1H,1'H,1''H,1'''H-2,2':5',5'':2'',2'''-quaterbenzimidazole | 862279-50-3

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 苯并咪唑类
• 英文名称: 1H,1'H,1''H,1'''H-2,2':5',5'':2'',2'''-quaterbenzimidazole
• 英文别名: 2-(1H-benzimidazol-2-yl)-6-[2-(1H-benzimidazol-2-yl)-3H-benzimidazol-5-yl]-1H-benzimidazole
• CAS: 862279-50-3
• 化学式: C₂₈H₁₈N₈
• 分子量: 466.505
• InChiKey: QBMSQACXLOHXIB-UHFFFAOYSA-N

物化性质

• 沸点：
  925.2±75.0 °C(Predicted)
• 密度：
  1.514±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  5.2
• 重原子数：
  36
• 可旋转键数：
  3
• 环数：
  8.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  115
• 氢给体数：
  4
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  1H,1'H,1''H,1'''H-2,2':5',5'':2'',2'''-quaterbenzimidazole 、 ammonium hexafluorophosphate 、 Λ-cis-[bis(2,2'-bipyridyl)bis(pyridine)ruthenium(II)][(+)-O,O'-dibenzoyl-L-tatrtrate] 、 水 以 乙二醇 为溶剂， 以73%的产率得到Λ4-[(Ru(bpy)2)4(bis(2,2'-bibenzimidazol)(-4H))](PF6)4*4water
  参考文献：
  名称：

  Syntheses of Homochiral Multinuclear Ru Complexes Based on Oligomeric Bibenzimidazoles

  摘要：

  The homochiral multinuclear Ru complexes of the oligomeric bibenzimidazoles were synthesized using Lambda-[Ru(bpy)(2)(PY)(2)][(-)-O,O-dibenzoyl-L-tartrate]-12H(2)O as an enantiornerically pure building block. The complexations proceed with the retention of configuration to provide well-defined mononuclear, dinuclear, tetranuclear, and octanuclear Ru complexes successfully. The optical purity and the absolute configurations of the complexes were determined by NMR and circular dichroism spectrometry. The rare X-ray structure of a tetranuclear complex Lambda(4)[(Ru(bpy)(2))(4)(bis(BiBzlm))](PF6)(4) was resolved, The crystallographic analysis reveals that all the four Ru centers have A octahedral configurations, with a Ru-Ru separation of 5.509 angstrom across the bridging bibenzimidazole ligand, which maintains near coplanarity. The UV-vis spectroscopic and electrochemical properties of the homochiral multinuclear assemblies were studied, indicating weak electronic communications between the metal centers.

  DOI：

  10.1021/ic062148a
• 作为产物：
  描述：

  3,3'-二氨基联苯胺 、 3-氧代-3,4-二氢-2-喹喔啉甲腈 在 溶剂黄146 作用下， 反应 7.0h， 以98%的产率得到1H,1'H,1''H,1'''H-2,2':5',5'':2'',2'''-quaterbenzimidazole
  参考文献：
  名称：

  暴露于1,2-二氨基苯时，3-氰基喹喔啉-2（1H）-的酸催化重排：2,2'-联苯并咪唑的合成。

  摘要：

  已开发出一种新颖且有效的方案，该方案可通过3-cyanoquinoxalin-2（1H）-ones与1,2-二氨基苯的反应合成各种取代的2,2'-联苯并咪唑，该方案通过依次进行亲核加成和亲电取代来进行随后进行了Mamedov重排。简明的一锅合成5,5'-bi（2,2'-联苯并咪唑）和2,2'-联苯并咪唑的氮杂类似物说明了该策略的合成效用。

  DOI：

  10.1021/acs.joc.9b01840

文献信息

• Efficient Synthesis and Characterization of Novel Bibenzimidazole Oligomers and Polymers as Potential Conjugated Chelating Ligands
  作者：Jun Yin、Ronald L. Elsenbaumer

  DOI：10.1021/jo051515h

  日期：2005.11.1

  synthesis of novel bibenzimidazole oligomers and polymers is reported here using methyl 2,2,2-trichloroacetimidate as a key starting material. The dimer, trimer, tetramer, and polymers of bibenzimidazole were synthesized as a new series of potential conjugated chelating ligands for metallopolymer studies. The polymers show a maximum absorption at around 400 nm. The optical band gap of the polymer was estimated

  本文报道了一种简单，温和的缩合路线，用于合成新型联苯并咪唑低聚物和聚合物，使用2,2,2-三氯乙亚氨酸甲酯作为关键原料。合成联苯并咪唑的二聚体，三聚体，四聚体和聚合物，作为用于金属聚合物研究的一系列潜在的共轭螯合配体。该聚合物在约400nm处显示出最大吸收。聚合物的光学带隙估计为2.68eV。
• Acid-Catalyzed Rearrangement of 3-Cyanoquinoxalin-2(1<i>H</i>)-ones When Exposed to 1,2-Diaminobenzenes: Synthesis of 2,2′-Bibenzimidazoles
  作者：Vakhid A. Mamedov、Nataliya A. Zhukova、Milyausha S. Kadyrova、Victor V. Syakaev、Tat’yana N. Beschastnova、Daina N. Buzyurova、Il’dar Kh. Rizvanov、Shamil K. Latypov、Oleg G. Sinyashin

  DOI：10.1021/acs.joc.9b01840

  日期：2019.11.1

  A novel and efficient protocol for the synthesis of diversely substituted 2,2'-bibenzimidazoles from the reaction of 3-cyanoquinoxalin-2(1H)-ones with 1,2-diaminobenzenes has been developed, which proceeds through sequential nucleophilic addition and electrophilic substitution followed by a Mamedov rearrangement. The synthetic utility of this strategy was illustrated by the concise, one-pot synthesis

  已开发出一种新颖且有效的方案，该方案可通过3-cyanoquinoxalin-2（1H）-ones与1,2-二氨基苯的反应合成各种取代的2,2'-联苯并咪唑，该方案通过依次进行亲核加成和亲电取代来进行随后进行了Mamedov重排。简明的一锅合成5,5'-bi（2,2'-联苯并咪唑）和2,2'-联苯并咪唑的氮杂类似物说明了该策略的合成效用。
• Syntheses of Homochiral Multinuclear Ru Complexes Based on Oligomeric Bibenzimidazoles
  作者：Jun Yin、Ronald L. Elsenbaumer

  DOI：10.1021/ic062148a

  日期：2007.8.1

  The homochiral multinuclear Ru complexes of the oligomeric bibenzimidazoles were synthesized using Lambda-[Ru(bpy)(2)(PY)(2)][(-)-O,O-dibenzoyl-L-tartrate]-12H(2)O as an enantiornerically pure building block. The complexations proceed with the retention of configuration to provide well-defined mononuclear, dinuclear, tetranuclear, and octanuclear Ru complexes successfully. The optical purity and the absolute configurations of the complexes were determined by NMR and circular dichroism spectrometry. The rare X-ray structure of a tetranuclear complex Lambda(4)[(Ru(bpy)(2))(4)(bis(BiBzlm))](PF6)(4) was resolved, The crystallographic analysis reveals that all the four Ru centers have A octahedral configurations, with a Ru-Ru separation of 5.509 angstrom across the bridging bibenzimidazole ligand, which maintains near coplanarity. The UV-vis spectroscopic and electrochemical properties of the homochiral multinuclear assemblies were studied, indicating weak electronic communications between the metal centers.