N,N'-bis[4-(diphenylamino)benzylidene]azine | 53338-51-5

• 分子结构分类: 有机化合物 - 有机氮化合物
• 英文名称: N,N'-bis[4-(diphenylamino)benzylidene]azine
• 英文别名: 4,4'-hydrazine-1,2-diylidenebis(methan-1-yl-1-ylidene)bis(N,N-diphenylaniline)；N,N-diphenyl-4-[[[4-(N-phenylanilino)phenyl]methylidenehydrazinylidene]methyl]aniline
• CAS: 53338-51-5
• 化学式: C₃₈H₃₀N₄
• 分子量: 542.683
• InChiKey: OSCSTTXJOACNQJ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  9.8
• 重原子数：
  42
• 可旋转键数：
  9
• 环数：
  6.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  31.2
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  三苯胺 在 一水合肼 、 三氯氧磷 作用下， 以 乙醇 为溶剂， 生成 N,N'-bis[4-(diphenylamino)benzylidene]azine
  参考文献：
  名称：

  Photophysical properties of isoelectronic oligomers with vinylene, imine, azine and ethynylene spacers bearing triphenylamine and carbazole end-groups

  摘要：

  Ten symmetrical oligomers containing either triphenylamine or carbazole substituents as end-groups and 1,4-phenylenevinylene, 1,4-phenylene imine, azine and 1,4-phenylene ethynylene as pi-spacers, have been synthesized by polycondensation reactions between aromatic aldehydes (4-formyltriphenylamine and 3-formyl N-hexylcarbazole) or iodides (4-iodotriphenylamine and 3-iodo N-hexylcarbazole) with bisphosphonate derivative, 1,4-diaminobenzene, hydrazine or 1,4-diethynylbenzene, respectively. These oligomers are models for the corresponding conducting polymers, have a well-defined molecular structure, can be highly purified using common methods and processed as thin films by vacuum evaporation, dip or spin coating. The oligomers preserve all of the properties and potential applications of the corresponding polymers. The structural characterization of these oligomers was performed using usual spectroscopic methods (H-1-RMN, FT-IR and DSC) and their photophysical properties were analyzed by UV-Vis and fluorescence spectroscopy. Their redox properties were studied by cyclic voltammetry. (C) 2013 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.dyepig.2013.01.025

文献信息

• Azine based AIEgens with multi-stimuli response towards picric acid
  作者：Munusamy Sathiyaraj、Kumaravelu Pavithra、Viruthachalam Thiagarajan

  DOI：10.1039/d0nj01324b

  日期：——

  substituents on the nitrogen atom of the amine moiety. Further, these azine derivatives sense the picric acid (PA) with high selectivity and sensitivity in both monomer and aggregated forms. The hydrogen bonding interaction of PA with any one side of the amine nitrogen leads to the formation of a new intramolecular charge transfer state which results in the formation of new absorption and emission spectra. Interestingly

  多功能聚集诱导发射发光剂（AIEgens）是新型材料，在包括生物医学，光电子学和传感器在内的各个领域都有重要的应用。为了更好地了解AIE机制，已经大力致力于AIEgens的战略开发和表征。在本文中，我们通过改变溶剂的极性和粘度来详细研究基于对称嗪（D–π–D）的AIEgens的光物理性质。嗪衍生物的AIE行为取决于胺部分的氮原子上的取代基。此外，这些嗪衍生物以单体形式和聚集形式都以高选择性和灵敏度来感测苦味酸（PA）。PA与胺氮的任一侧之间的氢键相互作用导致形成新的分子内电荷转移状态，从而导致形成新的吸收光谱和发射光谱。有趣的是，在PA的存在下，纯净的THF中的monomer嗪单体显示出荧光增强，而聚集的–嗪分子在THF和水的混合物中显示出荧光猝灭。
• N,N-disubstituted azines attenuate LPS-mediated neuroinflammation in microglia and neuronal apoptosis via inhibiting MAPK signaling pathways
  作者：Lalita Subedi、Oh Wook Kwon、Chaeho Pak、Goeun Lee、Kangwoo Lee、Hakwon Kim、Sun Yeou Kim

  DOI：10.1186/s12868-017-0399-3

  日期：2017.12

  effective anti-neuroinflammatory agent, we designed and synthesized a family of 13 new azine derivatives and investigated their anti-neuroinflammatory activities in LPS-activated BV-2 microglial cells.ResultsOut of 13 derivatives, compound 3 [4,4′-(1E,1′E,3E,3′E)-3,3′-(hydrazine-1,2-diylidene) bis-(prop-1-ene-1-yl-3-ylidene) bis-(2-methoxyphenol)] exhibited excellent anti-neuroinflammatory activities (IC50 = 12

  背景激活的小胶质细胞与星形胶质细胞和神经元细胞相互作用以诱导神经炎症，这可能有助于阿尔茨海默病和帕金森病的发病机制和进展。为了确定最有效的抗神经炎症药物，我们设计并合成了 13 种新的吖嗪衍生物家族，并研究了它们在 LPS 激活的 BV-2 小胶质细胞中的抗神经炎症活性。结果在 13 种衍生物中，化合物 3 [4,4' -(1E,1'E,3E,3'E)-3,3'-(hydrazine-1,2-diylidene) bis-(prop-1-ene-1-yl-3-ylidene) bis-(2 -甲氧基苯酚）]表现出优异的抗神经炎症活性（IC50 = 12.47 µM），可保护神经元免受小胶质细胞介导的神经毒性。具体来说，化合物 3 的抗神经炎症作用通过抑制 p38 和 JNK 介导的信号传导以及促炎细胞因子和炎症介质的产生来抑制 MAPK 信号通路。此外，化合物 3 通过抑制 LPS 介导的
• Excited state intramolecular proton transfer induced fluorescence in triphenylamine molecule: Role of structural conformation and reversible mechanofluorochromism
  作者：Anu Kundu、Subraminain Karthikeyan、Dohyun Moon、Savarimuthu Philip Anthony

  DOI：10.1016/j.molstruc.2018.05.042

  日期：2018.10

  conformation on excited state intramolecular proton transfer (ESIPT) induced fluorescence in both solution as well as solid state has been explored. 1 and 2, which are not hydrogen bonding donor to form intramolecular H-bonding, basis for ESIPT, are non-fluorescent in solution as well as solid. The incorporation of hydroxyl group in 3 and 4 promoted intramolecular H-bonding that could facilitate ESIPT

  摘要 合成了基于三苯胺 (TPA) 的席夫碱分子 (1-4)，并探索了分子结构和构象对激发态分子内质子转移 (ESIPT) 诱导荧光​​在溶液和固态中的作用。1 和 2 不是形成分子内 H 键的氢键供体，是 ESIPT 的基础，在溶液和固体中都不发荧光。在 3 和 4 中引入羟基促进了分子内 H 键合，这可以促进 ESIPT。有趣的是，3 在溶液（λmax = 489–540 nm，与标准荧光素相比，Φf = 0.337–0.018）和固态（λmax = 553 nm，Φf = 4.84%（绝对量子产率）中显示出强荧光，而结构相似 4没有显示荧光。由于非平面 TPA 的掺入，另外 3 还显示出可逆的机械荧光变色 (MFC)。固态结构分析证实了 3 和 4 中的分子内氢键，但 3 显示出 TPA 苯基和亚胺基团之间的共面构象，而 4 的不对称单元中的一个分子显示出轻微扭曲的构象。3 的粉末 X
• Comparative Studies of Structural, Thermal, Optical, and Electrochemical Properties of Azines with Different End Groups with Their Azomethine Analogues toward Application in (Opto)Electronics
  作者：Danuta Sek、Mariola Siwy、Katarzyna Bijak、Marzena Grucela-Zajac、Grzegorz Malecki、Karolina Smolarek、Lukasz Bujak、Sebastian Mackowski、Ewa Schab-Balcerzak

  DOI：10.1021/jp407623u

  日期：2013.10.10

  Two series of azines and their azomethine analogues were prepared via condensation reaction of benzaldehyde, 2-hydroxybenzaldehyde, 4-pyridinecarboxaldehyde, 2-thiophenecarboxaldehyde, and 4-(diphenylamino)benzaldehyde with hydrazine monohydrate and 1,4-phenylenediamine, respectively. The structures of given compounds were characterized by FTIR, H-1 NMR, and C-13 NMR spectroscopy as well as elemental analysis. Optical, electrochemical, and thermal properties of all compounds were investigated by means of differential scanning calorimetry (DSC), UV-vis spectroscopy, stationary and time-resolved photoluminescence spectroscopy, and cycling voltammetry (CV). Additionally, the electronic properties, that is, orbital energies and resulting energy gap were calculated theoretically by density functional theory (DFT). Influence of chemical structure of the compounds on their properties was analyzed.
• Photophysical properties of isoelectronic oligomers with vinylene, imine, azine and ethynylene spacers bearing triphenylamine and carbazole end-groups
  作者：Mircea Grigoras、Loredana Vacareanu、Teofilia Ivan、Ana Maria Catargiu

  DOI：10.1016/j.dyepig.2013.01.025

  日期：2013.7

  Ten symmetrical oligomers containing either triphenylamine or carbazole substituents as end-groups and 1,4-phenylenevinylene, 1,4-phenylene imine, azine and 1,4-phenylene ethynylene as pi-spacers, have been synthesized by polycondensation reactions between aromatic aldehydes (4-formyltriphenylamine and 3-formyl N-hexylcarbazole) or iodides (4-iodotriphenylamine and 3-iodo N-hexylcarbazole) with bisphosphonate derivative, 1,4-diaminobenzene, hydrazine or 1,4-diethynylbenzene, respectively. These oligomers are models for the corresponding conducting polymers, have a well-defined molecular structure, can be highly purified using common methods and processed as thin films by vacuum evaporation, dip or spin coating. The oligomers preserve all of the properties and potential applications of the corresponding polymers. The structural characterization of these oligomers was performed using usual spectroscopic methods (H-1-RMN, FT-IR and DSC) and their photophysical properties were analyzed by UV-Vis and fluorescence spectroscopy. Their redox properties were studied by cyclic voltammetry. (C) 2013 Elsevier Ltd. All rights reserved.