4-(phenylazo)-2,2′-bipyridine | 825621-05-4

• 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: 4-(phenylazo)-2,2′-bipyridine
• 英文别名: 4-PAbipy；4-[(E)-Phenyldiazenyl]-2,2'-bipyridine；phenyl-(2-pyridin-2-ylpyridin-4-yl)diazene
• CAS: 825621-05-4
• 化学式: C₁₆H₁₂N₄
• 分子量: 260.298
• InChiKey: NWXODWYMRIDIHV-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.3
• 重原子数：
  20
• 可旋转键数：
  3
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  50.5
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  iron(II) triflate 、 4-(phenylazo)-2,2′-bipyridine 、 potassium thioacyanate 以 乙腈 为溶剂， 以88%的产率得到Fe((4-phenylazo)-2,2'-bipyridine)2(NCS)2
  参考文献：
  名称：

  Thermal and Light‐Induced Spin Transitions of Fe ^II Complexes with 4‐ and 5‐(Phenylazo)‐2,2′‐bipyridine Ligands: Intra‐ vs. Intermolecular Effects

  摘要：

  AbstractFive new spin crossover complexes with 4‐ and 5‐(phenylazo)‐2,2‐bipyridine (4‐/5‐PAbipy) ligands were synthesized and investigated with respect to their spin crossover (SCO) behavior. The results are compared to the thermal and light‐induced spin transition properties of the parent SCO complexes [Fe(bpz)2(bipy)] (1) and [Fe(bipy)2(NCS)2] (2). [Fe(bpz)2(4‐PAbipy)] (1a) undergoes a stepwise spin transition whereas [Fe(bpz)2(5‐PAbipy)] (1b) exhibits a one‐step transition with a 6 K‐wide hysteresis. For [Fe(bpz)2(tBu5‐PAbipy)] (1c) the spin transition to the low‐spin state is incomplete. Qualitatively similar changes of the SCO behavior are observed for the complexes [Fe(4‐PAbipy)2(NCS)2] (2a) and [Fe(5‐PAbipy)2(NCS)2] (2b). In comparison to the parent system 2, a strengthening of intermolecular interactions leads to a stabilization of the low‐spin state. Evidence for the LIESST behavior could be obtained for all new compounds by means of magnetic susceptibility measurements as well as UV/Vis and resonance Raman spectroscopy.

  DOI：

  10.1002/ejic.201501252
• 作为产物：
  描述：

  4-氨基-2-溴吡啶 在 吡啶 、 四(三苯基膦)钯 、 三甲基苯基氢氧化铵 作用下， 以 间二甲苯 为溶剂， 反应 5.0h， 生成 4-(phenylazo)-2,2′-bipyridine
  参考文献：
  名称：

  Thermal and Light‐Induced Spin Transitions of Fe ^II Complexes with 4‐ and 5‐(Phenylazo)‐2,2′‐bipyridine Ligands: Intra‐ vs. Intermolecular Effects

  摘要：

  AbstractFive new spin crossover complexes with 4‐ and 5‐(phenylazo)‐2,2‐bipyridine (4‐/5‐PAbipy) ligands were synthesized and investigated with respect to their spin crossover (SCO) behavior. The results are compared to the thermal and light‐induced spin transition properties of the parent SCO complexes [Fe(bpz)2(bipy)] (1) and [Fe(bipy)2(NCS)2] (2). [Fe(bpz)2(4‐PAbipy)] (1a) undergoes a stepwise spin transition whereas [Fe(bpz)2(5‐PAbipy)] (1b) exhibits a one‐step transition with a 6 K‐wide hysteresis. For [Fe(bpz)2(tBu5‐PAbipy)] (1c) the spin transition to the low‐spin state is incomplete. Qualitatively similar changes of the SCO behavior are observed for the complexes [Fe(4‐PAbipy)2(NCS)2] (2a) and [Fe(5‐PAbipy)2(NCS)2] (2b). In comparison to the parent system 2, a strengthening of intermolecular interactions leads to a stabilization of the low‐spin state. Evidence for the LIESST behavior could be obtained for all new compounds by means of magnetic susceptibility measurements as well as UV/Vis and resonance Raman spectroscopy.

  DOI：

  10.1002/ejic.201501252

文献信息

• Thermal and Light‐Induced Spin Transitions of Fe ^II Complexes with 4‐ and 5‐(Phenylazo)‐2,2′‐bipyridine Ligands: Intra‐ vs. Intermolecular Effects
  作者：Sven Olaf Schmidt、Holger Naggert、Axel Buchholz、Hannah Brandenburg、Alexander Bannwarth、Winfried Plass、Felix Tuczek

  DOI：10.1002/ejic.201501252

  日期：2016.5

  AbstractFive new spin crossover complexes with 4‐ and 5‐(phenylazo)‐2,2‐bipyridine (4‐/5‐PAbipy) ligands were synthesized and investigated with respect to their spin crossover (SCO) behavior. The results are compared to the thermal and light‐induced spin transition properties of the parent SCO complexes [Fe(bpz)2(bipy)] (1) and [Fe(bipy)2(NCS)2] (2). [Fe(bpz)2(4‐PAbipy)] (1a) undergoes a stepwise spin transition whereas [Fe(bpz)2(5‐PAbipy)] (1b) exhibits a one‐step transition with a 6 K‐wide hysteresis. For [Fe(bpz)2(tBu5‐PAbipy)] (1c) the spin transition to the low‐spin state is incomplete. Qualitatively similar changes of the SCO behavior are observed for the complexes [Fe(4‐PAbipy)2(NCS)2] (2a) and [Fe(5‐PAbipy)2(NCS)2] (2b). In comparison to the parent system 2, a strengthening of intermolecular interactions leads to a stabilization of the low‐spin state. Evidence for the LIESST behavior could be obtained for all new compounds by means of magnetic susceptibility measurements as well as UV/Vis and resonance Raman spectroscopy.