5,5'-((2,5-dimethoxy-1,4-phenylene)bis(ethene-2,1-diyl))bis(benzo[d][1,3]dioxole)

• 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: 5,5'-((2,5-dimethoxy-1,4-phenylene)bis(ethene-2,1-diyl))bis(benzo[d][1,3]dioxole)
• 英文别名: 5-[(E)-2-[4-[(E)-2-(1,3-benzodioxol-5-yl)ethenyl]-2,5-dimethoxyphenyl]ethenyl]-1,3-benzodioxole
• 化学式: C₂₆H₂₂O₆
• 分子量: 430.457
• InChiKey: HTOANDCRHRZSEH-FCXRPNKRSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6
• 重原子数：
  32
• 可旋转键数：
  6
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.15
• 拓扑面积：
  55.4
• 氢给体数：
  0
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  甲醇 、 5,5'-((2,5-dimethoxy-1,4-phenylene)bis(ethene-2,1-diyl))bis(benzo[d][1,3]dioxole) 在 氢氧化钾 作用下， 生成
  参考文献：
  名称：

  Solid State Behaviour of Vinyl Quinones

  摘要：

  2,5-Bisvinyl-1,4-benzoquinones 1 and 2-vinyl-1,4-benzoquinones 2 substituted with aryl or ester end groups have been synthesized. The 2,5-bisstyryl-1,4-benzoquinones 1 (R=phenyl, p-tolyl, o-tolyl) crystallize with a 7 Angstrom-stacking axis. But only for the o-tolyl derivative the contacts between the vinyl groups are close enough to allow a four-center type photopolymerization. The ester derivative 1 (R=COOEt) has a layer structure and can be photooligomerized in the crystal. The generated cyclobutane subgroups have twofold symmetry. The vinylquinones 2 (R=aryl) may be dimerized photochemically in the crystal at the vinyl groups to centrosymmetric cyclobutanes. Crystals with 4 Angstrom stacking axis are also photoreactive.

  DOI：

  10.1080/10587259608039394
• 作为产物：
  描述：

  diethyl (benzo[d][1,3]dioxol-5-ylmethyl)phosphonate 、 2,5-二甲氧基苯-1,4-二甲醛 在 sodium methylate 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 生成 5,5'-((2,5-dimethoxy-1,4-phenylene)bis(ethene-2,1-diyl))bis(benzo[d][1,3]dioxole)
  参考文献：
  名称：

  Solid State Behaviour of Vinyl Quinones

  摘要：

  2,5-Bisvinyl-1,4-benzoquinones 1 and 2-vinyl-1,4-benzoquinones 2 substituted with aryl or ester end groups have been synthesized. The 2,5-bisstyryl-1,4-benzoquinones 1 (R=phenyl, p-tolyl, o-tolyl) crystallize with a 7 Angstrom-stacking axis. But only for the o-tolyl derivative the contacts between the vinyl groups are close enough to allow a four-center type photopolymerization. The ester derivative 1 (R=COOEt) has a layer structure and can be photooligomerized in the crystal. The generated cyclobutane subgroups have twofold symmetry. The vinylquinones 2 (R=aryl) may be dimerized photochemically in the crystal at the vinyl groups to centrosymmetric cyclobutanes. Crystals with 4 Angstrom stacking axis are also photoreactive.

  DOI：

  10.1080/10587259608039394

文献信息

• One-pot synthesis and study of spectroscopic properties of oligo(phenylenevinylene)s
  作者：Krupa N. Patel、Ashutosh V. Bedekar

  DOI：10.1016/j.tetlet.2015.10.033

  日期：2015.11

  Two series of OPVs (oligo(phenylenevinylene)), that is, ((1E,1'E)-(2,5-dimethoxy-1,4-phenylene)bis (ethene-2,1-diyl))dibenzene derivatives and 4-((E)-4-((E)-styryl)styryl)pyridine derivatives with different functional groups of varying electronic properties have been synthesized by one-pot Wittig-Heck methodology. The synthesized derivatives have been studied for their optical properties. Amongst them the ((1E,1'E)-(2,5-dimethoxy-1,4-phenylene)bis(ethene-2,1-diyl))dibenzene derivatives with appropriate changes in the end group showed a significant impact on the UV absorption and emission spectra. Particularly NO2-OPV showed distinct solvatochromism in the wavelength range of 218 nm in different solvents. Whereas 4-((E)-4((E)-styryl)styryl)pyridine derivatives showed clear acidochromism which can be detected visually as well as spectroscopically. (C) 2015 Elsevier Ltd. All rights reserved.
• Solid State Behaviour of Vinyl Quinones
  作者：Hermann Irngartinger、Jochen Lichtenthäler、Rüdiger Herpich、Birgit Stadler

  DOI：10.1080/10587259608039394

  日期：1996.2

  2,5-Bisvinyl-1,4-benzoquinones 1 and 2-vinyl-1,4-benzoquinones 2 substituted with aryl or ester end groups have been synthesized. The 2,5-bisstyryl-1,4-benzoquinones 1 (R=phenyl, p-tolyl, o-tolyl) crystallize with a 7 Angstrom-stacking axis. But only for the o-tolyl derivative the contacts between the vinyl groups are close enough to allow a four-center type photopolymerization. The ester derivative 1 (R=COOEt) has a layer structure and can be photooligomerized in the crystal. The generated cyclobutane subgroups have twofold symmetry. The vinylquinones 2 (R=aryl) may be dimerized photochemically in the crystal at the vinyl groups to centrosymmetric cyclobutanes. Crystals with 4 Angstrom stacking axis are also photoreactive.