2,9-Bis(p-carboxyphenyl)-1,10-phenanthroline | 157523-12-1

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 喹啉及其衍生物
• 英文名称: 2,9-Bis(p-carboxyphenyl)-1,10-phenanthroline
• 英文别名: 2,9-bis(4-carboxyphenyl)-1,10-phenanthroline；4,4'-(1,10-phenanthroline-2,9-diyl)dibenzoic acid；4-[9-(4-Carboxyphenyl)-1,10-phenanthrolin-2-yl]benzoic acid；4-[9-(4-carboxyphenyl)-1,10-phenanthrolin-2-yl]benzoic acid
• CAS: 157523-12-1
• 化学式: C₂₆H₁₆N₂O₄
• 分子量: 420.424
• InChiKey: LWWYULDEKNKUOL-UHFFFAOYSA-N

物化性质

• 沸点：
  727.1±60.0 °C(Predicted)
• 密度：
  1.402±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4.8
• 重原子数：
  32
• 可旋转键数：
  4
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  100
• 氢给体数：
  2
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  2,9-Bis(p-carboxyphenyl)-1,10-phenanthroline 在 草酰氯 作用下， 以 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， 反应 18.0h， 生成 2,9-bis<4-(6-methylpyridin-2-ylcarbamoyl)phenyl>-1,10-phenanthroline
  参考文献：
  名称：

  Self-Assembling, Chromogenic Receptors for the Recognition of Dicarboxylic Acids

  摘要：

  The synthesis of ligands (2,9-disubstituted phenanthrolines) bearing one or two acylaminopyridine binding sites, compounds 1 and 2 respectively, is described. Each ligand can assemble on a Cu(I) template, forming two different receptors for dicarboxylic acids, Cu(1)(2)(BF4-)-B-+ and Cu(2)(2)(BF4-)-B-+. These orange Cu(I) complexes are shown to bind (K-a > 10(4) M(-1)) to a variety of dicarboxylic acids in chloroform, with a slight preference for the C-5-dicarboxylic acids, glutaric and N-CBz-glutamic acids, over shorter and longer substrates. Complexation is analyzed both by NMR chemical shift changes and UV-visible absorption changes. The data indicate formation of 1:1 complexes for Cu(1)(2)(BF4-)-B-+ and 2:1 complexes for Cu(2)(2)(BF4-)-B-+, with the dicarboxylic acid substrate hydrogen bonding simultaneously to an acylaminopyridine binding site on each ligand. For Cu(2)(2)(BF4-)-B-+, the complexation event results in large shifts in the visible absorption bands and a color change from orange to red. The change in the visible absorbance, and therefore the chromogenicity, was found to be substrate dependent. The chromogenic effect is explained by a conformational change in the receptors resulting from hydrogen bond formation with the substrate.

  DOI：

  10.1021/ja00137a021
• 作为产物：
  描述：

  2-((4-bromobenzyl)oxy)tetrahydro-2H-pyran 在 manganese(IV) oxide 、 正丁基锂 、 jones reagent 、 对甲苯磺酸 作用下， 以 乙醚 、 乙醇 、 丙酮 为溶剂， 反应 19.0h， 生成 2,9-Bis(p-carboxyphenyl)-1,10-phenanthroline
  参考文献：
  名称：

  Spectral sensitization of large-band-gap semiconductors (thin films and ceramics) by a carboxylated bis(1,10-phenanthroline)copper(I) complex

  摘要：

  Photoelectrochemical cells based on colloidal films of titanium dioxide and zinc oxide ceramic electrodes sensitized by a bis(2,9-diphenyl-1,10-phenanthroline)copper(i) complex modified at the para positions with NaO2C groups, were investigated in an aqueous medium using hydroquinone as electron donor. The sensitizing effect is greater with the films due to the enhanced geometric area projection. The photocurrent-action spectrum obtained with this complex covers almost the whole of the solar visible region. The quantum efficiency was found to depend on the degree of surface coverage by the complex. In a solar-cell arrangement the open-circuit photovoltage was 0.6 V with a small short-circuit photocurrent of ca. 0.6 mA cm-2 in iodide-containing propylene carbonate.

  DOI：

  10.1039/dt9940001649

文献信息

• A two-dimensional metal–organic framework assembled from scandium-based cages for the selective capture of sulfur hexafluoride
  作者：Hao Wang、Le Shi、Zhangyi Xiong、Si Ma、Honghao Cao、Shijia Cai、Zhiwei Qiao、Jun Pan、Zhijie Chen

  DOI：10.1039/d3cc05087d

  日期：——

  we report the synthesis of a two-dimensional metal–organic framework (MOF), assembled from octahedral metal–organic cages featuring phenanthroline-based carboxylate linkers and μ3-oxo-centered trinuclear Sc(III) inorganic building blocks. We study the performance of this MOF towards the capture of sulfur hexafluoride (SF6). On account of its structural features and porous nature, this MOF displays an

  在此，我们报道了二维金属有机框架（MOF）的合成，该框架由八面体金属有机笼组装而成，具有基于菲咯啉的羧酸酯连接体和μ3-氧中心三核Sc（ III ）无机构建块。我们研究了这种 MOF 捕获六氟化硫 (SF 6 ) 的性能。由于其结构特征和多孔性质，该MOF在0.1 bar下表现出0.92 mmol g -1的SF 6吸收容量和约30.7 kJ mol -1的SF 6等量吸附热，说明了其在从N 2中选择性捕获SF 6 。此外，我们通过分子模拟研究了该MOF内部SF 6和N 2的吸附结合机制。
• Self-Assembling, Chromogenic Receptors for the Recognition of Dicarboxylic Acids
  作者：M. Scott Goodman、Andrew D. Hamilton、Jean Weiss

  DOI：10.1021/ja00137a021

  日期：1995.8

  The synthesis of ligands (2,9-disubstituted phenanthrolines) bearing one or two acylaminopyridine binding sites, compounds 1 and 2 respectively, is described. Each ligand can assemble on a Cu(I) template, forming two different receptors for dicarboxylic acids, Cu(1)(2)(BF4-)-B-+ and Cu(2)(2)(BF4-)-B-+. These orange Cu(I) complexes are shown to bind (K-a > 10(4) M(-1)) to a variety of dicarboxylic acids in chloroform, with a slight preference for the C-5-dicarboxylic acids, glutaric and N-CBz-glutamic acids, over shorter and longer substrates. Complexation is analyzed both by NMR chemical shift changes and UV-visible absorption changes. The data indicate formation of 1:1 complexes for Cu(1)(2)(BF4-)-B-+ and 2:1 complexes for Cu(2)(2)(BF4-)-B-+, with the dicarboxylic acid substrate hydrogen bonding simultaneously to an acylaminopyridine binding site on each ligand. For Cu(2)(2)(BF4-)-B-+, the complexation event results in large shifts in the visible absorption bands and a color change from orange to red. The change in the visible absorbance, and therefore the chromogenicity, was found to be substrate dependent. The chromogenic effect is explained by a conformational change in the receptors resulting from hydrogen bond formation with the substrate.
• Spectral sensitization of large-band-gap semiconductors (thin films and ceramics) by a carboxylated bis(1,10-phenanthroline)copper(I) complex
  作者：Nicol�s Alonso-Vante、Jean-Fran�ois Nierengarten、Jean-Pierre Sauvage

  DOI：10.1039/dt9940001649

  日期：——

  Photoelectrochemical cells based on colloidal films of titanium dioxide and zinc oxide ceramic electrodes sensitized by a bis(2,9-diphenyl-1,10-phenanthroline)copper(i) complex modified at the para positions with NaO2C groups, were investigated in an aqueous medium using hydroquinone as electron donor. The sensitizing effect is greater with the films due to the enhanced geometric area projection. The photocurrent-action spectrum obtained with this complex covers almost the whole of the solar visible region. The quantum efficiency was found to depend on the degree of surface coverage by the complex. In a solar-cell arrangement the open-circuit photovoltage was 0.6 V with a small short-circuit photocurrent of ca. 0.6 mA cm-2 in iodide-containing propylene carbonate.