1,3-Benzenedicarboxylic acid,5-[[4-[(4-ethynylphenyl)ethynyl]phenyl]ethynyl]-, dimethyl ester | 797761-31-0

• 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: 1,3-Benzenedicarboxylic acid,5-[[4-[(4-ethynylphenyl)ethynyl]phenyl]ethynyl]-, dimethyl ester
• 英文别名: 5-[4-(4-Ethynyl-phenylethynyl)-phenylethynyl]-isophthalic acid dimethyl ester
• CAS: 797761-31-0
• 化学式: C₂₈H₁₈O₄
• 分子量: 418.449
• InChiKey: JBLTVSDCXBZRRZ-UHFFFAOYSA-N

物化性质

• 沸点：
  593.9±50.0 °C(Predicted)
• 密度：
  1.27±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4.04
• 重原子数：
  32.0
• 可旋转键数：
  2.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.07
• 拓扑面积：
  52.6
• 氢给体数：
  0.0
• 氢受体数：
  4.0

反应信息

• 作为反应物：
  描述：

  1,3-Benzenedicarboxylic acid,5-[[4-[(4-ethynylphenyl)ethynyl]phenyl]ethynyl]-, dimethyl ester 、 4-iodo-2,2'-bipyridine 在 四(三苯基膦)钯 哌啶 、 copper(l) iodide 作用下， 以41%的产率得到5-[4-(4-[2,2']Bipyridinyl-4-ylethynyl-phenylethynyl)-phenylethynyl]-isophthalic acid dimethyl ester
  参考文献：
  名称：

  Excited State Electron Transfer from Ru(II) Polypyridyl Complexes Anchored to Nanocrystalline TiO₂ through Rigid-Rod Linkers

  摘要：

  Rigid-rod linkers varying in length were used to bind Ru(II) polypyridyl complexes to the surface of TiO2 (anatase) and of ZrO2 nanoparticle thin films. The linkers were made of p-phenyleneethynylene (Ph-E), bridges carrying two COOR anchoring groups at the end and were capped with Ru(II) polypyridyl complexes as the sensitizing chromophores. Two series of rigid-rod sensitizers were prepared: Ru complexes having bpy or 4,4'-(Cl)(2)-bpy as the ancillary ligands. In the first series, the excited state was localized on the rigid-rod linker, in the second series, the excited states were localized on the 4,4'-(Cl)(2)-bpy ligands. The rigid-rod sensitizers with Ru(bpy)(2) complexes did bind strongly (K-ad similar to 10(5) M-1) with high surface coverages (similar to10(-8) mol/cm(2)) on the nanostructured metal oxide films, ZrO2 and anatase TiO2. The length of the fully conjugated rigid-rod linker influences the photophysical properties of the sensitizer, and nanosecond transient absorption measurements indicated long-lived metal-to-ligand charge-transfer (MLCT) excited states (similar to2 mus) with evidence for delocalization onto the rigid-rod linker. The interfacial electron transfer behavior on TiO2 was found to be dependent on the Bronsted acidity or basicity of the surface. On base pretreated TiO2, the excited state electron injection yields were low and could be increased by addition of LiClO4 to an external CH3CN solution. Under these conditions, a fraction of the injection process could be time resolved on a 10 ns time scale. On acidic TiO2, ultrafast excited state electron injection was observed for both series. Recombination was found to be second order with average rate constants independent of which rigid-rod sensitizer was excited. For rigid-rod sensitizers with Ru(4,4'-(Cl)(2)-bpy)(2), there was evidence for a direct interaction between the 4,4'(Cl)(2)-bpy ligands and the TiO2 surface. Photophysical and interfacial electron transfer properties of these Cl-substituted complexes were nearly independent of the rigid-rod length.

  DOI：

  10.1021/jp047454t
• 作为产物：
  描述：

  Dimethyl 5-[2-[4-(2-trimethylsilylethynyl)phenyl]ethynyl]benzene-1,3-dicarboxylate 在 四丁基氟化铵 、 lithium hexamethyldisilazane 作用下， 以 四氢呋喃 、 正己烷 为溶剂， 反应 6.5h， 生成 1,3-Benzenedicarboxylic acid,5-[[4-[(4-ethynylphenyl)ethynyl]phenyl]ethynyl]-, dimethyl ester
  参考文献：
  名称：

  Excited State Electron Transfer from Ru(II) Polypyridyl Complexes Anchored to Nanocrystalline TiO₂ through Rigid-Rod Linkers

  摘要：

  Rigid-rod linkers varying in length were used to bind Ru(II) polypyridyl complexes to the surface of TiO2 (anatase) and of ZrO2 nanoparticle thin films. The linkers were made of p-phenyleneethynylene (Ph-E), bridges carrying two COOR anchoring groups at the end and were capped with Ru(II) polypyridyl complexes as the sensitizing chromophores. Two series of rigid-rod sensitizers were prepared: Ru complexes having bpy or 4,4'-(Cl)(2)-bpy as the ancillary ligands. In the first series, the excited state was localized on the rigid-rod linker, in the second series, the excited states were localized on the 4,4'-(Cl)(2)-bpy ligands. The rigid-rod sensitizers with Ru(bpy)(2) complexes did bind strongly (K-ad similar to 10(5) M-1) with high surface coverages (similar to10(-8) mol/cm(2)) on the nanostructured metal oxide films, ZrO2 and anatase TiO2. The length of the fully conjugated rigid-rod linker influences the photophysical properties of the sensitizer, and nanosecond transient absorption measurements indicated long-lived metal-to-ligand charge-transfer (MLCT) excited states (similar to2 mus) with evidence for delocalization onto the rigid-rod linker. The interfacial electron transfer behavior on TiO2 was found to be dependent on the Bronsted acidity or basicity of the surface. On base pretreated TiO2, the excited state electron injection yields were low and could be increased by addition of LiClO4 to an external CH3CN solution. Under these conditions, a fraction of the injection process could be time resolved on a 10 ns time scale. On acidic TiO2, ultrafast excited state electron injection was observed for both series. Recombination was found to be second order with average rate constants independent of which rigid-rod sensitizer was excited. For rigid-rod sensitizers with Ru(4,4'-(Cl)(2)-bpy)(2), there was evidence for a direct interaction between the 4,4'(Cl)(2)-bpy ligands and the TiO2 surface. Photophysical and interfacial electron transfer properties of these Cl-substituted complexes were nearly independent of the rigid-rod length.

  DOI：

  10.1021/jp047454t