2-(thiophen-2-yl)-4-(trifluoromethyl)pyridine

• 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: 2-(thiophen-2-yl)-4-(trifluoromethyl)pyridine
• 英文别名: 2-Thiophen-2-yl-4-(trifluoromethyl)pyridine
• 化学式: C₁₀H₆F₃NS
• 分子量: 229.226
• InChiKey: XGUCTHVDLHVQJL-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.1
• 重原子数：
  15
• 可旋转键数：
  1
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.1
• 拓扑面积：
  41.1
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  iridium(III) chloride trihydrate 、 2-(thiophen-2-yl)-4-(trifluoromethyl)pyridine 以 乙二醇乙醚 、 水 为溶剂， 生成
  参考文献：
  名称：

  基于噻吩-嘧啶/吡啶衍生物的黄-红色磷光铱(III)配合物的合成、光物理性质和DFT计算

  摘要：

  一系列杂配磷光铱 (III) 配合物 [Ir(C^N) 2 (O^O)] (C^N = 2-(thiophen-2-yl)pyrimidine (tppm), 2-(benzo[b]噻吩-2-基)嘧啶 (btppm), 2-(噻吩-2-基)-4-(三氟甲基)吡啶 (cf 3 thp), 2-(苯并[b]噻吩-2-基)-4-(三氟甲基)吡啶 (cf 3 btp)；O^O = 乙酰丙酮 (acacH)) 已被合成和表征，并报道了它们的光物理性质。所有这些配合物在室温下在 CH 2 Cl 2溶液中在558–647 nm 的光谱范围内发出黄红色，量子产率为 20.1–50.9%，发射寿命为 0.23–0.33 μs。密度泛函理论（DFT）和时间相关-DFT （ TD-DFT) 对这些配合物的计算有助于详细分配吸收和发射过程中涉及的激发态，即金属到配体和以配体为中心的电荷转移 (MLCT/LC) 跃迁。这些电荷转移型带由

  DOI：

  10.1002/jccs.202200370
• 作为产物：
  描述：

  2-噻吩硼酸 、 2-溴-4-(三氟甲基)吡啶 在 (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride 、 potassium phosphate monohydrate 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 10.0h， 以85.9%的产率得到2-(thiophen-2-yl)-4-(trifluoromethyl)pyridine
  参考文献：
  名称：

  Iridium(III) complexes adopting thienylpyridine derivatives for yellow-to-deep red OLEDs with low efficiency roll-off

  摘要：

  By introduction of trifluoromethyl and phenyl groups to 2-(2-thienyl)pyridine (thp), four new phosphorescent bis-cyclometalated iridium(III) complexes, (thp)(2)Ir(tpip), (cf(3)thp)(2)Ir(tpip), (cf(3)btp)(2)Ir(tpip) and (3-cf(3)btp)(2)Ir (tpip) (cf(3)thp = 2-(thiophen-2-yl)-4-(trifluoromethyl)pyridine, cf(3)btp = 2-(benzo[b]thiophen-2-yl)-4-(trifluoromethyl)pyridine, 3-cf(3)btp = 2-(benzo[b]thiophen-3-yl)-4-(trifluoromethyl)pyridine, tpip = tetraphenylimidodiphosphinate), were synthesized and fully characterized. The density functional theory and time dependent DFT calculations show that the frontier orbitals are mainly localized in the Ir(III) ion and the cyclometalated ligands. Thus, the photophysical properties were dominated by the cyclometalated C boolean AND N ligand, attributed to (MLCT)-M-3 and (ILCT)-I-3 transition. These Ir(III) complexes emit in the yellow-to-deep red region with photoluminescence quantum yields in the range 40.5-86.4% in CH2Cl2 solutions at 298 K. The organic light-emitting diodes (OLEDs) using (thp)(2)Ir(tpip), (cf(3)thp)(2)Ir(tpip) and (cf(3)btp)(2)Ir(tpip) as yellow, orange and deep red emitters display good electroluminescent performance with low efficiency roll-off. Notably, the device based on (cf(3)thp)(2)Ir(tpip) possesses very high EL efficiencies with the maximum luminance efficiency and external quantum efficiency (EQE) of 53.9 cd A(-1) and 17.9%, respectively. Furthermore, the EQE for this complex could be still retained as 15.4% at a luminance of 1000 cd m(-2).

  DOI：

  10.1016/j.dyepig.2018.11.017

文献信息

• Luminescence device, display apparatus and metal coordination compound
  申请人：CANON KABUSHIKI KAISHA

  公开号：EP1191612A2

  公开（公告）日：2002-03-27

  A luminescence device is principally constituted by a pair of electrodes and an organic compound layer disposed therebetween. The layer contains a metal coordination compound represented by the following formula (1): wherein M denotes Ir, Rh or Pd; n is 2 or 3; CyN denotes a substituted or unsubstituted cyclic group containing a nitrogen atom connected to M and capable of containing another nitrogen atom and/or a sulfur atom; and CyC denotes a substituted or unsubstituted cyclic group containing a carbon atom connected to M and capable of containing a nitrogen atom and/or a sulfur atom, CyN and CyC being connected to each other via a covalent bond, and each of substituents for CyN and CyC being selected from the group consisting of a halogen atom; nitro group; a trialkylsilyl group containing three linear or branched alkyl groups each independently having 1 - 8 carbon atoms; and a linear or branched alkyl group having 1 - 20 carbon atoms capable of including one or at least two non-neighboring methylene groups which can be replaced with -O-, -S-, -CO-, -CO-O-, -O-CO-, -CH=CH- or -C≡C- and capable of including a hydrogen atom which can be replaced with a fluorine atom; with the proviso that a sum of nitrogen atom and sulfur atom present in ring structures of CyN and CyC is at least 2.

  发光器件主要由一对电极和置于其间的有机化合物层构成。该层含有下式（1）所代表的金属配位化合物： 其中 M 表示 Ir、Rh 或 Pd；n 为 2 或 3；CyN 表示含有一个与 M 相连的氮原子并能含有另一个氮原子和/或一个硫原子的取代或未取代的环状基团；CyC 表示含有一个与 M 相连的碳原子并能含有一个氮原子和/或一个硫原子的取代或未取代的环状基团，CyN 和 CyC 通过共价键相互连接，CyN 和 CyC 的每个取代基均选自由卤素原子、硝基、三烷基、四烷基、五烷基、六烷基、七烷基、八烷基和九烷基组成的组；硝基； 三烷基硅烷基，包含三个各自独立具有 1 - 8 个碳原子的直链或支链烷基；具有 1-20 个碳原子的直链或支链烷基，该烷基可包括一个或至少两个非相邻的亚甲基，该亚甲基可被-O-、-S-、-CO-、-CO-O-、-O-CO-、-CH=CH-或-C≡C-取代，并可包括一个氢原子，该氢原子可被一个氟原子取代；但在 CyN 和 CyC 的环结构中存在的氮原子和硫原子之和至少为 2。
• Metal coordination compound, luminescence device and display apparatus
  申请人：CANON KABUSHIKI KAISHA

  公开号：EP1211257A2

  公开（公告）日：2002-06-05

  An organic EL device includes a luminescence layer containing, as a luminescent material allowing a high-luminescence and high-efficiency luminescence for a long period of time, a metal coordination compound represented by the following formula (1): LmML'n, wherein M denotes Ir, Pt, Ph or Pd; L denotes a bidentate ligand; L' denotes a bidentate ligand different from L; m is an integer of 1, 2 or 3; and n is an integer of 0, 1 or 2 with the proviso that the sum of m and n is 2 or 3. The partial structure MLm is represented by a formula (2) or a formula (3) shown below, and the partial structure ML'n is represented by a formula (4) or a formula (5) shown below: wherein CyN1, CyN2 and CyN3 independently denote a substituted or unsubstituted cyclic group containing a nitrogen atom connected to M; CyN4 denotes a cyclic group containing 8-quinoline or its derivative having a nitrogen atom connected to M; CyC1, CyC2 and CyC3 independently denote a substituted or unsubstituted cyclic group containing a carbon atom connected to M, with the proviso that the metal coordination compound is represented by the formula (2) when n is 0.

  一种有机电致发光器件包括一个发光层，该发光层含有下式(1)表示的金属配位化合物，该金属配位化合物是一种发光材料，可以长时间发出高亮度和高效率的荧光：LmML'n，其中 M 表示 Ir、Pt、Ph 或 Pd；L 表示双齿配体；L'表示不同于 L 的双齿配体；m 是 1、2 或 3 的整数；n 是 0、1 或 2 的整数，但 m 和 n 之和为 2 或 3。部分结构 MLm 用下图中的式 (2) 或式 (3) 表示，部分结构 ML'n 用下图中的式 (4) 或式 (5) 表示： 其中 CyN1、CyN2 和 CyN3 独立地表示含有与 M 相连的氮原子的取代或未取代的环状基团；CyN4 表示含有与 M 相连的氮原子的 8-喹啉或其衍生物的环状基团；CyC1、CyC2 和 CyC3 独立地表示含有与 M 相连的碳原子的取代或未取代的环状基团，但当 n 为 0 时，金属配位化合物由式（2）表示。
• Limuninescence device, display apparatus and metal coordination compound
  申请人：——

  公开号：US20020063516A1

  公开（公告）日：2002-05-30

  A luminescence device is principally constituted by a pair of electrodes and an organic compound layer disposed therebetween. The layer contains a metal coordination compound represented by the following formula (1): 1 wherein M denotes Ir, Rh or Pd; n is 2 or 3; CyN denotes a substituted or unsubstituted cyclic group containing a nitrogen atom connected to M and capable of containing another nitrogen atom and/or a sulfur atom; and CyC denotes a substituted or unsubstituted cyclic group containing a carbon atom connected to M and capable of containing a nitrogen atom and/or a sulfur atom, CyN and CyC being connected to each other via a covalent bond, and each of substituents for CyN and CyC being selected from the group consisting of a halogen atom; nitro group; a trialkylsilyl group containing three linear or branched alkyl groups each independently having 1-8 carbon atoms; and a linear or branched alkyl group having 1-20 carbon atoms capable of including one or at least two non-neighboring methylene groups which can be replaced with —O—, —S—, —CO—, —CO—O—, —O—CO—, —CH═CH— or —C≡C— and capable of including a hydrogen atom which can be replaced with a fluorine atom; with the proviso that a sum of nitrogen atom and sulfur atom present in ring structures of CyN and CyC is at least 2.

  发光器件主要由一对电极和置于其间的有机化合物层构成。该层含有下式（1）所代表的金属配位化合物： 1 其中 M 表示 Ir、Rh 或 Pd；n 为 2 或 3；CyN 表示取代或未取代的环状基团，该基团含有一个与 M 相连的氮原子，并可含有另一个氮原子和/或硫原子；以及 CyC 表示取代或未取代的环状基团，该基团含有一个与 M 相连的氮原子，并可含有另一个氮原子和/或硫原子；CyC 表示一个取代或未取代的环状基团，其中含有一个与 M 相连的碳原子，并可含有一个氮原子和/或一个硫原子，CyN 和 CyC 通过共价键相互连接，CyN 和 CyC 的每个取代基均选自由卤素原子、硝基组成的组；含有三个各自独立具有 1-8 个碳原子的直链或支链烷基的三烷基硅烷基；以及具有 1-20 个碳原子的直链或支链烷基，该烷基可包括一个或至少两个非相邻亚甲基，这些亚甲基可用-O-、-S-、-CO-、-CO-O-、-O-CO-、-CH&boxH；CH-或-C≡C-，并能包括一个可被氟原子取代的氢原子；但在 CyN 和 CyC 的环结构中存在的氮原子和硫原子之和至少为 2。
• Luminescence device and display apparatus
  申请人：CANON KABUSHIKI KAISHA

  公开号：EP1191612B1

  公开（公告）日：2009-09-09
• US6821646B2
  申请人：——

  公开号：US6821646B2

  公开（公告）日：2004-11-23