4,4'-(phenylazanediyl)dibenzoic acid | 181188-86-3

• 分子结构分类: 有机化合物 - 有机氮化合物
• 英文名称: 4,4'-(phenylazanediyl)dibenzoic acid
• 英文别名: 4-(N-(4-carboxyphenyl)anilino)benzoic acid
• CAS: 181188-86-3
• 化学式: C₂₀H₁₅NO₄
• 分子量: 333.343
• InChiKey: CTTCNCPHKDSWGJ-UHFFFAOYSA-N

物化性质

• 沸点：
  582.2±35.0 °C(Predicted)
• 密度：
  1.356±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4.2
• 重原子数：
  25
• 可旋转键数：
  5
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  77.8
• 氢给体数：
  2
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  4,4'-(phenylazanediyl)dibenzoic acid 在 草酰氯 、 N,N-二甲基甲酰胺 作用下， 以 二氯甲烷 为溶剂， 反应 15.0h， 以95%的产率得到4-(N-(4-carbonochloridoylphenyl)anilino)benzoyl chloride
  参考文献：
  名称：

  Triphenylamine-based receptor for selective recognition of dicarboxylates

  摘要：

  A new triphenylamine-based receptor 1 has been designed and synthesized for the recognition of aliphatic dicarboxylates of various chain lengths. This receptor has been designed to utilize an amide-urea conjugate for binding dicarboxylates. The receptor 1 is found to bind the dicarboxylates with moderate binding strength under a semi rigid, propeller shaped, fluorescent triphenylamine spacer. The binding behavior was studied in CH3CN using H-1 NMR, fluorescence and UV-vis spectroscopic methods. The conformational behavior of 1 and its complexation modes have been investigated using classical and quantum mechanical theoretical methods. The receptor is found to be selective for long chain suberate. (C) 2009 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2009.11.021
• 作为产物：
  描述：

  三苯胺 在 potassium permanganate 、 potassium carbonate 、 三氯氧磷 作用下， 以 水 、 丙酮 为溶剂， 反应 14.17h， 生成 4,4'-(phenylazanediyl)dibenzoic acid
  参考文献：
  名称：

  一系列基于吡啶的发色团的合成，晶体结构和双光子吸收特性

  摘要：

  设计并合成了一系列具有分子内“推挽”结构的2、2'：6'，2''-三联吡啶基生色团（L1，L2，L3和L4）。L1，L2和L4的单晶通过X射线衍射分析获得并解决。通过理论和实验研究了生色团的光物理行为以及结构与性质之间的联系。结果表明，发色团表现出灵敏的单光子激发荧光发射，具有高量子产率，强的两光子激发荧光和大的两光子吸收截面，尤其是在DMF溶液中。还发现甲酸酯甲基单元作为连接至三苯胺部分的外围基团明显影响发色团的结构，光物理性质。

  DOI：

  10.1016/j.dyepig.2012.03.020

文献信息

• Structure and performances of three metal coordination polymers synthesized from 4,4′- (phenylazanediy1) dibenzoic acid
  作者：Guanlin Guo、Lun Zhao、Lingshu Meng、Xin Liu

  DOI：10.1016/j.molstruc.2020.129053

  日期：2021.3

  [Zn(L)(bimb)0.5]n (2) [Ni(L)(bifu)](H2O)4}n(3) (H2L = 4,4′-(phenylazanediy1)dibenzoic acid, bifu = 2,7-bis(1-imidazoly)fluorene, bimb = 1,4-bis(imidazol-l-yl)), were obtained under different solvents. Three crystals were also evaluated by elemental analysis, PXRD, single-crystal X-ray diffraction, TGA and FTIR. The result indicated that 3D network structures 1 crystallized in a monoclinic space group P21/n

  摘要 三种新型 3D 配位聚合物 (CPs)，[Cd(L)(bifu)]n (1) 和 [Zn(L)(bimb)0.5]n (2) [Ni(L)(bifu)](H2O )4}n(3) (H2L = 4,4'-(phenylazanediy1)dibenzoic acid, bifu = 2,7-bis(1-imidazoly)芴, bimb = 1,4-bis(imidazol-1-yl)) , 是在不同溶剂下获得的。三种晶体还通过元素分析、PXRD、单晶 X 射线衍射、TGA 和 FTIR 进行了评估。结果表明，3D网络结构1在单斜空间群P21/n中结晶，2在正交空间群Pbca中结晶，3在三斜空间群P-1中结晶。值得注意的是，染料吸附部分表明 1 具有吸附有机染料甲基橙 (MO) 和荧光素钠 (FS) 的必要能力。此外，还研究了3的电化学分析。
• Syntheses, characterizations and luminescence properties of four novel coordination polymers based on 4,4′-(phenylazanediyl)dibenzoic acid with two rigid N-donor imidazol ligand
  作者：Changjiang Zhao、Lun Zhao、Min Zhang

  DOI：10.1016/j.ica.2017.09.019

  日期：2018.1

  Abstract Four novel coordination polymers (CPs), namely, [ZnL(bimb)]·DMF (1), [ZnL(bimb)]·6(H2O)0.5 (2), [ZnL(bimp)0.5]·3H2O (3) and [ZnL(bimp)]·7H2O (4), (H2L = 4,4′-(phenylazanediyl)dibenzoic acid, bimb = 1,4-bis(imidazol-1-yl)benzene, bimp = 3,5-bis(1-imidazoly)pyridine), have been synthesized under hydrothermal conditions with different solvents and decreased temperature rates. Their structures

  摘要四种新型的配位聚合物（CPs），即[ZnL（bimb）]·DMF（1），[ZnL（bimb）]·6（H2O）0.5（2），[ZnL（bimp）0.5]·3 （3 ）和[ZnL（bimp）]·7 （4），（H2L = 4,4'-（苯基氮杂二基）二苯甲酸，bimb = 1,4-双（咪唑-1-基）苯，bimp = 3,5-双（1-咪唑基）吡啶）是在水热条件下用不同的溶剂和降低的温度速率合成的。它们的结构已通过单晶X射线衍射分析确定，并进一步通过红外光谱（IR），元素分析和热重分析（TGA）进行了表征。图1展示了具有（66）拓扑的无限4倍互穿三维（3D）框架。图2显示了2D起伏的薄片，从而以ABAB方式形成了层之间具有π-π相互作用的3D框架。图3展示了具有（412·63）拓扑的无限2倍互穿3D框架。图4显示具有42·63·8}拓扑结构的2D层。还研究了在环境温度下固态的1-4的光致发光特性。
• Fluorescent metal–organic frameworks based on mixed organic ligands: new candidates for highly sensitive detection of TNP
  作者：Dong Wang、Zhiyong Hu、Shasha Xu、Dandan Li、Qiong Zhang、Wen Ma、Hongping Zhou、Jieying Wu、Yupeng Tian

  DOI：10.1039/c8dt03811b

  日期：——

  novel metal–organic frameworks (AHU-TW1 to 6) were synthesized by a solvothermal method. Herein, accessible Lewis base sites originating from organic ligands within MOFs act as functional sites that can interact with the analyte possessing protons and then lead to obvious variations in the fluorescence spectra. Due to their superiority, AHU-TW1, 3, 4 and 6 are able to recognize trinitrophenol (TNP) with

  在这项研究中，通过合理设计采用混合的有机配体，并以金属离子作为初始反应物，通过溶剂热法合成了一系列新颖的金属-有机骨架（AHU-TW1至6）。在此，源自MOF中有机配体的易接近的Lewis碱基位点可以作为功能位点，可以与拥有质子的分析物相互作用，然后导致荧光光谱发生明显变化。由于它们的优势，AHU-TW1，3，4和6是能够识别具有高灵敏度和低检测限三硝基苯酚（TNP）。
• 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。
• Construction of three metal-organic frameworks based on the sterically hindered V-shaped carboxylate ligand
  作者：Ling Qin、Cao Mei、Wei-Juan Zuo、Ya-Guang Wu、Ru-Yong Yan、Yan-Qing Wang

  DOI：10.1016/j.mencom.2016.09.029

  日期：2016.9

  Three novel metal-organic frameworks based on an N-centered ligand H2L [4,4’-(phenylazanediyl)dibenzoic acid], namely, [Cd(L)(bimx)1/2], [Cd(L)(dpe)]·H2O, [Cu(L)(dpe)1/2]·H2O, [bimx = 1,4-bis(imidazol-1-ylmethyl)benzene, dpe = 1,2-di-(pyridin-4-yl)ethane], have been obtained and characterized by elemental analysis and X-ray single-crystal diffraction. Their thermal stability properties are also discussed

  基于N中心配体H2L [4,4'-（苯基氮杂二基）二苯甲酸]的三种新型金属有机骨架，即[Cd（L）（bimx）1/2]，[Cd（L）（dpe） ]·H2O，[Cu（L）（dpe）1/2]· ，[bimx = 1,4-双（咪唑-1-基甲基）苯，dpe = 1,2-二-（吡啶-4-基）乙烷]，已通过元素分析和X射线单晶衍射进行了表征。还详细讨论了它们的热稳定性能。