2,3-dimethoxy-N-(1,10-phenanthroline-5-yl)benzamide | 947185-28-6

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 菲咯啉
• 英文名称: 2,3-dimethoxy-N-(1,10-phenanthroline-5-yl)benzamide
• 英文别名: Me2-phencat
• CAS: 947185-28-6
• 化学式: C₂₁H₁₇N₃O₃
• 分子量: 359.384
• InChiKey: GCEYKPGCIPYFRH-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.05
• 重原子数：
  27.0
• 可旋转键数：
  4.0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.1
• 拓扑面积：
  73.34
• 氢给体数：
  1.0
• 氢受体数：
  5.0

反应信息

• 作为反应物：
  描述：

  2,3-dimethoxy-N-(1,10-phenanthroline-5-yl)benzamide 在 三溴化硼 、 水 作用下， 以 二氯甲烷 为溶剂， 反应 24.0h， 生成 H2-phencat
  参考文献：
  名称：

  Luminescent iridium complexes for detection of molybdate

  摘要：

  [Ir(C⁁N)2Cl]2 [HC⁁N = 2-(3-R-苯基)吡啶，2-(3-R-苯基吡唑) R = H，Me]与Me2-phencat的反应生成发光配合物[Ir(C⁁N)2(Me2-phencat)][PF6] (Me2-2a, b, c)[PF6]。用BBr3脱除甲氧基存在一定困难，因为同时发生环金属苯基基团的溴化反应。然而，用BBr3脱除Me2-phencat，然后与[Ir(C⁁N)2Cl]2发生配合反应，生成发光配合物[Ir(C⁁N)2(H2-phencat)][PF6] (H2-3a, c)[PF6]，该配合物是钼酸盐的发光传感器。

  DOI：

  10.1039/c1dt11360g

文献信息

• Synthesis, Characterization, Solid-State Structures, and Spectroscopic Properties of Two Catechol-Based Luminescent Chemosensors for Biologically Relevant Oxometalates
  作者：Helen D. Batey、Adrian C. Whitwood、Anne-K. Duhme-Klair

  DOI：10.1021/ic700554n

  日期：2007.8.1

  The new heteroditopic ligand 2,3-dihydroxy-N-(1,10-phenanthroline-5-yl)benzamide (H-2-L-3) was synthesized and coordinated to [Ru(bpy)(2)(phen)](2+)- and [ReBr(CO)(3)(phen)]-type luminophores (bpy = 2,2'-bipyridine and phen = 1,10-phenanthroline). The resulting chemosensors [Ru(bpy)(2)(H-2-L-3)](2+) and [ReBr(CO)(3)(H-2-L-3)] were fully characterized and their solid-state structures and spectroscopic properties were investigated to assess how the photophysical properties of the luminescent signaling units affect the performance of the sensors. [Ru(bpy)(2)(H-2-L-3)](2+) and [ReBr(CO)(3)(H-2-L-3)] both signal the presence and concentration of molybdate and vanadate in aqueous acetonitrile through a decrease in emission intensity. [ReBr(CO)(3)(H-2-L-3)] also detects tungstate. Due to the higher emission intensity of the Ru-based sensor, its detection limits for molybdate (43 mu g L-1) and vanadate (24 mu g L-1) are almost 1 order of magnitude lower than the ones achieved with the Re-based sensor. The optimum working pH of the chemosensors is determined by the pK(a) values of the 2-hydroxy-groups of the receptor units: pH 4 for [ReBr(CO)(3)(H-2-L-3)] and pH 3 for [Ru(bpy)(2)(H-2-L-3)](2+). Both sensors are selective: equimolar amounts of PO43-, SO42-, ReO4-, Mn(II), Fe(III), Co(II), Ni(II), Cu(II), and Zn(II) do not interfere with the detection of molybdate or vanadate.