2,7-bis(3-(dimethylamino)propyl)benzo[lmn][3,8]phenanthroline-1,3,6,8(2H,7H)-tetraone | 3436-54-2

• 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: 2,7-bis(3-(dimethylamino)propyl)benzo[lmn][3,8]phenanthroline-1,3,6,8(2H,7H)-tetraone
• 英文别名: 6,13-bis[3-(dimethylamino)propyl]-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: 3436-54-2
• 化学式: C₂₄H₂₈N₄O₄
• 分子量: 436.511
• InChiKey: JFCQULJQIZSKEP-UHFFFAOYSA-N

物化性质

• 熔点：
  204-206 °C
• 沸点：
  607.6±50.0 °C(Predicted)
• 密度：
  1.289±0.06 g/cm3(Predicted)
• 溶解度：
  可溶于甲醇、乙醇、三氟乙醇

计算性质

• 辛醇/水分配系数(LogP)：
  1.9
• 重原子数：
  32
• 可旋转键数：
  8
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.42
• 拓扑面积：
  81.2
• 氢给体数：
  0
• 氢受体数：
  6

安全信息

• 储存条件：
  2-8°C，惰性气体

反应信息

• 作为反应物：
  描述：

  2,7-bis(3-(dimethylamino)propyl)benzo[lmn][3,8]phenanthroline-1,3,6,8(2H,7H)-tetraone 在 双氧水 作用下， 以 乙醇 为溶剂， 反应 48.0h， 以80%的产率得到3-[13-[3-[dimethyl(oxido)azaniumyl]propyl]-5,7,12,14-tetraoxo-6,13-diazatetracyclo[6.6.2.04,16.011,15]hexadeca-1(15),2,4(16),8,10-pentaen-6-yl]-N,N-dimethylpropan-1-amine oxide
  参考文献：
  名称：

  具有与pH无关的分散性的石墨烯的两性离子共轭表面活性剂功能化：一种在酸性介质中进行氧气释放反应的高效电子介体。

  摘要：

  石墨烯的官能化已被广泛用作调节石墨烯的表面性质的有效途径，并且已经广泛地研究了通过官能化来增强石墨烯在水溶液中的分散稳定性，以扩展其在各种领域中的用途。在此，描述了一种有效的方法，用于通过非共价两性离子官能化来增强石墨烯在不同pH值下在水溶液中的分散性。结果表明，表面活性剂的骨架结构中具有电子不足的碳原子，且具有较大的π-π相互作用区域，可与石墨烯发生强相互作用，并且分子的两性离子侧端基可支持石墨烯在各种pH条件下的分散性。实验和计算研究证实，per二酰亚胺氨基N-氧化物（PDI-NO）可以通过PDI-NO诱导的水合排斥效应实现石墨烯的有效官能化和非pH依赖性分散。PDI-NO官能化的石墨烯已成功地用于氧释放反应中，作为电子介体，可增强基于Ru的多金属氧酸盐催化剂在酸性介质中的电催化活性。所提出的策略有望在水不依赖于pH的稳定性的水性介质中生产高度分散的石墨烯方面取得重大进展，从而拓宽了石

  DOI：

  10.1002/smll.201906635
• 作为产物：
  描述：

  N,N-二甲基-1,3-二氨基丙烷 以92 %的产率得到2,7-bis(3-(dimethylamino)propyl)benzo[lmn][3,8]phenanthroline-1,3,6,8(2H,7H)-tetraone
  参考文献：
  名称：

  NAPHTHALENE DIIMIDE COMPOUND AND REDOX FLOW BATTERY CONTAINING THE SAME

  摘要：

  The present disclosure relates to a novel naphthalene diimide compound, an electrolyte solution for a redox flow battery containing the same, and a redox flow battery containing the same. The naphthalene diimide compound according to one embodiment exhibits a robust redox behavior, has high solubility in water, and has an advantage of being able to operate at neutral pH. In addition, since the naphthalene diimide compound according to one embodiment may improve the energy density by combining two electrons, it is useful as an additive for an electrolyte solution for a redox flow battery.

  公开号：

  US20240243327A1

文献信息

• Self-stacking of naphthalene bis(dicarboximide)s probed by NMR †
  作者：Vera Steullet、Dabney W. Dixon

  DOI：10.1039/a801441h

  日期：——

  The self-stacking in water of a series of naphthalene-1,8∶4,5-bis(dicarboximide)s (also known as naphthalene diimides, NDIs) bearing cationic side chains has been studied using NMR techniques. The position of the charge in the side chain has a strong effect on the propensity of the NDI to self-stack. Examples with a cationic center three atoms away from the NDI ring in general do not self-stack; those with cationic centers further out on the side chains are prone to self-stack at NMR concentrations. The size of the side chain per se does not appear to be a significant controlling factor; even a derivative with biotin side chains shows no evidence of self-stacking. Increasing the ionic strength of the solution can also induce stacking. Derivatives with aromatic side chains can show intramolecular self-stacking of the side chain with the central NDI ring. This is significant for side chains with isoquinoline and bipyridine groups but not significant for side chains with pyridine groups. An example of an NDI that undergoes both intramolecular and intermolecular stacking is the derivative bearing side chains ending in Ru(bpy)32+ moieties. In methanol, the shift patterns of the aromatic resonances of the bipyridine rings are very close to those of a model compound. However, a more complicated chemical shift pattern is seen in water. This indicates that conformations with the Ru(bpy)32+ moieties lying at least partly within the shielding cone of the aromatic NDI system are favored. Molecular modeling indicates that conformations in which the bipyridine ring interacts with the NDI ring are readily achievable. The temperature dependence of the chemical shifts for this molecule indicates that both intramolecular interactions of the bipyridine rings with the NDI ring and self-stacking of the NDI rings are significant.

  使用核磁共振技术研究了一系列带有阳离子侧链的萘-1,8‖4,5-双(二氧亚胺)(也称为萘二亚胺,NDI)在水中的自堆叠现象。侧链上的电荷位置对NDI的自堆叠倾向有强烈影响。通常,阳离子中心与NDI环相隔三原子的例子不会自堆叠;而阳离子中心位于侧链更远处的则倾向于在核磁共振浓度下自堆叠。侧链的大小本身似乎不是重要的控制因素;甚至带有生物素侧链的衍生物也未显示出自堆叠的证据。增加溶液的离子强度也可以诱导堆叠。带有芳香侧链的衍生物可以显示侧链与中央NDI环的分子内自堆叠。这对于带有异喹啉和联吡啶基团的侧链是显著的,但对于带有吡啶基团的侧链则不显著。一个同时经历分子内和分子间堆叠的NDI例子是带有侧链末端为Ru(bpy)32+基团的衍生物。在甲醇中,联吡啶环的芳香共振位移模式与模型化合物非常接近。然而,在水中的化学位移模式更为复杂。这表明,Ru(bpy)32+基团至少部分位于芳香NDI系统的屏蔽锥内的构象是受青睐的。分子模拟表明,联吡啶环与NDI环相互作用的构象容易实现。该分子化学位移的温度依赖性表明,联吡啶环与NDI环的分子内相互作用以及NDI环的自堆叠都是显著的。
• [EN] NAPHTHALENE DIIMIDE COMPOUNDS INTERACTING WITH G-QUADRUPLEX REGIONS IN DNA<br/>[FR] COMPOSÉS DE NAPHTALÈNE DIIMIDES INTERAGISSANT AVEC LES STRUCTURES EN G-QUADRUPLEXE DE L'ADN
  申请人：UNIV LONDON PHARMACY

  公开号：WO2009068916A1

  公开（公告）日：2009-06-04

  The invention relates to novel compounds which are naphthalene diimides of general formula (I). The compounds are used in therapy, particularly in cancer treatment.

  该发明涉及一种新型化合物，其为一般式(I)的萘二酰亚胺。这些化合物被用于治疗，特别是在癌症治疗中。
• [EN] REDOX FLOW BATTERY AND NEW COMPOUNDS USEFUL THEREIN<br/>[FR] BATTERIE À FLUX REDOX ET NOUVEAUX COMPOSÉS UTILES DANS CELLE-CI
  申请人：RIVUS AB

  公开号：WO2020201405A1

  公开（公告）日：2020-10-08

  The present invention relates to a redox flow battery comprising: a positive compartment containing a positive electrode in contact with a first aqueous-based electrolyte solution comprising a positive electrolyte dissolved in a first aqueous-based solvent; a negative compartment containing a negative electrode in contact with a second aqueous-based electrolyte solution comprising a negative electrolyte being an organic redox-active molecule dissolved in a second aqueous-based solvent; means for establishing electrical conduction between said positive electrode and said negative electrode, and an external load for directing electrical energy into or out of the redox flow battery; a separator component that separates the first aqueous-based electrolyte solution in the positive compartment from the second aqueous-based electrolyte solution in the negative compartment and substantially prevents the positive electrolyte in the positive compartment and the negative electrolyte in the negative compartment from intermingling with each other, while permitting the passage of non-redox-active species between the electrolyte solutions in the positive and negative compartments; and means capable of establishing flow of the electrolyte solutions past said positive and negative electrodes, respectively, and wherein the organic redox-active molecule is a naphthalene diimide (NDI); and a modified NDI.

  本发明涉及一种氧化还原流动电池，包括：一个正极间隔，其中含有与第一基于水的电解质溶液接触的正极，该溶液包括溶解在第一基于水的溶剂中的正电解质；一个负极间隔，其中含有与第二基于水的电解质溶液接触的负极，该溶液包括溶解在第二基于水的溶剂中的有机氧化还原活性分子作为负电解质；用于在正极和负极之间建立电传导的手段，以及用于将电能引导进入或离开氧化还原流动电池的外部负载；一种分隔组件，将正极间隔中的第一基于水的电解质溶液与负极间隔中的第二基于水的电解质溶液分离，并且实质上防止正极间隔中的正电解质和负极间隔中的负电解质相互混合，同时允许非氧化还原活性物种在正极和负极间的电解质溶液之间通行；以及能够建立电解质溶液在正极和负极电极之间流动的手段，其中所述的有机氧化还原活性分子是萘二酰亚胺（NDI）；以及一种改性的NDI。
• Enhanced efficiency of polymer photovoltaic cells via the incorporation of a water-soluble naphthalene diimide derivative as a cathode interlayer
  作者：Kang Zhao、Long Ye、Wenchao Zhao、Shaoqing Zhang、Huifeng Yao、Bowei Xu、Mingliang Sun、Jianhui Hou

  DOI：10.1039/c5tc02172c

  日期：——

  A novel water-soluble naphthalene diimide derivative was utilized as a cathode interlayer for two types of high performance polymer photovoltaic cells.

  一种新型水溶性萘二酰亚胺衍生物被用作两种高性能聚合物光伏电池的阴极中间层。
• Controlling intermolecular redox-doping of naphthalene diimides
  作者：Simon B. Schmidt、Till Biskup、Xuechen Jiao、Christopher R. McNeill、Michael Sommer

  DOI：10.1039/c9tc00721k

  日期：——

  is used to n-dope a series of NDI derivatives of varying energy levels. We demonstrate a photoinduced, intermolecular redox-doping process in which a dimethylpropyl amine side chain attached to one NDI reduces another NDI derivative to form radical anions. The influence of the aromatic core substituents on energy levels, doping efficacy and radical anion stability is studied by cyclic voltammetry,

  带有叔胺侧链的萘二酰亚胺（NDI）用于对一系列能级不同的NDI衍生物进行n掺杂。我们证明了光诱导的分子间氧化还原掺杂过程，其中连接到一个NDI的二甲基丙胺侧链还原了另一个NDI衍生物以形成自由基阴离子。通过循环伏安法，UV-Vis和电子顺磁共振（EPR）光谱研究了芳族核取代基对能级，掺杂效率和自由基阴离子稳定性的影响。通常，NDI的HOMO能级负责掺杂过程，而LUMO负责所产生的自由基阴离子的空气稳定性。具有两个氰基取代基的最缺乏电子的NDI衍生物显示出最高的掺杂产率，并产生光和热诱导掺杂的空气稳定的自由基阴离子。