5,5'-bis(diacetylcyanomethyl)-2,2'-bithiophene | 1252668-56-6

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 双噻吩和低聚噻吩
• 英文名称: 5,5'-bis(diacetylcyanomethyl)-2,2'-bithiophene
• CAS: 1252668-56-6
• 化学式: C₂₀H₁₆N₂O₄S₂
• 分子量: 412.49
• InChiKey: KHVUTXZJXUPOLA-UHFFFAOYSA-N

反应信息

• 作为产物：
  描述：

  2,2’-([2,2’-bithiophene]-5,5’-diyl)diacetonitrile 、 乙酰氯 在 sodium hydride 作用下， 以50%的产率得到5,5'-bis(diacetylcyanomethyl)-2,2'-bithiophene
  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