N,N'-dioctyl-2,6-bis(trimethylsilylethynyl)-1,4,5,8-naphthalene tetracarboxylicacid diimide | 1296623-61-4

• 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'-dioctyl-2,6-bis(trimethylsilylethynyl)-1,4,5,8-naphthalene tetracarboxylicacid diimide
• 英文别名: 6,13-Dioctyl-2,9-bis(2-trimethylsilylethynyl)-6,13-diazatetracyclo[6.6.2.04,16.011,15]hexadeca-1(15),2,4(16),8,10-pentaene-5,7,12,14-tetrone；6,13-dioctyl-2,9-bis(2-trimethylsilylethynyl)-6,13-diazatetracyclo[6.6.2.04,16.011,15]hexadeca-1(15),2,4(16),8,10-pentaene-5,7,12,14-tetrone
• CAS: 1296623-61-4
• 化学式: C₄₀H₅₄N₂O₄Si₂
• 分子量: 683.051
• InChiKey: ZKFDFCOUOVOZGX-UHFFFAOYSA-N

物化性质

• 沸点：
  728.9±60.0 °C(Predicted)
• 密度：
  1.12±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  9.21
• 重原子数：
  48
• 可旋转键数：
  18
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.55
• 拓扑面积：
  74.8
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  N,N'-dioctyl-2,6-bis(trimethylsilylethynyl)-1,4,5,8-naphthalene tetracarboxylicacid diimide 在 sodiumsulfide nonahydrate 、 溶剂黄146 作用下， 以 乙醇 为溶剂， 反应 15.0h， 以32%的产率得到N,N′-dioctyl-2,7-bis(trimethylsilyl)naphtho-[2,3-b:6,7-b′]dithiophene-4,5,9,10-diimide
  参考文献：
  名称：

  Naphthodithiophenediimide (NDTI): Synthesis, Structure, and Applications

  摘要：

  A straightforward synthesis of alpha,beta-unsubstituted and alpha-halogenated naphtho[2,3-b:6,7-b']-dithiophenediimides (NDTIs) is described. Electrochemical and optical studies of N,N-dioctyl-NDTI demonstrate that the compound has a low-lying LUMO energy level (4.0 eV below the vacuum level) and a small HOMO-LUMO gap (similar to 2.1 eV). With its interesting electronic and optical properties, in addition to its planar structure, NDTI is a promising building block for the development of novel pi-functional materials. In fact, it afforded n-channel, p-channel, and ambipolar materials, depending on the molecular modification.

  DOI：

  10.1021/ja404753r
• 作为产物：
  描述：

  2,6-二溴-N,N'-二-正辛基-1,8:4,5-萘四甲酰基二酰亚胺 、 三甲基乙炔基硅 在 copper(l) iodide 、 四(三苯基膦)钯 作用下， 以 四氢呋喃 、 三乙胺 为溶剂， 反应 1.5h， 以98%的产率得到N,N'-dioctyl-2,6-bis(trimethylsilylethynyl)-1,4,5,8-naphthalene tetracarboxylicacid diimide
  参考文献：
  名称：

  基于核取代的萘二酰亚胺的Chemodosimer用于氟离子检测

  摘要：

  我们已经证明了带有核取代的萘二酰亚胺（c-NDI）带有三甲基甲硅烷基乙炔部分的使用，该部分能够用作阴离子的比色和荧光化学计量仪。阴离子的检测是通过使检测器脱甲硅基来进行的。甲显著变化，肉眼可见的，只是在加入的F观察-离子; 另外其他离子，如Cl的- ，溴- ，HSO4--，ACO -和H2个采购订单4--导致没有明显变化。通过紫外可见光谱，荧光和1 H NMR光谱分析了添加氟离子后c-NDI的电子性能的变化。

  DOI：

  10.1016/j.tetlet.2011.02.080

文献信息

• Catalyst-Free Reaction of Ethynyl-π-Extended Electron Acceptors with Amines
  作者：Atsuro Takai、Masayuki Takeuchi

  DOI：10.1246/bcsj.20170287

  日期：2018.1.15

  amino-functionalized electron-accepting π-conjugated systems. The reaction between the ethynyl group of the electron acceptor and an amine proceeds almost quantitatively, without a catalyst, to give a Michael-addition-type product that shows remarkable changes in its optical properties, redox properties, and dipole moment. The progress of the reaction can be visually monitored in various media. On the basis

  以萘二亚胺 (NDI)、苝二酰亚胺 (PDI) 或二酮吡咯并吡咯 (DPP) 为代表的基于酰亚胺或酰胺的 π 系统由于其特有的光学性质、电子结构等而被广泛研究。在这里，我们展示了 NDI、PDI 和带有乙炔基取代基的 DPP 的合成，以及它们作为合成氨基官能化电子接受 π 共轭系统的新构建块的用途。电子受体的乙炔基与胺之间的反应几乎定量进行，无需催化剂，得到迈克尔加成型产物，其光学性质、氧化还原性质和偶极矩发生显着变化。可以在各种介质中目视监测反应进程。
• A chemodosimer based on a core-substituted naphthalene diimide for fluoride ion detection
  作者：Dale Buckland、Sheshanath V. Bhosale、Steven J. Langford

  DOI：10.1016/j.tetlet.2011.02.080

  日期：2011.4

  We have demonstrated the use of a core-substituted naphthalene diimide (c-NDI) bearing trimethylsilylacetylene moieties which is capable of being utilised as a colorimetric and fluorescent chemodosimeter for anions. The detection of anions was carried out by desilylation of the detector. A significant change, visible to the naked eye, was observed only upon addition of F− ions; addition of other ions

  我们已经证明了带有核取代的萘二酰亚胺（c-NDI）带有三甲基甲硅烷基乙炔部分的使用，该部分能够用作阴离子的比色和荧光化学计量仪。阴离子的检测是通过使检测器脱甲硅基来进行的。甲显著变化，肉眼可见的，只是在加入的F观察-离子; 另外其他离子，如Cl的- ，溴- ，HSO4--，ACO -和H2个采购订单4--导致没有明显变化。通过紫外可见光谱，荧光和1 H NMR光谱分析了添加氟离子后c-NDI的电子性能的变化。
• Naphthodithiophenediimide (NDTI): Synthesis, Structure, and Applications
  作者：Yuta Fukutomi、Masahiro Nakano、Jian-Yong Hu、Itaru Osaka、Kazuo Takimiya

  DOI：10.1021/ja404753r

  日期：2013.8.7

  A straightforward synthesis of alpha,beta-unsubstituted and alpha-halogenated naphtho[2,3-b:6,7-b']-dithiophenediimides (NDTIs) is described. Electrochemical and optical studies of N,N-dioctyl-NDTI demonstrate that the compound has a low-lying LUMO energy level (4.0 eV below the vacuum level) and a small HOMO-LUMO gap (similar to 2.1 eV). With its interesting electronic and optical properties, in addition to its planar structure, NDTI is a promising building block for the development of novel pi-functional materials. In fact, it afforded n-channel, p-channel, and ambipolar materials, depending on the molecular modification.