biphenyl-4,4'-dicarboxylic acid-bis(1-adamantanemethylamide)

• 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: biphenyl-4,4'-dicarboxylic acid-bis(1-adamantanemethylamide)
• 英文别名: N-(1-adamantylmethyl)-4-[4-(1-adamantylmethylcarbamoyl)phenyl]benzamide
• 化学式: C₃₆H₄₄N₂O₂
• 分子量: 536.758
• InChiKey: XAKVIFHTOBZVQF-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  7.9
• 重原子数：
  40
• 可旋转键数：
  7
• 环数：
  10.0
• sp3杂化的碳原子比例：
  0.61
• 拓扑面积：
  58.2
• 氢给体数：
  2
• 氢受体数：
  2

反应信息

• 作为产物：
  描述：

  檀香(SANTALUMALBUM)提取物 在 氯化亚砜 、 三乙胺 作用下， 以 二氯甲烷 为溶剂， 反应 0.5h， 生成 biphenyl-4,4'-dicarboxylic acid-bis(1-adamantanemethylamide)
  参考文献：
  名称：

  Noncovalent Binding of Sensitizers for Lanthanide(III) Luminescence in an EDTA-bis(β-cyclodextrin) Ligand

  摘要：

  EDTA-linked beta-cyclodextrin dimer 3 was synthesized from EDTA bis(anhydride) I and mono(propylamino) -appended beta-cyclodextrin 2. p-tert-Butylbenzoate 5, bound by the beta-cyclodextrin cavities of 3 with an association constant of 10(4) M-1 in water, acts as a sensitizer for the Eu-III and Tb-III complexes of 3. Luminescence spectroscopy, microcalorimetry, and Gd-III-induced NMR relaxation rate measurements prove that 3 forms a 1:2 complex with 5 and that one of the beta-cyclodextrin-bound sensitizers coordinates to the EDTA-encapsulated Ln(III) ion. The Eu-III complex of 3 forms strong 1:1 complexes (K approximate to 10(7) M-1) with bis(propylamido adamantyl)-functionalized biphenyl sensitizers 7 and 8 in water. Both beta-cycloclextrins of 3 are involved in the binding of these guests. The amide functionality adjacent to the biphenyl unit in 7 and 8 coordinates to the EDTA-encapsulated Ln(III) ion. For these biphenyl-based antennae both binding to beta-cyclodextrin and coordination to the Ln(III) center are crucial for efficient sensitization.

  DOI：

  10.1021/ja017025y

文献信息

• Noncovalent Binding of Sensitizers for Lanthanide(III) Luminescence in an EDTA-bis(β-cyclodextrin) Ligand
  作者：Jasper J. Michels、Jurriaan Huskens、David N. Reinhoudt

  DOI：10.1021/ja017025y

  日期：2002.3.1

  EDTA-linked beta-cyclodextrin dimer 3 was synthesized from EDTA bis(anhydride) I and mono(propylamino) -appended beta-cyclodextrin 2. p-tert-Butylbenzoate 5, bound by the beta-cyclodextrin cavities of 3 with an association constant of 10(4) M-1 in water, acts as a sensitizer for the Eu-III and Tb-III complexes of 3. Luminescence spectroscopy, microcalorimetry, and Gd-III-induced NMR relaxation rate measurements prove that 3 forms a 1:2 complex with 5 and that one of the beta-cyclodextrin-bound sensitizers coordinates to the EDTA-encapsulated Ln(III) ion. The Eu-III complex of 3 forms strong 1:1 complexes (K approximate to 10(7) M-1) with bis(propylamido adamantyl)-functionalized biphenyl sensitizers 7 and 8 in water. Both beta-cycloclextrins of 3 are involved in the binding of these guests. The amide functionality adjacent to the biphenyl unit in 7 and 8 coordinates to the EDTA-encapsulated Ln(III) ion. For these biphenyl-based antennae both binding to beta-cyclodextrin and coordination to the Ln(III) center are crucial for efficient sensitization.