1-azido-4-hexylbenzene | 1220349-31-4

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: 1-azido-4-hexylbenzene
• 英文别名: 1-azido-4-n-hexylbenzene
• CAS: 1220349-31-4
• 化学式: C₁₂H₁₇N₃
• 分子量: 203.287
• InChiKey: KLBCPFLFUAUSHH-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.5
• 重原子数：
  15
• 可旋转键数：
  6
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  14.4
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  2-乙炔基吡啶 、 1-azido-4-hexylbenzene 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87%的产率得到2-(1-(4-hexylphenyl)-1H-1,2,3-triazol-4-yl)pyridine
  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 copper(l) iodide 、 sodium azide 、 sodium ascorbate 、 N,N′-dimethyl-1,2-ethanediamine 作用下， 以 乙醇 为溶剂， 反应 0.75h， 以92%的产率得到1-azido-4-hexylbenzene
  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

• Water-soluble benzo- and naphtho-thiadiazole-based bistriazoles and their metal-binding properties
  作者：Scott M. Brombosz、Anthony Lucas Appleton、Andrew J. Zappas II、Uwe H. F. Bunz

  DOI：10.1039/b920484a

  日期：——

  A click reaction furnishes water-soluble acenothiadiazole-based bistriazoles with red-shifted absorption and emission characteristics.

  通过点击反应生成了具有红移吸收和发射特性的水溶性苊噻二唑双三唑。
• A Simple and Effective Synthesis of Aryl Azides via Arenediazonium Tosylates
  作者：Victor Filimonov、Joseph Parello、Ksenia Kutonova、Marina Trusova、Pavel Postnikov

  DOI：10.1055/s-0033-1339648

  日期：——

  Aromatic azides are formed in high yield from arenediazonium tosylates and sodium azide in water at room temperature or from aromatic amines via diazotization in the presence of p-TsOH. Besides being experimentally simple, these methods do not require any metal catalysis and provide clean products without purification.
• New type of ruthenium sensitizers with a triazole moiety as a bridging group
  作者：Sanghyun Paek、Chul Baik、Moon-sung Kang、Hongsuk Kang、Jaejung Ko

  DOI：10.1016/j.jorganchem.2009.12.021

  日期：2010.3

  A new type of ruthenium sensitizers JK-91 and JK-92 with a triazole moiety as a bridging group were designed and synthesized in an attempt to increase the pi-conjugated system. Two compounds work as highly efficient sensitizers for the dye-sensitized nanocrystalline TiO2 solar cell. Under standard AM 1.5 sunlight, the sensitizer JK-91 yielded a short-circuit photocurrent density of 12.55 mA/cm(2), an open-circuit voltage of 0.73 V, and a fill factor of 0.73, corresponding to an overall conversion efficiency of 6.75%. (C) 2010 Elsevier B.V. All rights reserved.
• US4280819A
  申请人：——

  公开号：US4280819A

  公开（公告）日：1981-07-28
• 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.