2-(1H-indol-3'-yl)-1H-anthra[1,2-d]imidazole-6,11-dione

• 分子结构分类: 有机化合物 - 苯类化合物 - 蒽
• 英文名称: 2-(1H-indol-3'-yl)-1H-anthra[1,2-d]imidazole-6,11-dione
• 化学式: C₂₃H₁₃N₃O₂
• 分子量: 363.375
• InChiKey: HTQWZDCBPHABRA-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.49
• 重原子数：
  28.0
• 可旋转键数：
  1.0
• 环数：
  6.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  78.61
• 氢给体数：
  2.0
• 氢受体数：
  3.0

反应信息

• 作为产物：
  描述：

  3-吲哚甲醛 、 1,2-二氨基蒽醌 在 phosphotungstic acid 、 氧气 作用下， 反应 3.0h， 以82%的产率得到2-(1H-indol-3'-yl)-1H-anthra[1,2-d]imidazole-6,11-dione
  参考文献：
  名称：

  一锅方案在好氧条件下PEG-400中磷钨酸催化J聚集的蒽并咪唑二酮†

  摘要：

  已经开发出一种精确且高效的一锅绿色方案，用于蒽的化学选择性合成[1,2- d在有氧条件下，使用磷钨酸（PTA）作为可重复使用的催化剂在聚乙二醇-400（PEG-400）载体上使用]咪唑-6,11-二酮。它涉及一种简单的合成方法，可用于从1,2-二氨基蒽醌和具有π富集的芳族/杂芳族环和亲脂性烷基链的各种醛类中制备各种蒽咪唑二酮。在惰性气氛中，反应遵循不同的途径，从而产生独特的萘喹喔啉衍生物。合成的蒽咪唑二酮衍生物显示出受取代模式影响的不同自聚集形态。还观察到晶体堆积图案和具有J-聚集形态的光物理性质之间的良好协议。

  DOI：

  10.1039/c5ra19190d

文献信息

• Cyanide and fluoride colorimetric sensing by novel imidazo-anthraquinones functionalised with indole and carbazole
  作者：Rosa M.F. Batista、Elisabete Oliveira、Susana P.G. Costa、Carlos Lodeiro、M. Manuela M. Raposo

  DOI：10.1080/10610278.2013.824082

  日期：2014.2.1

  Novel imidazo-anthraquinones functionalised with indole and carbazole have been synthesised and characterised and their evaluation as colorimetric chemosensors was carried out in acetonitrile as well as in acetonitrile/H2O (97:3) in the presence of several anions such as F-, Cl-, Br-, I-, CN-, NO3-, ClO4-, AcO-, BzO(-), NO3-, ClO4-, HSO4-, and H2PO4-. In addition, their behaviour in the presence of H+ and OH- was also studied. Upon addition of CN- and F- to acetonitrile solutions of compounds 1-3, a marked colour change from yellow to orange was observed and the fluorescence emission of 1 and 2 was switched on'. The recognition in organic aqueous solution leads to the selective and sensitive naked-eye detection (mM) of CN- for all receptors, with an easily detectable colour change from yellow to orange. The binding stoichiometry between the receptors and the anions was found to be 2:1. The binding process was also followed by H-1 NMR titrations showing that two different binding modes occurred in the presence of fluoride or cyanide anions, which is in agreement with the spectrophotometric titrations.