1,3-bis(8-(p-nitrophenylaminocarbonylamino)-3,6-di-tertbutyl-9H-carbazol-1-yl)urea

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吲哚及其衍生物
• 英文名称: 1,3-bis(8-(p-nitrophenylaminocarbonylamino)-3,6-di-tertbutyl-9H-carbazol-1-yl)urea
• 英文别名: 1,3-bis[3,6-ditert-butyl-8-[(4-nitrophenyl)carbamoylamino]-9H-carbazol-1-yl]urea
• 化学式: C₅₅H₆₀N₁₀O₇
• 分子量: 973.144
• InChiKey: DUUZHHSPYODOLC-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  12.9
• 重原子数：
  72
• 可旋转键数：
  10
• 环数：
  8.0
• sp3杂化的碳原子比例：
  0.29
• 拓扑面积：
  247
• 氢给体数：
  8
• 氢受体数：
  7

反应信息

• 作为产物：
  描述：

  3,6-二叔丁基咔唑 在 palladium on activated charcoal 、 硝酸 、 乙酸酐 、 溶剂黄146 、 三氟乙酸 、 肼 作用下， 以 四氢呋喃 、 乙醇 、 二氯甲烷 、 水 、 N,N-二甲基甲酰胺 为溶剂， 反应 6.0h， 生成 1,3-bis(8-(p-nitrophenylaminocarbonylamino)-3,6-di-tertbutyl-9H-carbazol-1-yl)urea
  参考文献：
  名称：

  Bis(carbazolyl)ureas as Selective Receptors for the Recognition of Hydrogenpyrophosphate in Aqueous Media

  摘要：

  Recognition properties of the novel bis(carbazole) tris-ureidic-based receptors 1 and 2 toward different anions have been studied by H-1 NMR and absorption and emission spectroscopy, as well as by DFT calculations. Receptor 1, in which the two urea-functionalized arms are decorated with p-nitrophenyl rings, behaves as a highly selective chromogenic molecular probe for hydrogenpyrophosphate anion in a competitive medium (acetonitrile/water, 70/30). Receptor 2, bearing two urea arms decorated with photoactive pyrenyl rings, acts as a highly selective fluorescent molecular probe for hydrogenpyrophosphate anion in either acetonitrile or an aqueous mixture (acetonitrile/water, 85/15). Receptor 2 exhibits a dual monomer-excimer emission spectrum and undergoes a remarked ratiometry in acetonitrile in the presence of hydrogenpyrophosphate: the excimer band disappears, whereas the monomer band is slightly increased. However, in the aqueous mixture, a strong increase of the excimer emission band was observed, while the monomer emission bands remained almost unaffected. The resulting binding modes and spectroscopic features are explained by suitable structures of model complexes for both receptors. In such complexes, a peripheral cooperative effect was found, alleviating the excess of negative charge in the guest toward the outer surface of the host, as well as the required enlargement on its internal cavity.

  DOI：

  10.1021/jo401430d

文献信息

• Bis(carbazolyl)ureas as Selective Receptors for the Recognition of Hydrogenpyrophosphate in Aqueous Media
  作者：Guzman Sanchez、Arturo Espinosa、David Curiel、Alberto Tarraga、Pedro Molina

  DOI：10.1021/jo401430d

  日期：2013.10.4

  Recognition properties of the novel bis(carbazole) tris-ureidic-based receptors 1 and 2 toward different anions have been studied by H-1 NMR and absorption and emission spectroscopy, as well as by DFT calculations. Receptor 1, in which the two urea-functionalized arms are decorated with p-nitrophenyl rings, behaves as a highly selective chromogenic molecular probe for hydrogenpyrophosphate anion in a competitive medium (acetonitrile/water, 70/30). Receptor 2, bearing two urea arms decorated with photoactive pyrenyl rings, acts as a highly selective fluorescent molecular probe for hydrogenpyrophosphate anion in either acetonitrile or an aqueous mixture (acetonitrile/water, 85/15). Receptor 2 exhibits a dual monomer-excimer emission spectrum and undergoes a remarked ratiometry in acetonitrile in the presence of hydrogenpyrophosphate: the excimer band disappears, whereas the monomer band is slightly increased. However, in the aqueous mixture, a strong increase of the excimer emission band was observed, while the monomer emission bands remained almost unaffected. The resulting binding modes and spectroscopic features are explained by suitable structures of model complexes for both receptors. In such complexes, a peripheral cooperative effect was found, alleviating the excess of negative charge in the guest toward the outer surface of the host, as well as the required enlargement on its internal cavity.