1,3,5-tris(octadecyloxy)benzene | 119891-48-4

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯酚醚
• 英文名称: 1,3,5-tris(octadecyloxy)benzene
• 英文别名: 1,3,5-Trioctadecoxybenzene
• CAS: 119891-48-4
• 化学式: C₆₀H₁₁₄O₃
• 分子量: 883.563
• InChiKey: AVGIOXAAXZEKAP-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  28.3
• 重原子数：
  63
• 可旋转键数：
  54
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.9
• 拓扑面积：
  27.7
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  1,3,5-tris(octadecyloxy)benzene 、 N,N-二甲基甲酰胺 在 三氯氧磷 作用下， 生成 2,4,6-tris(octadecyloxy)benzaldehyde
  参考文献：
  名称：

  Structural Requirements for Producing Solvent-Free Room Temperature Liquid Fullerenes

  摘要：

  A new class of solvent-free room temperature liquid fullerenes was synthesized by attaching a single substituent of 1,3,5-tris(alkyloxy)benzene unit to C-60 or C-70 under the Prato conditions. Although the C-60 monoadducts were single components after chromatographic purification, the C-70 monoadducts were isomeric mixtures due to the prolate spheroidal pi-chromophore. The alkyl chain length of the substituents significantly affected both melting points and rheological behavior of the fullerene derivatives. When the alkyl chains were short, the intermolecular pi-pi interactions of adjacent fullerene cores led to a melting point higher than room temperature. In contrast, in the case of exceedingly long alkyl chains, such as eicosyl (-C20H41) and docosanyl (-C22H45) groups, the van der Waals interactions among neighboring alkyl chains became dominant. Accordingly, only medium alkyl chain lengths could provide solvent-free fluidic fullerenes with low melting points. The rheological measurements of the liquid fullerenes at 25 degrees C revealed their unique liquid characteristics; molecular-level friction (or viscosity) and nanometer-scale clustering were noticed. It is generally thought that alkyl chains serve as a stabilizer of the fullerene core units. Thus, a longer chain or higher plasticity of the stabilizers would promote the disturbance of the core core interactions. It was indeed shown that longer alkyl chains resulted in a lower fluid viscosity. It was also found that metastable solid phases were produced by the noticeable van der Waals interaction between the long alkyl chains especially when a symmetric C-60 core was adopted. This interesting finding enabled the comparison of electrochemical activities of the C-60 unit between the solvent free liquid and metastable solid form, which revealed a superior electrochemical activity in the liquid state.

  DOI：

  10.1021/la400969f
• 作为产物：
  描述：

  间苯三酚 、 硬脂基溴 在 potassium carbonate 、 potassium iodide 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 生成 1,3,5-tris(octadecyloxy)benzene
  参考文献：
  名称：

  Structural Requirements for Producing Solvent-Free Room Temperature Liquid Fullerenes

  摘要：

  A new class of solvent-free room temperature liquid fullerenes was synthesized by attaching a single substituent of 1,3,5-tris(alkyloxy)benzene unit to C-60 or C-70 under the Prato conditions. Although the C-60 monoadducts were single components after chromatographic purification, the C-70 monoadducts were isomeric mixtures due to the prolate spheroidal pi-chromophore. The alkyl chain length of the substituents significantly affected both melting points and rheological behavior of the fullerene derivatives. When the alkyl chains were short, the intermolecular pi-pi interactions of adjacent fullerene cores led to a melting point higher than room temperature. In contrast, in the case of exceedingly long alkyl chains, such as eicosyl (-C20H41) and docosanyl (-C22H45) groups, the van der Waals interactions among neighboring alkyl chains became dominant. Accordingly, only medium alkyl chain lengths could provide solvent-free fluidic fullerenes with low melting points. The rheological measurements of the liquid fullerenes at 25 degrees C revealed their unique liquid characteristics; molecular-level friction (or viscosity) and nanometer-scale clustering were noticed. It is generally thought that alkyl chains serve as a stabilizer of the fullerene core units. Thus, a longer chain or higher plasticity of the stabilizers would promote the disturbance of the core core interactions. It was indeed shown that longer alkyl chains resulted in a lower fluid viscosity. It was also found that metastable solid phases were produced by the noticeable van der Waals interaction between the long alkyl chains especially when a symmetric C-60 core was adopted. This interesting finding enabled the comparison of electrochemical activities of the C-60 unit between the solvent free liquid and metastable solid form, which revealed a superior electrochemical activity in the liquid state.

  DOI：

  10.1021/la400969f

文献信息

• Thermal Properties and Crystal Structures of Ionic Liquids from Ruthenium Sandwich Complexes with Trialkoxybenzene Ligands: Effects of Substituent Positions and Alkyl Chain Lengths
  作者：Takahiro Ueda、Tomoyuki Mochida

  DOI：10.1021/acs.organomet.5b00021

  日期：2015.4.13

  A series of ionic liquids containing [Ru(C5H5)(arene)]+, where the arene ligands are 1,2,3-C6H3(OCnH2n+1)3 and 1,3,5-C6H3(OCnH2n+1)3 (n = 6, 12, and 18), were synthesized. The counteranions were PF6 and FSA (bis(fluorosulfonyl)amide). The melting points of the PF6 and FSA salts were 33–93 °C and −18–62 °C, respectively. In the PF6 salts, the melting points of the 1,3,5-derivatives were lower than those

  一系列含有[Ru（C 5 H 5）（arene）] +的离子液体，其中的芳烃配体是1,2,3-C 6 H 3（OC n H 2 n +1）3和1,3，合成了5-C 6 H 3（OC n H 2 n +1）3（n＝ 6、12和18）。抗衡阴离子为PF 6和FSA（双（氟磺酰基）酰胺）。PF 6和FSA盐的熔点分别为33-93°C和-18-62°C。在PF 6中1,3-，5-衍生物的熔点比1,2,3-衍生物的熔点低28-55°C，而在FSA盐中未观察到这种趋势。X射线晶体学显示在固态的1,2,3-衍生物的PF 6盐中形成了层状结构。在这些晶体中，通常观察到通过C Cp H···F H键状相互作用的阳离子-阴离子对。几种1,3,5-衍生物显示出亚稳相，其熔点低于稳定相。还合成并表征了1,2,3-衍生物的盐（n = 2）。