diethyl 5-[(4-ethynylphenyl)ethynyl]isophthaloate | 368455-21-4

• 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: diethyl 5-[(4-ethynylphenyl)ethynyl]isophthaloate
• 英文别名: diethyl 5-[(4-ethynylphenyl)ethynyl]isophthalate；1,3-Diethylcarboxylate-5-[(4-(ethynyl)phenyl)ethynyl]benzene；diethyl 5-[2-(4-ethynylphenyl)ethynyl]benzene-1,3-dicarboxylate
• CAS: 368455-21-4
• 化学式: C₂₂H₁₈O₄
• 分子量: 346.383
• InChiKey: OYJDRBLZJROANU-UHFFFAOYSA-N

物化性质

• 沸点：
  500.2±50.0 °C(Predicted)
• 密度：
  1.20±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4.6
• 重原子数：
  26
• 可旋转键数：
  9
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.18
• 拓扑面积：
  52.6
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  diethyl 5-[(4-ethynylphenyl)ethynyl]isophthaloate 在 哌啶 、 copper(l) iodide 、 四(三苯基膦)钯 、 乙醇 作用下， 以 二氯甲烷 为溶剂， 反应 4.0h， 生成 diethyl 5-[(4-[(4-ethynylphenyl)ethynyl]phenyl)ethynyl]isophthaloate
  参考文献：
  名称：

  Tetrahedral Onsager Crosses for Solubility Improvement and Crystallization Bypass

  摘要：

  Pure organic molecules exhibiting a suitable concave rigid shape are expected to give porous glasses in the solid state. Such a feature opens new opportunities to avoid crystallization and to improve molecular solubility in relation to the high internal energy of these solid phases. To quantitatively explore the latter strategy, a series of rigid tetrahedral conjugated molecules nC and the corresponding models nR have been synthesized. Related to the present purpose, several properties have been investigated using UV absorption, steady-state fluorescence emission, differential scanning calorimetry, H-1 NMR translational self-diffusion, magic angle spinning C-13 NMR, and multiple-beam interferometry experiments. The present tetrahedral crosses are up to 8 orders of magnitude more soluble than the corresponding model compounds after normalization to the same molecular length. In addition, they give concentrated monomeric solutions that can be used to cover surfaces with homogeneous films whose thickness goes down to the nanometer range. Such attractive features make cross-like molecular architectures promising for many applications.

  DOI：

  10.1021/ja010019h
• 作为产物：
  描述：

  diethyl 5-iodoisophthalate 在 哌啶 、 copper(l) iodide 、 四(三苯基膦)钯 、 乙醇 、 caesium carbonate 作用下， 以 二氯甲烷 为溶剂， 反应 8.0h， 生成 diethyl 5-[(4-ethynylphenyl)ethynyl]isophthaloate
  参考文献：
  名称：

  Tetrahedral Onsager Crosses for Solubility Improvement and Crystallization Bypass

  摘要：

  Pure organic molecules exhibiting a suitable concave rigid shape are expected to give porous glasses in the solid state. Such a feature opens new opportunities to avoid crystallization and to improve molecular solubility in relation to the high internal energy of these solid phases. To quantitatively explore the latter strategy, a series of rigid tetrahedral conjugated molecules nC and the corresponding models nR have been synthesized. Related to the present purpose, several properties have been investigated using UV absorption, steady-state fluorescence emission, differential scanning calorimetry, H-1 NMR translational self-diffusion, magic angle spinning C-13 NMR, and multiple-beam interferometry experiments. The present tetrahedral crosses are up to 8 orders of magnitude more soluble than the corresponding model compounds after normalization to the same molecular length. In addition, they give concentrated monomeric solutions that can be used to cover surfaces with homogeneous films whose thickness goes down to the nanometer range. Such attractive features make cross-like molecular architectures promising for many applications.

  DOI：

  10.1021/ja010019h

文献信息

• An Isoreticular Series of Metal-Organic Frameworks with Dendritic Hexacarboxylate Ligands and Exceptionally High Gas-Uptake Capacity
  作者：Daqiang Yuan、Dan Zhao、Daofeng Sun、Hong-Cai Zhou

  DOI：10.1002/anie.201001009

  日期：——

  Holding gas: One of the isoreticular metal–organic frameworks (MOFs) that have been synthesized and characterized structurally, PCN‐68 (see structure), has a Langmuir surface area of as high as 6033 m2 g−1. The MOFs also display excellent gas (H2, CH4, and CO2) adsorption capacity.

  保藏气体：PCN-68（参见结构）是一种已经合成并具有结构特征的等孔金属有机骨架（MOF），其朗缪尔表面积高达6033 m 2  g -1。MOF还显示出出色的气体（H 2，CH 4和CO 2）吸附能力。
• Metal–Organic Framework Materials with Ultrahigh Surface Areas: Is the Sky the Limit?
  作者：Omar K. Farha、Ibrahim Eryazici、Nak Cheon Jeong、Brad G. Hauser、Christopher E. Wilmer、Amy A. Sarjeant、Randall Q. Snurr、SonBinh T. Nguyen、A. Özgür Yazaydın、Joseph T. Hupp

  DOI：10.1021/ja3055639

  日期：2012.9.12

  We have synthesized, characterized, and computationally simulated/validated the behavior of two new metal organic framework (MOF) materials displaying the highest experimental Brunauer-Emmett-Teller (BET) surface areas of any porous materials reported to date (similar to 7000 m(2)/g). Key to evacuating the initially solvent-filled materials without pore collapse, and thereby accessing the ultrahigh areas, is the use of a supercritical CO2 activation technique. Additionally, we demonstrate computationally that by shifting from phenyl groups to "space efficient" acetylene moieties as linker expansion units, the hypothetical maximum surface area for a MOF material is substantially greater than previously envisioned (similar to 14600 m(2)/g (or greater) versus similar to 10500 m(2)/g).