1,3-Bis(3,4-dicarboxyphenyl)-1,1,3,3-tetramethyldisiloxane dianhydride

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 英文名称: 1,3-Bis(3,4-dicarboxyphenyl)-1,1,3,3-tetramethyldisiloxane dianhydride
• 英文别名: 1,3-bis(4'-phthalic anhydride)-tetramethyldisiloxane；tetramethyldisiloxane-1,3-bis(4-phthalic anhydride)；5-[[(1,3-Dioxo-2-benzofuran-5-yl)-dimethylsilyl]oxy-dimethylsilyl]-2-benzofuran-1,3-dione
• 化学式: C₂₀H₁₈O₇Si₂
• 分子量: 426.53
• InChiKey: RXJJOQVOLXJBOL-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.85
• 重原子数：
  29
• 可旋转键数：
  4
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.2
• 拓扑面积：
  96
• 氢给体数：
  0
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  1,3-Bis(3,4-dicarboxyphenyl)-1,1,3,3-tetramethyldisiloxane dianhydride 以 甲苯 为溶剂， 反应 12.0h， 生成 5-[[[1,3-Dioxo-2-(3-trimethoxysilylpropyl)isoindol-5-yl]-dimethylsilyl]oxy-dimethylsilyl]-2-(3-trimethoxysilylpropyl)isoindole-1,3-dione
  参考文献：
  名称：

  Synthesis of [(Trialkoxysilyl)propyl]imides

  摘要：

  Imidization reactions between anhydrides and (alkoxysilyl)propylamines containing alkoxysilane groups result in hydrolysis and condensation of the,alkoxysilane groups and formation of SiOSi bonds. As a result, the direct reaction of various anhydrides with (gamma-aminopropyl)trialkoxysilanes did not afford [(trialkoxysilyl)propyl]imides but instead resulted in insoluble crosslinked materials. A successful two-step synthesis of [(trialkoxysilyl)propyl] imides is reported. In the first step, an intermediate imide was prepared by reaction of an anhydride with 2-aminopyridine. Following removal of the water of imidization, addition of an (gamma-aminopropyl)trialkoxysilane resulted in a transimidization equilibrium which favored displacement of 2-aminopyridine and formation of a [(trialkoxysilyl)propyl]imide in high yield. Synthesis of a moisture-curable polyimide containing alkoxysilane endcaps is briefly described.

  DOI：

  10.1021/jo00089a029
• 作为产物：
  描述：

  1,2-二氯四甲基二硅烷 、 氯化偏苯三酸酐 在 二(氰基苯)二氯化钯 、 三苯基膦 作用下， 生成 1,3-Bis(3,4-dicarboxyphenyl)-1,1,3,3-tetramethyldisiloxane dianhydride
  参考文献：
  名称：

  Tuning of the color of the emitted light from new polyperyleneimides containing oxadiazole and siloxane moieties

  摘要：

  Four new aromatic poly(peryleneimides) containing electron-withdrawing oxadiazole rings and flexible tetramethyldisiloxane units in the backbone were prepared by a one step polycondensation reaction at high temperature of four aromatic diamines containing preformed oxadiazole units with a mixture, in different ratios, of perylenetetracarboxylic dianhydride and tetramethyldisiloxane-1,3-bis(4-phthalic anhydride). The structure of these polymers was confirmed by FT-IR and H-1 NMR spectroscopy. The solubility, thermal stability and glass transition temperature of the poly(peryleneimides) were measured and discussed in correlation with their chemical structure. The solid polymers were studied by X-ray diffraction which revealed a semicrystalline state consisting in face-to-face arranged columns of perylenediimide units for two of the polymers. The film-forming ability and the morphology of the resulting thin films were investigated using scanning electron microscopy which showed that two of the polymer films were organized into self-assembled rod-like structures. An extensive study of the photo-optical properties of these polymers highlighted the ability of the color of the emitted light to be modulated as a function of the excitation wavelengths, as was surveyed in the chromaticity diagrams. The Forster excitation energy transfer phenomenon from oxadiazole to perylenediimide chromophores was observed to occur for some of the polymers, for which the oxygen bridge appears to be responsible. In solution, high fluorescence quantum yields were obtained, up to 24%, while, in the solid state, low fluorescence emission was attained due to aggregation. These poly(peryleneimides) could be considered as promising candidates for high-performance materials to be used in novel optoelectronic applications, e.g. chemiluminescent sensors. (C) 2013 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.dyepig.2013.04.035

文献信息

• Bruma, Maria; Sava, Ion; Damaceanu, Mariana Dana, Revue Roumaine de Chimie, 2008, vol. 53, # 9, p. 803 - 811
  作者：Bruma, Maria、Sava, Ion、Damaceanu, Mariana Dana、Belomoina, Nataliya M.、Robison, Jenifer

  DOI：——

  日期：——
• Wengrovius Jeffrey H., Powell Virginia M., Webb Jimmy L., J. Org. Chem, 59 (1994) N 10, S 2813-2817
  作者：Wengrovius Jeffrey H., Powell Virginia M., Webb Jimmy L.

  DOI：——

  日期：——
• Tuning of the color of the emitted light from new polyperyleneimides containing oxadiazole and siloxane moieties
  作者：Mariana-Dana Damaceanu、Catalin-Paul Constantin、Maria Bruma、Mariana Pinteala

  DOI：10.1016/j.dyepig.2013.04.035

  日期：2013.10

  Four new aromatic poly(peryleneimides) containing electron-withdrawing oxadiazole rings and flexible tetramethyldisiloxane units in the backbone were prepared by a one step polycondensation reaction at high temperature of four aromatic diamines containing preformed oxadiazole units with a mixture, in different ratios, of perylenetetracarboxylic dianhydride and tetramethyldisiloxane-1,3-bis(4-phthalic anhydride). The structure of these polymers was confirmed by FT-IR and H-1 NMR spectroscopy. The solubility, thermal stability and glass transition temperature of the poly(peryleneimides) were measured and discussed in correlation with their chemical structure. The solid polymers were studied by X-ray diffraction which revealed a semicrystalline state consisting in face-to-face arranged columns of perylenediimide units for two of the polymers. The film-forming ability and the morphology of the resulting thin films were investigated using scanning electron microscopy which showed that two of the polymer films were organized into self-assembled rod-like structures. An extensive study of the photo-optical properties of these polymers highlighted the ability of the color of the emitted light to be modulated as a function of the excitation wavelengths, as was surveyed in the chromaticity diagrams. The Forster excitation energy transfer phenomenon from oxadiazole to perylenediimide chromophores was observed to occur for some of the polymers, for which the oxygen bridge appears to be responsible. In solution, high fluorescence quantum yields were obtained, up to 24%, while, in the solid state, low fluorescence emission was attained due to aggregation. These poly(peryleneimides) could be considered as promising candidates for high-performance materials to be used in novel optoelectronic applications, e.g. chemiluminescent sensors. (C) 2013 Elsevier Ltd. All rights reserved.
• Synthesis of [(Trialkoxysilyl)propyl]imides
  作者：Jeffrey H. Wengrovius、Virginia M. Powell、Jimmy L. Webb

  DOI：10.1021/jo00089a029

  日期：1994.5

  Imidization reactions between anhydrides and (alkoxysilyl)propylamines containing alkoxysilane groups result in hydrolysis and condensation of the,alkoxysilane groups and formation of SiOSi bonds. As a result, the direct reaction of various anhydrides with (gamma-aminopropyl)trialkoxysilanes did not afford [(trialkoxysilyl)propyl]imides but instead resulted in insoluble crosslinked materials. A successful two-step synthesis of [(trialkoxysilyl)propyl] imides is reported. In the first step, an intermediate imide was prepared by reaction of an anhydride with 2-aminopyridine. Following removal of the water of imidization, addition of an (gamma-aminopropyl)trialkoxysilane resulted in a transimidization equilibrium which favored displacement of 2-aminopyridine and formation of a [(trialkoxysilyl)propyl]imide in high yield. Synthesis of a moisture-curable polyimide containing alkoxysilane endcaps is briefly described.