2-(1-benzothiophen-2-yl)-5-trifluoromethylpyridine | 405282-51-1

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 苯并噻吩类
• 英文名称: 2-(1-benzothiophen-2-yl)-5-trifluoromethylpyridine
• 英文别名: 2-benzo[b]thiophen-2-yl-5-trifluoromethyl-pyridine；Hbtfmp；2-[5-(Trifluoromethyl)-2-pyridyl]benzo[b]thiophene；2-(1-benzothiophen-2-yl)-5-(trifluoromethyl)pyridine
• CAS: 405282-51-1
• 化学式: C₁₄H₈F₃NS
• 分子量: 279.285
• InChiKey: GQWCRENJRGIVAF-UHFFFAOYSA-N

物化性质

• 沸点：
  368.8±37.0 °C(Predicted)
• 密度：
  1.362±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4.5
• 重原子数：
  19
• 可旋转键数：
  1
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.07
• 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：

  氯化铱(III) 水合物 、 2-(1-benzothiophen-2-yl)-5-trifluoromethylpyridine 以 乙二醇乙醚 、 水 为溶剂， 生成 di[bis(2-benzo[b]thiophen-2-yl-5-trifluoromethyl-pyridinato-N,C(3'))iridium(III)(μ-chloro)]
  参考文献：
  名称：

  Tuning iridium(III) complexes containing 2-benzo[b]thiophen-2-yl-pyridine based ligands in the red region

  摘要：

  Synthesis and characterization of four iridium(III) complexes containing 2-benzo[b]thiophen-2-yl-pyridine based ligands are reported. The absorption, emission, electrochemistry, and thermostability of the complexes were systematically investigated. The (btmp)(2)Ir(acac) (btmp = 2-benzo[b]thiophen-2-yl-4-methyl-pyridyl, acac = acetyl acetone) was characterized using X-ray crystallography. Calculation on the electronic ground state for (btmp)(2)Ir(acac) was carried out using B3LYP density functional theory, HOMO levels are a mixture of Ir and btmp ligand orbitals, while the LUMO is predominantly btmp ligand based. Introduction of substituents (CH3, CF3) into pyridyl ring in a typical red emitter (btp)(2)Ir(acac) leads to a marked decrease in the sublimation temperature, which is more suitable for OLEDs process. Electrochemical studies showed that (btmp)(2)Ir(acac) has a slightly lower oxidation potential, but (btfmp)(2)Ir(acac), (btfmp)(2)Ir(dbm), and (btfmp)(2)Ir(pic) (btfmp = 2-benzo[b]thiophen-2-yl-5-trifluoromethyl-pyridine, dbm = dibenzoylmethane, pic = 2-picolinic acid) containing CF3 group are much difficult to oxidate than (btp)(2)Ir(acac). The emission characteristics of these complexes can be tuned by either changing the substituents and their position on 2-benzo[b]thiophen-2-yl-pyridine or using different monoanionic ligands, showing emission lambda(max) values from 604 to 638 nm in CH2Cl2 solution at room temperature. (c) 2007 Elsevier B.V. All rights reserved.

  DOI：

  10.1016/j.ica.2007.03.023
• 作为产物：
  描述：

  苯并噻吩-2-硼酸 、 2-溴-5-(三氟甲基)吡啶 在 palladium bis[bis(diphenylphosphino)ferrocene] dichloride 、 potassium carbonate 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 10.0h， 以71.6%的产率得到2-(1-benzothiophen-2-yl)-5-trifluoromethylpyridine
  参考文献：
  名称：

  红光铱配合物及其制备方法和应用

  摘要：

  本发明公开了红光铱配合物及其制备方法和应用，该红光铱配合物的制备方法，包括以下步骤：①由取代的2‑卤代吡啶与2‑硼酸苯并噻吩经suzuki偶联反应得到第一中间体；②由水合三氯化铱与步骤①得到的第一中间体反应得到第二中间体；③由二（二苯基膦酰）胺或其钾盐与步骤②得到的第二中间体反应得到目标产物。上述红光铱配合物在制备有机发光二极管上的应用。本发明的红光铱配合物以含氟取代的2‑吡啶苯并噻吩作为主结构，同时以二（二苯基膦酰）胺作为辅助配体，该结构的红光铱配合物发光亮度高，发光稳定性好，将其应用到有机发光二极管中能够显著提高发光效率和使用寿命。

  公开号：

  CN108997434B

文献信息

• Triplet Excited States Modulated by Push–Pull Substituents in Monocyclometalated Iridium(III) Photosensitizers
  作者：Shin-ya Takizawa、Sora Katoh、Atsushi Okazawa、Naoya Ikuta、Satoko Matsushima、Fanyang Zeng、Shigeru Murata

  DOI：10.1021/acs.inorgchem.0c03802

  日期：2021.4.5

  A series of novel monocyclometalated [Ir(tpy)(btp)Cl]+ complexes (Ir2–Ir5) were synthesized using 2,2′:6′,2″-terpyridine (tpy) and 2-(2-pyridyl)benzo[b]thiophene (btp) ligands, as well as their derivatives bearing electron-donating tert-butyl (t-Bu) and electron-withdrawing trifluoromethyl (CF3) groups. Ir2–Ir5 exhibited visible-light absorption stronger than that of the known complex [Ir(tpy)(ppy)Cl]+

  使用2,2'：6'，2''-吡啶（tpy）和2-（2-吡啶基）苯并[ ]合成了一系列新型的单环金属化[Ir（tpy）（btp）Cl] +配合物（Ir2 - Ir5）。b ]噻吩（btp）配体及其带有给电子叔丁基（t -Bu）和吸电子三氟甲基（CF 3）基团的衍生物。Ir2 – Ir5的可见光吸收性强于已知络合物[Ir（tpy）（ppy）Cl] +（Ir1; ppy ＝ 2-苯基吡啶）。光谱和计算研究表明，激发态动力学涉及两个三重态。一种是弱发射和短寿命的配体到配体的电荷转移（LLCT）状态，其起源是从btp到tpy配体的电荷转移。另一个是位于btp配体上的高发射态且寿命长的以配体为中心的状态（LC）。有趣的是，在tpy和btp配体上都引入取代基后，具有3 LLCT主导的激发态已完全变为3 LC状态。例如，母体配合物Ir2的激发态在CH 2 Cl 2中微弱发射（Φ= 2％），寿命短（τ= 110
• 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。
• 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。
• Phosphorescent and luminescent conjugated polymers and their use in electroluminescent assemblies
  申请人：Marsitzky Dirk

  公开号：US20060093852A1

  公开（公告）日：2006-05-04

  The invention relates to phosphorescent or luminescent conjugated polymers, whose emission is based on the phosphorescence of covalently bonded metal complexes, optionally combined with the fluorescence of the polymer chain. The invention also relates to a method for producing said polymers and to their use in electroluminescent assemblies.

  本发明涉及磷光或发光共轭聚合物，其发射基于共价键金属络合物的磷光，可选择与聚合物链的荧光相结合。本发明还涉及生产上述聚合物的方法及其在电致发光组件中的应用。
• Luminescence device and display apparatus
  申请人：CANON KABUSHIKI KAISHA

  公开号：EP1191612B1

  公开（公告）日：2009-09-09