1,1,1,3,3,3-hexafluoro-2-pyrazol-1-ylmethyl-propan-2-ol | 847373-35-7

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑类
• 英文名称: 1,1,1,3,3,3-hexafluoro-2-pyrazol-1-ylmethyl-propan-2-ol
• 英文别名: 1,1,1,3,3,3-hexafluoro-2-pyrazol-1-ylmethylpropan-2-ol；1-[2-Hydroxy-2-(trifluoromethyl)-3,3,3-trifluoropropyl]-1H-pyrazole；1,1,1,3,3,3-hexafluoro-2-(pyrazol-1-ylmethyl)propan-2-ol
• CAS: 847373-35-7
• 化学式: C₇H₆F₆N₂O
• 分子量: 248.128
• InChiKey: PRNRLIWUNOOZNH-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.6
• 重原子数：
  16
• 可旋转键数：
  2
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.57
• 拓扑面积：
  38
• 氢给体数：
  1
• 氢受体数：
  8

反应信息

• 作为反应物：
  描述：

  1,1,1,3,3,3-hexafluoro-2-pyrazol-1-ylmethyl-propan-2-ol 、 di-μ-chlorotetrakis[4,6-bis(trifluoromethyl)-2-(4-methyl-2-pyridinyl-κN)phenyl-κC]diiridium 在 RbOH 作用下， 以 水 、 1,2-二氯乙烷 为溶剂， 以59%的产率得到bis[4,6-bis(trifluoromethyl)-2-(4-methyl-2-pyridinyl-κN)phenyl-κC],[α,α-bis(trifluoromethyl)-2-pyrazol-1-ylmethyl-propan-2-olatoκN1,κO2]iridium
  参考文献：
  名称：

  Synthesis, structural characterization, and initial electroluminescent properties of bis-cycloiridiated complexes of 2-(3,5-bis(trifluoromethyl)phenyl)-4-methylpyridine

  摘要：

  A series of bis-cyclometalated Ir(III) complexes (8-10, 12, 15, 17, 19, 21, 23, 25, 28, 29 and 33) bearing two chromophoric N boolean AND C cyclometalated ligands derived from 2-(3,5-bis(trifluoromethyl)phenyl)-4-methylpyridine (1) and a third nonchromophoric ligand has been synthesized. A palladium-catalyzed cross-coupling reaction between 2-chloro-4-methylpyridine (2) and 3,5-bis(trifluoromethyl)phenylboronic acid (3) was used to prepare 2-(3,5-bis(trifluoromethyl)phenyl)-4-methylpyridine (1). Cyclometalation of (1) by IrCl3 was carried out in (MeO)(3)P = O, with the formation of chloro-bridged dimer [N boolean AND C](2)Ir(mu-Cl)(2)Ir[C boolean AND N](2) (8). Reaction of (8) with lithium 2,4-pentanedionate, lithium 2,2,6,6-tetramethyl-heptane-3,5-dionate (13), dipivaloyltrimethylsilylphosphine (14), 2,2-dimethyl-6,6,7,7,8,8,8-heptafluoro-3,5-octadione (16), 1,1,1,3,3,3-hexafluoro-2-pyridin-2-yl-propan-2-ol (18), 1,1,1,3,3,3-hexafluoro-2-pyrazol-1-ylmethyl-propan-2-ol (20), 2-diphenylphosphanylethanol (22), and 1-diphenylphosphanylpropan-2-ol (24), afforded octahedral iridium complexes 9, 12, 15, 17, 19, 21, 23 and 25, respectively. Complex 10, which contains three different ligands (L-1 = N boolean AND C of 1; L-2 = N boolean AND C of 4,4'-dimethyl-[2,2']bipyridinyl 4; L-3 = O boolean AND O of 2,4-pentanedione), and complex 11, which contains no cyclometalated ligands (L-1 = 4; L-2 = L-3 = Cl; L-4 = O boolean AND O of 2,4-pentanedione) were also isolated as minor products in a one-pot reaction between a 94:5 mixture of I and 4, IrCl3 and lithium 2,4-pentanedionate. Reaction of 8 with diphenylphosphanylmethanol (27) in 1,2-dichloroethane unexpectedly led to complexes 28 and 29. The reactions of 8 with benzoylformic acid resulted in the formation of hydroxyl-bridged dimer [N boolean AND C](2)Ir(mu-OH)(2)Ir[C boolean AND N](2) (33). According to X-ray analyses, Ir-to-Ir distances in the crystal cell increase from 6.86 angstrom for 10 to 13.31 angstrom for 33. The angle theta, which represents the twisting of two cyclometalated C-Ir-N planes relative to each other, varies from 97.5 degrees for 21 to 90.76 for complex 28. OLED devices were fabricated from several Ir complexes and preliminary results are discussed. (C) 2007 Elsevier B.V. All rights reserved.

  DOI：

  10.1016/j.jorganchem.2007.06.026
• 作为产物：
  描述：

  3,3,3,-三氟-2-(三氟甲基)-1,2-氧化丙烯 、 在 水 作用下， 以 四氢呋喃 为溶剂， 反应 2.0h， 以95%的产率得到1,1,1,3,3,3-hexafluoro-2-pyrazol-1-ylmethyl-propan-2-ol
  参考文献：
  名称：

  ELECTROLUMINESCENT BIS-CYCLOMETALLED IRIDIUM COMPOUNDS AND DEVICES MADE WITH SUCH COMPOUNDS

  摘要：

  公开号：

  EP2016154B1

文献信息

• Electroluminescent bis-cyclometalled iridium compounds and devices made with such compounds
  申请人：Ionkin Sergey Alex

  公开号：US20070259205A1

  公开（公告）日：2007-11-08

  One embodiment of this invention is bis-cyclometalled electroluminescent complexes of iridium(III). Another embodiment of this invention is electronic devices in which the active layer includes an bis-cyclometalled electroluminescent Ir(III) complex.

  本发明的一种实施例是铱（III）的双环金属电致发光配合物。本发明的另一种实施例是电子器件，其中活性层包括双环金属电致发光Ir（III）配合物。
• Syntheses, Structural Characterization, and First Electroluminescent Properties of Mono-cyclometalated Platinum(II) Complexes with Greater than Classical π−π Stacking and Pt−Pt Distances
  作者：Alex S. Ionkin、William J. Marshall、Ying Wang

  DOI：10.1021/om049211t

  日期：2005.2.1

  A series of mono-cyclometalated Pt(II) complexes (9, 10, 13, 15, and 17) bearing 2-(3,5-bis(trifluoromethyl)phenyl)-4-methylpyridine (1) as the same chromophoric Nboolean ANDC cyclometalated ligand and the second nonchromophoric bidenate ligands with increasing bulkiness were synthesized by the following steps. The palladium-catalyzed cross-coupling reaction between 2-chloro-4-methylpyridine (2) and 3,5-bis(trifluoromethyl)phenylboronic acid (3) was used to prepare 2-(3,5-bis(trifluoromethyl)phenyl)-4-methylpyridine (1). Di-tert-butyl(trimethylsilyl)anylmethylphosphine, tert-BU2P-CH2-SiMe3 (5), was used as a ligand for the Suzuki coupling. The cyclometalation of 1 by K2PtCl4 (7) was carried out in (MeO)(3)P=O (8) with the formation of a chloro-bridged dimer Nboolean ANDCPt(mu-Cl)(2)PtCboolean ANDN (9). The reactions of 9 with 2,2,6,6-tetramethylheptane-3,5-dionate (11), 1,1,1,3,3,3-hexafluoro-2-pyrazol-1-ylmethylpropan-2-ol (12), 2-[(diphenylphosphanyl)methyl]-1,1,1,3,3,3-hexafluoropropan-2-ol (14), and 2-[(di-tert-butylphosphanyl)methyl]-1,1,1,3,3,3-hexafluoropropan-2-ol(16) afforded square-planar Pt(II) complexes 10, 13, 15, and 17, correspondingly. According to X-ray analyses, the plane-to-plane distances of the pi-pi stacked complexes (10, 13, 15, and 17) increase from 3.478 Angstrom for 10 to 4.203 Angstrom for 15. The value of 4.203 Angstrom for aromatic- aromatic pi-pi interaction is greater than the usual range of 3.3-3.8 Angstrom for these phenomena. Pt-pt distances increase from 5.076 Angstrom for 13 to 8.123 Angstrom for 17. The geometry of complex 17 deviates greatly from square planar and is best described as "bowl-shaped". The effect of an increased pi-pi stacking distance on the electroluminescent properties of these Pt compounds is studied. The typical yellow luminescence band associated with the excimers of Pt compounds is absent for complex 15; however, it shows a green 540 nm electroluminesce band instead. An efficient LED constructed using compound 15 shows green electroluminescence with a peak efficiency of 6 cd/A.
• US7737277B2
  申请人：——

  公开号：US7737277B2

  公开（公告）日：2010-06-15
• [EN] ELECTROLUMINESCENT BIS-CYCLOMETALLED IRIDIUM COMPOUNDS AND DEVICES MADE WITH SUCH COMPOUNDS<br/>[FR] COMPOSÉS D'IRIDIUM ÉLECTROLUMINESCENT BIS-CYCLOMÉTALLÉS ET DISPOSITIFS RÉALISÉS AVEC DE TELS COMPOSÉS
  申请人：DU PONT

  公开号：WO2007133523A2

  公开（公告）日：2007-11-22

  [EN] One embodiment of this invention is bis-cyclometalled electroluminescent complexes of iridium(III). Another embodiment of this invention is electronic devices in which the active layer includes an bis-cyclometalled electroluminescent Ir(III) complex.
  [FR] Dans un mode de réalisation, l'invention concerne des complexes d'iridium (III) électroluminescents bis-cyclométallés. Dans un autre mode de réalisation, l'invention porte sur des dispositifs électroniques dont la couche active comprend un complexe électroluminescent d'Ir(III) bis-cyclométallé.