6-(5-trifluoromethylpyrazol-3-yl)-2,2'-bipyridine | 1005217-00-4

• 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
• 英文名称: 6-(5-trifluoromethylpyrazol-3-yl)-2,2'-bipyridine
• 英文别名: (fpzbpy)H；fpbpyH；6-[3-(Trifluoromethyl)-1H-pyrazole-5-yl]-2,2'-bipyridine；2-pyridin-2-yl-6-[5-(trifluoromethyl)-1H-pyrazol-3-yl]pyridine
• CAS: 1005217-00-4
• 化学式: C₁₄H₉F₃N₄
• 分子量: 290.247
• InChiKey: SDGLJRZZOHHXTN-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.4
• 重原子数：
  21
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.07
• 拓扑面积：
  54.5
• 氢给体数：
  1
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  6-(5-trifluoromethylpyrazol-3-yl)-2,2'-bipyridine 、 三甲基镓 以 乙醚 为溶剂， 以73%的产率得到[(fpzbpy)GaMe2]
  参考文献：
  名称：

  Synthesis, Characterization, and Photophysical Properties of Luminescent Gallium and Indium Complexes Constructed using Tridentate 6-Azolyl-2,2′-bipyridine Chelates

  摘要：

  Three systematically functionalized 6-azolyl-2,2'-bipyridine ligands were prepared from reactions initiated by 6-cyano-2,2'-bipyridine. These ligands readily reacted with the metal alkyl reagents GaMe3 and InMe3 to afford the pentacoordinate complexes [(fpzbpy)MMe2] (1a, M = Ga; 1b, M = In), [(ftzbpy)MMe2] (2a, M = Ga; 2b, M = In), and [(N4bpy)MMe2] (3a, M = Ga; 3b, M = In), in which (fpzbpy)H, (ftzbpy)H, and (N4bpy)H denote 6-pyrazolyl-, 6-triazolyl-, and 6-tetrazolyl-substituted 2,2'bipyridine, respectively. These complexes exhibited moderate blue-green emission ranging from 412 to 493 rim. On the other hand, treatment of the bidentate 2-pyridyl tetrazole ligand (pyN(4))H with InMe3 afforded the bridged dimer [Me2In(pyN(4))](2) (4). Calculation based on time-dependent density function theory (TDDFT) showed that the S, state of complexes 1-3 is mainly attributed to an allowed intraligand pi -> pi* electronic transition located at tridentate chelating moieties, together with a small contribution (< 10%) of gallium (or indium) -> pi* (ligand) charge transfer transition. Accordingly, the corresponding emission properties of 1a-3a (or 1b-3b) can be rationalized using the correlation between the substituent effect of azolyl groups and the relative HOMO/LUMO energy level.

  DOI：

  10.1021/om700577y
• 作为产物：
  描述：

  1-(2,2’-bipyridine-6-yl)-4,4,4-trifluorobutane-1,3-dione 在 肼 作用下， 以 乙醇 为溶剂， 反应 12.0h， 以40%的产率得到6-(5-trifluoromethylpyrazol-3-yl)-2,2'-bipyridine
  参考文献：
  名称：

  RUTHENIUM COMPLEXES WITH TRIDENTATE HETEROCYCLIC LIGAND AND DYE-SENSITIZED SOLAR CELLS USING THE SAME

  摘要：

  提供具有RuL1L2X化学式的钌配合物。该化学式包括以下式（I）所代表的结构式：其中，X是一种单齿阴离子配体，L1和L2分别代表具有以下结构式（II）所示结构的杂环三齿配体和具有以下结构式（III）所示结构的双吡啶配体衍生物：其中，L1和L2的R1、R2、R4和R5是相同或不同的取代基，代表烷基、烷氧基、氨基烷基、卤代烷烃或取代苯基、羧酸基或其酸基盐、磺酸基或其酸基盐、磷酸基或其酸基盐或氢原子。R3代表全氟烷基、烷氧基、烷基、氨基、卤素或氢原子。这些钌配合物适用于用作染料敏化太阳能电池的染料敏化剂。

  公开号：

  US20080114174A1

文献信息

• Iridium(III) Bis-tridentate Complexes with 6-(5-Trifluoromethylpyrazol-3-yl)-2,2′-bipyridine Chelating Ligands: Synthesis, Characterization, and Photophysical Properties
  作者：Jing-Lin Chen、Yu-Hui Wu、Li-Hua He、He-Rui Wen、Jinsheng Liao、Ruijin Hong

  DOI：10.1021/om100186k

  日期：2010.7.12

  A novel family of iridium(III) bis-tridentate complexes are reported that contain the deprotonated, N∧N∧N-coordinated 6-(5-trifluoromethylpyrazol-3-yl)-2,2′-bipyridine (fpbpyH) ligand. The monocationic homoleptic iridium(III) complex [Ir(fpbpy)2](PF6) (1) was first prepared by treatment of IrCl3·3H2O with 2.2 equiv of fpbpyH in degassed ethylene glycol at 196 °C and structurally characterized by single-crystal

  铱的新家族（III）双-三齿络合物报告包含去质子化，N ∧ Ñ ∧ N-二协调6-（5-三氟甲基吡啶-3-基）-2,2'-联吡啶（fpbpyH）配体。首先通过在196°C的脱气乙二醇中用2.2当量的fpbpyH处理IrCl 3 ·3H 2 O来制备单阳离子均铱铱（III）络合物[Ir（fpbpy）2 ]（PF 6）（1）。通过单晶X射线晶体学。Ir（tpy）Cl 3与等摩尔量的fpbpyH在相当条件下的反应生成了阳离子杂多铱（III）络合物[Ir（fpbpy）（tpy）]（PF 6）图2（2）以一个2,2'：6'2''-三联吡啶（tpy）代替一个fpbpy为特征。还通过无溶剂方法成功提供了电荷中性的杂合配合物[Ir（fpbpy）（dppy）]（3）（dppyH 2 = 2,6-二苯基吡啶），得到了一个结合了Ir的dppy的配合物。 III）离子通过两个碳原子进行环金属化反应。配合1 - 3
• Improved redox couple for electrochemical and optoelectronic devices
  申请人：Ecole Polytechnique Fédérale de Lausanne (EPFL)

  公开号：EP2492277A1

  公开（公告）日：2012-08-29

  The present invention provides an improved redox couple for electrochemical and optoelectronic devices. The redox couple is based on a complex of a first row transition metal, said complex containing at least one mono-, bi-, or tridentate ligand comprising a substituted or unsubstituted ring or ring system comprising a five-membered N-containing heteroring and/or a six-membered ring comprising at least two heteroatoms, at least one of which being a nitrogen atom, said five- or six-membered heteroring, respectively, comprising at least one double bond. The invention also relates to electrolytes and to the devices containing the complex, and to the use of the complex as a redox couple.

  本发明提供了一种改进的氧化还原偶对，用于电化学和光电子器件。该氧化还原偶对基于第一行过渡金属的配合物，所述配合物至少含有一个单、双或三齿配体，包括一个取代或未取代的环或环系统，其中包括一个五元N-含杂环和/或一个至少含有两个杂原子的六元环，其中至少一个是氮原子，所述的五元或六元杂环分别包括至少一个双键。该发明还涉及电解质、含有该配合物的器件，以及将该配合物用作氧化还原偶对的用途。
• REDOX COUPLE FOR ELECTROCHEMICAL AND OPTOELECTRONIC DEVICES
  申请人：Nazeeruddin Mohammad Khaja

  公开号：US20140060641A1

  公开（公告）日：2014-03-06

  The present invention provides an improved redox couple for electrochemical and optoelectronic devices. The redox couple is based on a complex of a first row transition metal, said complex containing at least one mono-, bi-, or tridentate ligand comprising a substituted or unsubstituted ring or ring system comprising a five-membered N-containing heteroring and/or a six-membered ring comprising at least two heteroatoms, at least one of which being a nitrogen atom, said five- or six-membered heteroring, respectively, comprising at least one double bond. The invention also relates to electrolytes and to the devices containing the complex, and to the use of the complex as a redox couple. The invention further provides electrochemical and/or optoelectronic devices comprising a first and a second electrode and, between said first and second electrode, a charge transport layer, said a charge transport layer comprising tetracyanoborate ([B(CN) 4 ] − ) and a cationic metal complex functioning as redox-couple.

  本发明提供了一种改进的氧化还原偶对，用于电化学和光电子器件。该氧化还原偶对基于第一行过渡金属的配合物，该配合物包含至少一种单、双或三齿配体，包括一个取代或未取代的环或环系统，其中包括一个含氮的五元杂环和/或至少包含两个杂原子的六元环，其中至少一个是氮原子，该五元或六元杂环，分别包括至少一个双键。本发明还涉及电解质、含有该配合物的器件以及将该配合物用作氧化还原偶对的用途。本发明进一步提供了电化学和/或光电子器件，包括第一和第二电极，以及在该第一和第二电极之间的电荷传输层，该电荷传输层包括四氰硼酸盐([B(CN)4]−)和作为氧化还原偶对的阳离子金属配合物。
• METAL COMPLEXES FOR USE AS DOPANTS AND OTHER USES
  申请人：Ecole Polytechnique Federale de Lausanne (EPFL)

  公开号：US20160233439A1

  公开（公告）日：2016-08-11

  The invention relates to electrochemical devices comprising complexes of cobalt comprising at least one ligand with a 5- or six membered, N-containing heteroring. The complex are useful as p- and n-dopants, as over of electrochemical devices, in particular in organic semiconductors. The complexes are further useful as over-discharge prevention and overvoltage protection agents.

  本发明涉及一种包含钴配合物的电化学器件，该配合物至少包含一种含有5或6个成员的N-含杂环配体。该配合物可用作p-和n-掺杂剂，用于电化学器件，特别是有机半导体中。此外，该配合物还可用作过放电防止和过电压保护剂。
• ORGANOMETALLIC COMPOUND, ORGANIC LIGHT-EMITTING DEVICE INCLUDING THE ORGANOMETALLIC COMPOUND, AND DIAGNOSIS COMPOSITION INCLUDING THE ORGANOMETALLIC COMPOUND
  申请人：Samsung Electronics Co., Ltd.

  公开号：EP3130595B1

  公开（公告）日：2018-10-17