1,2-二苯并咪唑苯 | 4506-61-0

• 物质功能分类: 有机原料 - 杂环化合物
• 分子结构分类: 有机化合物 - 有机杂环化合物 - 苯并咪唑类
• 中文名称: 1,2-二苯并咪唑苯
• 英文名称: 1,2-bis(2-benzimidazolyl)benzene
• 英文别名: 1,2-bis(benzimidazol-2-yl)benzene；2-[2-(1H-benzimidazol-2-yl)phenyl]-1H-benzimidazole
• CAS: 4506-61-0
• 化学式: C₂₀H₁₄N₄
• 分子量: 310.358
• InChiKey: NQVCKXMOMGRVES-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.5
• 重原子数：
  24
• 可旋转键数：
  2
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  57.4
• 氢给体数：
  2
• 氢受体数：
  2

安全信息

• 危险性防范说明：
  P261,P280,P301+P312,P302+P352,P305+P351+P338
• 危险性描述：
  H302,H315,H319,H335
• 储存条件：
  存放在2-8℃的环境中，应保持干燥并密封。

反应信息

• 作为反应物：
  描述：

  1,2-二苯并咪唑苯 生成 di(benzimidazol-2-yl)benzene
  参考文献：
  名称：

  Blue to green shifted fluorescence in inter- and intramolecular hydrogen bonded di(benzimidazol-2-yl)benzene

  摘要：

  分子间 H 键的二(苯并咪唑-2-基)苯相互转化为分子内 H 键异构体时，会产生强烈的蓝绿荧光偏移。

  DOI：

  10.1039/b907745f
• 作为产物：
  描述：

  1,2,9,18-Tetrazahexacyclo[15.7.0.02,10.03,8.011,16.019,24]tetracosa-3,5,7,9,11,13,15,17,19,21,23-undecaene 在 肼 作用下， 以 甲醇 为溶剂， 以100%的产率得到1,2-二苯并咪唑苯
  参考文献：
  名称：

  Cyclodehydrogenation of di- and tetra(benzimidazol-2-yl)benzenes to give model heteroaromatic discotic systems

  摘要：

  二、四（苯并咪唑-2-基）苯在氧化过程中会发生环氢化反应，形成 N-N 键，从而形成平面化多环化合物，这些化合物是含杂原子盘状材料核心的模型，并且很容易还原成原始化合物，从而证明了分子氧化还原转换。

  DOI：

  10.1039/b301512m

文献信息

• Synthesis, characterization and catecholase biomimetic activity of novel cobalt(II), copper(II), and iron(II) complexes bearing phenylene-bis-benzimidazole ligand
  作者：Juan Chirinos、Darmenia Ibarra、Ángel Morillo、Ligia Llovera、Teresa González、Jeannette Zárraga、Oswaldo Larreal、Mayamarú Guerra

  DOI：10.1016/j.poly.2021.115232

  日期：2021.7

  rather than the steric hindrance of the ligand. Kinetic parameters (Vmax, kcat, KM) were estimated by mean of the Michaelis–Menten model and Lineweaver–Burk plot. Catechol oxidation rates of complexes 2–4 are in the same order of magnitudes of mononuclear and dinuclear Cu(II) complexes bearing imidazole-based ligands but lower than observed for the catecholase enzyme.

  钴（II），铜（II）和Fe的过渡金属配合物（II）的轴承的刚性对称2,2' - （1,2-亚苯基）双（1H-苯并咪唑）配体，PhBIm 2，合成并充分通过ESI-MS，FT-IR，1 H NMR（用于顺磁性物质），UV-Vis光谱学和显微分析技术进行表征。此外，钴配合物是X射线结构分析的主题。PhBIm 2 Co（II）Cl 2配合物的分子晶体结构显示出伪四面体环境中的金属中心，配体螯合后，PhBIm 2骨架中的键没有明显的延长或压缩。所有复合催化的有氧氧化Ø -catechol到Ø-醌在温和的条件下。结果表明，氧化速率取决于对金属中心的电子稳定作用，而不是取决于配体的空间位阻。动力学参数（V max，k cat，K M）通过Michaelis–Menten模型和Lineweaver–Burk图进行估算。复合物的儿茶酚氧化速率2 - 4是在单核的大小的相同的顺序和双核铜（II）络合物轴承
• Green Synthesis of Polycyclic Benzimidazole Derivatives and Organic Semiconductors
  作者：Masashi Mamada、César Pérez-Bolívar、Pavel Anzenbacher

  DOI：10.1021/ol201973w

  日期：2011.9.16

  Polycyclic benzimidazole derivatives, an important class of compounds in organic electronics and photovoltaics, were prepared using a solvent-free “green” process based on heating carboxylic acid anhydrides and arylene diamines in the presence of zinc acetate in the solid state. Products were isolated and purified directly by train sublimation of the crude reaction mixtures. The reaction conditions

  多环苯并咪唑衍生物是有机电子产品和光伏产品中的一类重要化合物，是使用无溶剂的“绿色”工艺制备的，该工艺基于在固态乙酸锌存在下加热羧酸酐和亚芳基二胺的方法。产物的分离和纯化是通过将粗反应混合物直接升华进行的。使用各种羧酸酐优化反应条件。还描述了这些材料的光学和电化学性质。
• Highly efficient anion transport mediated by 1,3-bis(benzimidazol-2-yl)benzene derivatives bearing electron-withdrawing substituents
  作者：Chen-Chen Peng、Meng-Jia Zhang、Xiao-Xiao Sun、Xiong-Jie Cai、Yun Chen、Wen-Hua Chen

  DOI：10.1039/c6ob01461e

  日期：——

  1,3-Bis(benzimidazol-2-yl)benzene derivatives bearing strong electron-withdrawing substituents were found to exhibit highly efficient anion transport.

  1,3-双(苯并咪唑-2-基)苯衍生物携带强电子吸引取代基被发现具有高效的阴离子传输能力。
• Ti (IV) Complexes of Some Heterocyclic Ligands Synthesis, Characterization and Ethylene Polymerization Activity
  作者：Hamdi Elagab

  DOI：10.13005/ojc/320177

  日期：2016.3.25

  31 complexes of bis - (benzimidazole, benzothiazole and benzoxazole) compounds with Ti (IV) metal centers were synthesized, characterized, activated with methylalumoxane (MAO) and then tested for catalytic ethylene polymerization. The activities of the various catalysts were found to be functions of the hetero atoms in the ligand frameworks. The highest activity was obtained with 39 / MAO (573 kg PE / mol cat. h). The produced polyethylenes showed high molecular weights (up to 1.5 ×106 g/mol) and broad molecular weight distributions (PD = 65). This could result from different interactions of the MAO counterion with the heteroatoms of the catalyst ligand generating different active sites.

  合成了31个双-（苯并咪唑、苯并噻唑和苯并恶唑）化合物与钛（IV）金属中心的配合物，进行了表征，并用甲基铝氧烷（MAO）激活，然后测试了其在催化乙烯聚合中的活性。各种催化剂的活性被发现与配体框架中的杂原子有关。39 / MAO获得了最高活性（573 kg PE / mol cat. h）。所产生的聚乙烯具有高分子量（最高可达1.5 × 10^6 g/mol）和宽的分子量分布（PD = 65）。这可能是由于MAO反离子与催化剂配体中的杂原子之间不同的相互作用生成了不同的活性位点。
• Preparation and characterization of new soluble benzimidazole–imide copolymers
  作者：M. Berrada、F. Carriere、Y. Abboud、A. Abourriche、A. Benamara、N. Lajrhed、M. Kabbaj、M. Berrada

  DOI：10.1039/b205150h

  日期：——

  The present necessity to use heat-resistant materials in electronics justifies the scientific interest in different heterocyclic polymers. This paper is especially concerned with the preparation of novel heat-resistant polyimides having bisbenzimidazole moieties in the main chain and their applications as dielectric films. A soluble copolyimide was prepared by a two-step synthesis from aromatic dianhydrides and aromatic diamines. The bisbenzimidazole diamine was prepared by reduction of the corresponding dinitro compound. The diamine was reacted with various aromatic dianhydrides to prepare a series of alternating benzimidazole–imide copolymers via the poly(amic acid) precursors and thermal or chemical imidization. Monomers and polymers were characterized by conventional methods and their physical properties such as solution viscosity, solubility properties, thermal stability and thermal behaviour were studied. All copolymers were obtained in high yields having inherent viscosities ηinh that ranged from 0.60 to 0.98 dL g−1. Thin films of the copolymer were tough and flexible, having tensile strengths as high as 100 MPa. Glass transition temperatures were observed between 275 and 328 °C. Thermogravimetric analyses indicated that the thermal degradation of poly(benzimidazole–imide) occurs around 530 °C, which is ca. 80 °C higher than polyimide, confirming that the introduction of the bisbenzimidazole component improved the thermal stability of polyimide.

  目前电子领域对耐热材料的需求使得不同的杂环聚合物引起了科学界的关注。本文特别关注含有双苯并咪唑基团的新型耐热聚酰亚胺的制备及其作为绝缘薄膜的应用。通过对芳香二酐和芳香二胺的两步合成，制备了一种可溶性共聚酰亚胺。双苯并咪唑二胺是通过还原相应的二硝基化合物制备的。该二胺与多种芳香二酐反应，通过聚（酰胺酸）前驱体及热或化学酰亚胺化反应制备出一系列交替的苯并咪唑-酰亚胺共聚物。单体和聚合物通过常规方法进行了表征，并研究了其物理性质，如溶液粘度、溶解特性、热稳定性和热行为。所有共聚物都以高产率获得，固有粘度ηinh范围为0.60至0.98 dL g⁻¹。共聚物的薄膜坚韧且柔韧，拉伸强度高达100 MPa。玻璃转变温度在275至328°C之间。热重分析表明，聚（苯并咪唑-酰亚胺）的热降解发生在约530°C，这比聚酰亚胺高出约80°C，确认了双苯并咪唑组分的引入提高了聚酰亚胺的热稳定性。