1-(3-(trifluoromethyl)phenyl)isoquinoline | 910923-26-1

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡啶及其衍生物
• 英文名称: 1-(3-(trifluoromethyl)phenyl)isoquinoline
• 英文别名: 1-[3-(Trifluoromethyl)phenyl]isoquinoline
• CAS: 910923-26-1
• 化学式: C₁₆H₁₀F₃N
• 分子量: 273.257
• InChiKey: AGRCKFAUVYPTQO-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.6
• 重原子数：
  20
• 可旋转键数：
  1
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.06
• 拓扑面积：
  12.9
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  1-(3-(trifluoromethyl)phenyl)isoquinoline 、 在 乙二醇甲醚 、 silver trifluoromethanesulfonate 作用下， 以 neat (no solvent, solid phase) 为溶剂， 生成
  参考文献：
  名称：

  用于快速高效合成三环金属化铱 （III） 配合物的固态机械化学

  摘要：

  Tris-环金属化铱 （III） 配合物作为有机发光二极管 （OLED）、光氧化还原催化剂和生物成像探针等有吸引力的前瞻性材料而受到广泛关注。然而，它们的制备通常需要较长的反应时间、大量的高沸点溶剂、多步合成和惰性气体管路技术。遗憾的是，从生产成本和环境角度来看，这些要求都存在重大缺陷。在此，我们表明，使用球磨的两步机械化学方案能够从相对便宜的氯化铱 （III） 水合物中快速有效地合成各种三环金属化铱 （III） 络合物，而无需在空气中使用大量有机溶剂。值得注意的是，还演示了直接的一锅程序。目前的固态方法有望激发为这些有价值的铱基配合物开发经济高效且及时的生产方法，以及发现新的磷光材料、传感器和催化剂。

  DOI：

  10.1039/d3sc05796h
• 作为产物：
  描述：

  3-(三氟甲基)苯甲酰氯 在 双氧水 、 三氟乙酸 、 sodium hydroxide 作用下， 以 乙醚 、 乙酸乙酯 为溶剂， 反应 12.5h， 生成 1-(3-(trifluoromethyl)phenyl)isoquinoline
  参考文献：
  名称：

  有机酸催化的芳基酰基过氧化物对杂环的 Minisci 型芳基化

  摘要：

  已经报道了一种用芳基酰基过氧化物对杂环进行 Minisci 型芳基化的无金属方法。这种策略可以在没有金属催化剂的情况下从市售的起始材料快速简单地合成一系列 Minisci 型加合物。提出了用于这种转变的自由基途径机制。

  DOI：

  10.1039/d2ob01187e

文献信息

• Deep-Red and Near-Infrared Iridium Complexes with Fine-Tuned Emission Colors by Adjusting Trifluoromethyl Substitution on Cyclometalated Ligands Combined with Matched Ancillary Ligands for Highly Efficient Phosphorescent Organic Light-Emitting Diodes
  作者：Shuonan Chen、Hai Bi、Wenjing Tian、Yu Liu

  DOI：10.3390/molecules27010286

  日期：——

  Six novel Ir(C^N)2(L^X)-type heteroleptic iridium complexes with deep-red and near-infrared region (NIR)-emitting coverage were constructed through the cross matching of various cyclometalating (C^N) and ancillary (LX) ligands. Here, three novel C^N ligands were designed by introducing the electron-withdrawing group CF3 on the ortho (o-), meta (m-), and para (p-) positions of the phenyl ring in the 1-phenylisoquinoline (piq) group, which were combined with two electron-rich LX ligands (dipba and dipg), respectively, leading to subsequent iridium complexes with gradually changing emission colors from deep red (≈660 nm) to NIR (≈700 nm). Moreover, a series of phosphorescent organic light-emitting diodes (PhOLEDs) were fabricated by employing these phosphors as dopant emitters with two doping concentrations, 5% and 10%, respectively. They exhibited efficient electroluminescence (EL) with significantly high EQE values: >15.0% for deep red light0 (λmax = 664 nm) and >4.0% for NIR cases (λmax = 704 nm) at a high luminance level of 100 cd m−2. This work not only provides a promising approach for finely tuning the emission color of red phosphors via the easily accessible molecular design strategy, but also enables the establishment of an effective method for enriching phosphorescent-emitting molecules for practical applications, especially in the deep-red and near-infrared region (NIR).

  通过交叉匹配不同的环金属(C^N)和辅助(LX)配体，构建了六种新型Ir(C^N)2(L^X)异核配位的铱配合物，具有深红色和近红外区域(NIR)发射覆盖。在此基础上，设计了三种新型C^N配体，通过在1-苯基异喹啉(piq)基团的邻(ortho)、间(meta)和对(para)位引入电子吸引基CF3，分别与两种电子富集的LX配体(dipba和dipg)结合，导致铱配合物的发射颜色逐渐变化，从深红色(≈660 nm)到NIR(≈700 nm)。此外，通过将这些荧光体作为掺杂发射体，制备了一系列磷光有机电致发光二极管(PhOLEDs)，分别采用5%和10%的掺杂浓度。它们在高亮度水平(100 cd m−2)下表现出高效的电致发光(EQE)：对于深红光(λmax = 664 nm)，EQE值>15.0%，对于NIR情况(λmax = 704 nm)，EQE值>4.0%。这项工作不仅提供了一种有前途的方法，通过易于访问的分子设计策略来精细调节红色荧光体的发射颜色，而且还实现了一种有效的方法，用于丰富磷光发射分子的实际应用，特别是在深红色和近红外区域(NIR)。
• METAL COMPLEX, POLYMER, AND ELEMENT OBTAINED USING SAME
  申请人：Sumitomo Chemical Company, Limited

  公开号：EP2492276B1

  公开（公告）日：2014-10-08
• Studies of the 5‘-Substituted Phenylisoquinoline-Based Iridium Complexes Using Density Functional Theory
  作者：Cheng-Hsien Yang、Wei-Lin Su、Kai-Hung Fang、Shao-Pin Wang、I-Wen Sun

  DOI：10.1021/om060323p

  日期：2006.9.1

  To examine the effects of coordination sites and the nature of ligands reported for color-tuning of a few cyclometalated Ir(III) complexes, a series of 3'-substituted (F, CH3, OCH3, and CF3) phenylisoquinoline (piq) ligands were synthesized and successfully used to prepare iridium complexes, including bis[1-(5'-methyl) phenylisoquinolinato-N,C-2'] iridium(III) (acetylacetonate) (6a1), bis[1-(5'-trifluoromethyl) phenylisoquinolinato-N, C-2'] iridium(III) (acetylacetonate) (6a2), bis[1-(5'-methoxy) phenylisoquinolinato-N, C-2']iridium( III) (acetylacetonate) (6a3), and bis[1-(5'-fluoro) phenylisoquinolinato-N, C-2'] iridium(III) (acetylacetonate) (6a4). Density functional theory results indicate that two conflicting effects, electronic and steric, can be applied to account for the substitution-sensitive coordination sites of piq: the methoxyl- or fluoro-substituted ligand generates both 2'-coordinated and 6'-coordinated isomers. Coordination of methoxy substitution prefers 6'-coordination of piq dominated by steric effects, while coordination of fluoro substitution prefers 2'-coordination, arising from better back-donation of the iridium center. Correlations of HOMO-LUMO gaps with electroluminescence (EL) data are discussed. More importantly, the EL data are well predicted by time-dependent density functional theory calculations.
• METAL COMPLEX, POLYMER COMPOUND AND DEVICE USING THE SAME
  申请人：Okamura Rei

  公开号：US20120205585A1

  公开（公告）日：2012-08-16

  A metal complex represented by the following formula (1): wherein R 1 to R 6 , R 8 and R 11 to R 20 represent a hydrogen atom, a halogen atom, an alkyl group, an alkoxy group, an alkylthio group, an aryl group, an aryloxy group, an arylthio group, an arylalkyl group, an arylalkoxy group, an arylalkylthio group, an acyl group, an acyloxy group, an amide group, an acid imide group, an imine residue, a substituted amino group, a substituted silyl group, a substituted silyloxy group, a substituted silylthio group, a substituted silylamino group, a monovalent heterocyclic group, a heteroaryloxy group, a heteroarylthio group, an arylalkenyl group, an arylalkynyl group, a substituted carboxyl group or a cyano group; Z 1 to Z 5 represent —C(R*)═ or a nitrogen atom, wherein R* represents a hydrogen atom or a substituent, provided that at least two of Z 1 to Z 5 are nitrogen atoms; m represents 1 or 2.
• Organic acid catalysed Minisci-type arylation of heterocycles with aryl acyl peroxides
  作者：Yani Ouyang、Xiaoguang Yue、Jiehai Peng、Jiashun Zhu、Qiuyuan Shen、Wanmei Li

  DOI：10.1039/d2ob01187e

  日期：——

  A metal-free method for the Minisci-type arylation of heterocycles with aryl acyl peroxides has been reported. This strategy enables the rapid and simple synthesis of a series of Minisci-type adducts from commercially available starting materials without metal catalysts. A free-radical-pathway mechanism is suggested for this transformation.

  已经报道了一种用芳基酰基过氧化物对杂环进行 Minisci 型芳基化的无金属方法。这种策略可以在没有金属催化剂的情况下从市售的起始材料快速简单地合成一系列 Minisci 型加合物。提出了用于这种转变的自由基途径机制。