2-[3,5-双(三氟甲基)苯基]-4-甲基吡啶 | 583052-20-4

• 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
• 中文名称: 2-[3,5-双(三氟甲基)苯基]-4-甲基吡啶
• 英文名称: 2-(3,5-bis(trifluoromethyl)phenyl)-4-methylpyridine
• 英文别名: Pyridine, 2-[3,5-bis(trifluoromethyl)phenyl]-4-methyl-；2-[3,5-bis(trifluoromethyl)phenyl]-4-methylpyridine
• CAS: 583052-20-4
• 化学式: C₁₄H₉F₆N
• 分子量: 305.223
• InChiKey: QTHYYZWLKATFHB-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.6
• 重原子数：
  21
• 可旋转键数：
  1
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.21
• 拓扑面积：
  12.9
• 氢给体数：
  0
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  2-[3,5-双(三氟甲基)苯基]-4-甲基吡啶 在 tetrabutylammonium hydroxide 作用下， 以 四氢呋喃 、 水 为溶剂， 生成 platinum(II) [4,6-bis(trifluoromethyl)-2-(4-methyl-2-pyridinyl-κN)phenyl-κC][α,α-bis(trifluoromethyl)-2-pyrazol-1-ylmethylpropan-2-olato-κN1,κO]
  参考文献：
  名称：

  Syntheses, Structural Characterization, and First Electroluminescent Properties of Mono-cyclometalated Platinum(II) Complexes with Greater than Classical π−π Stacking and Pt−Pt Distances

  摘要：

  A series of mono-cyclometalated Pt(II) complexes (9, 10, 13, 15, and 17) bearing 2-(3,5-bis(trifluoromethyl)phenyl)-4-methylpyridine (1) as the same chromophoric Nboolean ANDC cyclometalated ligand and the second nonchromophoric bidenate ligands with increasing bulkiness were synthesized by the following steps. The palladium-catalyzed cross-coupling reaction between 2-chloro-4-methylpyridine (2) and 3,5-bis(trifluoromethyl)phenylboronic acid (3) was used to prepare 2-(3,5-bis(trifluoromethyl)phenyl)-4-methylpyridine (1). Di-tert-butyl(trimethylsilyl)anylmethylphosphine, tert-BU2P-CH2-SiMe3 (5), was used as a ligand for the Suzuki coupling. The cyclometalation of 1 by K2PtCl4 (7) was carried out in (MeO)(3)P=O (8) with the formation of a chloro-bridged dimer Nboolean ANDCPt(mu-Cl)(2)PtCboolean ANDN (9). The reactions of 9 with 2,2,6,6-tetramethylheptane-3,5-dionate (11), 1,1,1,3,3,3-hexafluoro-2-pyrazol-1-ylmethylpropan-2-ol (12), 2-[(diphenylphosphanyl)methyl]-1,1,1,3,3,3-hexafluoropropan-2-ol (14), and 2-[(di-tert-butylphosphanyl)methyl]-1,1,1,3,3,3-hexafluoropropan-2-ol(16) afforded square-planar Pt(II) complexes 10, 13, 15, and 17, correspondingly. According to X-ray analyses, the plane-to-plane distances of the pi-pi stacked complexes (10, 13, 15, and 17) increase from 3.478 Angstrom for 10 to 4.203 Angstrom for 15. The value of 4.203 Angstrom for aromatic- aromatic pi-pi interaction is greater than the usual range of 3.3-3.8 Angstrom for these phenomena. Pt-pt distances increase from 5.076 Angstrom for 13 to 8.123 Angstrom for 17. The geometry of complex 17 deviates greatly from square planar and is best described as "bowl-shaped". The effect of an increased pi-pi stacking distance on the electroluminescent properties of these Pt compounds is studied. The typical yellow luminescence band associated with the excimers of Pt compounds is absent for complex 15; however, it shows a green 540 nm electroluminesce band instead. An efficient LED constructed using compound 15 shows green electroluminescence with a peak efficiency of 6 cd/A.

  DOI：

  10.1021/om049211t
• 作为产物：
  描述：

  2-氯-4-甲基吡啶 、 3,5-双(三氟甲基)苯硼酸 在 四(三苯基膦)钯 、 sodium carbonate 作用下， 以 乙醇 、 水 、 甲苯 为溶剂， 反应 8.0h， 以60%的产率得到2-[3,5-双(三氟甲基)苯基]-4-甲基吡啶
  参考文献：
  名称：

  辅助配体在用于蓝色 OLED 的铱 (III) 配合物中的作用

  摘要：

  在这项研究中，新的深蓝色发光混合配体铱 (III) 配合物包含一个环金属化、两个相互反式的膦和两个顺式辅助配体，如 Ir{(CF3)2Meppy}(PPh3)2(H)(Cl ), [Ir{(CF3)2Meppy}(PPh3)2(H)(NCMe)]+ 和 Ir{(CF3)2Meppy} (PPh3)2(H)(CN), [(CF3)2Meppy = 2-(合成并研究了 3',5'-双-三氟甲基苯基)-4-甲基吡啶]以将磷光波长调整到深蓝色区域并提高发光效率。我们研究了辅助配体的强场能力，以深入了解导致发光颜色变化和不同发光效率的因素。这项工作代表了设计深蓝色磷光铱配合物的策略。苯环上取代的吸电子三氟甲基，吡啶环上的给电子甲基和氰基强场辅助配体增加了 HOMO-LUMO 间隙以实现发射颜色的低色移。结果，Ir{(CF3)2Meppy}(PPh3)2(H)(Cl)、[Ir{(CF3)2Meppy}

  DOI：

  10.1080/15421400902945576

文献信息

• Novel catalysts useful for catalyzing the coupling of arylhalides with arylboronic acids
  申请人：Ionkin Sergey Alex

  公开号：US20060281923A1

  公开（公告）日：2006-12-14

  The present invention relates to a new method of cross-coupling aryl moieties comprising reacting an arylhalide with an arylboronic acid in the presence of a palladium compound and a compound comprising a di-alkylphosphine moiety.

  本发明涉及一种新的芳基偶联方法，包括在钯化合物和含有二烷基膦基团的化合物存在下，将芳基卤化物与芳基硼酸反应。
• Rare Organometallic Complex of Divalent, Four-Coordinate Iridium:  Synthesis, Structural Characterization, and First Insights into Reactivity
  作者：Alex S. Ionkin、William J. Marshall

  DOI：10.1021/om049444k

  日期：2004.12.1

  carbon monoxide and a THF solution of complex 2 led to the reduction to the IrI complex trans-Ir(CO)[η2-OC(CF3)2PtBu2][η1-tBu2PC(CF3)2OH] (11). The C-cyclometalated complex Ir[η2-OC(CF3)2PtBu2][η3-CH2CMe2P(tBu)C(CF3)2O] (12) is formed upon heating of aprotic solutions of complex 2. The square-pyramidal five-coordinate IrIII hydride 3 reacts with sterically small ligands to form coordinately saturated octahedral

  新型体积庞大的P∧O二齿膦t Bu 2 PC（CF 3）2 OH（1）在2-（3,5-双（三氟甲基）苯基）-4-甲基吡啶（4）环金属化中的应用。的IrCl 3导致铱的不寻常的配位状态的稳定化：从单核的罕见的例子，顺磁性的，正方形平面的Ir II络合物，反式-Ir [η 2 -OC（CF 3）2 P吨卜2 ] 2（2个），在配位不饱和，五配位的单氢化物，反式-Ir（H）[η 2 -OC（CF 3）2 P吨卜2 ] 2（3），和单环金属化配合物，C ∧ NIR（H ）（CO）[η 2 -OC（CF 3）2 P吨卜2 ]（6）。配合物2可以通过两种替代方法合成：在碱（例如Et 4 NOH）的催化存在下通过3的空中氧化或通过3的升华来合成。在真空下。Ir II络合物2经历加氢生成Ir III -H络合物3。一氧化碳和的复合物的THF溶液之间的反应2导致减少到IR我复杂反-Ir（CO）[η 2 -OC（CF
• Palladium-Catalyzed Cross-Coupling Reactions of 2-Pyridylborates with Air-Stable HASPO Preligands
  作者：Lutz Ackermann、Harish Potukuchi

  DOI：10.1055/s-0029-1218020

  日期：2009.10

  A novel, air-stable TADDOLP(O)H derivative bearing electron-withdrawing substituents allows for efficient Suzuki-Miyaura cross-couplings with challenging electron-deficient 2-pyr-idylborates as nucleophiles.

  一种新颖的空气稳定的TADDOLP(O)H衍生物，具有电子吸引取代基，可以与具有挑战性的电子缺乏的2-吡啶硼酸盐作为亲核试剂进行高效的铃木-宫浦交叉偶联反应。
• New trifluoromethyl modified iridium(III) complex for high-efficiency sky-blue phosphorescent organic light-emitting diode
  作者：Xiao-Kang Zheng、Fang-Qing Zhao、Meng-Na Yin、Cheng Qian、Shuai-Hang Bi、Peng Tao、Yan-Qin Miao、Shu-Juan Liu、Qiang Zhao

  DOI：10.1016/j.tetlet.2021.153181

  日期：2021.7

  efficiency (0.22). The incorporation of trifluoromethyl moiety into the complex not only enhances the robust chemical stability but also provides the steric hindrance beneficial to organic light-emitting diodes. The sky-blue OLEDs based on this complex show narrow emission band with full width at half maxima of 54 nm. The peak power efficiency, current efficiency and external quantum efficiency of electroluminescence

  以双（三氟甲基）修饰的4-甲基-2-苯基吡啶为环金属化配体，2-（1 H）配位化合物（Ir-CF 3 -咪唑-2-基)吡啶作为辅助配体。红外-CF 3显示强烈的天蓝色磷光（465 nm，肩峰为 494 nm），溶液光致发光效率高（0.22）。三氟甲基部分掺入复合物中不仅增强了强大的化学稳定性，而且还提供了有利于有机发光二极管的空间位阻。基于这种复合物的天蓝色 OLED 显示出窄发射带，半峰全宽为 54 nm。电致发光的峰值功率效率、电流效率和外量子效率分别高达36.05 lm/W、51.45 cd/A和21.74%。
• Electroluminescent bis-cyclometalled iridium compounds and devices made with such compounds
  申请人：Ionkin Sergey Alex

  公开号：US20070259205A1

  公开（公告）日：2007-11-08

  One embodiment of this invention is bis-cyclometalled electroluminescent complexes of iridium(III). Another embodiment of this invention is electronic devices in which the active layer includes an bis-cyclometalled electroluminescent Ir(III) complex.

  本发明的一种实施例是铱（III）的双环金属电致发光配合物。本发明的另一种实施例是电子器件，其中活性层包括双环金属电致发光Ir（III）配合物。