2,5-di(3-hexylthiophen-2-yl)thiophene-3-carboxylic acid | 1351205-83-8

• 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: 2,5-di(3-hexylthiophen-2-yl)thiophene-3-carboxylic acid
• 英文别名: 2,5-Bis(3-hexylthiophen-2-yl)thiophene-3-carboxylic acid；2,5-bis(3-hexylthiophen-2-yl)thiophene-3-carboxylic acid
• CAS: 1351205-83-8
• 化学式: C₂₅H₃₂O₂S₃
• 分子量: 460.726
• InChiKey: WNIDZBOZKOAXJK-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  9.8
• 重原子数：
  30
• 可旋转键数：
  13
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.48
• 拓扑面积：
  122
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  2,5-di(3-hexylthiophen-2-yl)thiophene-3-carboxylic acid 、 6,6'-二硫烷二基二(1-己醇) 在 4-二甲氨基吡啶 、 盐酸-N-乙基-Nˊ-(3-二甲氨基丙基)碳二亚胺 作用下， 以 二氯甲烷 为溶剂， 反应 38.0h， 以86%的产率得到bis[2,5-di(3-hexylthiophen-2-yl)thiophene-3-carboxyloxyhexanyl]disulfide
  参考文献：
  名称：

  Gold nanoparticle-templated assembly of oligothiophenes: preparation and film properties

  摘要：

  Terthiophene-appended gold nanoparticles were prepared by the reduction of AuCl4-(C8H17)(4)N+ with NaBH4 in the presence of bis[2,5-di(3-hexylthiophen-2-yl)thiophene-3-carboxyloxyhexanyl]disulfide. A hexagonal self-assembly of particles with gold core diameters (1.9 +/- 0.1 nm) was detected by high-angle annular dark-field scanning transmission electron microscopy. The electric conductivity of the iodine-doped film was 9.1 x 10(-6) S cm(-1), which was ascribable to the terthiophene-based inter-ligand pi-pi interactions. The Au/terthiophene hybrid spin-coated film consisted of a highly three-dimensional assembled structure of terthiophenes, as inferred from grazing-incidence small-angle X-ray scattering, indicating that such monodispersed and small-sized gold nanoparticles can serve as a template for this organization. In this study, a gold nanoparticle-templated assembly of oligothiophenes has been fabricated for proposing a method to develop tailor-made organizations of pi-conjugated oligomers. (C) 2011 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2011.10.032
• 作为产物：
  描述：

  2,5-二溴噻吩-3-羧酸甲酯 在 四(三苯基膦)钯 、 sodium carbonate 、 potassium hydroxide 作用下， 以 乙二醇二甲醚 、 乙醇 为溶剂， 反应 17.5h， 生成 2,5-di(3-hexylthiophen-2-yl)thiophene-3-carboxylic acid
  参考文献：
  名称：

  Gold nanoparticle-templated assembly of oligothiophenes: preparation and film properties

  摘要：

  Terthiophene-appended gold nanoparticles were prepared by the reduction of AuCl4-(C8H17)(4)N+ with NaBH4 in the presence of bis[2,5-di(3-hexylthiophen-2-yl)thiophene-3-carboxyloxyhexanyl]disulfide. A hexagonal self-assembly of particles with gold core diameters (1.9 +/- 0.1 nm) was detected by high-angle annular dark-field scanning transmission electron microscopy. The electric conductivity of the iodine-doped film was 9.1 x 10(-6) S cm(-1), which was ascribable to the terthiophene-based inter-ligand pi-pi interactions. The Au/terthiophene hybrid spin-coated film consisted of a highly three-dimensional assembled structure of terthiophenes, as inferred from grazing-incidence small-angle X-ray scattering, indicating that such monodispersed and small-sized gold nanoparticles can serve as a template for this organization. In this study, a gold nanoparticle-templated assembly of oligothiophenes has been fabricated for proposing a method to develop tailor-made organizations of pi-conjugated oligomers. (C) 2011 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2011.10.032

文献信息

• Gold nanoparticle-templated assembly of oligothiophenes: preparation and film properties
  作者：Ken-ichi Saitou、Ryuhei Nishiyabu、Masahiko Iyoda、Yuji Kubo

  DOI：10.1016/j.tet.2011.10.032

  日期：2011.12

  Terthiophene-appended gold nanoparticles were prepared by the reduction of AuCl4-(C8H17)(4)N+ with NaBH4 in the presence of bis[2,5-di(3-hexylthiophen-2-yl)thiophene-3-carboxyloxyhexanyl]disulfide. A hexagonal self-assembly of particles with gold core diameters (1.9 +/- 0.1 nm) was detected by high-angle annular dark-field scanning transmission electron microscopy. The electric conductivity of the iodine-doped film was 9.1 x 10(-6) S cm(-1), which was ascribable to the terthiophene-based inter-ligand pi-pi interactions. The Au/terthiophene hybrid spin-coated film consisted of a highly three-dimensional assembled structure of terthiophenes, as inferred from grazing-incidence small-angle X-ray scattering, indicating that such monodispersed and small-sized gold nanoparticles can serve as a template for this organization. In this study, a gold nanoparticle-templated assembly of oligothiophenes has been fabricated for proposing a method to develop tailor-made organizations of pi-conjugated oligomers. (C) 2011 Elsevier Ltd. All rights reserved.