5-phenyl-2-methylquinolin-8-ol | 423755-61-7

• 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: 5-phenyl-2-methylquinolin-8-ol
• 英文别名: 2-methyl-5-phenyl-8-hydroxyquinoline；8-hydroxy-5-(phenyl)-2-methyl-quinoline；HPhMq；2-methyl-5-phenylquinolin-8-ol；2-Methyl-5-phenylquinolin-8-ol
• CAS: 423755-61-7
• 化学式: C₁₆H₁₃NO
• 分子量: 235.285
• InChiKey: NRTGZNBJGGOTOO-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.9
• 重原子数：
  18
• 可旋转键数：
  1
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.06
• 拓扑面积：
  33.1
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  aluminium(III) phenoxide 、 5-phenyl-2-methylquinolin-8-ol 以 not given 为溶剂， 生成 aluminium(III) bis(2-methyl-5-phenyl-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 5-phenyl-2-methylquinolin-8-ol
  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

• Synthesis and Photophysical Properties of a Series of Dimeric Indium Quinolinates
  作者：Sang Woo Kwak、Ju Hyun Hong、Sang Hoon Lee、Min Kim、Yongseog Chung、Kang Mun Lee、Youngjo Kim、Myung Hwan Park

  DOI：10.3390/molecules26010034

  日期：——

  A novel class of quinolinol-based dimeric indium complexes (1–6) was synthesized and characterized using 1H and 13C(1H) NMR spectroscopy and elemental analysis. Compounds 1–6 exhibited typical low-energy absorption bands assignable to quinolinol-centered π–π* charge transfer (CT) transition. The emission spectra of 1–6 exhibited slight bathochromic shifts with increasing solvent polarity (p-xylene

  合成了一类新的基于喹啉醇的二聚铟配合物 (1-6)，并使用 1H 和 13C(1H) NMR 光谱和元素分析对其进行了表征。化合物 1-6 表现出典型的低能量吸收带，可归因于以喹啉醇为中心的 π-π* 电荷转移 (CT) 跃迁。1-6 的发射光谱随着溶剂极性的增加（对二甲苯 < 四氢呋喃 (THF) < 二氯甲烷 (DCM)）表现出轻微的红移。发射带也显示出逐渐红移，随着喹啉基团 C5 位取代基的给电子效应增加。化合物 1（在 THF 中为 11.2%，在薄膜中为 17.2%）和 4（在 THF 中为 17.8% 和 36）的绝对发射量子产率 (ΦPL)。
• Asymmetric Synthesis of a New 8-Hydroxyquinoline-Derived α-Amino Acid and Its Incorporation in a Peptidylsensor for Divalent Zinc
  作者：Nathalie Jotterand、Dierdre A. Pearce、Barbara Imperiali

  DOI：10.1021/jo001681j

  日期：2001.5.1
• 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.