2-[2-(3-Formylphenyl)ethynyl]-5-(2-trimethylsilylethynyl)benzaldehyde | 1380279-67-3

• 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-[2-(3-Formylphenyl)ethynyl]-5-(2-trimethylsilylethynyl)benzaldehyde
• 英文别名: 2-[2-(3-formylphenyl)ethynyl]-5-(2-trimethylsilylethynyl)benzaldehyde
• CAS: 1380279-67-3
• 化学式: C₂₁H₁₈O₂Si
• 分子量: 330.458
• InChiKey: SPFJIZPJYSGEOD-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.94
• 重原子数：
  24
• 可旋转键数：
  6
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.14
• 拓扑面积：
  34.1
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  2-[2-(3-Formylphenyl)ethynyl]-5-(2-trimethylsilylethynyl)benzaldehyde 在 bis-triphenylphosphine-palladium(II) chloride 、 copper(l) iodide 、 potassium carbonate 、 三乙胺 、 三苯基膦 作用下， 以 四氢呋喃 、 甲醇 、 二氯甲烷 为溶剂， 反应 27.0h， 生成 5-((2-formyl-4-((2-formyl-4-((2-formylphenyl)ethynyl)phenyl)ethynyl)phenyl)ethynyl)-2-((3-formylphenyl)ethynyl)benzaldehyde
  参考文献：
  名称：

  p-Phenyleneethynylene-based comb-like oligomers: the synthesis and self-assembling property

  摘要：

  This paper describes the self-assembling property of three series of p-phenyleneethynylene based comb-like oligomers, which carry multiple peripheral side chains of different polarity. The new oligomers are prepared readily through the formation of the hydrazone bonds from the corresponding aldehyde and gallic acid-derived benzohydrazides. In polar solvents such as methanol and ethanol, the oligomers that bear n-decyl or 2-(2-(dioctylamino)-2-oxoethyl-amino)-2-oxoethoxyl unit (DOAOE) segments as the side chains are revealed to form vesicular structures, while the oligomers carrying hydrophilic oligo(ethyleneglycol) side chains do not. The structures of the vesicles are evidenced by SEM, AFM, TEM, and dye-encapsulation experiments. UV-vis absorption spectroscopic experiments suggest that the vesicles are generated through the stacking of the conjugated backbones, which is promoted by the solvophobic interaction of the peripheral side chains. (C) 2012 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2012.01.082
• 作为产物：
  描述：

  2-formyl-4-((trimethylsilyl)ethynyl)phenyl trifluoromethanesulfonate 、 3-乙炔基苯甲醛 在 bis-triphenylphosphine-palladium(II) chloride 、 copper(l) iodide 、 三乙胺 、 三苯基膦 作用下， 以 四氢呋喃 为溶剂， 反应 24.0h， 以84%的产率得到2-[2-(3-Formylphenyl)ethynyl]-5-(2-trimethylsilylethynyl)benzaldehyde
  参考文献：
  名称：

  p-Phenyleneethynylene-based comb-like oligomers: the synthesis and self-assembling property

  摘要：

  This paper describes the self-assembling property of three series of p-phenyleneethynylene based comb-like oligomers, which carry multiple peripheral side chains of different polarity. The new oligomers are prepared readily through the formation of the hydrazone bonds from the corresponding aldehyde and gallic acid-derived benzohydrazides. In polar solvents such as methanol and ethanol, the oligomers that bear n-decyl or 2-(2-(dioctylamino)-2-oxoethyl-amino)-2-oxoethoxyl unit (DOAOE) segments as the side chains are revealed to form vesicular structures, while the oligomers carrying hydrophilic oligo(ethyleneglycol) side chains do not. The structures of the vesicles are evidenced by SEM, AFM, TEM, and dye-encapsulation experiments. UV-vis absorption spectroscopic experiments suggest that the vesicles are generated through the stacking of the conjugated backbones, which is promoted by the solvophobic interaction of the peripheral side chains. (C) 2012 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2012.01.082

文献信息

• p-Phenyleneethynylene-based comb-like oligomers: the synthesis and self-assembling property
  作者：Liu-Gang Wang、Tian-Guang Zhan、Xin Zhao、Xi-Kui Jiang、Zhan-Ting Li

  DOI：10.1016/j.tet.2012.01.082

  日期：2012.7

  This paper describes the self-assembling property of three series of p-phenyleneethynylene based comb-like oligomers, which carry multiple peripheral side chains of different polarity. The new oligomers are prepared readily through the formation of the hydrazone bonds from the corresponding aldehyde and gallic acid-derived benzohydrazides. In polar solvents such as methanol and ethanol, the oligomers that bear n-decyl or 2-(2-(dioctylamino)-2-oxoethyl-amino)-2-oxoethoxyl unit (DOAOE) segments as the side chains are revealed to form vesicular structures, while the oligomers carrying hydrophilic oligo(ethyleneglycol) side chains do not. The structures of the vesicles are evidenced by SEM, AFM, TEM, and dye-encapsulation experiments. UV-vis absorption spectroscopic experiments suggest that the vesicles are generated through the stacking of the conjugated backbones, which is promoted by the solvophobic interaction of the peripheral side chains. (C) 2012 Elsevier Ltd. All rights reserved.