3-trifluoromethyl-5-(2,2'-bipyridin-6-yl)-1,2,4-1H-triazole | 1005216-99-8

• 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: 3-trifluoromethyl-5-(2,2'-bipyridin-6-yl)-1,2,4-1H-triazole
• 英文别名: 3-trifluoromethyl-5-(2,2’-bipyridin-6-yl)-1,2,4-1H triazole；(ftzbpy)H；6-(3-Trifluoromethyl-1,2,4-triazolyl)-2,2'-bipyridine；2-pyridin-2-yl-6-[5-(trifluoromethyl)-1H-1,2,4-triazol-3-yl]pyridine
• CAS: 1005216-99-8
• 化学式: C₁₃H₈F₃N₅
• 分子量: 291.235
• InChiKey: OXWWKWWXEPNGRU-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.2
• 重原子数：
  21
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.08
• 拓扑面积：
  67.4
• 氢给体数：
  1
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  3-trifluoromethyl-5-(2,2'-bipyridin-6-yl)-1,2,4-1H-triazole 、 三甲基镓 以 乙醚 为溶剂， 以82%的产率得到[(ftzbpy)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：

  6-氰基-2,2'-联吡啶 在 一水合肼 作用下， 以 乙醇 为溶剂， 反应 14.0h， 生成 3-trifluoromethyl-5-(2,2'-bipyridin-6-yl)-1,2,4-1H-triazole
  参考文献：
  名称：

  BIPYRIDYL TRIAZOLE RARE EARTH COMPLEX AND PREPARATION PROCESS THEREFOR

  摘要：

  公开号：

  EP2868661B1

文献信息

• BIPYRIDINE TRIAZOLE TYPE RARE EARTH COMPLEX AND PREPARATION METHOD THEREOF
  申请人：GUANGDONG SYNYOO NEW MATERIAL CO., LTD.

  公开号：US20140288305A1

  公开（公告）日：2014-09-25

  A bipyridine triazole rare earth complex LnL 3 as shown in Formula 1 and a preparation method thereof. The rare earth complex has high thermal stability and is suitable for manufacturing devices by an evaporation film-forming process or manufacturing devices by a solution film-forming process. The preparation method has the advantages of high yield, good product purity, short reaction time and simplicity in operation, and can greatly reduce cost.

  一种双吡啶三唑稀土配合物LnL3，如公式1所示，及其制备方法。该稀土配合物具有高热稳定性，适用于通过蒸发膜形成工艺制造器件或通过溶液膜形成工艺制造器件。该制备方法具有高产率、良好产品纯度、短反应时间和操作简单的优点，能大大降低成本。
• Emissive mononuclear Eu(III) and Tb(III) complexes bearing deprotonated 2,2′-bipyridyl-1,2,4-triazole terdentate ligands
  作者：Jing-Lin Chen、Guo-Ping Gao、Bao-Sheng Di、Yan-Sheng Luo、Xue-Hua Zeng、Lu Qiu、Li-Hua He、Sui-Jun Liu、He-Rui Wen

  DOI：10.1080/00958972.2016.1226501

  日期：2016.10.1

  new emissive mononuclear Ln(III) complexes with deprotonated 2,2ʹ-bipyridyl-1,2,4-triazole terdentate ligands, [Ln(L)(DMF)2(NO3)2]∙n(solvent) (Ln = Eu (1 and 2), Tb (3 and 4), HL = 6-(5-trifluoromethyl-1,2,4-triazol-3-yl)-2,2′-bipyridine, 6-(5-trifluoromethyl-1,2,4-triazol-3-yl)-4,4′-dimethyl-2,2′-bipyridine), have been synthesized and characterized. As revealed by X-ray crystallography, each Ln(III)

  摘要 一系列具有去质子化的 2,2ʹ-联吡啶-1,2,4-三唑三齿配体[Ln(L)(DMF)2(NO3)2]∙n(溶剂)( Ln = Eu (1 and 2), Tb (3 and 4), HL = 6-(5-trifluoromethyl-1,2,4-triazol-3-yl)-2,2'-bipyridine, 6-(5-三氟甲基-1,2,4-三唑-3-基)-4,4'-二甲基-2,2'-联吡啶)，已合成并表征。正如 X 射线晶体学所揭示的那样，每个 Ln(III) 都有一个扭曲的三棱柱，由来自一个 2,2ʹ-bipyridyl-1,2,4-triazolate 螯合物的三个氮和来自两个 DMF 分子和两个螯合硝酸盐的六个氧生成，其中 2,2ʹ-联吡啶基-1,2,4-三唑通过 1,2,4-三唑基-NH 的去质子化作为单阴离子三齿螯合物。配合物 1-4 在室温下在溶液和固态下都是发光的，
• US8853399B1
  申请人：——

  公开号：US8853399B1

  公开（公告）日：2014-10-07
• CN113801651
  申请人：——

  公开号：——

  公开（公告）日：——
• Synthesis, Characterization, and Photophysical Properties of Luminescent Gallium and Indium Complexes Constructed using Tridentate 6-Azolyl-2,2′-bipyridine Chelates
  作者：Yi-Hwa Song、Yuan-Chieh Chiu、Yun Chi、Pi-Tai Chou、Yi-Ming Cheng、Chun-Wei Lin、Gene-Hsiang Lee、Arthur J. Carty

  DOI：10.1021/om700577y

  日期：2008.1.1

  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.