N,N′-bis(4-methoxylsalicylidene)-p-phenylenediamine | 157982-85-9

• 分子结构分类: 有机化合物 - 苯类化合物 - 酚类
• 英文名称: N,N′-bis(4-methoxylsalicylidene)-p-phenylenediamine
• 英文别名: N,N'-bis(4-methoxysalicylide)benzene-1,4-diamine；N,N'-bis(4-methoxysalicylidene)-p-phenylenediamine；2-[[4-[(2-Hydroxy-4-methoxyphenyl)methylideneamino]phenyl]iminomethyl]-5-methoxyphenol
• CAS: 157982-85-9
• 化学式: C₂₂H₂₀N₂O₄
• 分子量: 376.412
• InChiKey: GXUWPGZPXLPEBX-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.8
• 重原子数：
  28
• 可旋转键数：
  6
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.09
• 拓扑面积：
  83.6
• 氢给体数：
  2
• 氢受体数：
  6

反应信息

• 作为产物：
  描述：

  2-羟基-4-甲氧基苯甲醛 、 对苯二胺 以 乙醇 为溶剂， 反应 5.0h， 以0.83%的产率得到N,N′-bis(4-methoxylsalicylidene)-p-phenylenediamine
  参考文献：
  名称：

  通过甲氧基和硝基取代调节水杨醛席夫碱的可逆热致变色性质

  摘要：

  摘要 本研究为探索新型可逆热致变色材料，合成了四种被甲氧基和硝基取代的水杨醛席夫碱(BSP1-4)，并研究了它们的可逆热致变色性能。所有化合物均通过 HNMR、IR、UV-vis、TG-DSC 和 SEM 技术进行表征。通过 HNMR、IR 和 UV-vis 光谱，四种目标产物显示不同的颜色。UV-Vis 光谱表明，BSPs 取代基的类型和位置可以通过改变电子跃迁模式来控制吸收波长，从而导致样品颜色的差异。随着浅色样品的增加，ΔE1的含量逐渐增加，直至最大值为48.6。TG-DSC 结果表明 BSP 在 350 °C 以下具有良好的热稳定性。SEM图像显示四种BSP样品的表面形貌不同，包括片状、棒状和条状。使用变温 FT-IR 光谱、固体 UV-Vis 光谱和响应时间评估 BSP 样品的热致变色性能。进行 DFT 计算以合理化 Enol 和 Ketone 形式的 BSP 样品的光学行为。变温

  DOI：

  10.1016/j.molstruc.2019.01.012

文献信息

• Color- and Morphology-Controlled Self-Assembly of New Electron-Donor-Substituted Aggregation-Induced Emission Compounds
  作者：Caixia Niu、Liu Zhao、Tao Fang、Xuebin Deng、Hui Ma、Jiaxin Zhang、Na Na、Jingsa Han、Jin Ouyang

  DOI：10.1021/la404436v

  日期：2014.3.11

  Four electron-donor-substituted aggregation-induced emission (AIE) compounds, N,N'-bis(4-methoxylsalicylidene)-p-phenylenediamine (BSPD-OMe), N,N'-bis(4-methylsalicylidene)-p-phenylenediamine (BSPD-Me), N,N'-bis(salicylidene)-p-phenylenediamine (BSPD), and N,N'-bis(4-hydroxylsalicylidene)-p-phenylenediamine (BSPD-OH), are designed and synthesized. They are all found to exhibit controlled self-assembly behaviors and good thermal properties. By changing the terminal electron-donor groups, they are controlled to self-assemble into three emission colors (green, yellow, and orange) and four morphologies (microblocks, microparticles, microrods, and nanowires) in THF/water mixtures. Their self-assembled structures were investigated with scanning electron microscopy (SEM), fluorescent microscopy images, transmission electron microscopy (TEM), and powder X-ray diffraction (PXRD) techniques. In addition, the emission colors of BSPD-OH can be successfully controlled to three colors (green -> yellow -> orange) through simply changing the water fraction (f(w)). Their thermal gravimetric analysis (TGA) results indicate that their thermal decomposition temperatures (T-d, corresponding to 5% weight loss) range from 282 to 319 degrees C. Their differential scanning calorimetry (DSC) data show that BSPD-OH bears a glass-transition temperature (T-g) of 118 degrees C. The good T-d and T-g values will ensure them to be luminogens for organic light-emitting diodes (OLEDs). The theoretical calculations and single-crystal X-ray diffraction (XRD) analysis of BSPD-OMe and BSPD suggest that the stronger electron donor substituent can twist the molecular conformation, decrease the degree of pi conjugation, increase the energy gap, and then induce the emission colors' blue shift and morphology variation. The results are meaningful in controlling the emission colors and self-assembly shapes of these derivatives, and they also provide a novel but facile way to get color-tunable AIE luminogens for OLEDs.