar methods successfully employed for the synthesis of related dicyanomethylene- or ((alkyloxy)carbonyl)cyanomethylenc-substituted thienoquinoidals were not applicable, and thus a new synthetic route was developed. The introduced (acyl)cyanomethylene terminal groups act both as a solublizing group to facilitate solution processability and an electron-withdrawing group to keep the LUMO energy levels sufficiently low for n-channel organic semiconductors. The LUMO energy levels estimated from their reduction potential are similar to 4.2 eV below the vacuum level, which just falls in between those for the corresponding dicyanomethylene- and ((alkyloxy)carbonyl)cyanomethylene-substituted thienoquinoidals. This qualitatively agrees with the electron-withdrawing nature of the terminal groups; the order of the electron withdrawing nature is cyano- > acyl- > (alkyloxy)carbonyl- groups. Spin-coating chloroform solutions of (acyl)cyanomethylene-substituted thienoquinoidals gave homogeneous thin films on the Si/SiO2 substrates, and the thin films based on the terthienoquinoidal derivatives became highly crystalline upon thermal annealing. The annealed film acted as the active semiconducting channel in the FET devices under ambient conditions, and the electron mobilities extracted from the saturation regime were similar to 0.06 cm(2) V-1 s(-1). These n-channel FET characteristics are nearly the same or slightly better than those of the FETs based on the related ((alkyloxy)carbonyl)cyanomethylene-terminated terthienoquinoidal, indicating that the (acyl)cyanomethylene moiety is a useful terminal group on the thienoquinoidals for the development of soluble n-channel organic semiconductors.

  DOI：

  10.1021/cm102109p
• 作为产物：
  描述：

  1-(2-thienyl)-2-butanol 在 对甲苯磺酸 、 pyridinium chlorochromate 作用下， 以 二氯甲烷 、 苯 为溶剂， 生成 1-(2-thienyl)butan-2-one ethylene acetal
  参考文献：
  名称：

  Quinoidal Oligothiophenes with (Acyl)cyanomethylene Termini: Synthesis, Characterization, Properties, and Solution Processed n-Channel Organic Field-Effect Transistors

  摘要：

  A new class of oligothienoquinoidal derivatives with newly employed (acyl)cyanomethylene termini are reported. For the synthesis of (acyl)cyanomethylene-substituted thienoquinoidals, similar methods successfully employed for the synthesis of related dicyanomethylene- or ((alkyloxy)carbonyl)cyanomethylenc-substituted thienoquinoidals were not applicable, and thus a new synthetic route was developed. The introduced (acyl)cyanomethylene terminal groups act both as a solublizing group to facilitate solution processability and an electron-withdrawing group to keep the LUMO energy levels sufficiently low for n-channel organic semiconductors. The LUMO energy levels estimated from their reduction potential are similar to 4.2 eV below the vacuum level, which just falls in between those for the corresponding dicyanomethylene- and ((alkyloxy)carbonyl)cyanomethylene-substituted thienoquinoidals. This qualitatively agrees with the electron-withdrawing nature of the terminal groups; the order of the electron withdrawing nature is cyano- > acyl- > (alkyloxy)carbonyl- groups. Spin-coating chloroform solutions of (acyl)cyanomethylene-substituted thienoquinoidals gave homogeneous thin films on the Si/SiO2 substrates, and the thin films based on the terthienoquinoidal derivatives became highly crystalline upon thermal annealing. The annealed film acted as the active semiconducting channel in the FET devices under ambient conditions, and the electron mobilities extracted from the saturation regime were similar to 0.06 cm(2) V-1 s(-1). These n-channel FET characteristics are nearly the same or slightly better than those of the FETs based on the related ((alkyloxy)carbonyl)cyanomethylene-terminated terthienoquinoidal, indicating that the (acyl)cyanomethylene moiety is a useful terminal group on the thienoquinoidals for the development of soluble n-channel organic semiconductors.

  DOI：

  10.1021/cm102109p