5,6-bis(dodecyloxy)-2,1,3-benzoxadiazole | 1400694-91-8

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 苯并恶二唑类
• 英文名称: 5,6-bis(dodecyloxy)-2,1,3-benzoxadiazole
• CAS: 1400694-91-8
• 化学式: C₃₀H₅₂N₂O₃
• 分子量: 488.754
• InChiKey: AESBSNRWCFOGKL-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  9.82
• 重原子数：
  35.0
• 可旋转键数：
  24.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.8
• 拓扑面积：
  57.38
• 氢给体数：
  0.0
• 氢受体数：
  5.0

反应信息

• 作为反应物：
  描述：

  5,6-bis(dodecyloxy)-2,1,3-benzoxadiazole 在 溴 、 溶剂黄146 作用下， 以 二氯甲烷 为溶剂， 反应 72.0h， 以90%的产率得到4,7-dibromo-5,6-bis(dodecyloxy)-2,1,3-benzoxadiazole
  参考文献：
  名称：

  2,1,3-Benzoxadiazole and 2,1,3-benzothiadiazole-based fluorescent compounds: Synthesis, characterization and photophysical/electrochemical properties

  摘要：

  Six new fluorescent compounds derived from 2,1,3-benzoxadiazole and 2,1,3-benzothiadiazole hetero-cycles with varying numbers of alkoxy chains were successfully synthesized. Sonogashira cross-coupling was used as the key synthetic step to link the central and terminal aromatic units through an acetylenic linker unit which ensures molecular planarity and extension of the conjugation. All of the synthesized compounds showed UV-vis absorption in the 426-437 nm range with reasonably high molar extinction coefficients. All six compounds emit in the green region of the visible spectrum with reasonably large Stokes shifts (95-107 nm) and medium emission efficiencies (phi(f) = 0.27-0.32). Electrochemical studies showed that the compounds have closely spaced HOMO and LUMO energy levels and that they may present good electron transporting properties. (C) 2012 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.dyepig.2012.06.001
• 作为产物：
  描述：

  1,2-(二十二烷氧荃)苯 在 sodium azide 、 硫酸 、 四丁基溴化铵 、 硝酸 作用下， 以 二氯甲烷 、 甲苯 为溶剂， 反应 7.0h， 生成 5,6-bis(dodecyloxy)-2,1,3-benzoxadiazole
  参考文献：
  名称：

  2,1,3-Benzoxadiazole and 2,1,3-benzothiadiazole-based fluorescent compounds: Synthesis, characterization and photophysical/electrochemical properties

  摘要：

  Six new fluorescent compounds derived from 2,1,3-benzoxadiazole and 2,1,3-benzothiadiazole hetero-cycles with varying numbers of alkoxy chains were successfully synthesized. Sonogashira cross-coupling was used as the key synthetic step to link the central and terminal aromatic units through an acetylenic linker unit which ensures molecular planarity and extension of the conjugation. All of the synthesized compounds showed UV-vis absorption in the 426-437 nm range with reasonably high molar extinction coefficients. All six compounds emit in the green region of the visible spectrum with reasonably large Stokes shifts (95-107 nm) and medium emission efficiencies (phi(f) = 0.27-0.32). Electrochemical studies showed that the compounds have closely spaced HOMO and LUMO energy levels and that they may present good electron transporting properties. (C) 2012 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.dyepig.2012.06.001