4,5-dibromo-2,7-dioctyl-[3,8]phenanthrolino[1,10-abc]phenazine-1,3,6,8(2H,7H,9H,14H)-tetraone | 1217433-90-3

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 二氮杂萘
• 英文名称: 4,5-dibromo-2,7-dioctyl-[3,8]phenanthrolino[1,10-abc]phenazine-1,3,6,8(2H,7H,9H,14H)-tetraone
• 英文别名: 8,9-dibromo-5,12-dihydro-5,12-diazatetracene di-n-octylimide；17,18-Dibromo-14,21-dioctyl-3,10,14,21-tetrazahexacyclo[10.10.2.02,11.04,9.016,24.019,23]tetracosa-1,4,6,8,11,16,18,23-octaene-13,15,20,22-tetrone；17,18-dibromo-14,21-dioctyl-3,10,14,21-tetrazahexacyclo[10.10.2.02,11.04,9.016,24.019,23]tetracosa-1,4,6,8,11,16,18,23-octaene-13,15,20,22-tetrone
• CAS: 1217433-90-3
• 化学式: C₃₆H₄₀Br₂N₄O₄
• 分子量: 752.546
• InChiKey: YHALPBBIWYMYAG-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  10.4
• 重原子数：
  46
• 可旋转键数：
  14
• 环数：
  6.0
• sp3杂化的碳原子比例：
  0.44
• 拓扑面积：
  98.8
• 氢给体数：
  2
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  4,5-dibromo-2,7-dioctyl-[3,8]phenanthrolino[1,10-abc]phenazine-1,3,6,8(2H,7H,9H,14H)-tetraone 在 1,1'-双(二苯基膦)二茂铁 、 tris-(dibenzylideneacetone)dipalladium(0) 、 lead dioxide 作用下， 以 1,4-二氧六环 、 氯仿 为溶剂， 反应 0.62h， 生成 5-bromo-2,7-dioctyl-1,3,6,8-tetraoxo-1,2,3,6,7,8-hexahydro[3,8] phenanthrolino[1,10-abc]phenazine-4-carbonitrile
  参考文献：
  名称：

  Cyanated Diazatetracene Diimides with Ultrahigh Electron Affinity for n-Channel Field Effect Transistors

  摘要：

  Several diazatetracene diimides with high electron affinity (up to 4.66 eV!) were prepared and well characterized. The LUMO energy level of these electron-deficient molecules was found to be closely related to their material stability. Compound 7 with ultrahigh electron affinity suffered from reduction and hydrolysis in the presence of silica gel or water. The stable compounds 3 and 6 showed n-channel FET behavior with an average electron mobility of 0.002 and 0.005 cm(2) V-1 s(-1), respectively, using a solution processing method.

  DOI：

  10.1021/ol400082c
• 作为产物：
  描述：

  2,3,6,7-tetrabromo-1,4,5,8-naphthalenetetracarboxylic acid diimide 在 溶剂黄146 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 生成 4,5-dibromo-2,7-dioctyl-[3,8]phenanthrolino[1,10-abc]phenazine-1,3,6,8(2H,7H,9H,14H)-tetraone
  参考文献：
  名称：

  吸收红光的超分子发色团体系的合成与光物理

  摘要：

  为了寻找用于光收集应用的超分子天线系统，我们报告了一种短而有效的，融合的基于NDI-锌-Salphen的生色团（Salphen =双-Salicylimide苯撑）的合成及其光物理性质。超分子识别基序嵌入该化合物的发色π系统中。融合的π发色团表现为一种颜料，吸收600至750 nm之间的光并显示适度的斯托克斯位移。结合吡啶后，化合物（DATZnS）不会改变其氧化还原电位，不会经历任何内部激发态猝灭，并且不会明显改变其激发态寿命。这些显着的特性定义了DATZnS 作为超分子光收集架构中使用的基于卟啉的成分的替代品。

  DOI：

  10.1002/chem.201402398

文献信息

• A Pyridyl-Monoannulated Naphthalene Diimide Motif Self-Assembles into Tuneable Nanostructures by Means of Solvophobic Control
  作者：Sheshanath V. Bhosale、Mukund Adsul、Ganesh V. Shitre、Sharad R. Bobe、Sidhanath V. Bhosale、Steven H. Privér

  DOI：10.1002/chem.201300120

  日期：2013.6.3

  The supramolecular self‐assembly of the core‐substituted naphthalene diimide bearing pyridyl motifs leads to the formation of a variety of nanostructures with pH and solvent control. The detection of HCl can be monitored by UV/Vis and fluorescence spectroscopy, as well as the naked eye, with a change in colour (blue to red, see figure). The cycle is fully reversed by the addition of triethylamine (TEA)

  具有吡啶基基团的核心取代萘二酰亚胺的超分子自组装导致形成各种具有pH和溶剂控制的纳米结构。HCl的检测可以通过UV / Vis和荧光光谱以及肉眼进行监测，并且颜色会发生变化（蓝色到红色，见图）。通过添加三乙胺（TEA）可以完全逆转该循环。
• Solvophobic control of core-substituted naphthalene diimide nanostructures
  作者：Sheshanath V. Bhosale、Chintan Jani、Cecilia H. Lalander、Steven J. Langford

  DOI：10.1039/b920015k

  日期：——

  The requirements for the self-assembly of 2,3-annulated core-substituted NDIs into discrete worm-like nanostructures are explored in MeOH-CHCl(3) solutions. AFM was used to visualize and characterize the structures formed at precise proportions of solvent mixes.

  在MeOH-CHCl（3）解决方案中探讨了将2,3-环氧基取代的NDI自组装成离散的蠕虫状纳米结构的要求。AFM用于可视化和表征在精确比例的溶剂混合物中形成的结构。
• A Core-Substituted Naphthalene Diimide Fluoride Sensor
  作者：Sheshanath V. Bhosale、Sidhanath V. Bhosale、Mohan B. Kalyankar、Steven J. Langford

  DOI：10.1021/ol9022722

  日期：2009.12.3

  characterization of a highly fluorescent core-substituted naphthalene diimide sensor (ϕ = 0.34) bearing a bis-sulfonamide group is described. The compound shows a unique selectivity and reactivity for the fluoride ion over other anions in CHCl3 by a two-stage deprotonation process leading to a colorimetric response. In DMSO solution, the sensor is shown to be highly selective for fluoride (Ka ∼ 106 M−1) over other

  描述了带有双磺酰胺基团的高荧光核取代的萘二酰亚胺传感器（φ= 0.34）的合成和表征。通过两步去质子化过程，该化合物对氯离子在CHCl 3中相对于其他阴离子显示出独特的选择性和反应性，从而导致比色响应。在DMSO溶液中，传感器被示出为用于氟化物高度选择性（ķ一〜10 6中号-1）在具有在吸收特性更明显变化的其他阴离子。
• Synthesis and Photophysics of a Red-Light Absorbing Supramolecular Chromophore System
  作者：Jeroen A. Rombouts、Janneke Ravensbergen、Raoul N. Frese、John T. M. Kennis、Andreas W. Ehlers、J. Chris Slootweg、Eelco Ruijter、Koop Lammertsma、Romano V. A. Orru

  DOI：10.1002/chem.201402398

  日期：2014.8.11

  In search of supramolecular antenna systems for light‐harvesting applications, we report on a short and effective synthesis of a fused NDI–zinc–salphen‐based chromophore (salphen = bis‐salicylimide phenylene) and its photophysical properties. A supramolecular recognition motif is embedded into the chromophoric π‐system of this compound. The fused π‐chromophore behaves as one pigment, absorbs light

  为了寻找用于光收集应用的超分子天线系统，我们报告了一种短而有效的，融合的基于NDI-锌-Salphen的生色团（Salphen =双-Salicylimide苯撑）的合成及其光物理性质。超分子识别基序嵌入该化合物的发色π系统中。融合的π发色团表现为一种颜料，吸收600至750 nm之间的光并显示适度的斯托克斯位移。结合吡啶后，化合物（DATZnS）不会改变其氧化还原电位，不会经历任何内部激发态猝灭，并且不会明显改变其激发态寿命。这些显着的特性定义了DATZnS 作为超分子光收集架构中使用的基于卟啉的成分的替代品。
• Cyanated Diazatetracene Diimides with Ultrahigh Electron Affinity for <i>n</i>-Channel Field Effect Transistors
  作者：Qun Ye、Jingjing Chang、Kuo-Wei Huang、Xueliang Shi、Jishan Wu、Chunyan Chi

  DOI：10.1021/ol400082c

  日期：2013.3.15

  Several diazatetracene diimides with high electron affinity (up to 4.66 eV!) were prepared and well characterized. The LUMO energy level of these electron-deficient molecules was found to be closely related to their material stability. Compound 7 with ultrahigh electron affinity suffered from reduction and hydrolysis in the presence of silica gel or water. The stable compounds 3 and 6 showed n-channel FET behavior with an average electron mobility of 0.002 and 0.005 cm(2) V-1 s(-1), respectively, using a solution processing method.