4,4',4''-(benzene-1,3,5-triyltris(azanediyl))tribenzoic acid | 1258012-29-1

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: 4,4',4''-(benzene-1,3,5-triyltris(azanediyl))tribenzoic acid
• 英文别名: 4,4′,4″-(benzene-1,3,5-triyltris(azanediyl))-tribenzoic acid；4,4',4"-(benzene-1,3,5-triyltris(azanediyl))tribenzoic acid；4,4′,4''-(benzene-1,3,5-triyltris(azanediyl))tribenzoic acid；4,4',4''-(Benzene-1,3,5-triyltris(azanediyl))tribenzoic acid；4-[3,5-bis(4-carboxyanilino)anilino]benzoic acid
• CAS: 1258012-29-1
• 化学式: C₂₇H₂₁N₃O₆
• 分子量: 483.48
• InChiKey: QPDKZYKUPNCXJF-UHFFFAOYSA-N

物化性质

• 沸点：
  759.9±60.0 °C(Predicted)
• 密度：
  1.486±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  5.1
• 重原子数：
  36
• 可旋转键数：
  9
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  148
• 氢给体数：
  6
• 氢受体数：
  9

安全信息

• 危险性防范说明：
  P261,P280,P301+P312,P302+P352,P305+P351+P338
• 危险性描述：
  H302,H315,H319,H335
• 储存条件：
  室温，惰性气体

反应信息

• 作为反应物：
  描述：

  4,4',4''-(benzene-1,3,5-triyltris(azanediyl))tribenzoic acid 、 1,2-双吡啶基乙烯 以 甲醇 为溶剂， 生成
  参考文献：
  名称：

  等规三醚和三胺连接的芳族三羧酸的晶体工程：其共晶体和与双（吡啶基）衍生物形成的盐中的同构结构和合成子相互作用†

  摘要：

  已经研究了分别具有醚键和胺键的构型柔性三酸H 3 tcpb和H 3 btab，以检查其晶体结构以及与双吡啶基分子的共晶体和盐的分子和超分子相似性。两种酸在本文研究的所有晶体结构中均显示出不对称但几乎相同的几何形状。这些分子在其晶体结构中通过酸-酸均合成子表现出一维同构性。H 3 tcpb和H 3 btab分子的1D链分别通过C–H⋯O和N–H⋯O氢键进一步组装，形成2D层。酸H 3与H 3 btab（5）相比，tcpb显示出较少的趋势形成具有双吡啶基分子的复合物单晶（3 ）。在所有复合物中，发现酸-吡啶杂合子在分子组装中起重要作用。但是，在本文研究的八种络合物中，有四种均观察到了同型合成素I，且均来自胺连接的三酸（H 3 btab）。此外，H的配合物3 TCPB表现出红移的发光，而那些为h 3 BTAB表现出蓝移（λ EX。 = 330纳米）相对于母体酸。

  DOI：

  10.1039/c8nj04600j
• 作为产物：
  描述：

  triethyl 4,4',4''-(benzene-1,3,5-triyltris(azanediyl))tribenzoate 在 盐酸 、 sodium hydroxide 作用下， 以 四氢呋喃 、 甲醇 为溶剂， 以90%的产率得到4,4',4''-(benzene-1,3,5-triyltris(azanediyl))tribenzoic acid
  参考文献：
  名称：

  Two Series of Solvent-Dependent Lanthanide Coordination Polymers Demonstrating Tunable Luminescence and Catalysis Properties

  摘要：

  Two series of lanthanide-organic frameworks with the formulas [Ln(BTATB)(DMF)(2)(H2O)]center dot DMF center dot 2H(2)O (Ln = La (1a), Eu (2a), Tb (3a), Er (4a)) and [Ln(BTATB)(H2O)(2)]center dot 2DMA center dot 4H(2)O (Ln = Er (1b), Yb (2b), Lu (3b)), respectively, were solvothermally synthesized from 4,4',4 ''-(benzene-1,3,5-triyltris(azanediyl))tribenzoate (H(3)BTATB) and Ln(NO3)(3) under DMF or DMA media and characterized by thermogravimetric analyses, IR spectroscopy, X-ray powder diffraction, and single crystal X-ray diffraction. X-ray single-crystal diffraction analyses for these complexes revealed that series A features an interesting 2D interdigitated layer architecture with (6,3) topology. Series B exhibits a 2D bilayer structure. The luminescence properties were studied, and the results showed that complex 3a displayed strong fluorescent emission in the visible region, where the emission intensities of 3a are enhanced upon the addition of Zn2+, demonstrating Zn2+-modulated fluorescence. Yb(III) complex 2b emits typical near-infrared luminescence (983 nm) in DMF (lambda(ex) = 315 nm). The Knoevenagel condensation reaction (benzaldehyde and malononitrile or ethyl cyanoacetate in acetonitrile) was studied using 3a and 2b as catalysts. The results showed that the conversion rates of reactions catalyzed by 3a increased to 99 and 42%, respectively, whereas the reactions catalyzed by 2b exhibited lower conversion rates.

  DOI：

  10.1021/cg500286v

文献信息

• Extension of the Pd-catalyzed C N bond forming reaction to the synthesis of large polydentate ligands containing N H functions
  作者：Davide Balestri、Alessia Bacchi、Patrick Scilabra、Paolo Pelagatti

  DOI：10.1016/j.ica.2017.06.029

  日期：2018.1

  The use of Pd(0) mediated C-N coupling reaction for the synthesis of large polydentate ligands functionalized with NH groups is described. The protocol has been applied to the synthesis of polycarboxylic ligands and polypyridyl ligands, starting from common aryl halides containing a central phenyl or biphenyl core as electrophiles. Different aromatic amines or isonicotinamide have been used as nucleophiles. In all cases the ligands have been isolated in high yields and purity. The products have been characterized by means of FTIR, H-1 NMR, C-13H-1} NMR, EI-MS or CI-MS and elemental analysis. The X-ray structure of N, N'-(biphenyl-4,4'-diyl) diisonicotinamide has also been solved. (C) 2017 Elsevier B.V. All rights reserved.
• Functional Mesoporous Metal−Organic Frameworks for the Capture of Heavy Metal Ions and Size-Selective Catalysis
  作者：Qian-Rong Fang、Da-Qian Yuan、Julian Sculley、Jian-Rong Li、Zheng-Bo Han、Hong-Cai Zhou

  DOI：10.1021/ic101935f

  日期：2010.12.20

  By using Zn4O(CO2)(6) as secondary building units (SBUs) and two extended ligands containing amino functional groups, TATAB and BTATB (TATAB = 4,4',4 ''-s-triazine-1,3,5-triyltri-p-aminobenzoate and BTATB = 4,4',4 ''-(benzene-1,3,5-triyltris(azanediyl))tribenzoate), two isostructural mesoporous metal organic frameworks (MOFs) with cavities up to 2.73 nm, designated as PCN-100 and PCN-101 (PCN represents porous coordination network), have been synthesized. N-2 sorption isotherms of both PCN-100 and -101 showed typical type IV behavior, indicating their mesoporous nature. The TATAB ligand that comprises PCN-100 was employed to capture heavy metal ions (Cd(II) and Hg(II)) by constructing complexes within the pores with a possible coordination mode similar to that found in aminopyridinato complexes. This reveals that mesoporous materials such as PCN-100 can be applied in the elimination of heavy metal ions from waste liquid. In addition, both PCNs-100 and -101 exhibit size-selective catalytic activity toward the Knoevenagel condensation reaction.
• 10.1016/j.ica.2024.122227
  作者：Yu, Shufang、Ma, Linsheng、Liu, Chunlin

  DOI：10.1016/j.ica.2024.122227

  日期：——
• Two Series of Solvent-Dependent Lanthanide Coordination Polymers Demonstrating Tunable Luminescence and Catalysis Properties
  作者：Na Wei、Ming-Yang Zhang、Xiao-Nan Zhang、Guang-Ming Li、Xiang-Dong Zhang、Zheng-Bo Han

  DOI：10.1021/cg500286v

  日期：2014.6.4

  Two series of lanthanide-organic frameworks with the formulas [Ln(BTATB)(DMF)(2)(H2O)]center dot DMF center dot 2H(2)O (Ln = La (1a), Eu (2a), Tb (3a), Er (4a)) and [Ln(BTATB)(H2O)(2)]center dot 2DMA center dot 4H(2)O (Ln = Er (1b), Yb (2b), Lu (3b)), respectively, were solvothermally synthesized from 4,4',4 ''-(benzene-1,3,5-triyltris(azanediyl))tribenzoate (H(3)BTATB) and Ln(NO3)(3) under DMF or DMA media and characterized by thermogravimetric analyses, IR spectroscopy, X-ray powder diffraction, and single crystal X-ray diffraction. X-ray single-crystal diffraction analyses for these complexes revealed that series A features an interesting 2D interdigitated layer architecture with (6,3) topology. Series B exhibits a 2D bilayer structure. The luminescence properties were studied, and the results showed that complex 3a displayed strong fluorescent emission in the visible region, where the emission intensities of 3a are enhanced upon the addition of Zn2+, demonstrating Zn2+-modulated fluorescence. Yb(III) complex 2b emits typical near-infrared luminescence (983 nm) in DMF (lambda(ex) = 315 nm). The Knoevenagel condensation reaction (benzaldehyde and malononitrile or ethyl cyanoacetate in acetonitrile) was studied using 3a and 2b as catalysts. The results showed that the conversion rates of reactions catalyzed by 3a increased to 99 and 42%, respectively, whereas the reactions catalyzed by 2b exhibited lower conversion rates.
• Crystal engineering with isosteric triether and triamine linked aromatic tri-carboxylic acids: iso-structurality and synthon interplay in their co-crystals and salts with bis(pyridyl) derivatives
  作者：Debarati Das、Sandipan Roy、Kumar Biradha

  DOI：10.1039/c8nj04600j

  日期：——

  amine linkages, respectively, have been studied to examine the molecular and supramolecular similarities in their crystal structures and also in those of cocrystals and salts with bispyridyl molecules. Both the acids exhibited unsymmetrical but almost identical geometries in all the crystal structures studied here. In their crystal structures these molecules were found to exhibit one-dimensional isostructurality

  已经研究了分别具有醚键和胺键的构型柔性三酸H 3 tcpb和H 3 btab，以检查其晶体结构以及与双吡啶基分子的共晶体和盐的分子和超分子相似性。两种酸在本文研究的所有晶体结构中均显示出不对称但几乎相同的几何形状。这些分子在其晶体结构中通过酸-酸均合成子表现出一维同构性。H 3 tcpb和H 3 btab分子的1D链分别通过C–H⋯O和N–H⋯O氢键进一步组装，形成2D层。酸H 3与H 3 btab（5）相比，tcpb显示出较少的趋势形成具有双吡啶基分子的复合物单晶（3 ）。在所有复合物中，发现酸-吡啶杂合子在分子组装中起重要作用。但是，在本文研究的八种络合物中，有四种均观察到了同型合成素I，且均来自胺连接的三酸（H 3 btab）。此外，H的配合物3 TCPB表现出红移的发光，而那些为h 3 BTAB表现出蓝移（λ EX。 = 330纳米）相对于母体酸。