2-(2-carboxylphenyl)-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-(2-carboxylphenyl)-1H-imidazole-4,5-dicarboxylic acid
• 英文别名: 2-(2-carboxyphenyl)-1H-imidazole-4,5-dicarboxylic acid；2-(2-Carboxyphenyl)-1H-imidazole-4,5-dicarboxylic acid
• 化学式: C₁₂H₈N₂O₆
• 分子量: 276.205
• InChiKey: YOPQZSDWEFYVIM-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-(2-carboxylphenyl)-1H-imidazole-4,5-dicarboxylic acid 在 barium(II) nitrate 、 水 作用下， 反应 96.0h， 以61%的产率得到
  参考文献：
  名称：

  A Water-Stable Proton-Conductive Barium(II)-Organic Framework for Ammonia Sensing at High Humidity

  摘要：

  In view of environmental protection and the need for early prediction of major diseases, it is necessary to accurately monitor the change of trace ammonia concentration in air or in exhaled breath. However, the adoption of proton-conductive metal-organic frameworks (MOFs) as smart sensors in this field is limited by a lack of ultrasensitive gas-detecting performance at high relative humidity (RH). Here, the pellet fabrication of a water-stable proton-conductive MOF, Ba(o-CbPhH2IDC)(H2O)(4)](n) (1) (o-CbPhH4IDC = 2-(2-carboxylphenyl)-1H-imidazole-4,5-dicarboxylic acid) is reported. The MOF 1 displays enhanced sensitivity and selectivity to NH3 gas at high RHs (>85%) and 30 degrees C, and the sensing mechanism is suggested. The electrochemical impedance gas sensor fabricated by MOF 1 is a promising sensor for ammonia at mild temperature and high RHs.

  DOI：

  10.1021/acs.inorgchem.8b00806

文献信息

• Three metal–organic frameworks constructed from imidazole-based multi-carboxylate ligands: Syntheses, structures and photoluminescent properties
  作者：Wenyan Zhou、Lijia Zhao、Zilong An、Gang Li

  DOI：10.1016/j.poly.2016.05.059

  日期：2016.10

  Abstract Three metal–organic frameworks, [Ba(o-CPhH2IDC)]n (1), [Ca(o-CPhH2IDC)(H2O)2]·H2O}n (2), (o-CPhH4IDC = 2-(2-carboxylphenyl)-1H-imidazole-4,5-dicarboxylic acid) and [Cd(m-CPhH2IDC)(phen)]·H2O}n (3) (m-CPhH4IDC = 2-(3-carboxylphenyl)-1H-imidazole-4,5-dicarboxylic acid and phen = 1,10-phenanthroline), have been solvothermally synthesized and structurally characterized by elemental analyses

  摘要三种金属有机骨架，[Ba（o-CPhH2IDC）] n（1），[Ca（o-CPhH2IDC）（H2O）2]· } n（2），（o-CPhH4IDC = 2-（2 -羧基苯基）-1H-咪唑-4,5-二羧酸）和[Cd（m-CPhH2IDC）（phen）]· } n（3）（m-CPhH4IDC = 2-（3-羧基苯基）-1H-溶剂热合成咪唑（4,5-二羧酸和phen = 1,10-菲咯啉），并通过元素分析，红外光谱，热重分析和单晶X射线衍射对其结构进行了表征。化合物1是（5,5）连接的3D结构。化合物2显示无限的一维双链结构。复数3通过相邻之字形链的π–π相互作用呈现出一种波状结构。咪唑基多羧酸盐配体具有很强的配位能力和多种配位方式。此外，
• Proton conduction in two Cu/Zn dimer-based hydrogen-bonded supramolecular frameworks from imidazole multi-carboxylate
  作者：Qingxu Wang、Zhejun Ye、Guoqing Shi、Kaimeng Guo、Gang Li

  DOI：10.1039/d0nj01189d

  日期：——

  At 98% RH and 100 °C, two dimer-based HSFs show the best σ values of 3.13 × 10⁻⁴ S cm⁻¹ for 1 and 0.55 × 10⁻⁴ S cm⁻¹ for 2, which can be compared to the values of reported HSFs.

  在98%相对湿度和100°C下，两种基于二聚体的HSF显示出最佳的σ值，分别为1的3.13 × 10⁻⁴ S cm⁻¹和2的0.55 × 10⁻⁴ S cm⁻¹，这可以与已报道的HSF值进行比较。
• Two imidazole multicarboxylate-based MOFs: syntheses, structures and proton conductive properties
  作者：Zhongcheng Guo、Yimeng Zhang、Jinggang Liu、Bingxue Han、Gang Li

  DOI：10.1039/d1nj03002g

  日期：——

  5-imidazole dicarboxylic acid (o-CPH4IDC) was selected by us. Consequently, two highly water-stable Ba(II) and Cd(II) MOFs, [Cd(o-CPH2IDC)(4,4′-bipy)0.5(H2O)2]·3H2O}n (1) (4,4′-bipy = 4,4′-bipyridine) and [Ba(o-CPH2IDC)]n (2) were made. The further study of water-assisted proton conduction for 1 and 2 demonstrated that both were temperature- and humidity-dependent proton conductors, and their best proton

  考虑到 N-杂环羧酸盐配体在构建金属有机骨架 (MOF) 中的配位优势，我们希望采用它们来构建结构更稳定的 MOF，用于质子传导研究。因此，我们选择了2-(2-羧基苯基)-4,5-咪唑二羧酸( o- CPH 4 IDC)的多功能配体。因此，两种高度水稳定的 Ba( II ) 和 Cd( II ) MOF，[Cd( o -CPH 2 IDC)(4,4'-bipy) 0.5 (H 2 O) 2 ]·3H 2 O} n ( 1 ) (4,4'-bipy = 4,4'-联吡啶) 和 [Ba( o -CPH2 IDC)] n ( 2 )。对1和2的水辅助质子传导的进一步研究表明，两者都是温度和湿度相关的质子导体，它们的最佳质子传导率在100°C和98% RH下可达到10 -4 S·cm -1。通过计算活化能和分析它们的晶体结构，可以为1和2提出车辆机制。显然，MOFs 中吸附的水分子和羧酸根基团在
• Water-assisted proton conductivity of two highly stable imidazole multi-carboxylate-based MOFs
  作者：Yin Qin、Yilin Li、Kaimeng Guo、Huabiao Tang、Lifen Hou、Gang Li

  DOI：10.1039/c9nj00400a

  日期：——

  The proton conduction and proton mechanisms of two highly stable imidazole multi-carboxylate-based MOFs have been investigated and discussed.

  研究并讨论了两种高度稳定的咪唑多羧酸基 MOF 的质子传导和质子机制。
• 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)( )]n (3) 五种三维或二维聚合物被制成、[n (4)和[Cd3(m-CPhH2IDC)2( )8]-2 }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。