5,5''-dibromo-2,2':5',2''-terthiophene-4,4''-dicarboxylic acid | 342023-18-1

• 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''-dibromo-2,2':5',2''-terthiophene-4,4''-dicarboxylic acid
• 英文别名: 2-bromo-5-[5-(5-bromo-4-carboxythiophen-2-yl)thiophen-2-yl]thiophene-3-carboxylic acid
• CAS: 342023-18-1
• 化学式: C₁₄H₆Br₂O₄S₃
• 分子量: 494.205
• InChiKey: QIRVNEJQLAXVCW-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.13
• 重原子数：
  23.0
• 可旋转键数：
  4.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  74.6
• 氢给体数：
  2.0
• 氢受体数：
  5.0

反应信息

• 作为反应物：
  描述：

  5,5''-dibromo-2,2':5',2''-terthiophene-4,4''-dicarboxylic acid 在 氯化亚砜 、 三乙胺 作用下， 以 四氢呋喃 为溶剂， 反应 8.0h， 生成 2-bromo-5-[5-[5-bromo-4-(octylcarbamoyl)thiophen-2-yl]thiophen-2-yl]-N-octylthiophene-3-carboxamide
  参考文献：
  名称：

  Synthesis and liquid crystal properties of a novel family of oligothiophene derivatives

  摘要：

  In order to develop novel oligothiophene-based liquid crystals capable of hydrogen bonding, new terthiophene derivatives containing an alkylamide group, N,N'-dialkyl-5,5"-dichloro-2,2:5',2"-terthiophene-4,4"-dicarboxamide (DNC(n)DCl3T, n=8, 18), N,N"-dialkyl-5,5"-dibromo-2,2':5',2"-terthiophene-4,4"-dicarboxamide (DNC(n)DBr3T, n=5, 8, 16, 18), or N,N'-dialkyl-5,5"-diiodo-2,2:5',2"-terthiophene-4,4"-dica-rboxamide (DNC(n)DI3T, n=8, 18), were designed and synthesized, and their thermal behaviour was examined. It was found that DNC(18)DC13T, DNC(n)DBr3T and DNC(n)DBr3T (n=8, 16, 18) form a smectic A phase and that the alkyl chain length greatly affects liquid crystal phase formation. The absence of liquid crystallinity in the corresponding ester derivatives suggests that intermolecular hydrogen bonding also plays a role in the formation of a liquid crystal phases in the DNC(n)DBr3T system. (C) 2004 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2004.04.029
• 作为产物：
  描述：

  alpha-三联噻吩 在 N-溴代丁二酰亚胺(NBS) 、 正丁基锂 、 二异丙胺 作用下， 以 四氢呋喃 、 氯仿 为溶剂， 反应 5.0h， 生成 5,5''-dibromo-2,2':5',2''-terthiophene-4,4''-dicarboxylic acid
  参考文献：
  名称：

  Synthesis and liquid crystal properties of a novel family of oligothiophene derivatives

  摘要：

  In order to develop novel oligothiophene-based liquid crystals capable of hydrogen bonding, new terthiophene derivatives containing an alkylamide group, N,N'-dialkyl-5,5"-dichloro-2,2:5',2"-terthiophene-4,4"-dicarboxamide (DNC(n)DCl3T, n=8, 18), N,N"-dialkyl-5,5"-dibromo-2,2':5',2"-terthiophene-4,4"-dicarboxamide (DNC(n)DBr3T, n=5, 8, 16, 18), or N,N'-dialkyl-5,5"-diiodo-2,2:5',2"-terthiophene-4,4"-dica-rboxamide (DNC(n)DI3T, n=8, 18), were designed and synthesized, and their thermal behaviour was examined. It was found that DNC(18)DC13T, DNC(n)DBr3T and DNC(n)DBr3T (n=8, 16, 18) form a smectic A phase and that the alkyl chain length greatly affects liquid crystal phase formation. The absence of liquid crystallinity in the corresponding ester derivatives suggests that intermolecular hydrogen bonding also plays a role in the formation of a liquid crystal phases in the DNC(n)DBr3T system. (C) 2004 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2004.04.029