4,7-bis((3,4-bis(dodecyloxy)phenyl)ethynyl)-5,6-bis(dodecyloxy)-2,1,3-benzothiadiazole | 1400694-88-3

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 苯并噻二唑类
• 英文名称: 4,7-bis((3,4-bis(dodecyloxy)phenyl)ethynyl)-5,6-bis(dodecyloxy)-2,1,3-benzothiadiazole
• CAS: 1400694-88-3
• 化学式: C₉₄H₁₅₆N₂O₆S
• 分子量: 1442.35
• InChiKey: RONUYXVQOBPICL-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  30.29
• 重原子数：
  103.0
• 可旋转键数：
  72.0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.77
• 拓扑面积：
  81.16
• 氢给体数：
  0.0
• 氢受体数：
  9.0

反应信息

• 作为产物：
  描述：

  4,7-二溴-5,6-双(十二烷基氧代)-2,1,3-苯并噻二唑 、 1,2-bis(dodecyloxy)-4-ethynylbenzene 在 bis-triphenylphosphine-palladium(II) chloride 、 copper(l) iodide 、 三乙胺 、 三苯基膦 作用下， 反应 0.33h， 以51%的产率得到4,7-bis((3,4-bis(dodecyloxy)phenyl)ethynyl)-5,6-bis(dodecyloxy)-2,1,3-benzothiadiazole
  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