5,5'-bis(4,4-di-p-tolyl-4H-indeno[1,2-b]thien-2-yl)-2,2'-bithiophene | 1113063-40-3

• 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(4,4-di-p-tolyl-4H-indeno[1,2-b]thien-2-yl)-2,2'-bithiophene
• 英文别名: 2-[5-[5-[4,4-Bis(4-methylphenyl)indeno[1,2-b]thiophen-2-yl]thiophen-2-yl]thiophen-2-yl]-4,4-bis(4-methylphenyl)indeno[1,2-b]thiophene
• CAS: 1113063-40-3
• 化学式: C₅₈H₄₂S₄
• 分子量: 867.235
• InChiKey: AKTJXSTVWNDLJR-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  16.8
• 重原子数：
  62
• 可旋转键数：
  7
• 环数：
  12.0
• sp3杂化的碳原子比例：
  0.1
• 拓扑面积：
  113
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  2-bromo-4,4-di-p-tolyl-4H-indeno[1,2-b]thiophene 、 5,5'-二溴-2,2'-联噻吩 在 正丁基锂 、 三甲基氯化锡 作用下， 以 四氢呋喃 、 正己烷 为溶剂， 反应 0.5h， 以0.27 g的产率得到5,5'-bis(4,4-di-p-tolyl-4H-indeno[1,2-b]thien-2-yl)-2,2'-bithiophene
  参考文献：
  名称：

  Quaterthiophenes with Terminal Indeno[1,2-b]thiophene Units as p-Type Organic Semiconductors

  摘要：

  Quaterthiophenes 4T, Oct-4T, and Tol-4T based on a central 2,2'-bithiophene core alpha,omega,-terminated with 4,4-unsubstituted and 4,4-disubstituted n-octyl or p-tolyl indeno[1,2-b]thiophene have been synthesized by Stille or Miyaura-Suzuki couplings. Compound 4T was also synthesized by an alternative route involving a soluble precursor bearing solubilizing trimethylsilyl groups which have been eliminated in the last step. The electronic properties of the compounds have been analyzed by cyclic voltammetry, UV-vis absorption and fluorescence emission spectroscopy. Thermal evaporation of 4T and Oct-4T leads to crystalline thin films and UV-vis absorption and X-ray diffraction data for these films suggest that the molecules adopt a quasi-vertical orientation onto the substrate. Strong pi-pi intermolecular interactions have been observed for 4T but not for molecules Oct-4T due to the presence of n-octyl chains. Sublimed thin films of Tol-4T show an amorphous character. The characterization of field-effect transistors fabricated from these three materials gave a hole-mobility of 2.2 x 10(-2) cm(2) V-1 s(-1) with an on/off ratio of 2.2 x 10(4) for 4T while no field-effect was observed for Oct-4T and Tol-4T.

  DOI：

  10.1021/jo802028n

文献信息

• Quaterthiophenes with Terminal Indeno[1,2-<i>b</i>]thiophene Units as <i>p</i>-Type Organic Semiconductors
  作者：Laurent Pouchain、Olivier Alévêque、Yohann Nicolas、Agathe Oger、Charles-Henri Le Régent、Magali Allain、Philippe Blanchard、Jean Roncali

  DOI：10.1021/jo802028n

  日期：2009.2.6

  Quaterthiophenes 4T, Oct-4T, and Tol-4T based on a central 2,2'-bithiophene core alpha,omega,-terminated with 4,4-unsubstituted and 4,4-disubstituted n-octyl or p-tolyl indeno[1,2-b]thiophene have been synthesized by Stille or Miyaura-Suzuki couplings. Compound 4T was also synthesized by an alternative route involving a soluble precursor bearing solubilizing trimethylsilyl groups which have been eliminated in the last step. The electronic properties of the compounds have been analyzed by cyclic voltammetry, UV-vis absorption and fluorescence emission spectroscopy. Thermal evaporation of 4T and Oct-4T leads to crystalline thin films and UV-vis absorption and X-ray diffraction data for these films suggest that the molecules adopt a quasi-vertical orientation onto the substrate. Strong pi-pi intermolecular interactions have been observed for 4T but not for molecules Oct-4T due to the presence of n-octyl chains. Sublimed thin films of Tol-4T show an amorphous character. The characterization of field-effect transistors fabricated from these three materials gave a hole-mobility of 2.2 x 10(-2) cm(2) V-1 s(-1) with an on/off ratio of 2.2 x 10(4) for 4T while no field-effect was observed for Oct-4T and Tol-4T.