2-methyl-5-(4-dimethylaminophenyl)-8-hydroxyquinoline | 1028353-74-3

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 喹啉及其衍生物
• 英文名称: 2-methyl-5-(4-dimethylaminophenyl)-8-hydroxyquinoline
• 英文别名: 8-hydroxy-5-(4-dimethyl-amino-phenyl)-2-methyl-quinoline；HMe2NC6H4Mq；5-(4-(dimethylamino)phenyl)-2-methylquinolin-8-ol；5-[4-(Dimethylamino)phenyl]-2-methylquinolin-8-ol；5-[4-(dimethylamino)phenyl]-2-methylquinolin-8-ol
• CAS: 1028353-74-3
• 化学式: C₁₈H₁₈N₂O
• 分子量: 278.354
• InChiKey: GKTKECICQDFPBN-UHFFFAOYSA-N

物化性质

• 熔点：
  160-162 °C(Solv: isopropanol (67-63-0))
• 沸点：
  444.0±45.0 °C(Predicted)
• 密度：
  1.185±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4
• 重原子数：
  21
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.17
• 拓扑面积：
  36.4
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  2-methyl-5-(4-dimethylaminophenyl)-8-hydroxyquinoline 、 aluminium(III) phenoxide 以 not given 为溶剂， 生成 aluminium(III) bis(2-methyl-5-(4-dimethylaminophenyl)-8-quinolinolate)phenolate
  参考文献：
  名称：

  True Blue:  Blue-Emitting Aluminum(III) Quinolinolate Complexes

  摘要：

  Blue-emitting heteroleptic aluminum(III) bis(2-methyl-8-quinolinolate) phenolate complexes were synthesized. A tunable, blue-to-green emission is achieved by attaching electron-withdrawing modulators to the emisssive quinaldinate ligand. The electronic nature of modulator substituents attached to the position of the highest HOMO (highest occupied molecular orbital) density is used to modulate ligand HOMO levels to achieve effective emission tuning to obtain blue-emitting materials. Optical and electrochemical properties of the resulting complexes were investigated and compared to the results of density functional theory (DFT/B3LYP/6-31G*) studies. The resulting materials may find application as organic light-emitting device materials.

  DOI：

  10.1021/ic061051l
• 作为产物：
  描述：

  5-溴-8-甲氧基-2-甲基-喹啉 在 氢溴酸 、 palladium diacetate 、 potassium carbonate 、 三(邻甲基苯基)磷 作用下， 以 水 、 甲苯 为溶剂， 生成 2-methyl-5-(4-dimethylaminophenyl)-8-hydroxyquinoline
  参考文献：
  名称：

  Sensitized luminescence in dinuclear lanthanide(iii) complexes of bridging 8-hydroxyquinoline derivatives with different electronic properties

  摘要：

  以μ-苯酚模式合成并表征了{Eu(hfac)3(H2O)}2(μ-HPhMq)2 (2)和{Ln(hfac)3(H2O)}2(μ-HMe2NC6H4Mq)2 (Ln = Eu, 3. Nd, 4)三种新的双核镧系(III)配合物；其中 hfac- = 六氟乙酰丙酮，HPhMq = 2-甲基-5-苯基喹啉-8-醇，HMe2C6H4Mq = 5-(4-(二甲基氨基)苯基)-2-甲基喹啉-8-醇。与{Eu(hfac)3}2(μ-HMq)2（1，HMq = 2-甲基-8-羟基喹啉）的激发波长（400 nm）相比，通过在 8-羟基喹啉中引入苯基或 4-（二甲基氨基）苯基，2 的敏化镧系元素发光激发波长延长至约 420 nm，4 的敏化镧系元素发光激发波长延长至 500 nm。由于取代了配位水分子或与配位 H2O 和 μ-苯酚形成了强 O-H⋯F 氢键，从而显著抑制了非辐射 O-H 振荡器，这些双核镧系元素（III）配合物在强度和寿命方面都表现出明显的氟化物诱导镧系元素（III）发射增强。

  DOI：

  10.1039/c0dt01663b

文献信息

• Sensitized luminescence in dinuclear lanthanide(iii) complexes of bridging 8-hydroxyquinoline derivatives with different electronic properties
  作者：Hai-Bing Xu、Jia Li、Lin-Xi Shi、Zhong-Ning Chen

  DOI：10.1039/c0dt01663b

  日期：——

  Three new dinuclear lanthanide(III) complexes Eu(hfac)3(H2O)}2(μ-HPhMq)2 (2) and Ln(hfac)3(H2O)}2(μ-HMe2NC6H4Mq)2 (Ln = Eu, 3; Nd, 4) with 8-hydroxylquinoline derivatives in μ-phenol mode were synthesized and characterized, where hfac− = hexafluoroacetylacetonate, HPhMq = 2-methyl-5-phenylquinolin-8-ol, and HMe2C6H4Mq = 5-(4-(dimethylamino)phenyl)-2-methylquinolin-8-ol. Compared with that (400 nm) for Eu(hfac)3}2(μ-HMq)2 (1, HMq = 2-methy-8-hydroxylquinoline), the excitation wavelength for sensitized lanthanide luminescence is extended to ca. 420 nm for 2, and 500 nm for 4 by introducing a phenyl or 4-(dimethylamino)phenyl to 8-hydroxylquinoline. These dinuclear lanthanide(III) complexes exhibit distinctly fluoride-induced lanthanide(III) emission enhancement in both intensity and lifetime due to replacing coordination water molecules or formation of strong O–H⋯F hydrogen bonds with coordinated H2O and μ-phenol, thus suppressing significantly the non-radiative O–H oscillators.

  以μ-苯酚模式合成并表征了Eu(hfac)3(H2O)}2(μ-HPhMq)2 (2)和Ln(hfac)3(H2O)}2(μ-HMe2NC6H4Mq)2 (Ln = Eu, 3. Nd, 4)三种新的双核镧系(III)配合物；其中 hfac- = 六氟乙酰丙酮，HPhMq = 2-甲基-5-苯基喹啉-8-醇，HMe2C6H4Mq = 5-(4-(二甲基氨基)苯基)-2-甲基喹啉-8-醇。与Eu(hfac)3}2(μ-HMq)2（1，HMq = 2-甲基-8-羟基喹啉）的激发波长（400 nm）相比，通过在 8-羟基喹啉中引入苯基或 4-（二甲基氨基）苯基，2 的敏化镧系元素发光激发波长延长至约 420 nm，4 的敏化镧系元素发光激发波长延长至 500 nm。由于取代了配位水分子或与配位 H2O 和 μ-苯酚形成了强 O-H⋯F 氢键，从而显著抑制了非辐射 O-H 振荡器，这些双核镧系元素（III）配合物在强度和寿命方面都表现出明显的氟化物诱导镧系元素（III）发射增强。
• True Blue:  Blue-Emitting Aluminum(III) Quinolinolate Complexes
  作者：César Pérez-Bolívar、Victor A. Montes、Pavel Anzenbacher

  DOI：10.1021/ic061051l

  日期：2006.11.1

  Blue-emitting heteroleptic aluminum(III) bis(2-methyl-8-quinolinolate) phenolate complexes were synthesized. A tunable, blue-to-green emission is achieved by attaching electron-withdrawing modulators to the emisssive quinaldinate ligand. The electronic nature of modulator substituents attached to the position of the highest HOMO (highest occupied molecular orbital) density is used to modulate ligand HOMO levels to achieve effective emission tuning to obtain blue-emitting materials. Optical and electrochemical properties of the resulting complexes were investigated and compared to the results of density functional theory (DFT/B3LYP/6-31G*) studies. The resulting materials may find application as organic light-emitting device materials.