4-bromo-4'-(octylsulfanyl)-2,2'-bithiophene | 917395-49-4

• 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: 4-bromo-4'-(octylsulfanyl)-2,2'-bithiophene
• 英文别名: 2-(4-Bromothiophen-2-yl)-4-octylsulfanylthiophene；2-(4-bromothiophen-2-yl)-4-octylsulfanylthiophene
• CAS: 917395-49-4
• 化学式: C₁₆H₂₁BrS₃
• 分子量: 389.445
• InChiKey: JMXHIBUCOCIITQ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  7.6
• 重原子数：
  20
• 可旋转键数：
  9
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  81.8
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  4-bromo-4'-(octylsulfanyl)-2,2'-bithiophene 在 三氯化铁 作用下， 以 硝基甲烷 、 氯仿 为溶剂， 反应 20.0h， 以55%的产率得到2-[3-Bromo-5-[5-[5-[4-bromo-5-[5-(4-bromothiophen-2-yl)-3-octylsulfanylthiophen-2-yl]thiophen-2-yl]-3-octylsulfanylthiophen-2-yl]-4-octylsulfanylthiophen-2-yl]thiophen-2-yl]-5-(4-bromothiophen-2-yl)-3-octylsulfanylthiophene
  参考文献：
  名称：

  One-Pot Synthesis of Symmetric Octithiophenes from Asymmetric β-Alkylsulfanyl Bithiophenes

  摘要：

  Starting from 4-(octylsulfanyl)-2,2'-bithiophene, 4-bromo-4'-(octylsulfanyl)-2,2'-bithiophene, 4-iodo-4'-(octylsulfanyl)-2,2'-bithiophene, 4-bromo-4'-[(S)-2-methylbutylsulfanyl]-2,2'-bithiophene, and 4-iodo-4'-[(S)-2-methylbutylsulfanyl]-2,2'-bithiophene, a new series of symmetrically beta-substituted octithiophenes were synthesized by one-pot oxidative coupling with FeCl3. The octithiophenes obtained are soluble in common organic solvents and show different solvatochromic properties depending on the substitution type. In particular, the bromine atom exerts a positive influence on the supramolecular organization: the brominated octithiophenes display high filmability, solvatochromism, and CD induced by aggregation (when the chiral 2-methylbutylsulfanyl group is present), properties usually observed for polythiophenes. Density functional theory (DFT) calculations were carried out an a model bithiophene (4-substituted with a methylsulfanyl group) in order to understand the possible mechanism of the growth, the regiochemistry, and the reason for the polymerization leads to an octithiophene.

  DOI：

  10.1021/ma0614141
• 作为产物：
  描述：

  1-辛硫醇 在 四(三苯基膦)钯 N-溴代丁二酰亚胺(NBS) 、 正丁基锂 、 氢碘酸 、 对甲苯磺酸 、 二异丙胺 作用下， 以 四氢呋喃 、 正己烷 、 溶剂黄146 、 甲苯 、 苯 为溶剂， 反应 39.0h， 生成 4-bromo-4'-(octylsulfanyl)-2,2'-bithiophene
  参考文献：
  名称：

  One-Pot Synthesis of Symmetric Octithiophenes from Asymmetric β-Alkylsulfanyl Bithiophenes

  摘要：

  Starting from 4-(octylsulfanyl)-2,2'-bithiophene, 4-bromo-4'-(octylsulfanyl)-2,2'-bithiophene, 4-iodo-4'-(octylsulfanyl)-2,2'-bithiophene, 4-bromo-4'-[(S)-2-methylbutylsulfanyl]-2,2'-bithiophene, and 4-iodo-4'-[(S)-2-methylbutylsulfanyl]-2,2'-bithiophene, a new series of symmetrically beta-substituted octithiophenes were synthesized by one-pot oxidative coupling with FeCl3. The octithiophenes obtained are soluble in common organic solvents and show different solvatochromic properties depending on the substitution type. In particular, the bromine atom exerts a positive influence on the supramolecular organization: the brominated octithiophenes display high filmability, solvatochromism, and CD induced by aggregation (when the chiral 2-methylbutylsulfanyl group is present), properties usually observed for polythiophenes. Density functional theory (DFT) calculations were carried out an a model bithiophene (4-substituted with a methylsulfanyl group) in order to understand the possible mechanism of the growth, the regiochemistry, and the reason for the polymerization leads to an octithiophene.

  DOI：

  10.1021/ma0614141