2-(4-tert-butylphenyl)-1-phenyl-1H-benzo[d]imidazole | 948906-37-4

• 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-tert-butylphenyl)-1-phenyl-1H-benzo[d]imidazole
• 英文别名: 1-Phenyl-2-(4-tert-butylphenyl)benzimidazole；2-(4-tert-butylphenyl)-1-phenylbenzimidazole
• CAS: 948906-37-4
• 化学式: C₂₃H₂₂N₂
• 分子量: 326.441
• InChiKey: BUMJRLKONQTGBY-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.4
• 重原子数：
  25
• 可旋转键数：
  3
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.17
• 拓扑面积：
  17.8
• 氢给体数：
  0
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  iridium(III) chloride trihydrate 、 2-(4-tert-butylphenyl)-1-phenyl-1H-benzo[d]imidazole 以 乙二醇乙醚 、 水 为溶剂， 反应 24.0h， 生成
  参考文献：
  名称：

  Simple molecular structure design of iridium(III) complexes: Achieving highly efficient non-doped devices with low efficiency roll-off

  摘要：

  To construct efficient emitters suitable for non-doped devices and deeply understand the relationship between structures and performances, we designed and synthesized two heteroleptic iridium(III) complexes based on 1,2-diphenyl-1H-benzoimidazole (PBI) ligands whose substituents are varied simply from methyl (complex 2) to tert-butyl groups (complex 3). The parent complex 1 with non-substituent on PBI ligand has also been presented for a better comparison. Their photophysical, electrochemical and electroluminescent (EL) performances are investigated systematically. Despite their structural modification, all complexes exhibit almost identical emission and excited-state characters, which are rationalized by the quantum-chemical calculations. However, the obvious differences on device performances are found. Non-doped device employing 3 as emitting layer displays the highest EL performance with maximum current efficiency (eta(c), (max)) of 18.6 cd A(-1) and power efficiency (h(p, max)) of 16.2 lm W-1 accompanied by low efficiency roll-off values, which is much higher than those of complexes 1 and 2. The obtained results herein suggest that introduction of the simple substituent into PBI ligand is an effective and feasible approach to develop highly efficient non-doped phosphors. (C) 2016 Elsevier B.V. All rights reserved.

  DOI：

  10.1016/j.orgel.2016.05.002
• 作为产物：
  描述：

  在 溶剂黄146 作用下， 生成 2-(4-tert-butylphenyl)-1-phenyl-1H-benzo[d]imidazole
  参考文献：
  名称：

  Simple molecular structure design of iridium(III) complexes: Achieving highly efficient non-doped devices with low efficiency roll-off

  摘要：

  To construct efficient emitters suitable for non-doped devices and deeply understand the relationship between structures and performances, we designed and synthesized two heteroleptic iridium(III) complexes based on 1,2-diphenyl-1H-benzoimidazole (PBI) ligands whose substituents are varied simply from methyl (complex 2) to tert-butyl groups (complex 3). The parent complex 1 with non-substituent on PBI ligand has also been presented for a better comparison. Their photophysical, electrochemical and electroluminescent (EL) performances are investigated systematically. Despite their structural modification, all complexes exhibit almost identical emission and excited-state characters, which are rationalized by the quantum-chemical calculations. However, the obvious differences on device performances are found. Non-doped device employing 3 as emitting layer displays the highest EL performance with maximum current efficiency (eta(c), (max)) of 18.6 cd A(-1) and power efficiency (h(p, max)) of 16.2 lm W-1 accompanied by low efficiency roll-off values, which is much higher than those of complexes 1 and 2. The obtained results herein suggest that introduction of the simple substituent into PBI ligand is an effective and feasible approach to develop highly efficient non-doped phosphors. (C) 2016 Elsevier B.V. All rights reserved.

  DOI：

  10.1016/j.orgel.2016.05.002

文献信息

• A Bioinspired Catalytic Aerobic Oxidative CH Functionalization of Primary Aliphatic Amines: Synthesis of 1,2-Disubstituted Benzimidazoles
  作者：Khac Minh Huy Nguyen、Martine Largeron

  DOI：10.1002/chem.201502487

  日期：2015.9.1

  Aerobic oxidative CH functionalization of primary aliphatic amines has been accomplished with a biomimetic cooperative catalytic system to furnish 1,2‐disubstituted benzimidazoles that play an important role as drug discovery targets. This one‐pot atom‐economical multistep process, which proceeds under mild conditions, with ambient air and equimolar amounts of each coupling partner, constitutes a

  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。
• Sulfur‐Catalyzed Oxidative Coupling of Dibenzyl Disulfides with Amines: Access to Thioamides and Aza Heterocycles
  作者：Thanh Binh Nguyen、Le Phuong Anh Nguyen、Thi Thu Tram Nguyen

  DOI：10.1002/adsc.201801695

  日期：2019.4.16

  In the presence of catalytic amounts of elemental sulfur, dibenzyl disulfide/DMSO was found to be an excellent thiobenzoylating agent of amines to provide a wide range of thioamides. The reaction becomes autocatalytic when anilines substituted by an o‐cyclizable group were used as nucleophile, leading to the corresponding 2‐aryl aza heterocycles.

  发现在催化量的元素硫存在下，二苄基二硫化物/ DMSO是一种出色的胺硫代苯甲酰化剂，可提供多种硫酰胺。当被邻环化基团取代的苯胺用作亲核试剂时，该反应变为自催化反应，从而导致相应的2-芳基氮杂杂环。
• Low efficiency roll-off and high performance OLEDs employing alkyl group modified iridium(<scp>iii</scp>) complexes as emitters
  作者：Li-Li Wen、Jing Yu、Hai-Zhu Sun、Guo-Gang Shan、Wen-Fa Xie、Zhong-Min Su

  DOI：10.1039/c6ra24142e

  日期：——

  Four Ir(iii) dyes employing modified 1,2-diphenyl-1H-benzoimidazole ligands were synthesized. Doped device using tBu-Ir-PI with tert-butyl group as emitter achieves high η_c of 42.0 cd A⁻¹ and η_p of 27.0 lm W⁻¹, respectively.

  我们合成了四种使用改性 1,2-二苯基-1H-苯并咪唑配体的 Ir(iii) 染料。使用带有叔丁基的 tBu-Ir-PI 作为发射体的掺杂器件分别实现了 42.0 cd A-1 的高 ηc 和 27.0 lm W-1 的 ηp。
• METHOD OF MAKING BENZAZOLES
  申请人：Shi Jianmin

  公开号：US20130172570A1

  公开（公告）日：2013-07-04

  This present invention provides a method of making benzazoles comprising a process of making aryl or alkyl benzazoles from corresponding aryl acid chlorides or alkyl acid chlorides without applying hazard condensing agent. The benzazole compounds described in this invention have following formula I: Wherein: n is an integer of from 3 to 8; Z is O, NR or S; and R and R′ are individually hydrogen; alkyl of from 1 to 24 carbon atoms, for example, propyl, t-butyl, heptyl, and the like; aryl or hetero-atom substituted aryl of from 5 to 20 carbon atoms, for example, phenyl and naphthyl, furyl, thienyl, pyridyl, quinolinyl and other heterocyclic systems; or halo such as chloro, fluoro, bromo, cyano; or atoms necessary to complete a fused aromatic ring; and B is a linkage unit consisting of alkyl, aryl, substituted alkyl, or substituted aryl which conjugately or unconjugately connects the multiple benzazoles together.

  本发明提供了一种制备苯并咪唑的方法，包括从相应的芳基酸氯化物或烷基酸氯化物中制备芳基或烷基苯并咪唑的过程，而无需应用危险的缩合剂。本发明中描述的苯并咪唑化合物具有以下式I： 其中： n是从3到8的整数； Z是O、NR或S； R和R'分别为氢、1至24个碳原子的烷基（例如丙基、叔丁基、庚基等）、5至20个碳原子的芳基或杂原子取代的芳基（例如苯基和萘基、呋喃基、噻吩基、吡啶基、喹啉基和其他杂环系统）或卤素，例如氯、氟、溴、氰；或必要的原子以完成融合芳环；且 B是连接多个苯并咪唑的共轭或非共轭的烷基、芳基、取代烷基或取代芳基的连接单元。
• BIPOLAR HOSTS FOR LIGHT EMITTING DEVICES
  申请人：NITTO DENKO CORPORTION

  公开号：US20140163237A1

  公开（公告）日：2014-06-12

  Some embodiments provide a compound represented by Formula 1: wherein R 1 , R 2 , R 3 , R 4 , R 5 , R 6 , R 7 and R 8 are independently H, C 1 -C 3 alkyl, or C 1-3 perfluoroalkyl; HT is optionally substituted carbazoyl, optionally substituted phenylcarbazolyl, optionally substituted (phenylcarbazolyl)phenyl, optionally substituted phenylnaphthylamine, or optionally substituted diphenylamine; and ET optionally substituted benzimidazol-2-yl, optionally substituted benzothiazol-2-yl, optionally substituted benzoxazol-2-yl, optionally substituted 3,3′-bipyridin-5-yl, optionally substituted quinolin-8-yl, optionally substituted quinolin-5-yl, or optionally substituted quinoxalin-5-yl. Other embodiments provide an organic light-emitting diode device comprising a compound of Formula 1.

  其中，某些实施例提供一种由式1表示的化合物： 其中，R1、R2、R3、R4、R5、R6、R7和R8独立地表示H、C1-C3烷基或C1-3全氟烷基；HT是可选取代的卡巴唑基、可选取代的苯基卡巴唑基、可选取代的（苯基卡巴唑基）苯基、可选取代的苯基萘胺或可选取代的二苯胺；ET是可选取代的苯并咪唑-2-基、可选取代的苯并噻唑-2-基、可选取代的苯并噁唑-2-基、可选取代的3,3'-联吡啶-5-基、可选取代的喹啉-8-基、可选取代的喹啉-5-基或可选取代的喹啉并吡啶-5-基。其他实施例提供一种由式1表示的化合物的有机发光二极管器件。