3,8-dibromo-4,7-phenanthroline | 199867-78-2

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 喹啉及其衍生物
• 英文名称: 3,8-dibromo-4,7-phenanthroline
• 英文别名: 3,8-Dibromo-4,7-phenanthroline
• CAS: 199867-78-2
• 化学式: C₁₂H₆Br₂N₂
• 分子量: 338.001
• InChiKey: VJUIQVPPJHRZMD-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.5
• 重原子数：
  16
• 可旋转键数：
  0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  25.8
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  3,8-dibromo-4,7-phenanthroline 在 copper(l) iodide 、 四(三苯基膦)钯 、 三乙胺 、 sodium hydroxide 作用下， 以 甲醇 为溶剂， 反应 1.5h， 生成 3,8-Diethynyl-4,7-phenanthroline
  参考文献：
  名称：

  BN-二苯并[a，o] ene烯：未知多环芳烃的类似物

  摘要：

  反思合成的尖峰：虽然母体碳氢化合物不易获得，但可以用两步法从已知的原料制备BN取代的二苯并[ a，o ] pic烯的几个实例。这些非线性的庚并苯类似物是水稳定的材料。他们的制备利用了潜在的通用方法来制备难以合成的多环芳烃骨架的扩展BN类似物。

  DOI：

  10.1002/anie.201302911
• 作为产物：
  描述：

  4,7-dimethyl-4,7-phenanthroline-3,8(4H,7H)-dione 在 三溴化磷 、 三溴氧磷 作用下， 反应 36.0h， 以94%的产率得到3,8-dibromo-4,7-phenanthroline
  参考文献：
  名称：

  Adaptive Self-Assembly: Environment-Induced Formation and Reversible Switching of Polynuclear Metallocyclophanes

  摘要：

  Ligand 3 has been shown to self-assemble under coordination of copper(II) cations in a 1:1 ratio in acetonitrile to give equilibrating mixtures of a [2 x 2] grid-type tetranuclear structure 1 and a hexanuclear achitecture of hexagonal shape 2. The latter was confirmed by determination of the crystal structure which further indicated that 2 contained acetonitrile molecules and hydroxo groups bound to the copper(II) centers, which are therefore five-coordinate. The structures assigned to 1 and 2 were further supported by the spectral (mass, UV/Vis) data. The self-assembly process is strongly dependent on the conditions of the medium. An increase in concentration in acetronitrile increases the relative amount of hexamer 2, which appears to be the favored entity at the highest concentrations that can be reached before precipitation occurs. On the other hand, in nitromethane only the tetranuclear complex 1 was detected by mass spectrometry. Replacement of nitromethane by acetonitrile and vice versa indicated the reversible switching between a solution containing either 1 alone or an equilibrium mixture of 1 and 2, respectively. In conclusion, the system described presents several remarkable features: 1) self-assembly with substrate binding, 2) dynamic combinatorial structure generation, and 3) environment-induced structural switching amounting in effect to a process of adaptive self-assembly.

  DOI：

  10.1002/1521-3765(20001117)6:22<4140::aid-chem4140>3.0.co;2-5

文献信息

• Copper(I)-Assembled [3]Rotaxane Whose Two Rings Act as Flapping Wings
  作者：Antoine Joosten、Yann Trolez、Jean-Paul Collin、Valérie Heitz、Jean-Pierre Sauvage

  DOI：10.1021/ja210113y

  日期：2012.1.25

  A new copper-complexed [3]rotaxane consisting of two coordinating 30-membered rings threaded by a two-binding-site axis has been prepared in good yield from relatively simple organic fragments. The main specificity of the system originates from the stoppering reaction, based on "click" chemistry, and thus from the presence of two triazole groups at positions next to the bidentate chelates of the axis

  已从相对简单的有机碎片中以良好的收率制备了一种新的铜络合 [3] 轮烷，其由两个由两个结合位点轴连接的 30 元配位环组成。该系统的主要特异性源于基于“点击”化学的终止反应，因此源于在轴中心部分的双齿螯合物旁边的位置处存在两个三唑基团。属于轴的配位原子的几何形状使得当金属中心为 5 配位时，三唑基团可以是配位碎片的一部分，或者当后者为 4 配位时根本不参与与金属的配位. 更具体地说，当两个络合金属中心是一价铜（I）中心时，三唑不包括在金属配位球中，而当金属中心是 Cu(II) 或 Zn(2+) 时，三唑基团与金属结合。这很容易通过以下事实来解释：Cu(I) 优选为 4-配位，而 Cu(II) 和 Zn(2+) 为 5-配位。两种情况（4-或5-坐标）之间的相互转化可以通过金属交换（Cu（I）/Zn（2+））或氧化还原过程（Cu（II）/Cu（I））定量诱导。它会导致重要的几何变化，特别是导
• Copper(i)-induced threading of two bis-macrocycles on two rods: a cyclic [4]rotaxane
  作者：Jean-Paul Collin、Julien Frey、Val?rie Heitz、Efstathia Sakellariou、Jean-Pierre Sauvage、Christian Tock

  DOI：10.1039/b601703g

  日期：——

  A cyclic pseudo-rotaxane tetramer has been synthesised quantitatively at room temperature by threading two two-coordination site rods through two bis-macrocycles in the presence of copper(I) as a template.

  以铜（I）为模板，通过将两个双配位点棒穿过两个双大环，在室温下定量合成了环状假轮烷四聚体。
• 一种以4，7-二氮杂菲为受体的化合物及其应 用
  申请人：西安瑞联新材料股份有限公司

  公开号：CN109608453B

  公开（公告）日：2021-09-21

  本发明公开了一种以4，7‑二氮杂菲为受体的化合物及其应用，属于有机电致发光材料技术领域。该类化合物的结构通式如下式(I‑1)或(I‑2)所示：其中，L为亚苯基，n为0‑3之间的任意整数，D1、D2、D3、D4相同或者不同，D1、D2、D3、D4各自独立为给电子基团。本发明提供的化合物作为OLED的掺杂材料和/或主体材料可以实现有机电致发光器件高亮度、低电压、高效率、使用寿命长；这些化合物制成的材料具有较高的热稳定性，可显著提高发光器件的发光稳定性，广泛应用于OLED发光器件及显示装置。
• Cyclic [2]Pseudorotaxane Tetramers Consisting of Two Rigid Rods Threaded through Two Bis-Macrocycles: Copper(I)-Templated Synthesis and X-ray Structure Studies
  作者：Julien Frey、Christian Tock、Jean-Paul Collin、Valérie Heitz、Jean-Pierre Sauvage、Kari Rissanen

  DOI：10.1021/ja801924y

  日期：2008.8.1

  Variously substituted coordinating rigid rods have been synthesized which incorporate a central 4,7-phenanthroline nucleus attached to two 2-pyridyl groups via its 3 and 8 positions, so as to yield bis-bidentate chelates, the two-coordinating axes of the chelates being parallel to one another. Regardless of the nature of the substituents borne by the rods, the copper(I)-induced threading reaction of two such rods through the rings of two bis-macrocycles affords in a quantitative yield the 4-copper(I) threaded assembly. The [2]pseudorotaxane tetramers thus obtained have been fully characterized in solution and, for one of them, an X-ray structure could be obtained, confirming the threaded nature of the complex and providing important structural information.
• Adaptive Self-Assembly: Environment-Induced Formation and Reversible Switching of Polynuclear Metallocyclophanes
  作者：Paul N. W. Baxter、Richard G. Khoury、Jean-Marie Lehn、Gerhard Baum、Dieter Fenske

  DOI：10.1002/1521-3765(20001117)6:22<4140::aid-chem4140>3.0.co;2-5

  日期：2000.11.17

  Ligand 3 has been shown to self-assemble under coordination of copper(II) cations in a 1:1 ratio in acetonitrile to give equilibrating mixtures of a [2 x 2] grid-type tetranuclear structure 1 and a hexanuclear achitecture of hexagonal shape 2. The latter was confirmed by determination of the crystal structure which further indicated that 2 contained acetonitrile molecules and hydroxo groups bound to the copper(II) centers, which are therefore five-coordinate. The structures assigned to 1 and 2 were further supported by the spectral (mass, UV/Vis) data. The self-assembly process is strongly dependent on the conditions of the medium. An increase in concentration in acetronitrile increases the relative amount of hexamer 2, which appears to be the favored entity at the highest concentrations that can be reached before precipitation occurs. On the other hand, in nitromethane only the tetranuclear complex 1 was detected by mass spectrometry. Replacement of nitromethane by acetonitrile and vice versa indicated the reversible switching between a solution containing either 1 alone or an equilibrium mixture of 1 and 2, respectively. In conclusion, the system described presents several remarkable features: 1) self-assembly with substrate binding, 2) dynamic combinatorial structure generation, and 3) environment-induced structural switching amounting in effect to a process of adaptive self-assembly.