2,3-bis(4-methoxyphenyl)-5-hydroxyquinoxaline | 1338054-03-7

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 二氮杂萘
• 英文名称: 2,3-bis(4-methoxyphenyl)-5-hydroxyquinoxaline
• 英文别名: 2,3-Bis(4-methoxyphenyl)quinoxalin-5-ol；2,3-bis(4-methoxyphenyl)quinoxalin-5-ol
• CAS: 1338054-03-7
• 化学式: C₂₂H₁₈N₂O₃
• 分子量: 358.397
• InChiKey: VODAQIJKBPLOLQ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.1
• 重原子数：
  27
• 可旋转键数：
  4
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.09
• 拓扑面积：
  64.5
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  2,3-bis(4-methoxyphenyl)-5-hydroxyquinoxaline 、 zinc(II) acetate dihydrate 在 Na₂CO₃ 作用下， 以 乙二醇甲醚 为溶剂， 以88%的产率得到
  参考文献：
  名称：

  First examples of luminescent zinc(II)-bisquinoxalinato complexes: Synthesis, spectroscopic and theoretical studies

  摘要：

  Four novel homoleptic zinc(II) complexes were prepared in high yield from para-substituted 2,3-diphenyl-5-hydroxyquinoxaline ligands, LHn, giving [Zn(L-n)(2)]. Density functional theoretical calculations were performed to probe the influence of the variation in para-substitution on the ligands. The calculations suggest that ligand-centred character appears to dominate the HOMO and LUMOs. Experimental electro-chemical and spectroscopic characterisation showed that the subtle variations in absorption and emission wavelengths are due to ligand-dominated transitions that are influenced by electronic nature of the para-substituted phenyl units in coordinated L-n, in both solution and the solid states. (C) 2012 Elsevier B. V. All rights reserved.

  DOI：

  10.1016/j.ica.2012.01.008
• 作为产物：
  描述：

  2-氨基-3-硝基苯酚 、 4,4'-二甲氧基苯酚酯 在 盐酸 、 锌 作用下， 以 乙醇 、 水 为溶剂， 反应 30.0h， 以96%的产率得到2,3-bis(4-methoxyphenyl)-5-hydroxyquinoxaline
  参考文献：
  名称：

  New 2,3-disubstituted-5-hydroxyquinoxaline ligands and their coordination chemistry with cyclometallated iridium(iii): syntheses, structures and tunable electronic properties

  摘要：

  我们合成了一系列新的对位取代的 2,3-二苯基-5-羟基喹喔啉配体（LHn），并对其进行了表征。这些配体是通过两步合成法以高产率制备的。相应地，还制备出了四种新型杂色铱（III）配合物，并得到了高产率的[Ir(ppy)2(Ln)]。对 LH3 和[Ir(PY)2(L2)]进行了两次 X 射线晶体学研究，结果均证实了所提出的配方，其中络合物显示了喹喔啉配体的 O、N 配位模式。我们进行了密度泛函理论计算，首先是比较配位的喹喔啉配位体系和相关的喹啉配位类似物，其次是探究对位取代变化对辅助配体的影响。计算结果表明，无论是喹啉还是喹喔啉系统，配体中心特性似乎都主导着 HOMO 和 LUMO。实验电化学和光谱特性分析表明，吸收和发射波长的微妙变化可能是由于配体主导的转变，而配体主导的转变受到配位 Ln 中对位取代的苯基单元的电子性质的影响。

  DOI：

  10.1039/c1dt10707k

文献信息

• New 2,3-disubstituted-5-hydroxyquinoxaline ligands and their coordination chemistry with cyclometallated iridium(iii): syntheses, structures and tunable electronic properties
  作者：Andrew J. Hallett、Benson M. Kariuki、Simon J. A. Pope

  DOI：10.1039/c1dt10707k

  日期：——

  A new series of para-substituted 2,3-diphenyl-5-hydroxyquinoxaline ligands (LHn) were synthesised and characterised. These ligands were prepared in high yield via a two-step synthetic method. Four novel heteroleptic iridium(III) complexes were correspondingly prepared in high yield giving [Ir(ppy)2(Ln)]. Two X-ray crystallographic studies were undertaken on LH3 and [Ir(ppy)2(L2)] with each confirming the proposed formulations, with the complex showing the O,N-coordination mode of the quinoxalinato ligand. Density functional theoretical calculations were performed, firstly to compare the coordinated quinoxalinato system with the related quinolinato analogue, and secondly to probe the influence of the variation in para-substitution on the ancillary ligand. The calculations suggest that for either the quinoline or quinoxaline systems ligand-centred character appears to dominate the HOMO and LUMOs. Experimental electrochemical and spectroscopic characterisation showed that the subtle variations in absorption and emission wavelengths are probably due to ligand-dominated transitions that are influenced by the electronic nature of the para-substituted phenyl units in coordinated Ln.

  我们合成了一系列新的对位取代的 2,3-二苯基-5-羟基喹喔啉配体（LHn），并对其进行了表征。这些配体是通过两步合成法以高产率制备的。相应地，还制备出了四种新型杂色铱（III）配合物，并得到了高产率的[Ir(ppy)2(Ln)]。对 LH3 和[Ir(PY)2(L2)]进行了两次 X 射线晶体学研究，结果均证实了所提出的配方，其中络合物显示了喹喔啉配体的 O、N 配位模式。我们进行了密度泛函理论计算，首先是比较配位的喹喔啉配位体系和相关的喹啉配位类似物，其次是探究对位取代变化对辅助配体的影响。计算结果表明，无论是喹啉还是喹喔啉系统，配体中心特性似乎都主导着 HOMO 和 LUMO。实验电化学和光谱特性分析表明，吸收和发射波长的微妙变化可能是由于配体主导的转变，而配体主导的转变受到配位 Ln 中对位取代的苯基单元的电子性质的影响。
• First examples of luminescent zinc(II)-bisquinoxalinato complexes: Synthesis, spectroscopic and theoretical studies
  作者：Andrew J. Hallett、Simon J.A. Pope

  DOI：10.1016/j.ica.2012.01.008

  日期：2012.5

  Four novel homoleptic zinc(II) complexes were prepared in high yield from para-substituted 2,3-diphenyl-5-hydroxyquinoxaline ligands, LHn, giving [Zn(L-n)(2)]. Density functional theoretical calculations were performed to probe the influence of the variation in para-substitution on the ligands. The calculations suggest that ligand-centred character appears to dominate the HOMO and LUMOs. Experimental electro-chemical and spectroscopic characterisation showed that the subtle variations in absorption and emission wavelengths are due to ligand-dominated transitions that are influenced by electronic nature of the para-substituted phenyl units in coordinated L-n, in both solution and the solid states. (C) 2012 Elsevier B. V. All rights reserved.