2-(4-carboxyphenyl)-1H-imidazole-4,5-dicarboxylic acid

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑类
• 英文名称: 2-(4-carboxyphenyl)-1H-imidazole-4,5-dicarboxylic acid
• 英文别名: 2-(4-carboxylphenyl)-1H-imidazole-4,5-dicarboxylic acid；2-(4-Carboxyphenyl)-1H-imidazole-4,5-dicarboxylic acid
• 化学式: C₁₂H₈N₂O₆
• 分子量: 276.205
• InChiKey: VISJKRXFOOOCNB-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1
• 重原子数：
  20
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  141
• 氢给体数：
  4
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  2-(4-carboxyphenyl)-1H-imidazole-4,5-dicarboxylic acid 在 水 、 三乙胺 、 calcium chloride 作用下， 反应 72.0h， 以51%的产率得到
  参考文献：
  名称：

  Syntheses, crystal structures, and thermal properties of two complexes built by imidazole-based multi-carboxylate ligands

  摘要：

  Based on two promising p-CPhH4IDC and o-CPhH4IDC ligands, one 2D coordination polymer, [Ca(p-CPhH2IDC)(H2O)] (n) (p-CPhH4IDC = 2-(4-carboxylphenyl)-1H-imidazole-4,5-dicarboxylic acid) (I) and one novel dimeric complex, [Cd-2(o-CPhH2IDC)(2)(H2O)(6)] center dot 4H(2)O (o-CPhH4IDC = 2-(2-carboxylphenyl)-1H-imidazole-4,5-dicarboxylic acid) (II) have been hydrothermally synthesized and structurally characterized by elemental analyses, IR spectroscopy, and single crystal X-ray diffraction (CIF files CCDC nos. 929826 (I), 959841 (II)). Polymer I exhibits a graceful 2D grid sheet structure. Polymer II is a binuclear complex in which two Cd2+ ions are bridged by two carboxyates from two o-CPhH2IDC2- ligands. Four and two types of coordination environments around the Ca and Cd atoms, respectively can be observed. Furthermore, the solid-state photoluminescence and thermal properties of the two complexes have been investigated.

  DOI：

  10.1134/s1070328415080072
• 作为产物：
  描述：

  2,3-bis(nitrooxy)succinic acid 、 对醛基苯甲酸 在 ammonium hydroxide 作用下， 以 水 为溶剂， 反应 24.0h， 以48%的产率得到2-(4-carboxyphenyl)-1H-imidazole-4,5-dicarboxylic acid
  参考文献：
  名称：

  由混合桥接 N-供体和 2-(4-羧基苯基)-4,5-咪唑二羧酸配体组装的两种 Zn(II) 配位聚合物的合成、结构、发光和光催化性能

  摘要：

  摘要 两种新的 Zn(II) 配位聚合物，其分子式为 {[Zn3(HCpIDC)2(4,4'-bipy)(H2O)]·4H2O}n (1) 和 {[Zn2(CpIDC)(BIMB)] ·H2O}n (2) [H4CpIDC = 2-(4-carboxyphenyl)-4,5-咪唑二羧酸，4,4'-bipy = 4,4'-联吡啶，BIMB = 1,4-bis(1 -咪唑基)苯]已成功合成。复合物 1 和 2 均具有 3D 框架，其中 HCpIDC3- 和 CpIDC4- 配体的 IDC 基团连接金属节点，导致无限 21 螺旋链。HCpIDC3- 和 CpIDC4− 阴离子表现出两种配位模式（μ4-kN,O: kN',O': kO",O‴: kO"" 和 μ5-kN,O: kN',O': kO",O ‴: kO″″: kO) 在不同的协调环境中。进一步的结构分析表明，1 和 2 分别是拓扑双峰

  DOI：

  10.1016/j.molstruc.2017.01.023

文献信息

• Two Highly Stable Proton Conductive Cobalt(II)–Organic Frameworks as Impedance Sensors for Formic Acid
  作者：Rui‐Lan Liu、Zhi‐Qiang Shi、Xin‐Yue Wang、Zi‐Feng Li、Gang Li

  DOI：10.1002/chem.201902169

  日期：2019.11.7

  favorable to the proton transfer. By measuring the impedance values after exposure to formic acid vapor at 98 % or 68 % RH and 25 °C, both MOFs indicate reproducibly high sensitivity to the analyte. The detection limit of formic acid vapor is as low as 35 ppm for 1 and 70 ppm for 2. Meanwhile, both MOFs also show commendable selectivity towards formic acid among interfering solutions. The proton conducting

  近年来，金属有机框架（MOF）已作为一种先进的化学传感器进行了广泛的探索。但是，关于MOFs作为酸性气体传感器的研究很少，特别是质子传导性MOFs。在这项工作中，两个新的质子传导3D MOF Co3（p-CPhHIDC）2（4,4'-bipy）（H2 O）]⋅2H2 O} n（1）（p-CPhH4 IDC = 2 -（4-羧基苯基）-1 H-咪唑-4,5-二羧酸; 4,4'-bipy = 4,4'-联吡啶）和[Co3（p-CPhHIDC）2（bpe）（H2 O） ]⋅3H2 O} n（2）（bpe =反式-1,2-双（4-吡啶基）乙烯）已被溶剂热制备并研究了它们的甲酸传感性能。MOF 1和MOF 2均显示出温度和湿度相关的质子传导特性，并且在98％相对湿度（RH）和100°C时分别表现出1.04×10-3和7.02×10-4 S cm的优化质子电导率。框架内大量的不配位的羧酸位点，游
• Four d10 metal coordination polymers based on 2-(4-carboxyphenyl)-1H-imidazole-4,5-dicarboxylic acid and auxiliary N-containing ligands: Syntheses, structures, photoluminescence and sensing properties
  作者：Gang Yuan、Chao Zhang、De-Jun Xu、Kui-Zhan Shao、Xiu-Mei Li、Xiang-Rong Hao、Zhong-Min Su

  DOI：10.1016/j.poly.2020.114430

  日期：2020.4

  and further characterized by infrared spectra (IR), elemental analyses and thermogravimetric analyses (TGA). The H4CpIDC ligands can be deprotonated into H2CpIDC2−, HCpIDC3− or CpIDC4− anions and they can coordinate to the metal centers in monodentate, μ3, μ4 or μ5 modes in the four complexes. Complex 1 possesses a 3D framework with a new (3,4,5)-connected topology constructed from interconnected trz-Zn-CpIDC

  摘要四个新的CP [Zn5（HCpIDC）2（trz）4（H2O）2] n（1），[Cd2（HCpIDC）（ttz）（H2O）2]∙H2O]} n（2），[ Zn（H2CpIDC）（tib）]∙4H2O]} n（3）和[Zn3（HCpIDC）2（tib）（H2O）2]∙H2O]} n（4）[H4CpIDC = 2-（4-羧基苯基） -1H-咪唑-4,5-二羧酸，Htrz = 1,2,4-三唑，Httz = 1H-四唑，tib = 1,3,5-三（1H-咪唑-1-基）苯）]，通过精细控制合成条件已经水热合成。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。H4CpIDC配体可以被去质子化为H2CpIDC2-，HCpIDC3-或CpIDC4-阴离子，并且它们可以在四个络合物中以单齿，μ3，μ4或μ5模式与金属中心配位。复合体1具有3D框架，其中包含一个新的（3
• A water-stable Tb(III) coordination polymer based on 2-(4-carboxyphenyl)-1H-imidazole-4,5-dicarboxylic acid: Synthesis, structure, color-tunable fluorescence and sensing properties
  作者：Gang Yuan、Chao Zhang、De-Jun Xu、Kui-Zhan Shao、Xiu-Mei Li、Xiang-Rong Hao、Zhong-Min Su

  DOI：10.1016/j.inoche.2021.108458

  日期：2021.3

  43}246.66.83} formed by HCpIDC3− anions μ4 − bridging Tb(III) ions. The solid-state luminescent property of CP 1 was characterized and the results revealed that it exhibits fascinating excitation-wavelength dependent fluorescence property and may be a potential color-tunable fluorescence material. In addition, the luminescent emissions of CP 1 can be enhanced by addition of trace amount of Al3+ demonstrating

  一种新型的水稳定性基于Tb（III）的配位聚合物（CP）[Tb（HCpIDC）（H 2 O）2 ]·2H 2 O} n（1）（H 4 CpIDC = 2-（4-羧苯基） ）-4,5-咪唑二羧酸）是在水热条件下合成的，并通过单晶和粉末X射线衍射分析，红外分析，元素分析和热重分析进行了表征。CP 1展示了一个2D（3,6）连接的kgd网络，其点符号为4 3 } 2 4 6 .6 6 .8 3 }由HCpIDC 3-阴离子μ形成4- 桥接Tb（III）离子。对CP 1的固态发光特性进行了表征，结果表明，它具有令人着迷的激发波长依赖性荧光特性，并且可能是潜在的颜色可调荧光材料。另外，可以通过添加痕量的Al 3+来增强CP 1的发光，这证明了其在检测Al 3+离子方面的潜在应用。
• One Novel 2D Manganese(II) Coordination Polymer From Carboxylphenyl Imidazole Dicarboxylate: Synthesis, Crystal Structure, and Properties
  作者：Feng Wang、Chengfei Ruan、Yanbin Jiao、Gang Li

  DOI：10.1080/15533174.2015.1137032

  日期：2016.11.1

  been solvothermally synthesized and structurally characterized by elemental analysis, IR spectrum, as well as single-crystal X-ray diffraction analysis. The polymer can be regarded as a 2D sheet structure. Further, the solid-state photoluminescence and thermal properties of the polymer have been investigated.

  一种Mn（II）配位聚合物，[Mn（p- CPhH 2 IDC）（H 2 O）] n（1）（p -CPhH 4 IDC = 2-（4-羧基苯基）-1 H-咪唑-4,5 -二羧酸），已经溶剂热合成并通过元素分析，IR光谱以及单晶X射线衍射分析进行结构表征。该聚合物可以被视为2D片状结构。此外，已经研究了聚合物的固态光致发光和热性能。
• Construction of a series of coordination polymers from three imidazole-based multi-carboxylate ligands
  作者：Beibei Guo、Li Li、Yang Wang、Yanyan Zhu、Gang Li

  DOI：10.1039/c3dt51486b

  日期：——

  2-Carboxylphenyl, 3-carboxylphenyl and 4-carboxylphenyl groups were introduced into the 2-position of imidazole-4,5-dicarboxylate system, respectively, obtaining three multi-functional ligands 2-(2-carboxylphenyl)-1H-imidazole-4,5-dicarboxylic acid (o-CPhH4IDC), 2-(3-carboxylphenyl)-1H-imidazole-4,5-dicarboxylic acid (m-CPhH4IDC) and 2-(4-carboxylphenyl)-1H-imidazole-4,5-dicarboxylic acid (p-CPhH4IDC). Then the three organic ligands are employed to react with Sr(II) and Cd(II) ions. Subsequently, five 3D or 2D polymers, [Sr(o-CPhH2IDC)]n (1), [Sr3(m-CPhHIDC)2(H2O)3]n (2), [Sr(p-CPhH2IDC)(H2O)]n (3), [Cd(o-CPhH2IDC)(H2O)2]n (4) and [Cd3(m-CPhHIDC)2(H2O)8]·2H2O}n (5), have been hydro(solvo)thermally synthesized and structurally characterized. Compound 1 is a (5,5)-connected 3D structure with unique “H-shape” channels. Three kinds of coordination environments around the Sr atoms are exhibited in compound 2. Both compounds 1 and 2 contain unusual irregular cages. Compound 3 displays a (4,6)-connected 3D porous framework composed of right-handed helices connected by p-CPhH2IDC2− anions. Both compounds 4 and 5 present net-like layer structures. These various architectures demonstrate the versatile coordination abilities of the three imidazole-based multi-carboxylate ligands.

  在咪唑-4,5-二甲酸酯体系的 2 位分别引入 2-羧基苯基、3-羧基苯基和 4-羧基苯基，得到三种多功能配体 2-(2-羧基苯基)-1H-咪唑-4、5-二羧酸（o-CPH4IDC）、2-（3-羧基苯基）-1H-咪唑-4,5-二羧酸（m-CPH4IDC）和 2-（4-羧基苯基）-1H-咪唑-4,5-二羧酸（p-CPH4IDC）。然后，这三种有机配体与 Sr(II) 和 Cd(II) 离子发生反应。随后，[Sr(o-CPh2IDC)]n (1)、[Sr3(m-CPh2IDC)2(H2O)3]n (2)、[Sr(p-CPh2IDC)(H2O)]n (3) 五种三维或二维聚合物被制成、[n (4)和[Cd3(m-CPhH2IDC)2(H2O)8]-2H2O}n (5)进行了水（溶）热合成和结构表征。化合物 1 是一种 (5,5) 连接的三维结构，具有独特的 "H 形 "通道。在化合物 2 中，Sr 原子周围呈现出三种配位环境。化合物 1 和 2 都含有不寻常的不规则笼。化合物 3 显示了一个 (4,6) 连接的三维多孔框架，由对-CPH2IDC2-阴离子连接的右手螺旋组成。化合物 4 和 5 都呈现出网状层结构。这些不同的结构展示了这三种咪唑基多羧酸配体的多功能配位能力。