N,N’-bis(2-bromoethyl)-1,4,5,8-naphthalenetetracarboxylic 1,8:4,5-diimide | 861091-38-5

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡啶及其衍生物
• 英文名称: N,N’-bis(2-bromoethyl)-1,4,5,8-naphthalenetetracarboxylic 1,8:4,5-diimide
• 英文别名: N,N-bis(2-bromoethyl)naphthalene diimide；2,7-bis-(2-bromo-ethyl)-benzo[lmn][3,8]phenanthroline-1,3,6,8-tetraone；2,7-Bis-(2-brom-aethyl)-benzo[lmn][3,8]phenanthrolin-1,3,6,8-tetraon
• CAS: 861091-38-5
• 化学式: C₁₈H₁₂Br₂N₂O₄
• 分子量: 480.112
• InChiKey: HALVHQOIKWKZEV-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.82
• 重原子数：
  26.0
• 可旋转键数：
  4.0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.22
• 拓扑面积：
  74.76
• 氢给体数：
  0.0
• 氢受体数：
  4.0

反应信息

• 作为反应物：
  描述：

  N,N’-bis(2-bromoethyl)-1,4,5,8-naphthalenetetracarboxylic 1,8:4,5-diimide 、 二苯胺 在 potassium iodide 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 以9 mg的产率得到N,N’-bis[3-(diphenylamino)propyl]-1,4,5,8-naphthalenetetracarboxylic 1,8:4,5-diimide
  参考文献：
  名称：

  固态含烷基胺部分的萘二酰亚胺的光致变色和光机械效应

  摘要：

  在固态下已观察到带有烷基胺部分的萘二酰亚胺（NDI）的光致变色。颜色的变化归因于NDI自由基阴离子物种的产生，这可能是通过从烷基胺部分到NDI的光诱导电子转移过程而形成的。NDI的光敏性高度依赖于烷基胺部分的结构。晶体学分析，动力学分析，UV / Vis / NIR光谱测量和光产物分析表明，自由基阴离子是通过不可逆过程形成的，该过程是由胺自由基阳离子和中性胺部分之间的质子抽象引发的。如近红外光谱中的宽吸收带所示，自由基阴离子形成了包括混合价堆叠和自由基阴离子堆叠在内的堆叠。

  DOI：

  10.1002/chem.201304849
• 作为产物：
  描述：

  alkaline earth salt of/the/ methylsulfuric acid 在 氢溴酸 作用下， 生成 N,N’-bis(2-bromoethyl)-1,4,5,8-naphthalenetetracarboxylic 1,8:4,5-diimide
  参考文献：
  名称：

  关于萘并咪唑啉的制备

  摘要：

  DOI：

  10.1002/hlca.193802101182

文献信息

• Novel fluorescent markers for hypoxic cells of naphthalimides with two heterocyclic side chains for bioreductive binding
  作者：Yan Liu、Yufang Xu、Xuhong Qian、Jianwen Liu、Liyun Shen、Junhui Li、Yuanxing Zhang

  DOI：10.1016/j.bmc.2005.12.012

  日期：2006.5

  Novel naphthalimides with two heterocyclic side chains of 2-nitroimidazole for bioreductive binding were designed, synthesized, and used as fluorescent markers for hypoxic cells. Their evaluation for imaging tumor hypoxia was carried Out in V79 cells, CHO cells, and 95D cells in vitro by using fluorescence scan ascent. A(2) and A(4) showed a very large differential fluorescence between hypoxic and oxic cells (V79 cells) in vitro and are promising candidate markers for hypoxic cells. (c) 2005 Elsevier Ltd. All rights reserved.
• Free-Standing Monolayer Two-Dimensional Supramolecular Organic Framework with Good Internal Order
  作者：Martin Pfeffermann、Renhao Dong、Robert Graf、Wojciech Zajaczkowski、Tatiana Gorelik、Wojciech Pisula、Akimitsu Narita、Klaus Müllen、Xinliang Feng

  DOI：10.1021/jacs.5b09638

  日期：2015.11.18

  Utilizing dynamic self-assembly and self-sorting to obtain large-area, molecularly precise monolayered structures represents a promising approach toward two-dimensional supramolecular organic frameworks (2D SOF) or 2D supramolecular polymers. So far, related approaches suffer from small domain sizes, fragility and weak long-range internal order. Here we report on the self-assembly of a host-guest enhanced donor-acceptor interaction, consisting of a tris(methoxynaphthyl)-substituted truxene spacer, and a naphthalene diimide substituted with N-methyl viologenyl moieties as donor and acceptor monomers, respectively, in combination with cucurbit[8]uril as host monomer toward monolayers of an unprecedented 2D SOF. Featuring orthogonal solubility, the participating molecules self-assemble at a liquid-liquid interface, yielding exceptionally large-area, insoluble films, which were analyzed by transmission electron microscopy, atomic force microscopy and optical microscopy to be monolayers with a thickness of 1.8 nm, homogeneously covering areas up to 0.25 cm(2), and featuring the ability to be free-standing over holes of 10 mu m(2). Characterization with ultraviolet-visible absorption spectroscopy, solid-state nuclear magnetic resonance spectroscopy, infrared spectroscopy, and grazing incidence wide-angle X-ray scattering allowed for confirmation of a successful complexation of all three monomers toward an internal long-range order and gave indications to an expected hexagonal superstructure. Our results extend the existing variety of two-dimensional soft nanomaterials by a versatile supramolecular approach, whereas the possibility of varying the functional monomers is supposed to open adaptability to different applications like membranes, sensors, molecular sieves, and optoelectronics.