2-(1-(4-hexylphenyl)-1H-1,2,3-triazol-4-yl)pyridine | 1290143-09-7

• 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: 2-(1-(4-hexylphenyl)-1H-1,2,3-triazol-4-yl)pyridine
• 英文别名: 1-(4-hexyl phenyl)-4-(2-pyridyl)-1,2,3-triazole；2-[1-(4-Hexylphenyl)triazol-4-yl]pyridine；2-[1-(4-hexylphenyl)triazol-4-yl]pyridine
• CAS: 1290143-09-7
• 化学式: C₁₉H₂₂N₄
• 分子量: 306.41
• InChiKey: ZLYWUKKYAREIQZ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.9
• 重原子数：
  23
• 可旋转键数：
  7
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.32
• 拓扑面积：
  43.6
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  cis-dichlorobis(dimethylsulfoxide)platinum(II) 、 2-(1-(4-hexylphenyl)-1H-1,2,3-triazol-4-yl)pyridine 以 硝基甲烷 为溶剂， 以59%的产率得到dichloro(1-(4-hexyl 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：

  1-正己基-4-碘代苯 在 potassium fluoride 、 copper(l) iodide 、 sodium azide 、 tetrakis(actonitrile)copper(I) hexafluorophosphate 、 铜 、 sodium ascorbate 、 N,N-二异丙基乙胺 、 N,N′-dimethyl-1,2-ethanediamine 作用下， 以 甲醇 、 乙醇 、 二氯甲烷 为溶剂， 反应 72.75h， 生成 2-(1-(4-hexylphenyl)-1H-1,2,3-triazol-4-yl)pyridine
  参考文献：
  名称：

  “Click-chemistry” approach in the design of 1,2,3-triazolyl-pyridine ligands and their Ru(ii)-complexes for dye-sensitized solar cells

  摘要：

  本文介绍了通过“点击化学”合成的新型1,2,3-三唑基吡啶配体及其对应的Ru(L)(2,2′-联吡啶-4,4′-二羧酸)(NCS)2配合物（L = 1,2,3-三唑基吡啶）。这些配合物已在光物理和电化学特性方面进行了表征，并且作为染料敏化太阳能电池（DSSC）的敏化剂。在基于乙腈的电解质的DSSC中，包含Ru(2-(1-(4-己基苯基)-1H-1,2,3-三唑-4-基)吡啶)(2,2′-联吡啶-4,4′-二羧酸)(NCS)2的TBA盐1在全日光强度下表现出7.8%的整体能量转化效率，而Ru(2-(4-(4-己基苯基)-1H-1,2,3-三唑-1-基)吡啶)(2,2′-联吡啶-4,4′-二羧酸)(NCS)2的TBA盐2的效率为4.7%。瞬态光电压和光电流衰减测量表明，由于与染料2敏化器相比，染料1的电子运输速度更快且重组率更低，从而实现了更优的性能。此外，还使用2微米厚的TiO2膜和作为孔传输材料的螺旋-OMeTAD制备了固态器件。固态染料敏化太阳能电池的能量转化效率分别为1.92%和0.38%，对应于敏化剂1和2。

  DOI：

  10.1039/c0jm03750h

文献信息

• Triazole compounds and methods of making and using the same
  申请人：Bhattacharjee Ashoke

  公开号：US20100016955A1

  公开（公告）日：2010-01-21

  The present invention provides triazole macrocyclic compounds useful as therapeutic agents. More particularly, these compounds are useful as anti-infective, anti-proliferative, anti-inflammatory, and prokinetic agents.

  本发明提供了三唑大环化合物，作为治疗剂使用。更具体地说，这些化合物可用作抗感染、抗增殖、抗炎和促动力剂。
• 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.
• “Click-chemistry” approach in the design of 1,2,3-triazolyl-pyridine ligands and their Ru(ii)-complexes for dye-sensitized solar cells
  作者：Ilona Stengel、Amaresh Mishra、Nuttapol Pootrakulchote、Soo-Jin Moon、Shaik M. Zakeeruddin、Michael Grätzel、Peter Bäuerle

  DOI：10.1039/c0jm03750h

  日期：——

  The synthesis of new 1,2,3-triazolyl-pyridine ligands via “click-chemistry” and their corresponding Ru(L)(2,2′-bipyridyl-4,4′-dicarboxylic acid)(NCS)2 complexes (L = 1,2,3-triazolyl-pyridine) are presented. The complexes have been photophysically and electrochemically characterized and have been used as sensitizers in dye-sensitized solar cells (DSSC). In DSSCs with an acetonitrile-based electrolyte the cells comprising of Ru(2-(1-(4-hexylphenyl)-1H-1,2,3-triazol-4-yl)pyridine)(2,2′-bipyridyl-4,4′-dicarboxylic acid)(NCS)2 TBA salt 1 showed an overall power conversion efficiency of 7.8% under full sunlight intensity, and Ru(2-(4-(4-hexylphenyl)-1H-1,2,3-triazol-1-yl)pyridine)(2,2′-bipyridyl-4,4′-dicarboxylic acid)(NCS)2 TBA salt 2 an efficiency of 4.7%. Transient photovoltage and photocurrent decay measurements showed an enhanced performance for dye 1 due to faster electron transport into the TiO2 film and lower recombination rate in comparison to dye 2 sensitized devices. Additionally, solid-state devices were prepared with 2 μm thick TiO2 films using spiro-OMeTAD as a hole-transport material. The solid-state dye-sensitized solar cells showed power conversion efficiencies of 1.92% and 0.38% for sensitizer 1 and 2, respectively.

  本文介绍了通过“点击化学”合成的新型1,2,3-三唑基吡啶配体及其对应的Ru(L)(2,2′-联吡啶-4,4′-二羧酸)(NCS)2配合物（L = 1,2,3-三唑基吡啶）。这些配合物已在光物理和电化学特性方面进行了表征，并且作为染料敏化太阳能电池（DSSC）的敏化剂。在基于乙腈的电解质的DSSC中，包含Ru(2-(1-(4-己基苯基)-1H-1,2,3-三唑-4-基)吡啶)(2,2′-联吡啶-4,4′-二羧酸)(NCS)2的TBA盐1在全日光强度下表现出7.8%的整体能量转化效率，而Ru(2-(4-(4-己基苯基)-1H-1,2,3-三唑-1-基)吡啶)(2,2′-联吡啶-4,4′-二羧酸)(NCS)2的TBA盐2的效率为4.7%。瞬态光电压和光电流衰减测量表明，由于与染料2敏化器相比，染料1的电子运输速度更快且重组率更低，从而实现了更优的性能。此外，还使用2微米厚的TiO2膜和作为孔传输材料的螺旋-OMeTAD制备了固态器件。固态染料敏化太阳能电池的能量转化效率分别为1.92%和0.38%，对应于敏化剂1和2。