2-(3-(perfluoropropyl)-1H-1, 2, 4-triazole-5-yl)pyridine | 848093-61-8

• 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: 2-(3-(perfluoropropyl)-1H-1, 2, 4-triazole-5-yl)pyridine
• 英文别名: 3-(heptafluoropropyl)-5-(2-pyridyl)triazole；(hptz)H；3-(Heptafluoropropyl)-5-(2-pyridyl)-1H-1,2,4-triazole；2-[5-(1,1,2,2,3,3,3-heptafluoropropyl)-1H-1,2,4-triazol-3-yl]pyridine
• CAS: 848093-61-8
• 化学式: C₁₀H₅F₇N₄
• 分子量: 314.165
• InChiKey: YLECOUQNLABJIQ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.9
• 重原子数：
  21
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.3
• 拓扑面积：
  54.5
• 氢给体数：
  1
• 氢受体数：
  10

反应信息

• 作为反应物：
  描述：

  (1-(2,4-difluorophenyl)-1H-pyrazole)₂Ir(μ-Cl)₂Ir(1-(2,4-difluorophenyl)-1H-pyrazole)₂ 、 2-(3-(perfluoropropyl)-1H-1, 2, 4-triazole-5-yl)pyridine 在 Na₂CO₃ 作用下， 以 乙二醇乙醚 为溶剂， 以78%的产率得到[(dfpz)2Ir(hptz)]
  参考文献：
  名称：

  杂环金属化铱（III）配合物在室温下在溶液和固态下显示蓝色磷光。

  摘要：

  合成了一系列带有两个N-苯基取代的吡唑和一个2-吡啶基吡唑（或三唑）配体的Ir（III）杂合金属配合物1-3，并进行了表征，以实现高效的室温蓝色磷光。N-苯基吡唑配体dfpzH = 1-（2,4-二氟苯基）吡唑，fpzH = 1-（4-氟苯基）吡唑，dfmpzH = 1-（2,4-二氟苯基）-3,5-二甲基吡唑和fmpzH = 1-（4-氟苯基）-3,5-二甲基吡唑，相对于典型的环金属化（C（楔形）N）螯合物显示相似的反应模式，该螯合物利用其邻位取代的苯基链段与中心Ir（ III）原子，而第二个2-吡啶基吡唑（或三唑）配体，即fppzH = 3-（三氟甲基）-5-（2-吡啶基）吡唑，fptzH = 3-（三氟甲基）-5-（2-吡啶基）三唑 hptzH = 3-（七氟丙基）-5-（2-吡啶基）三唑，经过典型的阴离子（NN）螯合以完成八面体骨架。建立了复合物[（dfpz）（2）Ir（fppz）

  DOI：

  10.1021/ic050311g
• 作为产物：
  描述：

  庚氟丁酸乙酯 、 2-脒基吡啶盐酸盐 在 肼 、 sodium hydroxide 作用下， 以 四氢呋喃 为溶剂， 反应 4.0h， 以25%的产率得到2-(3-(perfluoropropyl)-1H-1, 2, 4-triazole-5-yl)pyridine
  参考文献：
  名称：

  Synthesis and characterization of new blue light emitting iridium complexes containing a trimethylsilyl group

  摘要：

  通过μ-氯桥接二聚体和全氟丙基三唑基辅助配体合成了以三甲基硅基为笨重电子供体的新型蓝色铱配合物--Ir(F2-p-三甲基硅基)2(ftp)和Ir(F2-m-三甲基硅基)2(ftp)，并利用各种光谱研究对其进行了表征。Ir(F2-p-三甲基硅基)2(ftp)和 Ir(F2-m-三甲基硅基)2(ftp)在薄膜中的光量子效率分别达到 75 ± 5% 和 76 ±5%。DFT 计算表明，与 FIrpic 相比，新型蓝铱配合物具有较宽的带隙，并且对位三甲基硅基的 Ir(F2-p-trimethylsilyl)2(fptp) 的 HOMO 水平比元位三甲基硅基的 Ir(F2-p-trimethylsilyl)2(fptp) 的 HOMO 水平略深。与 FIrpic 相比，复合物的紫外可见吸收和光致发光（PL）光谱发生了蓝移。使用 Ir(F2-p-三甲基硅基)2(ptp)的装置显示出 19.3% 的最大外部量子效率（0.00152 mA cm-2），国际照明委员会（CIE）坐标为 (0.145, 0.247)。

  DOI：

  10.1039/c2jm33084a

文献信息

• Phosphorescent Osmium (II) complexes and uses thereof
  申请人：Tao Ye

  公开号：US20050137400A1

  公开（公告）日：2005-06-23

  There is disclosed herein phosphorescent compounds, uses thereof, and devices including organic light emitting diode (OLEDs) including such compounds. Compounds of interest include: wherein A is Os or Ru The anionic chelating chromophores Ncircumflex over ( )}N, which are formed by connecting one pentagonal ring structure containing at least two nitrogen atoms to a hexagonal pyridine type of fragment via a direct carbon-carbon linkage. L is a neutral donor ligand; the typical example includes carbonyl, pyridine, phosphine, arsine and isocyanide; two neutral L's can also combine to produce the so-called chelating ligand such as 2,2′-bipyridine, 1,10-phenanthroline and N-heterocyclic carbene (NHC) ligand, or bidentate phosphorous ligands such as 1,2-bis(diphenylphosphino)ethane, 1,2-bis(diphenylphosphino)benzene. L can occupy either cis or trans orientation. When L occupies the trans position, the preferred structure contains both the hexagonal fragment of NAN as well as its pentagonal fragment located at the trans position respect to their counterparts of the second NAN chromophore. When L occupies the cis position, the preferred structure consists of the pentagonal unit of Ncircumflex over ( )}N chromophores residing opposite to the L. X 1 , X 2 and X 3 independently are C or N; when X 2 is N, R, is omitted, when X 3 is N, R 2 is omitted, R 1 is H, C1-C8 alkyl, C1-C8 substituted phenyl or C1-C4 perfluoroalkyl, R 2 is H, F or cyano substituent, X 4 is either C or N; X 4 may locate at any position of the hexagonal ring, when X 4 is N and R 3 and R 4 are not linked to X 4 , R 3 is H, methyl or C1-C3 small alkyl, R 4 is H, methyl or C1-C3 small alkyl, or R 3 and R 4 together form an additional conjugated unit with structure

  本文介绍了荧光化合物及其用途，以及包括这些化合物的有机发光二极管（OLED）在内的装置。感兴趣的化合物包括：其中A是Os或Ru。阴离子螯合色团Ncircumflex over ( )}N是通过将至少含有两个氮原子的五边形环结构与一个六边形吡啶类型的片段通过直接碳-碳键连接而形成的。L是一个中性给体配体；典型的例子包括羰基、吡啶、膦、砷和异氰酸酯；两个中性的L也可以组合成所谓的螯合配体，如2,2′-联吡啶、1,10-邻菲啰啉和N-杂环卡宾（NHC）配体，或者是双齿膦配体，如1,2-双(二苯基膦基)乙烷、1,2-双(二苯基膦基)苯。L可以占据顺式或反式位向。当L占据反式位置时，首选结构包含NAN的六边形片段以及其位于反向位置的五边形片段，相对于第二个NAN色团的对应物。当L占据顺式位置时，首选结构由Ncircumflex over ( )}N色团的五边形单元组成，位于L的对面。X1、X2和X3独立地是C或N；当X2为N时，省略R；当X3为N时，省略R2；R1为H、C1-C8烷基、C1-C8取代苯基或C1-C4全氟烷基；R2为H、F或氰基取代基；X4为C或N；当X4为N且R3和R4未与X4连接时，X4可以位于六边形环的任何位置；R3为H、甲基或C1-C3小烷基；R4为H、甲基或C1-C3小烷基；或者R3和R4共同形成具有结构的额外共轭单元。
• Platinum(II) Complexes with Pyridyl Azolate-Based Chelates:  Synthesis, Structural Characterization, and Tuning of Photo- and Electrophosphorescence
  作者：Sheng-Yuan Chang、Jakka Kavitha、Shih-Wen Li、Chan-Shou Hsu、Yun Chi、Yu-Shan Yeh、Pi-Tai Chou、Gene-Hsiang Lee、Arthur J. Carty、Yu-Tai Tao、Chin-Hsiung Chien

  DOI：10.1021/ic051393b

  日期：2006.1.1

  A new series of luminescent platinum(II) azolate complexes with a formula of [Pt(N Lambda N)(2)], in which N Lambda N = mppz (1), bppz (2a), bzpz (2b), bmpz (2c), bqpz (2d), fppz (3a), hppz (3b), bptz (4), hptz (5), were synthesized, and their photophyscial properties were examined. Single-crystal X-ray diffraction studies of 2c: and 3b revealed a planar molecular geometry, in which the N Lambda N chelates adopt a trans configuration and show notable interligand C-(HN)-N-... hydrogen bonding within the complex. Interesting intermolecular interactions were observed in the solid state. Complex 2c formed a slipped-stack structure with a (PtPt)-Pt-... separation distance of 6.432 angstrom, while complex 3b showed a columnar stacking with the molecules oriented in an alternating order in relation to the chain axis, giving a much reduced (PtPt)-Pt-... distance of 3.442 angstrom. The lowest absorption band for all complexes revealed strong state mixings between the singlet and triplet (MLCT and intraligand pi pi*) manifolds. Complexes 1 and 2 showed mixed (MLCT)-M-3 and (3)pi pi phosphorescence in fluid solution. While radiationless deactivation was apparently dominant for complxes 3-5 in solution, resulting in rather weak emission, strong phosphorescence was observed in the room-temperature solid state with the peak wavelength being significantly red shifted compared to that in solution. The emission nature has been tentatively assigned to be (MMLCT)-M-3 in character. OLED devices with a multilayer configuration of ITO/NPB/CBP:2a/BCP/Alq(3)/LiF/Al were successfully fabricated using a CBP layer doped with various amount of 2a, ranging from 6 to 100%, as the emitting layer. A substantial red shift with increasing doping concentrations was observed in electroluminescence. With a neat film of 2a, the device showed a green emission with lambda(max) at 556 nm and an external QE of similar to 1.6% at a driving current of 20 mA. Similarly, for the device using a neat film of 3a, an electroluminescence centered at 616 nm with a slightly reduced external QE of similar to 2.1% was recorded. Aggregation of platinum(II) complexes in the solid state was proposed to account for the large red-shift in electroluminescence.
• US7759490B2
  申请人：——

  公开号：US7759490B2

  公开（公告）日：2010-07-20
• Synthesis and characterization of new blue light emitting iridium complexes containing a trimethylsilyl group
  作者：Chul Young Kim、Dong-Gwang Ha、Hyun Hee Kang、Hui-Jun Yun、Soon-Ki Kwon、Jang-Joo Kim、Yun-Hi Kim

  DOI：10.1039/c2jm33084a

  日期：——

  New blue iridium complexes with a trimethylsilyl group as a bulky electron donating group, Ir(F2-p-trimethylsilyl)2(fptp) and Ir(F2-m-trimethylsilyl)2(fptp), were synthesized via μ-chloro-bridged dimer and perfluoropropylated triazole-based ancillary ligands and then characterized using various spectroscopic studies. Both Ir(F2-p-trimethylsilyl)2(fptp) and Ir(F2-m-trimethylsilyl)2(fptp) exhibited high photoluminescence quantum efficiencies of 75 ± 5% and 76 ± 5% in films, respectively. The DFT calculation demonstrated that the new blue iridium complexes have a wide bandgap compared with FIrpic and the Ir(F2-p-trimethylsilyl)2(fptp) with a trimethylsilyl group in the para position has a slightly deeper HOMO level than that of the Ir(F2-p-trimethylsilyl)2(fptp) with a trimethylsilyl group in the meta position. The UV-vis absorption and photoluminescent (PL) spectra of the complexes were blue shifted compared with those of FIrpic. The device using the Ir(F2-p-trimethylsilyl)2(fptp) exhibited a maximum external quantum efficiency of 19.3% (at 0.00152 mA cm−2) and commission Internationale de l'Eclairage (CIE) coordinates of (0.145, 0.247).

  通过μ-氯桥接二聚体和全氟丙基三唑基辅助配体合成了以三甲基硅基为笨重电子供体的新型蓝色铱配合物--Ir(F2-p-三甲基硅基)2(ftp)和Ir(F2-m-三甲基硅基)2(ftp)，并利用各种光谱研究对其进行了表征。Ir(F2-p-三甲基硅基)2(ftp)和 Ir(F2-m-三甲基硅基)2(ftp)在薄膜中的光量子效率分别达到 75 ± 5% 和 76 ±5%。DFT 计算表明，与 FIrpic 相比，新型蓝铱配合物具有较宽的带隙，并且对位三甲基硅基的 Ir(F2-p-trimethylsilyl)2(fptp) 的 HOMO 水平比元位三甲基硅基的 Ir(F2-p-trimethylsilyl)2(fptp) 的 HOMO 水平略深。与 FIrpic 相比，复合物的紫外可见吸收和光致发光（PL）光谱发生了蓝移。使用 Ir(F2-p-三甲基硅基)2(ptp)的装置显示出 19.3% 的最大外部量子效率（0.00152 mA cm-2），国际照明委员会（CIE）坐标为 (0.145, 0.247)。
• Heteroleptic Cyclometalated Iridium(III) Complexes Displaying Blue Phosphorescence in Solution and Solid State at Room Temperature
  作者：Cheng-Han Yang、Shih-Wen Li、Yun Chi、Yi-Ming Cheng、Yu-Shan Yeh、Pi-Tai Chou、Gene-Hsiang Lee、Chih-Hsiang Wang、Ching-Fong Shu

  DOI：10.1021/ic050311g

  日期：2005.10.1

  bearing two N-phenyl-substituted pyrazoles and one 2-pyridyl pyrazole (or triazole) ligands were synthesized and characterized to attain highly efficient, room-temperature blue phosphorescence. The N-phenylpyrazole ligands, dfpzH = 1-(2,4-difluorophenyl)pyrazole, fpzH = 1-(4-fluorophenyl)pyrazole, dfmpzH = 1-(2,4-difluorophenyl)-3,5-dimethylpyrazole, and fmpzH = 1-(4-fluorophenyl)-3,5-dimethylpyrazole

  合成了一系列带有两个N-苯基取代的吡唑和一个2-吡啶基吡唑（或三唑）配体的Ir（III）杂合金属配合物1-3，并进行了表征，以实现高效的室温蓝色磷光。N-苯基吡唑配体dfpzH = 1-（2,4-二氟苯基）吡唑，fpzH = 1-（4-氟苯基）吡唑，dfmpzH = 1-（2,4-二氟苯基）-3,5-二甲基吡唑和fmpzH = 1-（4-氟苯基）-3,5-二甲基吡唑，相对于典型的环金属化（C（楔形）N）螯合物显示相似的反应模式，该螯合物利用其邻位取代的苯基链段与中心Ir（ III）原子，而第二个2-吡啶基吡唑（或三唑）配体，即fppzH = 3-（三氟甲基）-5-（2-吡啶基）吡唑，fptzH = 3-（三氟甲基）-5-（2-吡啶基）三唑 hptzH = 3-（七氟丙基）-5-（2-吡啶基）三唑，经过典型的阴离子（NN）螯合以完成八面体骨架。建立了复合物[（dfpz）（2）Ir（fppz）