2,2'-Bis(2-pyridyl)-6,6'-bibenzimidazole | 135774-29-7

• 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: 2,2'-Bis(2-pyridyl)-6,6'-bibenzimidazole
• 英文别名: 2,2'-di-(2-pyridyl)-6,6'-bibenzimidazole；2-pyridin-2-yl-6-(2-pyridin-2-yl-3H-benzimidazol-5-yl)-1H-benzimidazole
• CAS: 135774-29-7
• 化学式: C₂₄H₁₆N₆
• 分子量: 388.431
• InChiKey: OHGIQXYAQDYDHI-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.9
• 重原子数：
  30
• 可旋转键数：
  3
• 环数：
  6.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  83.1
• 氢给体数：
  2
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  Os(bpy)₂Cl₂*2H₂O 、 sodium perchlorate 、 2,2'-Bis(2-pyridyl)-6,6'-bibenzimidazole 以 乙醇 、 水 为溶剂， 以63%的产率得到
  参考文献：
  名称：

  Synthesis and proton-coupled redox properties of mononuclear or asymmetric dinuclear complexes of ruthenium, rhodium and/or osmium containing 2,2′-bis(2-pyridyl)-6,6′-bibenzimidazole

  摘要：

  New mononuclear and heterodinuclear complexes. [ML(2)(H(2)L(1))](2+) and [L(2)'M(H(2)L(1))M'L(2)''](4+) [M, M' = Ru, Rh and/or Os; L' or L'' = 2.2'-bipyridine (bipy), 1,10-phenanthroline or 4,4'-dimethytbipyridine], containing the dinucleating ligand 2,2'-bis(2-pyridyl)-6,6'-bibenzimidazole (H(2)L(1)) have been prepared. The metal-to-ligand charge-transfer bands are almost unaltered when changing from the mono- to dinuclear complexes, indicating that the bridging H(2)L(1) ligand has slightly lower pi* orbital energy than that of bipy. The bridging H(2)L(1) ligand acts as a sigma/pi-donor ligand. Both the absorption spectra and the oxidation potentials of the: complexes are strongly dependent on the solution pH, which determines the NH deprotonation of the co-ordinated ligand H(2)L(1). The mononuclear complexes of Ru and Os act not only as basic acids but also as diacidic bases while the heterodinuclear complexes essentially act as dibasic acids. The proton-coupled redox reaction was demonstrated by plots of E, vs. pH (Pourbaix diagrams). The pK(a) values of the complexes reflect on both the type of metals and their oxidation states, M(II) and M(III). The introduction of asymmetry in the dinuclear complexes containing H(2)L(1) can provide not only a potential difference between the two metal sites but also a preferential protonation (or deprotonation) site.

  DOI：

  10.1039/dt9940000263
• 作为产物：
  描述：

  吡啶-2-甲醛 、 3,3'-二氨基联苯胺 以 硝基苯 为溶剂， 生成 2,2'-Bis(2-pyridyl)-6,6'-bibenzimidazole
  参考文献：
  名称：

  An Experimental and Computational Analysis on the Differential Role of the Positional Isomers of Symmetric Bis-2-(pyridyl)-1H-benzimidazoles as DNA Binding Agents

  摘要：

  Three symmetrical positional isomers of bis-2-(n-pyridyl)-1H-benzimidazoles (n = 2, 3, 4) were synthesized and DNA binding studies were performed with these isomeric derivatives. Like bisbenzimidazole compound Hoechst 33258, these molecules also demonstrate AT-specific DNA binding. The binding affinities of 3-pyridine (m-pyben) and 4-pyridine (p-pyben) derivatized bisbenzimidazoles to double-stranded DNA were significantly higher compared to 2-pyridine derivatized benzimidazole o-pyben. This has been established by combined experimental results of isothermal fluorescence titration, circular dichroism, and thermal denaturation of DNA. To rationalize the origin of their differential binding characteristics with double-stranded DNA, computational structural analyses of the uncomplexed ligands were performed using ab initio/Density Functional Theory. The molecular conformations of the symmetric head-to-head bisbenzimidazoles have been computed. The existence of intramolecular hydrogen bonding was established in o-pyben, which confers a conformational rigidity to the molecule about the bond connecting the pyridine and benzimidazole units. This might cause reduction in its binding affinity to double-stranded DNA compared to its para and meta counterparts. Additionally, the predicted stable conformations for p-, m-, and o-pyben at the B3LYP/6-31G* and RHF/6-31G* levels were further supported by experimental pK(a) determination. The results provide important information on the molecular recognition process of such symmetric head to head bisbenzimidazoles toward duplex DNA.

  DOI：

  10.1021/jo0619433

文献信息

• Temperature-Dependent Rates of Electron Transfers and Intersystem Crossing on the Laser Excitation of Ligand-Bridged Ru(II) and Co(III) Compounds
  作者：Akio Yoshimura、Koichi Nozaki、Noriaki Ikeda、Takeshi Ohno

  DOI：10.1021/jp9513982

  日期：1996.1.1

  electron transfers within ligand-bridged Ru(II) and Co(III) compounds of [(bpy)2Ru(L)Co(bpy)2]5+ (a, b, and c) were examined in butyronitrile by means of laser photolysis kinetic spectroscopy, where L is a bridging tetradentate ligand, 2,6-bis(2-pyridyl)benzodiimidazole for a, 2,2‘-bis(2-pyridyl)bibenzimidazole for b, and 1,5-bis[2-(2-pyridyl)benzimidazoyl]pentane for c. The temperature dependence of

  通过在丁腈中检测[[（bpy）2 Ru（L）Co（bpy）2 ] 5+（a，b和c）的配体桥联Ru（II）和Co（III）化合物内的光诱导分子内电子转移。光解动力学光谱学，其中L是桥联四齿配体，a是2,6-双（2-吡啶基）苯并二咪唑，b是2,2'-双（2-吡啶基）联苯并咪唑，1,5-bis [ c的2-（2-吡啶基）苯并咪唑基]戊烷。通过考虑吉布斯（Gibbs）能量变化和重组能的温度依赖性，分析了电子转移和系统间交叉速率的温度依赖性。皮秒激光激发a和b后在420 nm处观察到的瞬态差异吸收带不归因于激发的Ru（II）部分的形成，而是归因于Co（III）部分的反应产物（2 Co（II）） ，在270 K以下1 ns内衰变形成4 Co（II）的长寿命物种。2 Co（II）→ 4的系统间交叉的内球重组根据转变速率的温度依赖性，Co（II）估计为0.6 eV。电子从Ru（II）部分的激发MLCT状态到c的Co（III）在300
• A Fluorophoric-Axle-Based, Nonfluororescent, Metallo anti-[3]Pseudorotaxane: Recovery of Fluorescence by Means of an Axle Substitution Reaction
  作者：Subrata Saha、I. Ravikumar、Pradyut Ghosh

  DOI：10.1002/chem.201102627

  日期：2011.12.2

  characterized by the electrospray ionization mass spectroscopy (ESI‐MS), UV/Vis and EPR spectroscopy, and single‐crystal X‐ray data. The ESI‐MS showed peaks that support the formation of [3]pseudorotaxane. The UV/Vis spectrum of [3]pseudorotaxane in CH3CN showed a characteristic d–d band of a Cu2+ complex at 650 nm. Further, the X‐band in the EPR spectrum of [3]pseudorotaxane suggested a distorted square‐pyramidal

  在荧光轴上合成了以Cu 2+为模板的多核非荧光抗[3]假轮烷。Cu 2+模板[3]假轮烷的特征在于电喷雾电离质谱（ESI-MS），UV / Vis和EPR光谱以及单晶X射线数据。ESI-MS显示出支持[3]假轮烷的形成的峰。CH 3 CN中[3]假轮烷的UV / Vis光谱在650 nm处显示Cu 2+络合物的特征性d-d谱带。此外，[3]假轮烷的EPR光谱中的X波段表明Cu 2+的方锥几何形状畸变。重要的是，通过单晶X射线结构分析证实了[3]假轮烷的形成，这表明一个荧光轴被旋入两个具有反构象的Cu 2+大环轮（MC-Cu 2+）。进行了UV / Vis和荧光滴定实验，以追踪由MC-Cu 2+和荧光轴在CH 3 CN中形成[3]假轮烷的溶液状态。在两项研究中，S形曲线拟合均支持荧光轴和MC-Cu 2+的1：2络合物的形成。复杂的。其次，通过滴定具有更强的双齿螯合配体（例如1,10-菲咯啉）
• Haga, Masa-Aki; Ano, Tomo-Aki; Kano, Kenji, Inorganic Chemistry, 1991, vol. 30, # 20, p. 3843 - 3849
  作者：Haga, Masa-Aki、Ano, Tomo-Aki、Kano, Kenji、Yamabe, Shinichi

  DOI：——

  日期：——
• Precursors of Organometallic Compounds for Electroluminescent Materials
  申请人：Chin Sung-Min

  公开号：US20090108733A1

  公开（公告）日：2009-04-30

  The present invention relates to a precursor of metallic complex for electroluminescent material, a luminescent material comprised of said precursor of metallic complex and metal, and an electroluminescent device containing a luminescent material comprised of said precursor and metal. The luminescent material comprised of the precursor according to the present invention and metal is advantageous in that it shows excellent electric conductivity and light emitting property of high efficiency.
• An Experimental and Computational Analysis on the Differential Role of the Positional Isomers of Symmetric Bis-2-(pyridyl)-1<i>H</i>-benzimidazoles as DNA Binding Agents
  作者：Padmaparna Chaudhuri、Bishwajit Ganguly、Santanu Bhattacharya

  DOI：10.1021/jo0619433

  日期：2007.3.1

  Three symmetrical positional isomers of bis-2-(n-pyridyl)-1H-benzimidazoles (n = 2, 3, 4) were synthesized and DNA binding studies were performed with these isomeric derivatives. Like bisbenzimidazole compound Hoechst 33258, these molecules also demonstrate AT-specific DNA binding. The binding affinities of 3-pyridine (m-pyben) and 4-pyridine (p-pyben) derivatized bisbenzimidazoles to double-stranded DNA were significantly higher compared to 2-pyridine derivatized benzimidazole o-pyben. This has been established by combined experimental results of isothermal fluorescence titration, circular dichroism, and thermal denaturation of DNA. To rationalize the origin of their differential binding characteristics with double-stranded DNA, computational structural analyses of the uncomplexed ligands were performed using ab initio/Density Functional Theory. The molecular conformations of the symmetric head-to-head bisbenzimidazoles have been computed. The existence of intramolecular hydrogen bonding was established in o-pyben, which confers a conformational rigidity to the molecule about the bond connecting the pyridine and benzimidazole units. This might cause reduction in its binding affinity to double-stranded DNA compared to its para and meta counterparts. Additionally, the predicted stable conformations for p-, m-, and o-pyben at the B3LYP/6-31G* and RHF/6-31G* levels were further supported by experimental pK(a) determination. The results provide important information on the molecular recognition process of such symmetric head to head bisbenzimidazoles toward duplex DNA.