3-[(2S)-2-methyl-3,6,9,12,15-pentaoxahexadecyloxy]-4-methylthiophene

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 3-[(2S)-2-methyl-3,6,9,12,15-pentaoxahexadecyloxy]-4-methylthiophene
• 英文别名: 3-[(2s)-2-Methyl-3,6,9,12,15-pentaoxahexadecyloxy]-4-methylthiophene；3-[(2S)-2-[2-[2-[2-(2-methoxyethoxy)ethoxy]ethoxy]ethoxy]propoxy]-4-methylthiophene
• 化学式: C₁₇H₃₀O₆S
• 分子量: 362.488
• InChiKey: RJFKKWHZEBSSQB-INIZCTEOSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.6
• 重原子数：
  24
• 可旋转键数：
  16
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.76
• 拓扑面积：
  83.6
• 氢给体数：
  0
• 氢受体数：
  7

反应信息

• 作为产物：
  描述：

  3-methoxy-4-methylthiophene 、 (2S)-2-(2-{2-[2-(2-methoxyethoxy)ethoxy]ethoxy}ethoxy)propan-1-ol 在 对甲苯磺酸 作用下， 以 甲苯 为溶剂， 反应 72.0h， 以69%的产率得到3-[(2S)-2-methyl-3,6,9,12,15-pentaoxahexadecyloxy]-4-methylthiophene
  参考文献：
  名称：

  Highly Ordered Structures of Amphiphilic Polythiophenes in Aqueous Media

  摘要：

  Aqueous dispersions of a regioregular polythiophene, bearing enantiomerically pure oligo(ethylene oxide) side chains, are obtained by injecting small volumes of a THF solution of the polymer into water. The interplay of hydrophilic and hydrophobic interactions accounts for the unprecedented formation of hexagonal platelets, as well as other aggregates. Electron microscopy and selected area electron diffraction revealed that the platelets show diffraction patterns typical for single crystals. The relative amount of these highly ordered structures reaches 30% of all aggregates, in case of dispersions containing 10% (v/v) of THF in water. The effect of the organic solvent in controlling the formation of highly ordered assemblies is also investigated by means of UV-vis spectroscopy, where the occurrence of main chain organization gives rise to a distinct red-shifted absorption band. In the fluorescence spectra, the same situation accounts for quenching of the emission located at higher wavelengths with respect to the one in pure THF. The chiral information in the side chain is expressed at the supramolecular level in the highly ordered states, as revealed by CD spectroscopy. Notably, the intensity of the bisignated Cotton effect reaches its maximum at 10% (v/v) of THF, which coincides with the highest amount of single crystals in TEM. Thermochromic experiments show high thermal stability of the chiral assemblies in water.

  DOI：

  10.1021/ma011334r

文献信息

• Highly Ordered Structures of Amphiphilic Polythiophenes in Aqueous Media
  作者：F. Brustolin、F. Goldoni、E. W. Meijer、N. A. J. M. Sommerdijk

  DOI：10.1021/ma011334r

  日期：2002.1.1

  Aqueous dispersions of a regioregular polythiophene, bearing enantiomerically pure oligo(ethylene oxide) side chains, are obtained by injecting small volumes of a THF solution of the polymer into water. The interplay of hydrophilic and hydrophobic interactions accounts for the unprecedented formation of hexagonal platelets, as well as other aggregates. Electron microscopy and selected area electron diffraction revealed that the platelets show diffraction patterns typical for single crystals. The relative amount of these highly ordered structures reaches 30% of all aggregates, in case of dispersions containing 10% (v/v) of THF in water. The effect of the organic solvent in controlling the formation of highly ordered assemblies is also investigated by means of UV-vis spectroscopy, where the occurrence of main chain organization gives rise to a distinct red-shifted absorption band. In the fluorescence spectra, the same situation accounts for quenching of the emission located at higher wavelengths with respect to the one in pure THF. The chiral information in the side chain is expressed at the supramolecular level in the highly ordered states, as revealed by CD spectroscopy. Notably, the intensity of the bisignated Cotton effect reaches its maximum at 10% (v/v) of THF, which coincides with the highest amount of single crystals in TEM. Thermochromic experiments show high thermal stability of the chiral assemblies in water.