4,4,5,5,6,6,6-heptafluoro-1-(1-methyl-1H-pyrazol-4-yl)hexane-1,3-dione | 1448993-68-7

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 4,4,5,5,6,6,6-heptafluoro-1-(1-methyl-1H-pyrazol-4-yl)hexane-1,3-dione
• 英文别名: 4,4,5,5,6,6,6-Heptafluoro-1-(1-methyl-1h-pyrazol-4-yl)-1,3-hexanedione；4,4,5,5,6,6,6-heptafluoro-1-(1-methylpyrazol-4-yl)hexane-1,3-dione
• CAS: 1448993-68-7
• 化学式: C₁₀H₇F₇N₂O₂
• 分子量: 320.167
• InChiKey: YIJCAWHLKLIAOR-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：
  5
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  52
• 氢给体数：
  0
• 氢受体数：
  10

反应信息

• 作为反应物：
  描述：

  乙醇 、 、 4,4,5,5,6,6,6-heptafluoro-1-(1-methyl-1H-pyrazol-4-yl)hexane-1,3-dione 以81 %的产率得到tris[4,4,5,5,6,6,6-heptafluoro-1-(1-methyl-1H-pyrazol-4-yl)hexane-1,3-dionato](diethanol)europium(III)
  参考文献：
  名称：

  Synthesis, structure, and luminescent properties of neutral tris-complexes of Eu3+ and Sm3+ with 4,4,5,5,6,6,6-heptafluoro-1-(1-methyl-1H-pyrazol-4-yl)hexane-1,3-dione

  摘要：

  4,4,5,5,6,6,6-heptafluoro-1-(1-methyl-1H-pyrazol-4-yl)hexane-1、3-二酮 (HPyrC3F7)与新沉淀的水合铕(ɪɪɪ)和钐(ɪɪɪ)氢氧化物在 EtOH 中的反应生成了成分为 [Ln(PyrC3F7)3(EtOH)2]的结晶络合物、根据配体/金属的化学计量比，研究了它们的形成特点。通过单晶 X 射线衍射等理化方法对这些配合物的结构和组成进行了表征。详细研究了这些化合物在晶体状态和溶液中的发光特性。研究还考虑了[Eu(PyrC3F7)3(EtOH)2]复合物中电子激发转移的可能方式。

  DOI：

  10.1007/s11172-022-3645-5
• 作为产物：
  描述：

  七氟丁酸甲酯 、 1-(1-甲基吡唑)乙酮 在 sodium hydride 作用下， 以 乙醚 为溶剂， 生成 4,4,5,5,6,6,6-heptafluoro-1-(1-methyl-1H-pyrazol-4-yl)hexane-1,3-dione
  参考文献：
  名称：

  Synthesis, structure, and luminescent properties of neutral tris-complexes of Eu3+ and Sm3+ with 4,4,5,5,6,6,6-heptafluoro-1-(1-methyl-1H-pyrazol-4-yl)hexane-1,3-dione

  摘要：

  4,4,5,5,6,6,6-heptafluoro-1-(1-methyl-1H-pyrazol-4-yl)hexane-1、3-二酮 (HPyrC3F7)与新沉淀的水合铕(ɪɪɪ)和钐(ɪɪɪ)氢氧化物在 EtOH 中的反应生成了成分为 [Ln(PyrC3F7)3(EtOH)2]的结晶络合物、根据配体/金属的化学计量比，研究了它们的形成特点。通过单晶 X 射线衍射等理化方法对这些配合物的结构和组成进行了表征。详细研究了这些化合物在晶体状态和溶液中的发光特性。研究还考虑了[Eu(PyrC3F7)3(EtOH)2]复合物中电子激发转移的可能方式。

  DOI：

  10.1007/s11172-022-3645-5

文献信息

• Novel β-diketonate complexes of <mml:math xmlns:mml="http://www.w3.org/1998/Math/MathML" altimg="si1.gif" overflow="scroll"><mml:mrow><mml:msup><mml:mrow><mml:mtext>Eu</mml:mtext></mml:mrow><mml:mrow><mml:mn>3</mml:mn><mml:mo>+</mml:mo></mml:mrow></mml:msup></mml:mrow></mml:math> bearing pyrazole moiety for bright photo- and electroluminescence
  作者：V.M. Korshunov、S.A. Ambrozevich、I.V. Taydakov、A.A. Vashchenko、D.O. Goriachiy、A.S. Selyukov、A.O. Dmitrienko

  DOI：10.1016/j.dyepig.2018.12.006

  日期：2019.4

  Four novel 1,3-diketonate Eu3+ complexes bearing pyrazole moieties as main ligands and a 4,7-Diphenyl-1,10-phenanthroline (bathophenanthroline) ancillary ligand were synthesized. The number of fluorine atoms in the main ligand was varied from 3 to 13. From spectroscopic studies of the synthesized complexes we conclude that increasing the degree of fluorination results in a significant rise in the quantum yield and sensitization efficiency. With further extension of the fluorinated chain length, saturation of these characteristics was observed. The maximum obtained values of the quantum yield and sensitization efficiency were 56% and 99%, respectively. In order to reveal the potential of the complexes for OLED applications, electroluminescent devices based on these compounds were fabricated and their performance was studied. It was found that the quantum efficiencies of the OLEDs and the sensitization efficiencies exhibit similar behaviour depending on the degree of fluorination of the ligands in the complexes.
• Synthesis and luminescent properties of neutral Eu(III) and Gd(III) complexes with 1-(1,5-dimethyl-1h-pyrazol-4-yl)-4,4,4-trifluoro-1,3-butanedione and 4,4,5,5,6,6,6-heptafluoro-1-(1-methyl-1H-pyrazol-4-yl)-1,3-hexanedione
  作者：I. V. Taidakov、B. E. Zaitsev、A. N. Lobanov、A. G. Vitukhnovskii、N. P. Datskevich、A. S. Selyukov

  DOI：10.1134/s0036023613040190

  日期：2013.4

  Neutral [EuL(3)Phen] complexes were synthesized by the reaction of EuCl3 with heterocyclic diketones-1-(1,5-dimethyl-1H-pyrazol-4-yl)-4,4,4-trifluoro-1,3-butanedione and 4,4,5,5,6,6,6-heptafluoro-1-(1-methyl-1H-pyrazol-4-yl)-1,3-hexanedione-and 1,10-phenanthroline (Phen) in an aqueous alcohol solution in the presence of NaOH. The reaction of GdCl3 with the same diketones under analogous conditions, but without adding 1,10-phenanthroline, yielded [GdL3(H2O)(2)] complexes. The composition of the complexes was determined by elemental analysis, and their optical and luminescent properties were examined.
• Bright NIR-luminescent <mml:math xmlns:mml="http://www.w3.org/1998/Math/MathML" display="inline" id="d1e655" altimg="si55.svg"><mml:msup><mml:mrow><mml:mi mathvariant="normal">Nd</mml:mi></mml:mrow><mml:mrow><mml:mn>3</mml:mn><mml:mo>+</mml:mo></mml:mrow></mml:msup></mml:math> complexes with pyrazole-substituted 1,3-diketones demonstrated an unusual spectral lines branching ratios
  作者：D.A. Metlina、M.T. Metlin、S.A. Ambrozevich、A.S. Selyukov、N.P. Datskevich、D.F. Aminev、D.O. Goryachii、K.A. Lyssenko、A.A. Pavlov、A.O. Dmitrienko、I.V. Taydakov

  DOI：10.1016/j.dyepig.2020.108558

  日期：2020.10

  A series of novel highly NIR-emitting Nd3+ complexes with specially designed 1,3-diketones bearing a pyrazole moiety and a linear CxF2x+1 group (x = 1, 3,6) was obtained and exhaustively investigated. It was demonstrated that for the complexes with an increased number of fluorine atoms, the triplet level energy of the ligands is decreased and phonon relaxation processes are suppressed. This provides a remarkable increase in the photoluminescence quantum yield up to 1.1%, which is close to the highest values reported for Nd3+ complexes with 1,3-diketones. The photoluminescence spectra of the complexes exhibited the Stark splitting indicative of non-cubic symmetry. Low symmetry of coordination environment was confirmed by the X-ray structural data and analysis of calculated Judd-Ofelt intensity parameters. Besides, it was revealed that the most intense band in the PL spectrum is attributed to the F-4(3/2) -> I-4(9/2) transition (at 880 nm) which is commonly rather weak for simple diketonate complexes. The calculations showed that the unexpectedly high branching ratio of the F-4(3/2) -> (4)I9/ transition raises with elongation of the fluorinated chain and reaches 59% for the complex with x = 6. The studies were conducted for solutions of the complexes as well as for solid samples, and the corresponding changes in their optical behavior were discussed. Uncommon properties of the synthesized Nd3+ complexes make them promising materials for various state-of-the-art luminescent applications, e.g., luminescent markers with an unusual spectral intensity distribution. Based on the electroluminescence studies, we also estimated the potential of the complexes for purely NIR-emitting OLEDs fabrication.