2-hydroxynaphthylazopentafluorobenzene

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 英文名称: 2-hydroxynaphthylazopentafluorobenzene
• 化学式: C₁₆H₇F₅N₂O
• 分子量: 338.236
• InChiKey: SOVUVMHACVPVEY-GHVJWSGMSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.66
• 重原子数：
  24.0
• 可旋转键数：
  2.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  44.95
• 氢给体数：
  1.0
• 氢受体数：
  3.0

反应信息

• 作为反应物：
  描述：

  2-hydroxynaphthylazopentafluorobenzene 、 4-二甲氨基吡啶 、 三氟甲磺酸三甲基硅酯 以 氯苯 为溶剂， 反应 24.0h， 以97%的产率得到2-hydroxynaphthylazopentakis[4-(dimethylamino)-1-pyridinio]benzene pentakis(triflate)
  参考文献：
  名称：

  Electrostatics and Color:  Massive Electrostatic Perturbation of Chromophores by Ion Cluster Ligands

  摘要：

  The SASAPOS protocol, a general reaction sequence allowing complete exchange of various neutral ligands X in organic, elementorganic, and inorganic systems by cationic ligands L+, has been applied to a variety of pentafluorophenyl-substituted dyes of the general formula C6F5-XY-D (X, Y = N, CH; D = donor substituted arene), yielding the corresponding polycationically substituted dyes. The perturbation of the chromophores by the massive electrostatic effects introduced via the SASAPOS method led to bathochromic shifts of the absorption maxima of up 140 nm, 7600 cm(-1), respectively. A strong dependency of the specific shifts on the nature of the connecting pi linker -XY- (N vs CH) has been detected by UV-vis absorption spectroscopy. Additionally, the effects of resubstitution of cationic ligands L+ by OH and O- have been studied.

  DOI：

  10.1021/ja064907u
• 作为产物：
  描述：

  2,3,4,5,6-五氟苯胺 、 2-萘酚 在 nitrosonium tetrafluoroborate 作用下， 以 乙腈 为溶剂， 反应 1.0h， 以47%的产率得到2-hydroxynaphthylazopentafluorobenzene
  参考文献：
  名称：

  Electrostatics and Color:  Massive Electrostatic Perturbation of Chromophores by Ion Cluster Ligands

  摘要：

  The SASAPOS protocol, a general reaction sequence allowing complete exchange of various neutral ligands X in organic, elementorganic, and inorganic systems by cationic ligands L+, has been applied to a variety of pentafluorophenyl-substituted dyes of the general formula C6F5-XY-D (X, Y = N, CH; D = donor substituted arene), yielding the corresponding polycationically substituted dyes. The perturbation of the chromophores by the massive electrostatic effects introduced via the SASAPOS method led to bathochromic shifts of the absorption maxima of up 140 nm, 7600 cm(-1), respectively. A strong dependency of the specific shifts on the nature of the connecting pi linker -XY- (N vs CH) has been detected by UV-vis absorption spectroscopy. Additionally, the effects of resubstitution of cationic ligands L+ by OH and O- have been studied.

  DOI：

  10.1021/ja064907u

文献信息

• Electrostatics and Color:  Massive Electrostatic Perturbation of Chromophores by Ion Cluster Ligands
  作者：Robert Weiss、Frank G. Pühlhofer

  DOI：10.1021/ja064907u

  日期：2007.1.1

  The SASAPOS protocol, a general reaction sequence allowing complete exchange of various neutral ligands X in organic, elementorganic, and inorganic systems by cationic ligands L+, has been applied to a variety of pentafluorophenyl-substituted dyes of the general formula C6F5-XY-D (X, Y = N, CH; D = donor substituted arene), yielding the corresponding polycationically substituted dyes. The perturbation of the chromophores by the massive electrostatic effects introduced via the SASAPOS method led to bathochromic shifts of the absorption maxima of up 140 nm, 7600 cm(-1), respectively. A strong dependency of the specific shifts on the nature of the connecting pi linker -XY- (N vs CH) has been detected by UV-vis absorption spectroscopy. Additionally, the effects of resubstitution of cationic ligands L+ by OH and O- have been studied.