9-(4-(2-(pyridin-2-yl)-1H-benzo[d]imidazol-1-yl)phenyl)-9H-carbazole | 1226878-11-0

• 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: 9-(4-(2-(pyridin-2-yl)-1H-benzo[d]imidazol-1-yl)phenyl)-9H-carbazole
• 英文别名: 1-(4-(carbazol-9-yl)phenyl)-2-pyridinylbenzimidazole；1-(4-carbazol-9-ylphenyl)-2-pyridin-2-ylbenzimidazole；1-(4-carbazolylphenyl)-2-pyridinyl benzimidazole；1-(4-(9-carbazolyl)phenyl)-2-(pyridin-2-yl)benzimidazole；9-[4-(2-Pyridin-2-ylbenzimidazol-1-yl)phenyl]carbazole；9-[4-(2-pyridin-2-ylbenzimidazol-1-yl)phenyl]carbazole
• CAS: 1226878-11-0
• 化学式: C₃₀H₂₀N₄
• 分子量: 436.516
• InChiKey: QLOIYHSXMDNPBG-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.8
• 重原子数：
  34
• 可旋转键数：
  3
• 环数：
  7.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  35.6
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  顺-双(2,2-二吡啶)二氯化钌(II) 水合物 、 9-(4-(2-(pyridin-2-yl)-1H-benzo[d]imidazol-1-yl)phenyl)-9H-carbazole 以 乙二醇 为溶剂， 以38.8%的产率得到[Ru(2,2'-bipyridine)2(1-(4-carbazolylphenyl)-2-pyridinylbenzimidazole)]Cl2
  参考文献：
  名称：

  基于联吡啶和两个具有载流子传输单元的新型二亚胺配体的钌（II）聚吡啶基配合物：合成，光致发光和氧化还原性质

  摘要：

  一系列钌（II）配合物的，的[Ru（联吡啶）2 L] X 2（大号 = L1，L2; X =氯-，PF 6 -，SCN - ），是基于吡啶和两种新型二亚胺合成配位体L1 L2（L1 ＝ 1-（4-5′-苯基-1,3,4-恶二唑基苯基）-2-吡啶基-苯并咪唑，L2 ＝ 1-（4-咔唑基苯基）-2-吡啶基苯并咪唑）；并且还描述了[Ru（bpy）2 L1] Cl 2的晶体结构。还制备了[Ru（bpy）2（Pybm）] X 2（Pybm = 2-（2-吡啶）苯并咪唑）复合物作为参考样品。在UV-vis吸收光谱中，有一个强π  →  π*过渡和两个dπ（Ru）→  π *过渡。通过比较[Ru（bpy）2 L] X（L  = L1，L2）与参考配合物之间的光致发光性质，我们发现具有咔唑和恶唑的载流子传输基团的配合物具有更高的发射强度和量子效率。在范围0.80-1.00 V在其每一个被分配到所述金属氧化

  DOI：

  10.1016/j.jorganchem.2010.04.037
• 作为产物：
  描述：

  2-(2-吡啶)-苯并咪唑 、 9-(4-溴苯基)咔唑 在 N,N-二甲基丙烯基脲 、 copper(l) iodide 、 18-冠醚-6 、 potassium carbonate 作用下， 反应 48.0h， 以67%的产率得到9-(4-(2-(pyridin-2-yl)-1H-benzo[d]imidazol-1-yl)phenyl)-9H-carbazole
  参考文献：
  名称：

  基于联吡啶和两个具有载流子传输单元的新型二亚胺配体的钌（II）聚吡啶基配合物：合成，光致发光和氧化还原性质

  摘要：

  一系列钌（II）配合物的，的[Ru（联吡啶）2 L] X 2（大号 = L1，L2; X =氯-，PF 6 -，SCN - ），是基于吡啶和两种新型二亚胺合成配位体L1 L2（L1 ＝ 1-（4-5′-苯基-1,3,4-恶二唑基苯基）-2-吡啶基-苯并咪唑，L2 ＝ 1-（4-咔唑基苯基）-2-吡啶基苯并咪唑）；并且还描述了[Ru（bpy）2 L1] Cl 2的晶体结构。还制备了[Ru（bpy）2（Pybm）] X 2（Pybm = 2-（2-吡啶）苯并咪唑）复合物作为参考样品。在UV-vis吸收光谱中，有一个强π  →  π*过渡和两个dπ（Ru）→  π *过渡。通过比较[Ru（bpy）2 L] X（L  = L1，L2）与参考配合物之间的光致发光性质，我们发现具有咔唑和恶唑的载流子传输基团的配合物具有更高的发射强度和量子效率。在范围0.80-1.00 V在其每一个被分配到所述金属氧化

  DOI：

  10.1016/j.jorganchem.2010.04.037

文献信息

• Tuning the NLO response of bis-cyclometalated iridium(<scp>iii</scp>) complexes by modifying ligands: experimental and structural DFT analysis
  作者：Mansoor Akhtar、Ali Muhammad Arif、Shifa Ullah Khan、Guo-Gang Shan、Hong-liang Xu、Zhong-Min Su

  DOI：10.1039/d1nj00114k

  日期：——

  and Crbd (9-(4-(2-(pyridin-2-yl)-1H-benzo[d]imidazol-1-yl)phenyl)-9H-carbazole) as ancillary ligands. The aim of this paper is to study the effect of the substituent on the geometrical structures, electronic and second-order nonlinear optical (NLO) properties, and UV-vis absorption spectra. It is found that the first hyperpolarizabilities can be easily modulated by the introduction of Phbd and Crbd

  已经进行了密度泛函理论（DFT）计算，以研究两种合成的铱（III）配合物，它们具有取代的Phbd（1-苯基-2-（吡啶-2-基）-1 H-苯并[ d ]咪唑）和Crbd（ 9-（4-（2-（吡啶-2-基）-1 H-苯并[ d ]咪唑-1-基）苯基）-9 H-咔唑）作为辅助配体。本文的目的是研究取代基对几何结构，电子和二阶非线性光学（NLO）性质以及UV-vis吸收光谱的影响。发现通过引入Phbd和Crbd单位可以容易地调节第一超极化率。与具有Crbd作为辅助配体的复合物相比，具有Phbd的复合物具有更大的第一超极化率值。重要的是，第一超极化率的变化可以通过电荷转移模式定性地解释。可以预期，对这些铱（III）配合物的理论研究将有助于设计高性能和多功能的NLO材料。
• Synthesis and photoluminescence properties of four rhenium(I) complexes based on diimine ligands with oxadiazole/carbazole moiety
  作者：Jing Wu、Hong-Yan Li、Ling-Chen Kang、Dong-Ping Li、Huan-Rong Li、Xin-Hui Zhou、Yan Sui、You-Xuan Zheng、Jing-Lin Zuo、Xiao-Zeng You

  DOI：10.1016/j.jphotochem.2010.02.010

  日期：2010.4

  By introducing two carrier-transporting moieties (oxadiazole and carbazole) into two diimine ligands (2-(2-pyridine)-benzimidazole and 2,2'-dipyridylamine), respectively, four novel ligands (L1-L4) and their corresponding rhenium(I) complexes (1-4) have been synthesized and characterized by elemental analysis, H-1 NMR and IR spectra. Their photophysical properties, thermal analysis, along with the X-ray crystal structure analysis of 14 and corresponding complex 4 are also described. In absorption spectra, the 2-(2-pyridine)benzimidazole containing complexes 1,2 show the intraligand charge-transfer (pi -> pi* (L)) bands and metal-to-ligand charge-transfer d pi(Re) -> pi* MLCT bands, while the 2,2'-dipyridylamine containing complexes 3,4 only show the pi -> pi* bands. In the excitation spectra, all the complexes show strong M La bands. After excitation of pi -> pi* or MLCT bands, all the four Re(I) complexes exhibit broad bands around 550-560 nm due to the Re(I)-based (MLCT)-M-3 emission. The two complexes 1 (with oxadiazole moiety) and 2 (with carbazole moiety) show the photoluminescence quantum efficiency of 2.0% and 7.5% in solid state, respectively, indicating that the carbazole unit is the better chromophore to enhance the luminescence efficiency of diimine Re(I) complexes than the oxadiazole moiety. (C) 2010 Elsevier B.V. All rights reserved.
• Synthesis and photoluminescent properties of series ternary lanthanide (Eu(III), Sm(III), Nd(III), Er(III), Yb(III)) complexes containing 4,4,4-trifluoro-1-(2-naphthyl)-1,3-butanedionate and carbazole-functionalized ligand
  作者：Jing Wu、Hong-Yan Li、Qiu-Lei Xu、Yu-Cheng Zhu、Yun-Mei Tao、Huan-Rong Li、You-Xuan Zheng、Jing-Lin Zuo、Xiao-Zeng You

  DOI：10.1016/j.ica.2010.03.067

  日期：2010.8

  A series of new ternary lanthanide complexes Ln(TFNB)(3)L (where Ln = Eu, Sm, Nd, Er, Yb, TFNB = 4,4,4-trifluoro-1-(2-naphthyl)-1,3-butanedionate, L = 1-(4-carbazolylphenyl)-2-pyridinyl benzimidazole) have been synthesised. The photoluminescence properties and TGA of them are described in detail. The trifluorinated ligand TFNB displays excellent antenna effect to sensitize the Ln(III) ions to emit characteristic spectra. The carbazole-containing ligand L is testified to be an outstanding synergistic ligand. The luminescence properties investigated and the quantum efficiency measured in dichloromethane solution of Eu(TFNB)(3)L and Sm(TFNB)(3)L show that the carbazole moiety is good at absorbing energy to sensitize the metal-centered emitting states and can make the complexes more rigid, provide efficient shielding of the Ln(III) core towards external quenching compared with the reference complexes of Eu(TFNB)(3)(Pybm) and Sm(TFNB)(3)(Pybm) (Pybm = 2-(2-pyridine)-benzimidazole) which have no carbazole unit. The quantum efficiency of Eu(TFNB)(3)L in air-equilibrated CH2Cl2 solution is calculated to be 14.8% by using air-equilibrated aqueous [Ru(bpy)(3)](2+).2Cl solution as reference sample (Phi(std) = 2.8%). (C) 2010 Elsevier B.V. All rights reserved.
• Enhancing the luminescence properties and stability of cationic iridium(iii) complexes based on phenylbenzoimidazole ligand: a combined experimental and theoretical study
  作者：Guo-Gang Shan、Hai-Bin Li、Hai-Zhu Sun、Hong-Tao Cao、Dong-Xia Zhu、Zhong-Min Su

  DOI：10.1039/c3dt50358e

  日期：——

  Herein we designed and synthesized a series of cationic iridium(III) complexes with a phenylbenzoimidazole-based cyclometalated ligand, containing different numbers of carbazole moieties from zero to three (complexes 1–4). The photophysical and electrochemical properties of this series have been systematically investigated. The complexes exhibit strong luminescence in both solution and in neat films

  本文我们设计并合成了一系列阳离子铱（的III）配合物与基于苯基苯并咪唑-环金属化配体，从零至三个（络合物含有咔唑部分的不同数目的1 - 4）。已经对该体系的光物理和电化学性质进行了系统研究。络合物在溶液和纯净薄膜中均显示出强发光性，并具有出色的氧化还原可逆性。发现将咔唑基团引入配合物中可导致纯膜中光致发光的量子效率大大提高，但密度密度理论（DFT）结果支持该方法对发光颜色和激发态特性的影响很小。DFT计算还表明，功能化的配合物2–4显示出比1更佳的空穴传输性质。更重要的是，所有络合物在以金属为中心（3MC）激发态，表明它们的稳定性。进一步的研究表明，3 MC状态下结构开放的限制是由苯基苯并咪唑配体的独特分子构象引起的，这首先在没有分子内π-π堆积的阳离子铱（III）络合物中得到了证明。此处提出的这些结果将为设计和合成适用于光学器件的高效，稳定的阳离子铱（III）配合物提供有价值的信息。
• Ruthenium (II) polypyridyl complexes based on bipyridine and two novel diimine ligands with carrier-transporting unit: synthesis, photoluminescence and redox properties
  作者：Jing Wu、Hong-Yan Li、Ling-Chen Kang、Dong-Ping Li、Qiu-Lei Xu、Yu-Cheng Zhu、Yun-Mei Tao、You-Xuan Zheng、Jing-Lin Zuo、Xiao-Zeng You

  DOI：10.1016/j.jorganchem.2010.04.037

  日期：2010.8

  A series of ruthenium (II) complexes, [Ru(bpy)2L]X2 (L = L1, L2; X = Cl−, PF6−, SCN−), were synthesized based on bipyridine and two novel diimine ligands L1 and L2 (L1 = 1-(4-5′-phenyl-1,3,4-oxadiazolylphenyl)-2-pyridinyl-benzoimidazole, L2 = 1-(4-carbazolylphenyl)-2-pyridinylbenzimidazole); and the crystal structure of [Ru(bpy)2L1]Cl2 was also described. [Ru(bpy)2(Pybm)]X2 (Pybm = 2-(2-pyridine)benzimidazole)

  一系列钌（II）配合物的，的[Ru（联吡啶）2 L] X 2（大号 = L1，L2; X =氯-，PF 6 -，SCN - ），是基于吡啶和两种新型二亚胺合成配位体L1 L2（L1 ＝ 1-（4-5′-苯基-1,3,4-恶二唑基苯基）-2-吡啶基-苯并咪唑，L2 ＝ 1-（4-咔唑基苯基）-2-吡啶基苯并咪唑）；并且还描述了[Ru（bpy）2 L1] Cl 2的晶体结构。还制备了[Ru（bpy）2（Pybm）] X 2（Pybm = 2-（2-吡啶）苯并咪唑）复合物作为参考样品。在UV-vis吸收光谱中，有一个强π  →  π*过渡和两个dπ（Ru）→  π *过渡。通过比较[Ru（bpy）2 L] X（L  = L1，L2）与参考配合物之间的光致发光性质，我们发现具有咔唑和恶唑的载流子传输基团的配合物具有更高的发射强度和量子效率。在范围0.80-1.00 V在其每一个被分配到所述金属氧化