5-(4-((6-chlorohexyl)(methyl)amino)styryl)thiophene-2-carbaldehyde | 1478603-30-3

• 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: 5-(4-((6-chlorohexyl)(methyl)amino)styryl)thiophene-2-carbaldehyde
• CAS: 1478603-30-3
• 化学式: C₂₀H₂₄ClNOS
• 分子量: 361.936
• InChiKey: IHTDTCYRODXZMN-UHFFFAOYSA-N

物化性质

• 熔点：
  64.54 °C
• 沸点：
  535.0±50.0 °C(Predicted)
• 密度：
  1.183±0.06 g/cm3(Temp: 20 °C; Press: 760 Torr)(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  5.97
• 重原子数：
  24.0
• 可旋转键数：
  10.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.35
• 拓扑面积：
  20.31
• 氢给体数：
  0.0
• 氢受体数：
  3.0

反应信息

• 作为反应物：
  描述：

  4,4'-二羟基联苯 、 5-(4-((6-chlorohexyl)(methyl)amino)styryl)thiophene-2-carbaldehyde 在 potassium carbonate 、 potassium iodide 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 12.0h， 以52%的产率得到5-(4-((6-((4'-hydroxy-[1,1'-biphenyl]-4-yl)oxy)hexyl)(methyl)amino)styryl)thiophene-2-carbaldehyde
  参考文献：
  名称：

  A nunchaku-like nonlinear optical chromophore for improved temporal stability of guest–host electro-optic materials

  摘要：

  A novel nunchaku-like organic second order nonlinear optical chromophore containing a D-pi-A backbone and a rigid biphenylene unit was prepared. The UV vis absorption spectra studies demonstrated that the large rigid structure could suppress dipole dipole interactions effectively. The electro-optic coefficient of a poled film containing 20% wt of the new dye doped in amorphous polycarbonate afforded a value of 39 pm/V at 1310 nm. Compared with results obtained from a similar D-pi-A chromophore without the rigid isolated group, the new dye gave better performance. Moreover, the electrooptic film prepared with the new dye gave greater temporal stability, compared to a similar D-pi-A doped poled film that was reported previously. These results indicated that the introduction of a biphenylene group could effectively reduce the intermolecular electrostatic interactions and aid the alignment of the chromophores. (C) 2013 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.dyepig.2013.06.034
• 作为产物：
  描述：

  4-((6-chlorohexyl)(methyl)amino)benzaldehyde 在 正丁基锂 、 sodium hydride 作用下， 以 四氢呋喃 、 乙醚 、 正己烷 为溶剂， 反应 26.0h， 生成 5-(4-((6-chlorohexyl)(methyl)amino)styryl)thiophene-2-carbaldehyde
  参考文献：
  名称：

  A nunchaku-like nonlinear optical chromophore for improved temporal stability of guest–host electro-optic materials

  摘要：

  A novel nunchaku-like organic second order nonlinear optical chromophore containing a D-pi-A backbone and a rigid biphenylene unit was prepared. The UV vis absorption spectra studies demonstrated that the large rigid structure could suppress dipole dipole interactions effectively. The electro-optic coefficient of a poled film containing 20% wt of the new dye doped in amorphous polycarbonate afforded a value of 39 pm/V at 1310 nm. Compared with results obtained from a similar D-pi-A chromophore without the rigid isolated group, the new dye gave better performance. Moreover, the electrooptic film prepared with the new dye gave greater temporal stability, compared to a similar D-pi-A doped poled film that was reported previously. These results indicated that the introduction of a biphenylene group could effectively reduce the intermolecular electrostatic interactions and aid the alignment of the chromophores. (C) 2013 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.dyepig.2013.06.034