tetrakis(1-(3,5-dicarboxyphenyl-1-ethynyl)-4-phenyl)ethylene

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 二芳基庚烷
• 英文名称: tetrakis(1-(3,5-dicarboxyphenyl-1-ethynyl)-4-phenyl)ethylene
• 英文别名: 5,5',5'',5'''-((Ethene-1,1,2,2-tetrayltetrakis(benzene-4,1-diyl))tetrakis(ethyne-2,1-diyl))tetraisophthalic acid；5-[2-[4-[1,2,2-tris[4-[2-(3,5-dicarboxyphenyl)ethynyl]phenyl]ethenyl]phenyl]ethynyl]benzene-1,3-dicarboxylic acid
• 化学式: C₆₆H₃₆O₁₆
• 分子量: 1085.0
• InChiKey: KSNOVFMPQCJVSZ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  12.3
• 重原子数：
  82
• 可旋转键数：
  20
• 环数：
  8.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  298
• 氢给体数：
  8
• 氢受体数：
  16

反应信息

• 作为反应物：
  描述：

  N,N-二乙基甲酰胺 、 zinc(II) nitrate hexahydrate 、 tetrakis(1-(3,5-dicarboxyphenyl-1-ethynyl)-4-phenyl)ethylene 以 乙醇 为溶剂， 反应 36.0h， 以77%的产率得到[Zn4(TDPEPE)(H2O)4(DEF)4]*(H2O)3(DEF)9.5
  参考文献：
  名称：

  Conformational Locking by Design: Relating Strain Energy with Luminescence and Stability in Rigid Metal–Organic Frameworks

  摘要：

  Minimization of the torsional barrier for phenyl ring flipping in a metal organic framework (MOF) based on the new ethynyl-extended octacarboxylate ligand H8TDPEPE leads to a fluorescent material with a near-dark state. Immobilization of the ligand in the rigid structure also unexpectedly causes significant strain. We used DFT calculations to estimate the ligand strain energies in our and all other topologically related materials and correlated these with empirical structural descriptors to derive general rules for trapping molecules in high-energy conformations within MOFs. These studies portend possible applications of MOFs for studying fundamental concepts related to conformational locking and its effects on molecular reactivity and chromophore photophysics.

  DOI：

  10.1021/ja3103154
• 作为产物：
  描述：

  5,5',5'',5'''-((乙烯-1,1,2,2-四基四(苯-4,1-二基))四(乙炔-2,1-二基))四间苯二甲酸 在 水 、 sodium hydroxide 作用下， 以 四氢呋喃 、 甲醇 为溶剂， 反应 24.0h， 以79%的产率得到tetrakis(1-(3,5-dicarboxyphenyl-1-ethynyl)-4-phenyl)ethylene
  参考文献：
  名称：

  Conformational Locking by Design: Relating Strain Energy with Luminescence and Stability in Rigid Metal–Organic Frameworks

  摘要：

  Minimization of the torsional barrier for phenyl ring flipping in a metal organic framework (MOF) based on the new ethynyl-extended octacarboxylate ligand H8TDPEPE leads to a fluorescent material with a near-dark state. Immobilization of the ligand in the rigid structure also unexpectedly causes significant strain. We used DFT calculations to estimate the ligand strain energies in our and all other topologically related materials and correlated these with empirical structural descriptors to derive general rules for trapping molecules in high-energy conformations within MOFs. These studies portend possible applications of MOFs for studying fundamental concepts related to conformational locking and its effects on molecular reactivity and chromophore photophysics.

  DOI：

  10.1021/ja3103154

文献信息

• Conformational Locking by Design: Relating Strain Energy with Luminescence and Stability in Rigid Metal–Organic Frameworks
  作者：Natalia B. Shustova、Anthony F. Cozzolino、Mircea Dincă

  DOI：10.1021/ja3103154

  日期：2012.12.5

  Minimization of the torsional barrier for phenyl ring flipping in a metal organic framework (MOF) based on the new ethynyl-extended octacarboxylate ligand H8TDPEPE leads to a fluorescent material with a near-dark state. Immobilization of the ligand in the rigid structure also unexpectedly causes significant strain. We used DFT calculations to estimate the ligand strain energies in our and all other topologically related materials and correlated these with empirical structural descriptors to derive general rules for trapping molecules in high-energy conformations within MOFs. These studies portend possible applications of MOFs for studying fundamental concepts related to conformational locking and its effects on molecular reactivity and chromophore photophysics.