3,3'-(2-amino-5-isopropyl-1,3-phenylenebis(ethyne-2,1-diyl))dibenzoic acid | 1255369-33-5

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 二芳基庚烷
• 英文名称: 3,3'-(2-amino-5-isopropyl-1,3-phenylenebis(ethyne-2,1-diyl))dibenzoic acid
• 英文别名: 3,3'-(2-Amino-5-iso-propyl-1,3-phenylene)bis(ethyne-2,1-diyl)dibenzoic acid；3-[2-[2-amino-3-[2-(3-carboxyphenyl)ethynyl]-5-propan-2-ylphenyl]ethynyl]benzoic acid
• CAS: 1255369-33-5
• 化学式: C₂₇H₂₁NO₄
• 分子量: 423.468
• InChiKey: GJQWCTGCRGULPM-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.5
• 重原子数：
  32
• 可旋转键数：
  7
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.11
• 拓扑面积：
  101
• 氢给体数：
  3
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  dimolybdenum(II) tetrakis(trifluoroacetate) 、 3,3'-(2-amino-5-isopropyl-1,3-phenylenebis(ethyne-2,1-diyl))dibenzoic acid 、 二甲基亚砜 以 二甲基亚砜 为溶剂， 生成 [Mo2(3,3'-(2-amino-5-isopropyl-1,3-phenylenebis(ethyne-2,1-diyl))dibenzoato)2(dimethyl sulfoxide)2]2*4(dimethyl sulfoxide)
  参考文献：
  名称：

  Ligand Bridging-Angle-Driven Assembly of Molecular Architectures Based on Quadruply Bonded Mo−Mo Dimers

  摘要：

  A systematic exploration of the assembly of Mo-2(O2C-)(4)-based metal-organic molecular architectures structurally controlled by the bridging angles of rigid organic linkers has been performed. Twelve bridging dicarboxylate ligands were designed to be of different sizes with bridging angles of 0, 60, 90, and 120 degrees while incorporating a variety of nonbridging functional groups, and these ligands were used as linkers. These dicarboxylate linkers assemble with quadruply bonded Mo-Mo clusters acting as nodes to give 13 molecular architectures, termed metal-organic polygons/polyhedra with metal cluster node arrangements of a linear shape, triangle, octahedron, and cuboctahedron/anti-cuboctahedron. The syntheses of these complexes have been optimized and their structures determined by single-crystal X-ray diffraction. The results have shown that the shape and size of the resulting molecular architecture can be controlled by tuning the bridging angle and size of the linker, respectively. Functionalization of the linker can adjust the solubility of the ensuing molecular assembly but has little or no effect on the geometry of the product. Preliminary gas adsorption, spectroscopic, and electrochemical properties of selected members were also studied. The present work is trying to enrich metal-containing supramolecular chemistry through the inclusion of well-characterized quadruply bonded Mo-Mo units into the structures, which can widen the prospect of additional electronic functionality, thereby leading to novel properties.

  DOI：

  10.1021/ja1080794
• 作为产物：
  描述：

  2,6-二溴-4-异丙苯胺 在 甲醇 、 copper(l) iodide 、 四(三苯基膦)钯 、 水 、 potassium carbonate 、 三乙胺 、 sodium hydroxide 作用下， 以 四氢呋喃 、 甲醇 、 二氯甲烷 为溶剂， 反应 29.0h， 生成 3,3'-(2-amino-5-isopropyl-1,3-phenylenebis(ethyne-2,1-diyl))dibenzoic acid
  参考文献：
  名称：

  通过分子笼的客体诱导荧光开启直接识别 HMX

  摘要：

  Octahydro-1,3,5,7-tetranitro-1,3,5,7-tetrazocine (HMX) 是使用最广泛的强力炸药之一。由于 HMX 的挥发性极低、还原潜力不利和缺乏芳环，因此在不需要专门设备的情况下直接和选择性地检测 HMX 仍然是一个巨大的挑战。在这里，我们报告了第一个基于设计的金属有机笼 (MOC) 以 ppb 灵敏度直接识别 HMX 的化学探针。笼子在腔内具有两个不饱和双铜单元和四个给电子氨基，提供多个结合位点以选择性地增强主客体事件。结果发现，与其他爆炸性分子相比，在空腔内捕获 HMX 会强烈调节宿主笼的发射行为，导致高度诱导的荧光“开启”（160 倍）。基于密度泛函理论 (DFT) 模拟，主客体之间大小和结合位点的相互拟合导致协同效应扰乱配体到金属电荷转移 (LMCT) 过程，这可能是起源这种选择性 HMX 诱导的开启行为。

  DOI：

  10.1016/j.cclet.2021.05.051

文献信息

• Direct identification of HMX via guest-induced fluorescence turn-on of molecular cage
  作者：Chen Wang、Jin Shang、Li Tian、Hongwei Zhao、Peng Wang、Kai Feng、Guokang He、Jefferson Zhe Liu、Wei Zhu、Guangtao Li

  DOI：10.1016/j.cclet.2021.05.051

  日期：2021.12

  a designed metal-organic cage (MOC). The cage features two unsaturated dicopper units and four electron donating amino groups inside the cavity, providing multiple binding sites to selectively enhance host-guest events. It was found that compared to other explosive molecules the capture of HMX inside the cavity would strongly modulate the emissive behavior of the host cage, resulting in highly induced

  Octahydro-1,3,5,7-tetranitro-1,3,5,7-tetrazocine (HMX) 是使用最广泛的强力炸药之一。由于 HMX 的挥发性极低、还原潜力不利和缺乏芳环，因此在不需要专门设备的情况下直接和选择性地检测 HMX 仍然是一个巨大的挑战。在这里，我们报告了第一个基于设计的金属有机笼 (MOC) 以 ppb 灵敏度直接识别 HMX 的化学探针。笼子在腔内具有两个不饱和双铜单元和四个给电子氨基，提供多个结合位点以选择性地增强主客体事件。结果发现，与其他爆炸性分子相比，在空腔内捕获 HMX 会强烈调节宿主笼的发射行为，导致高度诱导的荧光“开启”（160 倍）。基于密度泛函理论 (DFT) 模拟，主客体之间大小和结合位点的相互拟合导致协同效应扰乱配体到金属电荷转移 (LMCT) 过程，这可能是起源这种选择性 HMX 诱导的开启行为。
• Ligand Bridging-Angle-Driven Assembly of Molecular Architectures Based on Quadruply Bonded Mo−Mo Dimers
  作者：Jian-Rong Li、Andrey A. Yakovenko、Weigang Lu、Daren J. Timmons、Wenjuan Zhuang、Daqiang Yuan、Hong-Cai Zhou

  DOI：10.1021/ja1080794

  日期：2010.12.15

  A systematic exploration of the assembly of Mo-2(O2C-)(4)-based metal-organic molecular architectures structurally controlled by the bridging angles of rigid organic linkers has been performed. Twelve bridging dicarboxylate ligands were designed to be of different sizes with bridging angles of 0, 60, 90, and 120 degrees while incorporating a variety of nonbridging functional groups, and these ligands were used as linkers. These dicarboxylate linkers assemble with quadruply bonded Mo-Mo clusters acting as nodes to give 13 molecular architectures, termed metal-organic polygons/polyhedra with metal cluster node arrangements of a linear shape, triangle, octahedron, and cuboctahedron/anti-cuboctahedron. The syntheses of these complexes have been optimized and their structures determined by single-crystal X-ray diffraction. The results have shown that the shape and size of the resulting molecular architecture can be controlled by tuning the bridging angle and size of the linker, respectively. Functionalization of the linker can adjust the solubility of the ensuing molecular assembly but has little or no effect on the geometry of the product. Preliminary gas adsorption, spectroscopic, and electrochemical properties of selected members were also studied. The present work is trying to enrich metal-containing supramolecular chemistry through the inclusion of well-characterized quadruply bonded Mo-Mo units into the structures, which can widen the prospect of additional electronic functionality, thereby leading to novel properties.