N,N-bis(4-aminophenyl)-N',N'-diphenyl-1,4-phenylenediamine | 844658-09-9

• 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-aminophenyl)-N',N'-diphenyl-1,4-phenylenediamine
• 英文别名: 4-N-(4-aminophenyl)-4-N-[4-(N-phenylanilino)phenyl]benzene-1,4-diamine
• CAS: 844658-09-9
• 化学式: C₃₀H₂₆N₄
• 分子量: 442.563
• InChiKey: YYZATQWNKRMZSZ-UHFFFAOYSA-N

物化性质

• 沸点：
  668.7±50.0 °C(Predicted)
• 密度：
  1.242±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  7
• 重原子数：
  34
• 可旋转键数：
  6
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  58.5
• 氢给体数：
  2
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  N,N-bis(4-aminophenyl)-N',N'-diphenyl-1,4-phenylenediamine 、 三光气 以 1,2-二氯乙烷 为溶剂， 反应 8.0h， 生成 4-N,4-N-bis(4-isocyanatophenyl)-1-N,1-N-diphenylbenzene-1,4-diamine
  参考文献：
  名称：

  Preparation and electrochromic properties of two series of polyurethanes containing separated triphenylamine moiety with different blocks

  摘要：

  Two series of novel aromatic polyurethanes containing triphenylamine derivatives were synthesized via polycondensation of 4-(3,6-diisocyanato-9H-carbazol-9-yl) aniline, N,N-bis(4-isocyanatophenyl) benzene-1,4-diamine with various dihydroxy monomers such as phenolphthalein, 2,2-bis (4-hydroxyphenyl)-propane, 4,4'-dihydroxybiphenyl, 4, 4'-bishydroxy benzophenone and bisphenolfluorene, respectively. The variation of the backbone structure affected the electronic properties, solubility, molecular weight and thermal stability of polyurethanes. The thermal stability of polyurethanes was studied by the gravimetric analyzer. The electrochromic performance was investigated by cyclic voltammograms and spectroelectrochemical methods, which showed stable and reversible electrochromic properties. Besides, the color of polyurethanes can be varied from initial colorless to green then to blue via electro-oxidation, which indicates the polyurethanes will have potential applications for eletrochromic materials. In addition, the PUs exhibited memory characteristic. The result indicated the PUs could be applied in smart window and memory devices. (C) 2015 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.dyepig.2015.10.001
• 作为产物：
  描述：

  4-硝基苯基二苯胺 在 palladium on activated charcoal 、 sodium hydride 、 一水合肼 作用下， 以 乙醇 、 N,N-二甲基甲酰胺 为溶剂， 反应 7.0h， 生成 N,N-bis(4-aminophenyl)-N',N'-diphenyl-1,4-phenylenediamine
  参考文献：
  名称：

  New conjugated poly(pyridinium salt) derivative: AIE characteristics, the interaction with DNA and selective fluorescence enhancement induced by dsDNA

  摘要：

  基于具有AIE特性的新型共轭聚合物（吡啶盐），开发了具有出色灵敏度和选择性的荧光开启DNA传感器。该探针还成功地用于跟踪DNase I对DNA的切割过程。

  DOI：

  10.1039/c5ra22653h

文献信息

• Synthesis, luminescence and electrochromism of aromatic poly(amine–amide)s with pendent triphenylamine moieties
  作者：Guey-Sheng Liou、Sheng-Huei Hsiao、Tzy-Hsiang Su

  DOI：10.1039/b419183h

  日期：——

  A new triphenylamine-containing aromatic dicarboxylic acid monomer, N,N-bis(4-carboxyphenyl)-N′,N′-diphenyl-1,4-phenylenediamine (2), was synthesized from the amination reaction between 4-aminotriphenylamine and 4-fluorobenzonitrile and subsequent alkaline hydrolysis of the dinitrile intermediate. A series of novel aromatic poly(amine–amide)s with triphenylamine units in the main chain and as the pendent group were prepared from the newly synthesized dicarboxylic acid and various aromatic diamines. These poly(amine–amide)s were amorphous and readily soluble in many organic solvents. All the polymers could be solution-cast into flexible films with good mechanical properties. They had excellent levels of thermal stability associated with high glass-transition temperatures (226–261 °C). These polymers exhibited strong UV–vis absorption bands at 350–365 nm in NMP solution. Their photoluminescence spectra showed maximum bands around 512–543 nm in the green region. The hole-transporting and electrochromic properties are examined by electrochemical and spectroelectrochemical methods. Cyclic voltammograms of the poly(amine–amide) 5a prepared from the dicarboxylic acid monomer 2 with a structurally similar diamine monomer N,N-bis(4-aminophenyl)-N′,N′-diphenyl-1,4-phenylenediamine (4a) exhibited four reversible oxidation redox couples in acetonitrile solution at E1/2 = 0.60, 0.80, 0.97 and 1.13 V, respectively. All the poly(amine–amide)s exhibited excellent reversibility of electrochromic characteristics by continuous five cyclic scans between 0.0 to 1.30 V, with a color change from the original pale yellowish neutral form to the green and then to blue oxidized forms.

  一种新的含三苯胺的芳香族二羧酸单体--N,N-双（4-羧基苯基）-Nâ²,Nâ²-二苯基-1,4-苯二胺（2），是由 4-氨基三苯胺和 4-氟苯腈发生胺化反应，然后二腈中间体发生碱性水解而合成的。利用新合成的二羧酸和各种芳香族二胺，制备了一系列新型芳香族聚（胺）酰胺，其主链和悬垂基均含有三苯胺单元。这些聚（胺）酰胺呈无定形，易溶于多种有机溶剂。所有聚合物都可以溶液浇铸成具有良好机械性能的柔性薄膜。它们具有出色的热稳定性，玻璃转化温度高（226-261 °C）。在 NMP 溶液中，这些聚合物在 350- 365 纳米波长处显示出强烈的紫外可见吸收带。它们的光致发光光谱在绿色区域的 512- 543 nm 附近显示出最大波段。电化学和光谱电化学方法检测了空穴传输和电致变色特性。由二羧酸单体 2 与结构相似的二胺单体 N,N-双（4-氨基苯基）-Nâ²,Nâ²-二苯基-1,4-苯二胺（4a）制备的聚（胺酰胺）5a 在乙腈溶液中的循环伏安图显示出四个可逆氧化还原偶，E1/2 分别为 0.60、0.80、0.97 和 1.13 V。通过在 0.0 至 1.30 V 之间连续进行五次循环扫描，所有聚（胺酰胺）都表现出极佳的电致变色可逆性，颜色从最初的淡黄色中性形态变为绿色，然后再变为蓝色氧化形态。
• Novel anodic electrochromic aromatic polyamides with multi-stage oxidative coloring based on N,N,N′,N′-tetraphenyl-p-phenylenediamine derivatives
  作者：Cha-Wen Chang、Guey-Sheng Liou

  DOI：10.1039/b810750e

  日期：——

  A series of novel aromatic polyamides with pendent 4,4′-dimethoxy-substituted triphenylamine (TPA) units were prepared via the direct phosphorylation polycondensation from a new dicarboxylic acid monomer, N,N-bis(4-carboxyphenyl)-N′,N′-di(4-methoxyphenyl)-1,4-phenylenediamine (4), and various aromatic diamines. These polyamides were amorphous with good solubility in many organic solvents, such as N-methyl-2-pyrrolidinone (NMP) and N,N-dimethylacetamide (DMAc), and could be solution-cast into flexible polymer films. They had excellent levels of thermal stability associated with their relatively high glass-transition temperatures (233–308 °C). These polymers exhibited strong UV-vis absorption bands at 351–363 nm in NMP solution. Their photoluminescence spectra showed maximum bands around 450–504 nm. The hole-transporting and electrochromic properties are examined by electrochemical and spectroelectrochemical methods. Cyclic voltammograms of the polyamide 6g prepared from the dicarboxylic acid monomer (4) with a structurally similar diamine monomer N,N-bis(4-aminophenyl)-N′,N′-di(4-methoxyphenyl)-1,4-phenylenediamine (5g) exhibited four reversible oxidation redox couples in acetonitrile solution at Eonset = 0.35, E1/2 = 0.64, 0.84, and 0.99 V, respectively. After over 3000 cyclic switches for green color, the films of polyamide 6g still showed excellent continuous cyclic stability of electrochromism.

  一种新型二羧酸单体--N,N-双（4-羧基苯基）-Nâ²,Nâ²-二（4-甲氧基苯基）-1,4-苯二胺（4）和多种芳香族二胺通过直接磷酸化缩聚反应制备了一系列具有下垂的 4,4â²-二甲氧基取代三苯胺（TPA）单元的新型芳香族聚酰胺。这些聚酰胺是无定形的，在 N-甲基-2-吡咯烷酮（NMP）和 N,N-二甲基乙酰胺（DMAc）等多种有机溶剂中具有良好的溶解性，可以溶液浇铸成柔性聚合物薄膜。这些聚合物具有极佳的热稳定性，其玻璃化转变温度相对较高（233â308 °C）。在 NMP 溶液中，这些聚合物在 351- 363 nm 处显示出强烈的紫外-可见吸收带。它们的光致发光光谱在 450-504 nm 处显示出最大波段。电化学和光谱电化学方法检测了空穴传输和电致变色特性。由二羧酸单体（4）与结构相似的二胺单体 N,N-双（4-氨基苯基）-Nâ²,Nâ²-二（4-甲氧基苯基）-1,4-苯二胺（5g）制备的聚酰胺 6g 的循环伏安图显示，在乙腈溶液中，Eonset = 0.35、E1/2 = 0.64、0.84 和 0.99 V 时，存在四个可逆氧化还原偶。经过 3000 多次绿色循环切换后，聚酰胺 6g 薄膜的电致色性仍表现出极佳的连续循环稳定性。
• Novel Aromatic Poly(Amine-Imide)s Bearing A Pendent Triphenylamine Group:  Synthesis, Thermal, Photophysical, Electrochemical, and Electrochromic Characteristics
  作者：Shu-Hua Cheng、Sheng-Huei Hsiao、Tzy-Hsiang Su、Guey-Sheng Liou

  DOI：10.1021/ma048774d

  日期：2005.1.1

  A new triphenylamine-containing aromatic diamine, N,N-bis(4-aminophenyl)-N',N'-diphenyl-1,4-phenylenediamine, was synthesized from the amination reaction between 4-aminotriphenylamine and 4-fluoronitrobenzene and subsequent reduction of the dinitro intermediate. A series of novel aromatic poly(amine-imide)s with pendent triphenylamine units were prepared from the newly synthesized diamine and various tetracarboxylic dianhydrides by either a one-step or a conventional two-step polymerization process. All the poly(amine-imide)s were amorphous and readily soluble in many organic solvents such as N-methyl-2-pyrrolidone (NMP), N,N-dimethylacetamide, and chloroform. These polymers could be solution cast into transparent, tough, and flexible films with good mechanical properties. They had useful levels of thermal stability associated with relatively high glass transition temperatures (264-352 degreesC), 10% weight-loss temperatures in excess of 568 degreesC, and char yields at 800 degreesC in nitrogen higher than 63%. These polymers exhibited strong UV-vis absorption bands at 311-330 nm in NMP solution. The photoluminescence spectra showed maximum bands around 545-562 nm in the green region. The hole-transporting and electrochromic properties are examined by electrochemical and spectroelectrochemical methods. Cyclic voltammograms of the poly(amine-imide) films cast onto an indium-tin oxide (ITO)-coated glass substrate exhibited two reversible oxidation redox couples at 0.78 and 1.14 V versus Ag/AgCl in acetonitrile solution. The poly(amine-imide) films revealed excellent stability of electrochromic characteristics, with a color change from the pale yellowish neutral form to the green and blue oxidized forms at applied potentials ranging from 0.78 to 1.14 V.
• PROCESS FOR PRODUCING A DRY POLYAMIDE-IMIDE FILM WITH HIGH GALLING RESISTANCE ON A THREADED TUBULAR COMPONENT FROM AN AQUEOUS DISPERSION WHICH IS FREE OF CARCINOGENIC SUBSTANCES
  申请人：VALLOUREC OIL AND GAS FRANCE

  公开号：EP2895585B1

  公开（公告）日：2019-10-30