1-phenyl-3-methyl-4-(1-naphthoyl)pyrazol-5-one | 141704-27-0

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 英文名称: 1-phenyl-3-methyl-4-(1-naphthoyl)pyrazol-5-one
• 英文别名: 1-phenyl-3-methyl-4-(1-naphthoyl)-5-pyrazolone；3-Methyl-4-(1-naphthoyl)-1-phenyl-5(4H)-pyrazolone；5-methyl-4-(naphthalene-1-carbonyl)-2-phenyl-4H-pyrazol-3-one
• CAS: 141704-27-0
• 化学式: C₂₁H₁₆N₂O₂
• 分子量: 328.37
• InChiKey: IATZVCSONYEVMW-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.1
• 重原子数：
  25
• 可旋转键数：
  3
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.1
• 拓扑面积：
  49.7
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  gadolinium(III) nitrate hexahydrate 、 1-phenyl-3-methyl-4-(1-naphthoyl)pyrazol-5-one 在 sodium hydroxide 作用下， 以 乙醇 为溶剂， 生成 tris[1-phenyl-3-methyl-4-(1-naphthoyl)-5-pyrazolonato]gadolinium dihydrate
  参考文献：
  名称：

  Tuning the Triplet Energy Levels of Pyrazolone Ligands to Match the ⁵D₀ Level of Europium(III)

  摘要：

  Three pyrazolone-based ligands, namely 1-phenyl-3-methyl-4-(1- naphthoyl)-5-pyrazolone (HL1), 1-phenyl-3-methyl-4-(4-dimethylaminobenzoyl)-5-pyrazolone (HL2), and 1-phenyl-3-methyl-4-(4-cyanobenzoyl)-5-pyrazolone (W), were synthesized by introducing electron-poor or electron-rich aryl substituents at the 4-position of the pyrazolone ring. Their corresponding europium complexes Eu(LX)(3)(H2O)(2) and Eu(LX)(3)(TPPO)(H2O) (X = 1-3) were characterized by photophysical studies. The characteristic Eu(Ill) emission of these complexes with at most 9.2 x 10(-3) of fluorescent quantum yield was observed at room temperature. The results show that the modification of ligands tunes the triplet energy levels of three pyrazolone-based ligands to match the D-5(0) energy level of Eu3+ properly and improves the energy transfer efficiency from antenna to Eu3+, therefore enhancing the Eu(Ill) emission intensity. The highest energy transfer efficiency and probability of lanthanide emission of Eu(L1)(3)(H2O)(2) are 35.1% and 2.6%, respectively, which opens up broad prospects for improving luminescent properties of Eu(III) complexes by the modification of ligands. Furthermore, the electroluminescent properties of Eu(L1)(3)(TPPO)(H2O) were also investigated.

  DOI：

  10.1021/ic050844p

文献信息

• Copper(I) monophosphine complexes with functionalized acylpyrazolonate ligands: Syntheses of heterobimetallic Cu–Zn and Cu–Ru adducts
  作者：Augusto Cingolani、Fabio Marchetti、Claudio Pettinari、Riccardo Pettinari、Brian W. Skelton、Neil Somers、Allan H. White

  DOI：10.1016/j.poly.2005.07.020

  日期：2006.1

  Copper(I) acylpyrazolonate derivatives of formula [Cu(Q)(PPh3)(2)] (HQ = HQ(C2F5) = 1-phenyl-3-methyl4-pentafluoropropanoyl-pyrazol-5-one, HQ(CF3,CF3) = 1-(4-trifluoromethyl)phenyl-3-methyl-4-trifluoroacetylpyrazol-5-one, HQ(naph) = 1-phenyl-3-methyl-4-(1-naphthoyl)pyrazol-5-one, HQ(fur) = 1-phenyl-3-methyl-4-furylpyrazol-5-one, HQ(thi) = 1-phenyl-3-methyl-4-thienoylpyrazol-5-one, HQ(CF3,py) = 1-(2-pyridyl)-3-methyl-4-trifluoromethylpyrazol-5-one) have been synthesized and characterized, both in the solid state and in solution. The isomorphous crystal structures of [Cu(Q(fur))(PPh3)(2)] and [Cu(Q(thi))(PPh3)(2)] and of [CU(Q(C2F5))(PPh3)(2)] show their copper atoms in distorted tetrahedral environments. Apart from the derivative [Cu(Q(naph))(PPh3)(2)] they are fluxional in chloroform solution, dissociating partially to the [Cu(Q)(PR3)] fragment and free PR3, or existing in solution as [Cu(O-2-Q)(PR3)(2)] or [Cu(O-Q)(PR3)(2)] species, with CuO2P2 or CuOP2, metal environments, in equilibrium with each other. By contrast, in [Cu(Q(CF3,py))(PPh3)(2)] the Q(CF3.py) ligand is coordinated to copper through the nitrogen atoms of the pyrazole and pyridine rings. The latter compound reacts with Zn(BF4)(2)center dot xH(2)O and [Ru(p-cymene)Cl-2](2) affording ionic heterobimetallic adducts. (c) 2005 Elsevier Ltd. All rights reserved.