3,4,5-tris(2-(2-(2-methoxyethoxy)ethoxy)ethoxy)benzamide | 1566542-62-8

• 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: 3,4,5-tris(2-(2-(2-methoxyethoxy)ethoxy)ethoxy)benzamide
• 英文别名: 3,4,5-Tris[2-[2-(2-methoxyethoxy)ethoxy]ethoxy]benzamide
• CAS: 1566542-62-8
• 化学式: C₂₈H₄₉NO₁₃
• 分子量: 607.696
• InChiKey: FZBQCOKNHXFXEM-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.96
• 重原子数：
  42.0
• 可旋转键数：
  31.0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.75
• 拓扑面积：
  153.85
• 氢给体数：
  1.0
• 氢受体数：
  13.0

反应信息

• 作为反应物：
  描述：

  3,4,5-tris(2-(2-(2-methoxyethoxy)ethoxy)ethoxy)benzamide 在 水 、 溴 、 potassium hydroxide 作用下， 反应 12.0h， 以63%的产率得到3,4,5-tri(triethylene glycol monomethyl ether)phenylamine
  参考文献：
  名称：

  两亲有机笼：自组装成纳米管和增强的阴离子-π相互作用。

  摘要：

  合成了两亲有机笼，并用作自组装合成子，用于在溶液中制备新型功能性超分子结构。透射电子显微镜（TEM）结果表明，该两亲性笼在水溶液中自组装成直径为29±4nm的单层纳米管，浓度为0.05mgmL-1。有趣的是，该笼的自组装显着增强了阴离子-π相互作用，这表明自组装后Cl-与该两亲性笼之间的缔合常数（Ka）显着增加。具体而言，在相同浓度的2.26×10-5 M的水中自组装后，Ka从甲醇中的离散笼的223 M-1增加到聚集笼的6800 M-1。

  DOI：

  10.1002/cplu.202000143
• 作为产物：
  描述：

  对甲苯磺酸三缩乙二醇单甲醚酯 在 ammonium hydroxide 、 potassium carbonate 、 potassium bromide 作用下， 以 甲醇 、 乙腈 为溶剂， 反应 12.0h， 生成 3,4,5-tris(2-(2-(2-methoxyethoxy)ethoxy)ethoxy)benzamide
  参考文献：
  名称：

  两亲有机笼：自组装成纳米管和增强的阴离子-π相互作用。

  摘要：

  合成了两亲有机笼，并用作自组装合成子，用于在溶液中制备新型功能性超分子结构。透射电子显微镜（TEM）结果表明，该两亲性笼在水溶液中自组装成直径为29±4nm的单层纳米管，浓度为0.05mgmL-1。有趣的是，该笼的自组装显着增强了阴离子-π相互作用，这表明自组装后Cl-与该两亲性笼之间的缔合常数（Ka）显着增加。具体而言，在相同浓度的2.26×10-5 M的水中自组装后，Ka从甲醇中的离散笼的223 M-1增加到聚集笼的6800 M-1。

  DOI：

  10.1002/cplu.202000143

文献信息

• Understanding the Role of H-Bonding in Aqueous Self-Assembly of Two Naphthalene Diimide (NDI)-Conjugated Amphiphiles
  作者：Priya Rajdev、Mijanur Rahaman Molla、Suhrit Ghosh

  DOI：10.1021/la500089b

  日期：2014.3.4

  Supramolecular architectures with the synchronized combination of various directional noncovalent forces arc ubiquitous in biological systems. However, reports of such abiotic synthetic systems involving H-bonding in aqueous medium are rare due to the challenge faced in the formation of such structures by overcoming the competition from the water molecules. In this paper we have studied self-assembly of two structurally related naphthalene-diimide (NDI) conjugated bola-amphiphiles (NDI-1 and NDI-2) in water with an aim to realize the specific role of H-bonding among the hydrazide units present in one of the two building blocks (NDI-2) on the self-assembly. Both chromophores showed vesicular assembly in aqueous solution driven primarily by pi-stacking among the NDI chromophores, which could be probed by UV-vis absorption spectra. Contrary to common belief, the lack of an H-bonding group in NDI-1 was found to be a boon in disguise in terms of the stability of the aggregates. Whereas NDI-2 aggregates showed LCST around 65-70 degrees C owing to the breaking of the H-bonds with increased temperature, the NDI-1 aggregates were found to be structurally intact until 90 C, which may be attributed to the increased hydrophobicity introduced by the absence of the polar hydrazide group. Further concentration- and solvent-dependent UV-vis studies showed that NDI-1 formed assembled structure at greatly dilute solution and also in a solvent such as THF, confirming greater propensity for its self-assembly. As both bola-amphiphiles contain an electron-deficient NDI chromophore, interaction of their vesicles was studied with an externally added electron-rich pyrene derivative. Surprisingly, NDI-1 did not show any charge-transfer interaction with the donor, whereas NDI-2 could effectively intercalate, leading to a functional membrane with tunable surface functionalities. This was attributed to the additional stability of the intercalated state by H-bonding among the hydrazide units.