4-methacryloyloxy-3,5-dimethoxy-(E)-stilbene | 1346133-67-2

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 二苯乙烯类
• 英文名称: 4-methacryloyloxy-3,5-dimethoxy-(E)-stilbene
• 英文别名: [2,6-dimethoxy-4-[(E)-2-phenylethenyl]phenyl] 2-methylprop-2-enoate
• CAS: 1346133-67-2
• 化学式: C₂₀H₂₀O₄
• 分子量: 324.376
• InChiKey: AZNXSUGFVKFMFA-ZHACJKMWSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.9
• 重原子数：
  24
• 可旋转键数：
  7
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.15
• 拓扑面积：
  44.8
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  (E)-2,6-dimethoxy-4-(phenylethenyl)phenol 、 甲基丙烯酰氯 在 三乙胺 作用下， 以 四氢呋喃 为溶剂， 反应 17.0h， 以78%的产率得到4-methacryloyloxy-3,5-dimethoxy-(E)-stilbene
  参考文献：
  名称：

  Selective [2 + 2]-Cycloaddition in Methacrylic Stilbene Polymers without Interference from E/Z-Isomerization

  摘要：

  Stilbene is known to undergo two different reactions upon photochemical excitation. The first is an E/Z isomerization and the second is a [2 + 2]-cycloaddition of two stilbene molecules. Because both reactions occur in parallel their use is limited. Here we report on photorefractive polymers with a methacrylate backbone and covalently attached 4-hydroxy-(E)-stilbene or 3,5-dimethoxy-4-hydroxy-(E)-stilbene units in the side chain which show [2 + 2]-cycloaddition only. Both polymers, poly(4-methacryloyloxy-(E)-stilbene) (PMAES) and poly(4-methacryloyloxy-3,5-dimethoxy-(E)-stilbene) (PMADMES), show very high initial refractive indices of 1.6533 for PMAES and 1.6288 for PMADMES. The photochemical reaction upon laser irradiation with 355 nm was monitored by UV/vis, fluorescence, and IR spectroscopy. The light-induced changes of the refractive index at 633 nm measured by surface plasmon resonance (SPR) were found to be Delta n > 0.05 for PMAES and Delta n > 0.04 for PMADMES. The sensitivity of PMADMES is enhanced compared to PMAES due to the electron donating groups (EDG) as the direct comparison of both polymers shows. Both polymers are useful for optical devices because they do not show any absorption in the visible range and are noncrystalline as determined by wide-angle X-ray scattering (WAXS) and differential scanning calorimetry (DSC).

  DOI：

  10.1021/ma2015485

文献信息

• Selective [2 + 2]-Cycloaddition in Methacrylic Stilbene Polymers without Interference from <i>E</i>/<i>Z</i>-Isomerization
  作者：Martin Schraub、Helen Gray、Norbert Hampp

  DOI：10.1021/ma2015485

  日期：2011.11.22

  Stilbene is known to undergo two different reactions upon photochemical excitation. The first is an E/Z isomerization and the second is a [2 + 2]-cycloaddition of two stilbene molecules. Because both reactions occur in parallel their use is limited. Here we report on photorefractive polymers with a methacrylate backbone and covalently attached 4-hydroxy-(E)-stilbene or 3,5-dimethoxy-4-hydroxy-(E)-stilbene units in the side chain which show [2 + 2]-cycloaddition only. Both polymers, poly(4-methacryloyloxy-(E)-stilbene) (PMAES) and poly(4-methacryloyloxy-3,5-dimethoxy-(E)-stilbene) (PMADMES), show very high initial refractive indices of 1.6533 for PMAES and 1.6288 for PMADMES. The photochemical reaction upon laser irradiation with 355 nm was monitored by UV/vis, fluorescence, and IR spectroscopy. The light-induced changes of the refractive index at 633 nm measured by surface plasmon resonance (SPR) were found to be Delta n > 0.05 for PMAES and Delta n > 0.04 for PMADMES. The sensitivity of PMADMES is enhanced compared to PMAES due to the electron donating groups (EDG) as the direct comparison of both polymers shows. Both polymers are useful for optical devices because they do not show any absorption in the visible range and are noncrystalline as determined by wide-angle X-ray scattering (WAXS) and differential scanning calorimetry (DSC).