(Z,Z)-2,5-bis(α-cyano-α-hexanoxycarbonylmetylene)-2,5-dihydro-thieno[3,2-b]thiophene

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 噻吩并噻吩类
• 英文名称: (Z,Z)-2,5-bis(α-cyano-α-hexanoxycarbonylmetylene)-2,5-dihydro-thieno[3,2-b]thiophene
• 英文别名: hexyl (2Z)-2-cyano-2-[(5Z)-5-(1-cyano-2-hexoxy-2-oxoethylidene)thieno[3,2-b]thiophen-2-ylidene]acetate
• 化学式: C₂₄H₂₈N₂O₄S₂
• 分子量: 472.629
• InChiKey: DPEPFPUIQMXSCC-CLFAGFIQSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.3
• 重原子数：
  32
• 可旋转键数：
  14
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  151
• 氢给体数：
  0
• 氢受体数：
  8

反应信息

• 作为产物：
  描述：

  2,5-二溴噻吩并[3,2-B]噻吩 、 氰基乙酸己酯 在 sodium hydride 、 1,1'-双(二苯基膦)二茂铁 、 四(三苯基膦)钯 、 盐酸 作用下， 以 1,4-二氧六环 、 mineral oil 、 乙醇 、 水 为溶剂， 反应 0.5h， 以44%的产率得到(Z,Z)-2,5-bis(α-cyano-α-hexanoxycarbonylmetylene)-2,5-dihydro-thieno[3,2-b]thiophene
  参考文献：
  名称：

  ((Alkyloxy)carbonyl)cyanomethylene-Substituted Thienoquinoidal Compounds: a New Class of Soluble n-Channel Organic Semiconductors for Air-Stable Organic Field-Effect Transistors

  摘要：

  A new n-channel semiconductor class for organic field-effect transistors (OFETs) based on thienoquinoidal structures is reported. A newly employed terminal group, the ((alkyloxy)carbonyl)cyanomethylene moiety, plays two important roles in the thienoquinoidal compounds: i.e., as an electron-withdrawing group to keep the LUMO energy level sufficiently low for acting as an n-channel organic semiconductor and as a solubilizing group to facilitate solution processability. For the construction of this class of compounds, a new, straightforward synthetic method was established and applied to oligothienoquinoidal and fused thienoquinoidal systems. When both core and alkyl groups in the ester moiety were tuned, the thienoquinoidals exhibited good solubility, stability in the atmosphere, and electron-accepting properties, as well as solution processability. Solution-processed FETs based on the terthienoquinoid derivative with ((n-alkyloxy)carbonyl)cyanomethylene moieties exhibit good electron mobilities (mu similar to 0.015 cm(2) V-1 s(-1)) and I-on/I-off approximate to 10(5) under ambient conditions. Vapor-processed FETs using the benzodithienoquinoidal derivative showed similar n-channel FET characteristics.

  DOI：

  10.1021/ja103171y

文献信息

• ((Alkyloxy)carbonyl)cyanomethylene-Substituted Thienoquinoidal Compounds: a New Class of Soluble n-Channel Organic Semiconductors for Air-Stable Organic Field-Effect Transistors
  作者：Yuki Suzuki、Eigo Miyazaki、Kazuo Takimiya

  DOI：10.1021/ja103171y

  日期：2010.8.4

  A new n-channel semiconductor class for organic field-effect transistors (OFETs) based on thienoquinoidal structures is reported. A newly employed terminal group, the ((alkyloxy)carbonyl)cyanomethylene moiety, plays two important roles in the thienoquinoidal compounds: i.e., as an electron-withdrawing group to keep the LUMO energy level sufficiently low for acting as an n-channel organic semiconductor and as a solubilizing group to facilitate solution processability. For the construction of this class of compounds, a new, straightforward synthetic method was established and applied to oligothienoquinoidal and fused thienoquinoidal systems. When both core and alkyl groups in the ester moiety were tuned, the thienoquinoidals exhibited good solubility, stability in the atmosphere, and electron-accepting properties, as well as solution processability. Solution-processed FETs based on the terthienoquinoid derivative with ((n-alkyloxy)carbonyl)cyanomethylene moieties exhibit good electron mobilities (mu similar to 0.015 cm(2) V-1 s(-1)) and I-on/I-off approximate to 10(5) under ambient conditions. Vapor-processed FETs using the benzodithienoquinoidal derivative showed similar n-channel FET characteristics.