1-(2-trifluoromethyl-phenyl)-4-(2-pyridyl)-1,2,3-triazole | 1318914-62-3

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡啶及其衍生物
• 英文名称: 1-(2-trifluoromethyl-phenyl)-4-(2-pyridyl)-1,2,3-triazole
• 英文别名: 1-[2-(Trifluoromethyl)phenyl]-4-(2-pyridyl)-1H-1,2,3-triazole；2-[1-[2-(trifluoromethyl)phenyl]triazol-4-yl]pyridine
• CAS: 1318914-62-3
• 化学式: C₁₄H₉F₃N₄
• 分子量: 290.247
• InChiKey: ATKPJGGRHLHBLV-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.9
• 重原子数：
  21
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.07
• 拓扑面积：
  43.6
• 氢给体数：
  0
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  cis-dichlorobis(dimethylsulfoxide)platinum(II) 、 1-(2-trifluoromethyl-phenyl)-4-(2-pyridyl)-1,2,3-triazole 以 硝基甲烷 为溶剂， 以65%的产率得到dichloro(1-(2-trifluoromethyl phenyl)-4-(2-pyridyl)-1,2,3-triazole)platinum(II)
  参考文献：
  名称：

  Expanding the scope of ‘Click’ derived 1,2,3-triazole ligands: New palladium and platinum complexes

  摘要：

  Using the 'Click Protocol' the new ligands 1-(cyclohexyl)-4-(2-pyridyl)-1,2,3-triazole (1), 1-(2-trifluoromethyl phenyl)-4-(2-pyridyl)-1,2,3-triazole (2), 1-(4-hexyl phenyl)-4-(2-pyridyl)-1,2,3-triazole (3), 1-(2-mercaptomethyl phenyl)-4-(2-pyridyl)-1,2,3-triazole (4) and 1-(4-N, N-dimethylamino phenyl)-4-(2-pyridyl)-1,2,3-triazole (5) were prepared by reacting 2-ethynylpyridine with the corresponding azides. In the next step the ligands were reacted with suitable palladium and platinum precursors to yield the cis-dichloro-palladium complexes 1a-4a and platinum complexes 1b-4b. Investigation of the molecular structure of the free ligands 1 and 5 reveals the formation of infinite chains in the 3D structure which are governed by hydrogen bonds between the triazole units. Likewise the 3D structure of 1a shows infinite chains which are held together by multiple remarkably short C-H center dot center dot center dot Cl-Pd contacts. Electrochemical investigation of the free ligands by cyclic voltammetry showed irreversible reduction processes at highly negative potential. Upon metal complexation huge anodic shifts of the reduction potential were observed. To further characterize the electronic properties of all the compounds UV-Vis spectra were also analyzed. (C) 2011 Elsevier B.V. All rights reserved.

  DOI：

  10.1016/j.ica.2011.02.085
• 作为产物：
  描述：

  2-乙炔基吡啶 、 1-叠氮基-2-(三氟甲基)苯 在 copper(ll) sulfate pentahydrate 、 叔丁基三氯乙酰亚胺酯 、 (+)-sodium L-ascorbate 作用下， 以 二氯甲烷 、 水 、 叔丁醇 为溶剂， 反应 48.0h， 以93%的产率得到1-(2-trifluoromethyl-phenyl)-4-(2-pyridyl)-1,2,3-triazole
  参考文献：
  名称：

  Expanding the scope of ‘Click’ derived 1,2,3-triazole ligands: New palladium and platinum complexes

  摘要：

  Using the 'Click Protocol' the new ligands 1-(cyclohexyl)-4-(2-pyridyl)-1,2,3-triazole (1), 1-(2-trifluoromethyl phenyl)-4-(2-pyridyl)-1,2,3-triazole (2), 1-(4-hexyl phenyl)-4-(2-pyridyl)-1,2,3-triazole (3), 1-(2-mercaptomethyl phenyl)-4-(2-pyridyl)-1,2,3-triazole (4) and 1-(4-N, N-dimethylamino phenyl)-4-(2-pyridyl)-1,2,3-triazole (5) were prepared by reacting 2-ethynylpyridine with the corresponding azides. In the next step the ligands were reacted with suitable palladium and platinum precursors to yield the cis-dichloro-palladium complexes 1a-4a and platinum complexes 1b-4b. Investigation of the molecular structure of the free ligands 1 and 5 reveals the formation of infinite chains in the 3D structure which are governed by hydrogen bonds between the triazole units. Likewise the 3D structure of 1a shows infinite chains which are held together by multiple remarkably short C-H center dot center dot center dot Cl-Pd contacts. Electrochemical investigation of the free ligands by cyclic voltammetry showed irreversible reduction processes at highly negative potential. Upon metal complexation huge anodic shifts of the reduction potential were observed. To further characterize the electronic properties of all the compounds UV-Vis spectra were also analyzed. (C) 2011 Elsevier B.V. All rights reserved.

  DOI：

  10.1016/j.ica.2011.02.085

文献信息

• The redox series [Ru(bpy)₂(L)]ⁿ, n = +3, +2, +1, 0, with L = bipyridine, “click” derived pyridyl-triazole or bis-triazole: a combined structural, electrochemical, spectroelectrochemical and DFT investigation
  作者：Stephan Hohloch、David Schweinfurth、Michael G. Sommer、Fritz Weisser、Naina Deibel、Fabian Ehret、Biprajit Sarkar

  DOI：10.1039/c3dt52898g

  日期：——

  The compounds [Ru(bpy)2(L1)](ClO4)2 (1(ClO4)2), [Ru(bpy)2(L2)](ClO4)2 (2(ClO4)2), [Ru(bpy)2(L3)](ClO4)2 (3(ClO4)2), [Ru(bpy)2(L4)](ClO4)2 (4(ClO4)2), [Ru(bpy)2(L5)](ClO4)2 (5(ClO4)2), and [Ru(bpy)2(L6)](ClO4)26(ClO4)2 (bpy = 2,2′-bipyridine, L1 = 1-(4-isopropyl-phenyl)-4-(2-pyridyl)-1,2,3-triazole, L2 = 1-(4-butoxy-phenyl)-4-(2-pyridyl)-1,2,3-triazole, L3 = 1-(2-trifluoromethyl-phenyl)-4-(2-pyridyl)-1,2,3-triazole, L4 = 4,4′-bis-1-(2,6-diisopropyl-phenyl)}-1,2,3-triazole, L5 = 4,4′-bis-(1-phenyl)}-1,2,3-triazole, L6 = 4,4′-bis-1-(2-trifluoromethyl-phenyl)}-1,2,3-triazole) were synthesized from [Ru(bpy)2(EtOH)2](ClO4)2 and the corresponding “click”-derived pyridyl-triazole or bis-triazole ligands, and characterized by 1H-NMR spectroscopy, elemental analysis, mass spectrometry and X-ray crystallography. Structural analysis showed a distorted octahedral coordination environment about the Ru(II) centers, and shorter Ru–N(triazole) bond distances compared to Ru–N(pyridine) distances in complexes of mixed-donor ligands. All the complexes were subjected to cyclic voltammetric studies, and the results were compared to the well-known [Ru(bpy)3]2+ compound. The oxidation and reduction potentials were found to be largely uninfluenced by ligand changes, with all the investigated complexes showing their oxidation and reduction steps at rather similar potentials. A combined UV-vis-NIR and EPR spectroelectrochemical investigation, together with DFT calculations, was used to determine the site of electron transfer in these complexes. These results provided insights into their electronic structures in the various investigated redox states, showed subtle differences in the spectroscopic signatures of these complexes despite their similar electrochemical properties, and provided clues to the unperturbed redox potentials in these complexes with respect to ligand substitutions. The reduced forms of the complexes display structured absorption bands in the NIR region. Additionally, we also present new synthetic routes for the ligands presented here using Cu-abnormal carbene catalysts.

  化合物 [Ru(bpy)2(L1)](ClO4)2 (1(ClO4)2), [Ru(bpy)2(L2)](ClO4)2 (2(ClO4)2), [Ru(bpy)2(L3)](ClO4)2 (3(ClO4)2), [Ru(bpy)2(L4)](ClO4)2 (4(ClO4)2), [Ru(bpy)2(L5)](ClO4)2 (5(ClO4)2) 和 [Ru(bpy)2(L6)](ClO4)2 (6(ClO4)2)（bpy = 2,2′-联吡啶，L1 = 1-(4-异丙基-苯)-4-(2-吡啶基)-1,2,3-三唑，L2 = 1-(4-丁氧基-苯)-4-(2-吡啶基)-1,2,3-三唑，L3 = 1-(2-三氟甲基-苯)-4-(2-吡啶基)-1,2,3-三唑，L4 = 4,4′-双-1-(2,6-二异丙基-苯)}-1,2,3-三唑，L5 = 4,4′-双-(1-苯基)}-1,2,3-三唑，L6 = 4,4′-双-1-(2-三氟甲基-苯)}-1,2,3-三唑）是由 [Ru(bpy)2(EtOH)2](ClO4)2 与相应的“点击”衍生的吡啶-三唑或双三唑配体合成的，并通过 1H-NMR 光谱、元素分析、质谱和 X 射线晶体学进行表征。结构分析显示 Ru(II) 中心周围存在畸变的八面体配位环境，并且与混合供体配体的化合物相比，Ru–N(三唑) 键长较短而 Ru–N(吡啶) 键长较长。所有化合物都进行了循环伏安研究，并将结果与著名的 [Ru(bpy)3]2+ 化合物进行了比较。氧化和还原电位在很大程度上不受配体变化的影响，所有研究的化合物在相似的电位下表现出氧化和还原步骤。结合 UV-vis-NIR 和 EPR 光谱电化学研究，以及 DFT 计算，用于确定这些化合物中的电子转移位点。这些结果为它们在不同研究的氧化还原状态下的电子结构提供了见解，尽管这些化合物的电化学性质相似，但其光谱特征显示出微妙的差异，并为与配体替换有关的这些化合物中未受干扰的氧化还原电位提供了线索。化合物的还原形式在 NIR 区域表现出结构化的吸收带。此外，我们还展示了使用 Cu-不寻常的卡宾催化剂合成所呈现配体的新合成路线。
• Expanding the scope of ‘Click’ derived 1,2,3-triazole ligands: New palladium and platinum complexes
  作者：David Schweinfurth、Sabine Strobel、Biprajit Sarkar

  DOI：10.1016/j.ica.2011.02.085

  日期：2011.8

  Using the 'Click Protocol' the new ligands 1-(cyclohexyl)-4-(2-pyridyl)-1,2,3-triazole (1), 1-(2-trifluoromethyl phenyl)-4-(2-pyridyl)-1,2,3-triazole (2), 1-(4-hexyl phenyl)-4-(2-pyridyl)-1,2,3-triazole (3), 1-(2-mercaptomethyl phenyl)-4-(2-pyridyl)-1,2,3-triazole (4) and 1-(4-N, N-dimethylamino phenyl)-4-(2-pyridyl)-1,2,3-triazole (5) were prepared by reacting 2-ethynylpyridine with the corresponding azides. In the next step the ligands were reacted with suitable palladium and platinum precursors to yield the cis-dichloro-palladium complexes 1a-4a and platinum complexes 1b-4b. Investigation of the molecular structure of the free ligands 1 and 5 reveals the formation of infinite chains in the 3D structure which are governed by hydrogen bonds between the triazole units. Likewise the 3D structure of 1a shows infinite chains which are held together by multiple remarkably short C-H center dot center dot center dot Cl-Pd contacts. Electrochemical investigation of the free ligands by cyclic voltammetry showed irreversible reduction processes at highly negative potential. Upon metal complexation huge anodic shifts of the reduction potential were observed. To further characterize the electronic properties of all the compounds UV-Vis spectra were also analyzed. (C) 2011 Elsevier B.V. All rights reserved.