2-(4-fluorophenyl)-1-phenyl-1H-benzo[d]imidazole | 2622-70-0

• 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: 2-(4-fluorophenyl)-1-phenyl-1H-benzo[d]imidazole
• 英文别名: 1-Phenyl-2-(4-fluorphenyl)-benzimidazol；2-(4-fluorophenyl)-1-phenylbenzimidazole
• CAS: 2622-70-0
• 化学式: C₁₉H₁₃FN₂
• 分子量: 288.324
• InChiKey: IXJYNVUQHFCCSD-UHFFFAOYSA-N

物化性质

• 熔点：
  100-101 °C
• 沸点：
  464.2±47.0 °C(Predicted)
• 密度：
  1.18±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4.9
• 重原子数：
  22
• 可旋转键数：
  2
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  17.8
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  1,1,2-triphenyl-2-(9H-carbazol-2-yl)ethylene 、 2-(4-fluorophenyl)-1-phenyl-1H-benzo[d]imidazole 在 caesium carbonate 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 12.5h， 以69%的产率得到9-(4-(1-phenyl-1H-benzo[d]imidazol-2-yl)phenyl)-2-(1,2,2-triphenylvinyl)-9H-carbazole
  参考文献：
  名称：

  Engineering of aggregation-induced emission luminogens by isomeric strategy to achieve high-performance optoelectronic device

  摘要：

  Achieving non-doped organic light-emitting diodes (OLEDs) with high electroluminescent (EL) performance is essential for both illumination source and display applications. A source of this difficulty is the aggregation-induce quenching effect of emitters in the solid state, which results in low EL efficiency and severe roll-off. Herein, four isomeric aggregation-induced emission luminogens (AIEgens), namely TPE-3Cz-mPBI, TPE-3Cz-pPBI, TPE-2Cz-mPBI, and TPE-2Cz-pPBI, are constructed by varying the linkage positions of electron-accepter 1,2-diphenyl-1H-benzo[dlimidazole (PBI), electron-donor carbazole, and ME-active triphenylethene functional groups. A comprehensive investigation is carried out, and the results indicate that position isomerism dramatically affects electronic structures, photophysical properties, carrier transport capabilities, and device performances. Compared with TPE-3Cz-mPBI and TPE-3Cz-pPBI, TPE-2Cz-mPBI, and TPE-2C2-pPBI exhibit more excellent AIE-active with the fluorescence quantum yield up to 72.5% and 89.7% in the neat films. Moreover, TPE-2Cz-mPBI shows high electron transport property and appropriate energy level, which favor balanced charge carrier injection/transporting in OLEDs. Hence, non-doped device based on TPE-2Cz-mPBI exhibits the best EL performance with external quantum efficiency, current efficiency, and power efficiency of 3.2%, 7.8 cd A(-1), and 7.7 lm W-1, respectively. The isomeric strategy presents a promising method to extend the structural diversity of highly efficient AIE emitters, optimize optoelectronic properties, and construct high-performance non-doped devices. Due to intrinsic twisted structure and accessible protonated N-electron in molecular framework, the isomers exhibit impressive mechanochromism and acidochromism.

  DOI：

  10.1016/j.dyepig.2019.107912
• 作为产物：
  描述：

  对氟苄胺 、 邻氨基二苯胺 在 1-(3-amino-2,4-dihydroxyphenyl)-1-ethanone 、 copper(ll) bromide 作用下， 以 甲醇 为溶剂， 反应 24.0h， 以80%的产率得到2-(4-fluorophenyl)-1-phenyl-1H-benzo[d]imidazole
  参考文献：
  名称：

  生物启发的催化好氧氧化C ？H脂肪族伯胺的官能化：1,2-双取代苯并咪唑的合成

  摘要：

  脂肪族伯胺的好氧氧化CH功能已通过仿生协同催化系统完成，以提供1,2-二取代的苯并咪唑类化合物，这些化合物在药物发现目标中起着重要的作用。这种单罐原子经济的多步工艺在温和的条件下进行，在环境空气和等摩尔量的每个偶合配偶体的条件下进行，构成了一种方便的环保策略，以功能化非活化脂族胺，这些胺仍然是非酶催化好氧性底物系统。

  DOI：

  10.1002/chem.201502487

文献信息

• Conventional and Microwave-Assisted Synthesis of Benzimidazole Derivatives and Their<i>In Vitro</i>Inhibition of Human Cyclooxygenase
  作者：Daniela Secci、Adriana Bolasco、Melissa D'Ascenzio、Flavio della Sala、Matilde Yáñez、Simone Carradori

  DOI：10.1002/jhet.1058

  日期：2012.9

  A large series of 1,2‐diaryl‐benzimidazole and 2‐aryl‐1H‐benzimidazole derivatives were synthesized with slight differences using both microwave irradiation and conventional heating methods. Usually higher yields and time reactions reduction were obtained with the former method. All compounds were assayed for their in vitro ability to inhibit human cyclooxygenases, and most of them showed an encouraging

  使用微波辐照和常规加热方法合成了一系列1,2-二芳基-苯并咪唑和2-芳基-1 H-苯并咪唑衍生物，但略有差异。通常，使用前一种方法可获得更高的产率和时间反应的减少。分析了所有化合物在体外抑制人环氧化酶的能力，其中大多数在微摩尔范围内显示出令人鼓舞的抑制活性和同工型选择性。
• Iridium complexes as light emitting materials and organic light emitting diode device
  申请人：Cheng Chien-Hong

  公开号：US20050116626A1

  公开（公告）日：2005-06-02

  Phosphorescent iridium complexes having Formula I or Formula II: wherein X is chosen from a monoanionic bidentate ligand; Z is chosen from an atomic group wherein Z together with the buta-1,3-diene to which Z is attached form an aryl group or heteroaryl group; R, R 1 , and R 2 are independently chosen from a hydrogen atom or a substituent; m is an integer from 0 to 4; and n is an integer from 0 to the maximum number of possible substituents on Z, are disclosed. Light emitting devices using the phosphorescent iridium complexes are also disclosed.

  具有化学式I或化学式II的磷光铱配合物：其中X选择自单阴离子双齿配体；Z选择自原子团，其中Z与其连接的丁二烯共同形成芳基或杂环基；R、R1和R2独立选择自氢原子或取代基；m为0至4的整数；n为0至Z可能取代基的最大数量的整数。公开了使用这些磷光铱配合物的发光器件。
• Novel bluish green benzimidazole-based iridium(<scp>iii</scp>) complexes for highly efficient phosphorescent organic light-emitting diodes
  作者：Jin-Hui Zhao、Yong-Xu Hu、Yan Dong、Xin Xia、Hai-Jun Chi、Guo-Yong Xiao、Xiao Li、Dong-Yu Zhang

  DOI：10.1039/c6nj03634a

  日期：——

  N-di(p-tolyl)amino)phenyl)cyclohexane (TAPC) (20 nm)/4,4′-N,N′-dicarbazole-biphenyl (CBP):Ir(III) complex (30 nm)/1,3,5-tris(N-phenylbenzimidazol-2-yl)benzene (TPBi) (50 nm)/8-hydroxyquinolinato lithium (Liq) (2 nm)/Al were fabricated to evaluate the potential applications of these fluorinated Ir(III) complexes. Good device performance (current efficiency: 48.0–70.1 cd A−1 and external quantum efficiency:

  设计并合成了三种全氟苯并咪唑基铱[Ir（III）]配合物，分别缩写为1F-Ir，2F-Ir和3F-Ir。详细研究了它们的光致发光，热学和电化学性能。这些Ir（III）配合物表现出强的蓝绿色发射，量子效率为0.68–0.81。具有ITO / 1,1-双（4-（N，N-二（对甲苯基）氨基）苯基）环己烷（TAPC）简单结构的有机发光二极管（OLED ）（20 nm）/ 4,4 ′ -N，N′-二咔唑-联苯（CBP）：Ir（III）络合物（30 nm）/ 1,3,5-tris（N制备了-苯基苯并咪唑-2-基）苯（TPBi）（50 nm）/ 8-羟基喹啉基锂（Liq）（2 nm）/ Al，以评估这些氟化Ir（III）配合物的潜在应用。器件性能良好（电流效率：48.0–70.1 cd A -1和外部量子效率：15.6–21.7％）。特别地，具有2F-Ir作为掺杂剂发射极的OLED表现出最佳性能，其最大电流效率为70
• Synthesis of some fluorescent benzimidazole derivatives using cobalt(ii) hydroxide as highly efficient catalyst — spectral and physico-chemical studies and ESIPT process
  作者：J. Jayabharathi、V. Thanikachalam、K. Jayamoorthy

  DOI：10.1039/c3pp50083g

  日期：2013.10

  Some fluorescent benzimidazole derivatives have been designed and synthesized using cobalt(II) hydroxide as highly efficient catalyst. Synthesized compounds have been characterized by 1H and 13C-NMR and mass spectral analysis. The solvent effect on the absorption and fluorescence bands has been analyzed and supplemented by computational studies. Solvatochromic effects on the spectral position and profile

  已经使用氢氧化钴（II）作为高效催化剂设计和合成了一些荧光苯并咪唑衍生物。合成的化合物的特征是1 H和13C-NMR和质谱分析。分析了溶剂对吸收带和荧光带的影响，并通过计算研究进行了补充。溶剂变色效应对固定荧光光谱的光谱位置和分布的影响清楚地表明，在极性和非极性环境下研究的所有化合物的发射单重态的电荷转移（CT）特性。苯并咪唑的荧光衰减令人满意地适合单个指数动力学。HOMO和LUMO轨道图片[DFT / B3LYP / 6-31G（d，p）]证明了在含有羟基的苯并咪唑衍生物中存在激发态分子内质子转移（ESIPT）。
• Organometallic complex for organic electroluminescent device
  申请人：Lin Cheng-Hung

  公开号：US06936716B1

  公开（公告）日：2005-08-30

  An organometallic complex having formula (I) wherein M is a transition metal; each A 1 and A 2 is independently a monodentate ligand, or A 1 and A 2 are covalently joined together to form a bidentate ligand; R 1 is H, C 1-18 alkyl, C 1-18 alkoxy, C 3-18 heteroalkyl, C 3-20 aryl, C 3-20 heteroaryl, or C 3-20 cycloalkyl; R 2 is the same or different and is H, C 1-18 alkyl, C 1-18 alkoxy, C 3-18 heteroalkyl, C 3-20 aryl, C 3-20 heteroaryl, or C 3-20 cycloalkyl, or two R 2 groups link together with the carbon atoms to which they are attached to form a 4- to 12-member aromatic or heteroaromatic ring; R 3 is the same or different and is H, CN, tricyanovinyl, halogen, CX 3 , C 1-18 alkyl, C 1-18 alkoxy, C 3-18 heteroalkyl, C 3-20 aryl, C 3-20 heteroaryl, or C 3-20 cycloalkyl, wherein X is halogen; m is the charge of M; n is 1, 2, or 3.

  一种具有式（I）的有机金属配合物，其中M是过渡金属；每个A1和A2分别是单齿配体，或A1和A2被共价地连接在一起形成双齿配体；R1是H、C1-18烷基、C1-18烷氧基、C3-18杂烷基、C3-20芳基、C3-20杂芳基或C3-20环烷基；R2相同或不同，是H、C1-18烷基、C1-18烷氧基、C3-18杂烷基、C3-20芳基、C3-20杂芳基或C3-20环烷基，或两个R2基团通过它们连接的碳原子形成4-到12-成员的芳香或杂芳环；R3相同或不同，是H、CN、三氰基乙烯、卤素、CX3、C1-18烷基、C1-18烷氧基、C3-18杂烷基、C3-20芳基、C3-20杂芳基或C3-20环烷基，其中X是卤素；m是M的电荷；n为1、2或3。