2-naphtho[2,3-d]oxazol-2-ylphenol | 1008528-40-2

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑类
• 英文名称: 2-naphtho[2,3-d]oxazol-2-ylphenol
• 英文别名: 2-(2-hydroxyphenyl)naphthoxazole；2-Benzo[f][1,3]benzoxazol-2-ylphenol
• CAS: 1008528-40-2
• 化学式: C₁₇H₁₁NO₂
• 分子量: 261.28
• InChiKey: ZVFNXYODBMRTJE-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4
• 重原子数：
  20
• 可旋转键数：
  1
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  46.3
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  bis[2-(2,4-difluorophenyl)pyridinato-N,C6']iridium(III) chloride dimer 、 2-naphtho[2,3-d]oxazol-2-ylphenol 在 Na₂CO₃ 作用下， 以 乙二醇乙醚 为溶剂， 以73%的产率得到iridium(III) bis(2-(2,4-difluorophenyl)pyridinato-N,C(2'))(2-(naphthoxazolyl)phenolate)
  参考文献：
  名称：

  Highly Phosphorescent Iridium Complexes with Chromophoric 2-(2-Hydroxyphenyl)oxazole-Based Ancillary Ligands: Interligand Energy-Harvesting Phosphorescence

  摘要：

  We disclose a controlled phosphorescence color tuning in a Series of cyclometalated heteroleptic Ir(III) complexes (Ir(III) bis(2-(2,4-difluorophenyl)pyridinato-C,N-2') (LX)) containing chromophoric 2-(2-hydroxyphenyl)oxazole-derivative ancillary ligands (LX). From a cyclometalated chloride-bridged Ir(III) dimer, three highly emissive cyclometalated heteroleptic Ir(III) complexes were obtained in good yields, each with a different conjugative plane in the chromophoric ancillary ligand (i.e., 2-(2-hydroxyphenyl)-4-methyloxazole, 2-(2-hydroxyphenyl)-6-methylbenzoxazole, and 2-(2-hydroxyphenyl)naphthoxazole). The three Ir(Ill) complexes showed highly efficient greenish blue (500 nm), green (525 nm), and yellow (552 nm) phosphorescence, respectively; a regular ca. 0.11 eV bathochromic shift was observed for each additional phenyl ring fused to the oxazole ring in the ancillary ligand. From the absorption, electrochemical measurements, static and transient photoluminescence (PL), and time-dependent density functional theory (TD-DFT) calculations, it can be concluded that the Ir(Ill) complexes have a single emission center with dual excitation paths. Finally, this characteristic energy-harvesting phosphorescence was further demonstrated in electrophosphorescence devices.

  DOI：

  10.1021/ic701778f
• 作为产物：
  描述：

  2-phenylnaphtho[2,3-d]oxazole 在 sodium persulfate 、 palladium diacetate 作用下， 以 1,4-二氧六环 为溶剂， 反应 14.0h， 以61%的产率得到2-naphtho[2,3-d]oxazol-2-ylphenol
  参考文献：
  名称：

  Palladium catalyzed C_sp2–H activation for direct aryl hydroxylation: the unprecedented role of 1,4-dioxane as a source of hydroxyl radicals

  摘要：

  直接芳香族羟基化已通过使用多功能引导基团通过前所未有的1,4-二氧六环的羟基转移实现钯催化的Csp2-H活化。

  DOI：

  10.1039/c4cc06864e