4-bromo-N-[4-bromo-5-(4-methoxyphenyl)-3-phenyl-1H-pyrrol-2-yl]-5-(4-methoxyphenyl)-3-phenylpyrrol-2-imine | 490035-87-5

• 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-5-(4-methoxyphenyl)-3-phenyl-1H-pyrrol-2-yl]-5-(4-methoxyphenyl)-3-phenylpyrrol-2-imine
• CAS: 490035-87-5
• 化学式: C₃₄H₂₅Br₂N₃O₂
• 分子量: 667.399
• InChiKey: FVEDVKYTIBBKDL-UHFFFAOYSA-N

物化性质

• 沸点：
  776.0±70.0 °C(Predicted)
• 密度：
  1.45±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  8.9
• 重原子数：
  41
• 可旋转键数：
  7
• 环数：
  6.0
• sp3杂化的碳原子比例：
  0.06
• 拓扑面积：
  59
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  4-bromo-N-[4-bromo-5-(4-methoxyphenyl)-3-phenyl-1H-pyrrol-2-yl]-5-(4-methoxyphenyl)-3-phenylpyrrol-2-imine 、 三氟化硼 以 乙醚 、 二氯甲烷 为溶剂， 生成 氟硼溴代氮杂二吡咯甲烷
  参考文献：
  名称：

  Synthesis of BF₂chelates of tetraarylazadipyrromethenes and evidence for their photodynamic therapeutic behaviour

  摘要：

  描述了一类新的治疗窗口光敏剂的合成、光谱特性和体外细胞摄取特性，即3,5-二芳基-1H-吡咯-2-基-3,5-二芳基吡咯-2-亚胺的BF2配合物（四芳基氮双吡咯美烯），旨在开发一种新型的光动力治疗药物。

  DOI：

  10.1039/b204317c
• 作为产物：
  描述：

  (5-(4-methoxyphenyl)-3-phenyl-1H-pyrrol-2-yl)(5-(4-methoxyphenyl)-3-phenylpyrrol-2-ylidene)amine 在 N-溴代丁二酰亚胺(NBS) 作用下， 以 二氯甲烷 为溶剂， 以77%的产率得到4-bromo-N-[4-bromo-5-(4-methoxyphenyl)-3-phenyl-1H-pyrrol-2-yl]-5-(4-methoxyphenyl)-3-phenylpyrrol-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

• Azadipyrromethene Complexes of d⁸ Metal Centers: Rhodium(I), Iridium(I), Palladium(II), and Platinum(II)
  作者：Nihal Deligonul、Thomas G. Gray

  DOI：10.1021/ic4017239

  日期：2013.11.18

  comparisons are made to related dipyrromethene and tetra-azaporphyrin complexes. The electron-donating capacity of azadipyrromethene ligands is evaluated from C≡O stretching frequencies of three rhodium(I) carbonyl complexes and from density-functional theory calculations. Frontier orbitals are confined to the azadipyrromethene ligand. HOMO–LUMO energy gaps are almost unperturbed from those of the

  叠氮吡咯烷酮是蓝色颜料，可螯合主基团和d-嵌段路易斯酸。这里报道的是d 8个金属中心的叠氮二吡咯亚甲基络合物。新化合物是在与氯化有机金属前体的盐复分解反应中制备的。报告了十六个新的复合体。主要的吸收特征是在600 nm附近有一个强烈的峰并在紫外线下发生跃迁。所有这些都是氮杂二吡咯甲烷发色团的特征。所有化合物均为深色固体，会产生蓝色或蓝紫色溶液。在晶体学上表征了十个配合物。结构均匀地显示骨干应变，具有内消旋-氮原子，从纯SP瞳孔会放大2-杂交。对相关的二吡咯亚甲基和四氮杂卟啉配合物进行结构比较。氮杂二吡咯亚甲基配体的给电子能力是根据三种铑（I）羰基配合物的C≡O拉伸频率和密度泛函理论计算得出的。边界轨道限于氮杂二吡咯甲烷配体。HOMO-LUMO的能隙几乎不受游离的阴离子氮杂二吡咯亚甲基的影响。
• 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.
• Synthesis of BF₂chelates of tetraarylazadipyrromethenes and evidence for their photodynamic therapeutic behaviour
  作者：John Killoran、Lorcan Allen、John F. Gallagher、William M. Gallagher、Donal F. O′Shea

  DOI：10.1039/b204317c

  日期：——

  The synthesis, spectroscopic characteristics and in vitro cellular uptake properties of a new class of therapeutic window photosensitiser, namely the BF2 chelates of 3,5-diaryl-1H-pyrrol-2-yl-3,5-diarylpyrrol-2-ylidene amines (tetraarylazadipyrromethenes), are described with the aim of developing a novel class of photodynamic therapeutic agents.

  描述了一类新的治疗窗口光敏剂的合成、光谱特性和体外细胞摄取特性，即3,5-二芳基-1H-吡咯-2-基-3,5-二芳基吡咯-2-亚胺的BF2配合物（四芳基氮双吡咯美烯），旨在开发一种新型的光动力治疗药物。