2,5-dibromo-3-{[(4-(4'-cyano)terphenyloxy)carbonyl]methyl}thiophene | 1215807-68-3

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: 2,5-dibromo-3-{[(4-(4'-cyano)terphenyloxy)carbonyl]methyl}thiophene
• 英文别名: [4-[4-(4-Cyanophenyl)phenyl]phenyl] 2-(2,5-dibromothiophen-3-yl)acetate；[4-[4-(4-cyanophenyl)phenyl]phenyl] 2-(2,5-dibromothiophen-3-yl)acetate
• CAS: 1215807-68-3
• 化学式: C₂₅H₁₅Br₂NO₂S
• 分子量: 553.274
• InChiKey: QDVNZJLHEVWOBB-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  8
• 重原子数：
  31
• 可旋转键数：
  6
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.04
• 拓扑面积：
  78.3
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  3-噻吩乙酸 在 4-二甲氨基吡啶 、 N-溴代丁二酰亚胺(NBS) 、 N,N'-二环己基碳二亚胺 作用下， 以 四氢呋喃 、 N,N-二甲基甲酰胺 为溶剂， 反应 44.0h， 生成 2,5-dibromo-3-{[(4-(4'-cyano)terphenyloxy)carbonyl]methyl}thiophene
  参考文献：
  名称：

  Synthesis and Properties of Light-Emitting Polythiophene Derivatives Bearing Terphenyl Mesogenic Pendant

  摘要：

  A series of polythiophenes containing terphenyl mesogenic side chain at the third position through ester bonding was synthesized by dehalogenative polycondensation. The thiophene monomers 2,5-bromo-3-{[(4-(4'-cyano)terphenyloxy)carbonyl]-methyl]}-thiophene [M(CN)] and 2,5-bromo-3-{[(4-(4'-methoxy)terphenyloxy)-carbonyl]methyl}-thiophene [M(OCH3)] were prepared via Suzuki reation and esterification reactions, in sequence. The structures and properties of the monomers and polymers were characterized and evaluated with nuclear magnetic resonance, infrared spectroscopy, thermogravimetry, differential scanning calorimetry, polarized optical microscopy, ultraviolet spectroscopy, and photoluminescence. All of the polymers were stable, losing little of their weights when heated to epsilon 300 degrees C. The polymers showed good solubility and could be dissolved in common solvents such as CHCl3, THF, DMF, etc. The monomers exhibited enantiotropic SmAd phases with a bilayer arrangement in the heating and cooling processes. Due to short spacer methylene ester between the bulk terphenyl mesogenic side chain and rigid polythiophene main chain, the polymers could not exhibit liquid crystallinty at elevated temperature. The existence of the chromophoric terphenyl core endows the polymers with high photoluminescence. When their CH2Cl2 solutions were photoexcited, the polymers emitted a strong UV light about 400nm.

  DOI：

  10.1080/15421400903568047

文献信息

• Synthesis and Properties of Light-Emitting Polythiophene Derivatives Bearing Terphenyl Mesogenic Pendant
  作者：Lie Chen、Yiwang Chen、Weihua Zhou、Fan Li、Xiaohui He、Ben Zhong Tang

  DOI：10.1080/15421400903568047

  日期：2010.3.22

  A series of polythiophenes containing terphenyl mesogenic side chain at the third position through ester bonding was synthesized by dehalogenative polycondensation. The thiophene monomers 2,5-bromo-3-[(4-(4'-cyano)terphenyloxy)carbonyl]-methyl]}-thiophene [M(CN)] and 2,5-bromo-3-[(4-(4'-methoxy)terphenyloxy)-carbonyl]methyl}-thiophene [M(OCH3)] were prepared via Suzuki reation and esterification reactions, in sequence. The structures and properties of the monomers and polymers were characterized and evaluated with nuclear magnetic resonance, infrared spectroscopy, thermogravimetry, differential scanning calorimetry, polarized optical microscopy, ultraviolet spectroscopy, and photoluminescence. All of the polymers were stable, losing little of their weights when heated to epsilon 300 degrees C. The polymers showed good solubility and could be dissolved in common solvents such as CHCl3, THF, DMF, etc. The monomers exhibited enantiotropic SmAd phases with a bilayer arrangement in the heating and cooling processes. Due to short spacer methylene ester between the bulk terphenyl mesogenic side chain and rigid polythiophene main chain, the polymers could not exhibit liquid crystallinty at elevated temperature. The existence of the chromophoric terphenyl core endows the polymers with high photoluminescence. When their CH2Cl2 solutions were photoexcited, the polymers emitted a strong UV light about 400nm.