4-bromo-N-[4-bromo-3,5-bis(4-bromophenyl)-1H-pyrrol-2-yl]-3,5-bis(4-bromophenyl)pyrrol-2-imine | 1385015-26-8

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡咯
• 英文名称: 4-bromo-N-[4-bromo-3,5-bis(4-bromophenyl)-1H-pyrrol-2-yl]-3,5-bis(4-bromophenyl)pyrrol-2-imine
• CAS: 1385015-26-8
• 化学式: C₃₂H₁₇Br₆N₃
• 分子量: 922.931
• InChiKey: OAEJTOCIOKHWEX-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  11.8
• 重原子数：
  41
• 可旋转键数：
  5
• 环数：
  6.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  40.5
• 氢给体数：
  1
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  (二甲基苯基膦)氯化金 、 4-bromo-N-[4-bromo-3,5-bis(4-bromophenyl)-1H-pyrrol-2-yl]-3,5-bis(4-bromophenyl)pyrrol-2-imine 在 NaO-t-Bu 作用下， 以 四氢呋喃 为溶剂， 以47%的产率得到(3-bromo-5-((4-bromo-3,5-bis(4-bromophenyl)-2H-pyrrol-2-ylidene)amino)-2,4-bis(4-bromophenyl)-1H-pyrrol-1-yl)(dimethyl(phenyl)-l5-phosphaneyl)gold
  参考文献：
  名称：

  Gold(I) Complexes of Brominated Azadipyrromethene Ligands

  摘要：

  Azadipyrromethenes are luminescent, red-light absorbing dyes that readily bind BF2+ and metals. Their framework allows for structural modification at the phenyl arms and the two pyrrolic carbon positions. Here we report five new gold(I) complexes with azadipyrromethene ligands brominated at the pyrrolic carbons and/or the four phenyl substituents. New complexes are characterized by multinuclear NMR spectroscopy, X-ray crystallography, optical absorption and emission spectroscopy, and elemental analysis. The new compounds have a perturbed two-coordinate geometry in the crystalline state, with gold(I) binding one dimethylphenylphosphine ancillary ligand and one pyrrole nitrogen of the azadipyrromethene. The second azadipyrromethene pyrrole nitrogen perturbs the linear coordination. These complexes maintain the absorption features of the free ligands. Excitation in the near-ultraviolet generates emission in the near-UV and visible regions. Density-functional theory calculations indicate that the photoproperties of the new compounds arise almost entirely from the conjugated ligands and not from the (phosphine)gold(I) fragments.

  DOI：

  10.1021/ic300709n
• 作为产物：
  描述：

  1,3-bis(4-bromophenyl)-4-nitrobutan-1-one 在 N-溴代丁二酰亚胺(NBS) 、 ammonium acetate 作用下， 以 二氯甲烷 、 正丁醇 为溶剂， 反应 24.0h， 生成 4-bromo-N-[4-bromo-3,5-bis(4-bromophenyl)-1H-pyrrol-2-yl]-3,5-bis(4-bromophenyl)pyrrol-2-imine
  参考文献：
  名称：

  Gold(I) Complexes of Brominated Azadipyrromethene Ligands

  摘要：

  Azadipyrromethenes are luminescent, red-light absorbing dyes that readily bind BF2+ and metals. Their framework allows for structural modification at the phenyl arms and the two pyrrolic carbon positions. Here we report five new gold(I) complexes with azadipyrromethene ligands brominated at the pyrrolic carbons and/or the four phenyl substituents. New complexes are characterized by multinuclear NMR spectroscopy, X-ray crystallography, optical absorption and emission spectroscopy, and elemental analysis. The new compounds have a perturbed two-coordinate geometry in the crystalline state, with gold(I) binding one dimethylphenylphosphine ancillary ligand and one pyrrole nitrogen of the azadipyrromethene. The second azadipyrromethene pyrrole nitrogen perturbs the linear coordination. These complexes maintain the absorption features of the free ligands. Excitation in the near-ultraviolet generates emission in the near-UV and visible regions. Density-functional theory calculations indicate that the photoproperties of the new compounds arise almost entirely from the conjugated ligands and not from the (phosphine)gold(I) fragments.

  DOI：

  10.1021/ic300709n

文献信息

• Gold(I) Complexes of Brominated Azadipyrromethene Ligands
  作者：Lei Gao、Nihal Deligonul、Thomas G. Gray

  DOI：10.1021/ic300709n

  日期：2012.7.16

  Azadipyrromethenes are luminescent, red-light absorbing dyes that readily bind BF2+ and metals. Their framework allows for structural modification at the phenyl arms and the two pyrrolic carbon positions. Here we report five new gold(I) complexes with azadipyrromethene ligands brominated at the pyrrolic carbons and/or the four phenyl substituents. New complexes are characterized by multinuclear NMR spectroscopy, X-ray crystallography, optical absorption and emission spectroscopy, and elemental analysis. The new compounds have a perturbed two-coordinate geometry in the crystalline state, with gold(I) binding one dimethylphenylphosphine ancillary ligand and one pyrrole nitrogen of the azadipyrromethene. The second azadipyrromethene pyrrole nitrogen perturbs the linear coordination. These complexes maintain the absorption features of the free ligands. Excitation in the near-ultraviolet generates emission in the near-UV and visible regions. Density-functional theory calculations indicate that the photoproperties of the new compounds arise almost entirely from the conjugated ligands and not from the (phosphine)gold(I) fragments.