4-[4'-(3-{3-[2-(2-Ethoxy-ethoxy)-ethoxy]-2-[2-(2-ethoxy-ethoxy)-ethoxymethyl]-propoxy}-2-{3-[2-(2-ethoxy-ethoxy)-ethoxy]-2-[2-(2-ethoxy-ethoxy)-ethoxymethyl]-propoxymethyl}-propoxy)-biphenyl-4-yl]-2-methyl-but-3-yn-2-ol | 454664-60-9

• 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: 4-[4'-(3-{3-[2-(2-Ethoxy-ethoxy)-ethoxy]-2-[2-(2-ethoxy-ethoxy)-ethoxymethyl]-propoxy}-2-{3-[2-(2-ethoxy-ethoxy)-ethoxy]-2-[2-(2-ethoxy-ethoxy)-ethoxymethyl]-propoxymethyl}-propoxy)-biphenyl-4-yl]-2-methyl-but-3-yn-2-ol
• CAS: 454664-60-9
• 化学式: C₅₃H₈₈O₁₆
• 分子量: 981.272
• InChiKey: LXSPSNRCLIRJOT-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.02
• 重原子数：
  69.0
• 可旋转键数：
  48.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.74
• 拓扑面积：
  158.68
• 氢给体数：
  1.0
• 氢受体数：
  16.0

反应信息

• 作为反应物：
  描述：

  4-[4'-(3-{3-[2-(2-Ethoxy-ethoxy)-ethoxy]-2-[2-(2-ethoxy-ethoxy)-ethoxymethyl]-propoxy}-2-{3-[2-(2-ethoxy-ethoxy)-ethoxy]-2-[2-(2-ethoxy-ethoxy)-ethoxymethyl]-propoxymethyl}-propoxy)-biphenyl-4-yl]-2-methyl-but-3-yn-2-ol 在 氢氧化钾 、 四丁基碘化铵 作用下， 以 环己烷 、 水 为溶剂， 反应 24.0h， 以59.2%的产率得到4-(3-{3-[2-(2-Ethoxy-ethoxy)-ethoxy]-2-[2-(2-ethoxy-ethoxy)-ethoxymethyl]-propoxy}-2-{3-[2-(2-ethoxy-ethoxy)-ethoxy]-2-[2-(2-ethoxy-ethoxy)-ethoxymethyl]-propoxymethyl}-propoxy)-4'-ethynyl-biphenyl
  参考文献：
  名称：

  Amphiphilic Hairy Disks with Branched Hydrophilic Tails and a Hexa-peri-hexabenzocoronene Core

  摘要：

  Amphiphilic discotic molecules with hydrophilic side branches consisting of hexaphenyl hexa-peri-hexabenzocoronene and hexabiphenyl hexa-peri-hexabiphenylcoronene as the aromatic core and hexa-substituted oligoethers as the branched peripheral chains have been synthesized, and their microstructure has been characterized. The discotic molecules based on dibranched oligoether side chains have been observed to self-organize into a well-ordered hexagonal columnar structure within liquid crystalline phases, which possessed an exceptionally high thermal stability and an unusually wide temperature range over >300 degreesC. We suggest that a combination of the large lateral dimensions of the rigid cores and disordered structure of the oxygen-containing branches tails is a driving force to the formation of a highly ordered columnar structure in the bulk state with enhanced molecular segregation. In contrast to the thermotropic phase behavior that favors the formation of highly ordered columnar aggregates through a strong stacking interaction, the hexabenzocoronene cores are packed in a face-on arrangement at the air/water interface and on solid surfaces with surface domains composed of an array of 7 x 7 molecules. We suggest a crablike molecular conformation and cluster-segregated monolayers with 6-fold symmetry and unusual face-on packing on a solid surface. Preliminary spectroscopic studies in the bulk state have shown that the molecules based on a hexaaromatic-substituted core may serve as functional supramolecular materials with high energy transfer characteristic within the columns due to near-perfect columnar ordering, which is unchanged over a wide temperature range. We believe that an absence of the crystallization phenomenon of side-branched oligoether chains is critical for the formation of long-range columnar ordering with strong intracolumnar correlation of conjugated disks important for high carrier mobility.

  DOI：

  10.1021/ja017553+
• 作为产物：
  描述：

  Toluene-4-sulfonic acid 3-{3-[2-(2-ethoxy-ethoxy)-ethoxy]-2-[2-(2-ethoxy-ethoxy)-ethoxymethyl]-propoxy}-2-{3-[2-(2-ethoxy-ethoxy)-ethoxy]-2-[2-(2-ethoxy-ethoxy)-ethoxymethyl]-propoxymethyl}-propyl ester 在 copper(l) iodide 、 四(三苯基膦)钯 、 potassium carbonate 、 三乙胺 作用下， 以 乙醇 为溶剂， 反应 24.0h， 生成 4-[4'-(3-{3-[2-(2-Ethoxy-ethoxy)-ethoxy]-2-[2-(2-ethoxy-ethoxy)-ethoxymethyl]-propoxy}-2-{3-[2-(2-ethoxy-ethoxy)-ethoxy]-2-[2-(2-ethoxy-ethoxy)-ethoxymethyl]-propoxymethyl}-propoxy)-biphenyl-4-yl]-2-methyl-but-3-yn-2-ol
  参考文献：
  名称：

  Amphiphilic Hairy Disks with Branched Hydrophilic Tails and a Hexa-peri-hexabenzocoronene Core

  摘要：

  Amphiphilic discotic molecules with hydrophilic side branches consisting of hexaphenyl hexa-peri-hexabenzocoronene and hexabiphenyl hexa-peri-hexabiphenylcoronene as the aromatic core and hexa-substituted oligoethers as the branched peripheral chains have been synthesized, and their microstructure has been characterized. The discotic molecules based on dibranched oligoether side chains have been observed to self-organize into a well-ordered hexagonal columnar structure within liquid crystalline phases, which possessed an exceptionally high thermal stability and an unusually wide temperature range over >300 degreesC. We suggest that a combination of the large lateral dimensions of the rigid cores and disordered structure of the oxygen-containing branches tails is a driving force to the formation of a highly ordered columnar structure in the bulk state with enhanced molecular segregation. In contrast to the thermotropic phase behavior that favors the formation of highly ordered columnar aggregates through a strong stacking interaction, the hexabenzocoronene cores are packed in a face-on arrangement at the air/water interface and on solid surfaces with surface domains composed of an array of 7 x 7 molecules. We suggest a crablike molecular conformation and cluster-segregated monolayers with 6-fold symmetry and unusual face-on packing on a solid surface. Preliminary spectroscopic studies in the bulk state have shown that the molecules based on a hexaaromatic-substituted core may serve as functional supramolecular materials with high energy transfer characteristic within the columns due to near-perfect columnar ordering, which is unchanged over a wide temperature range. We believe that an absence of the crystallization phenomenon of side-branched oligoether chains is critical for the formation of long-range columnar ordering with strong intracolumnar correlation of conjugated disks important for high carrier mobility.

  DOI：

  10.1021/ja017553+