4,8-diethynyl-2,6-diphenyl-1,5-dihydrobenzo-[1,2-d:4,5-d′]diimidazole

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑类
• 英文名称: 4,8-diethynyl-2,6-diphenyl-1,5-dihydrobenzo-[1,2-d:4,5-d′]diimidazole
• 英文别名: 4,8-Diethynyl-2,6-diphenyl-3,5-dihydroimidazo[4,5-f]benzimidazole；4,8-diethynyl-2,6-diphenyl-3,5-dihydroimidazo[4,5-f]benzimidazole
• 化学式: C₂₄H₁₄N₄
• 分子量: 358.402
• InChiKey: ZDANIFBDJRBBQE-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.9
• 重原子数：
  28
• 可旋转键数：
  4
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  57.4
• 氢给体数：
  2
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  4,8-diethynyl-2,6-diphenyl-1,5-dihydrobenzo-[1,2-d:4,5-d′]diimidazole 在 bis-triphenylphosphine-palladium(II) chloride 、 copper(l) iodide 、 三乙胺 、 三氟乙酸 作用下， 以 四氢呋喃 、 二氯甲烷 为溶剂， 反应 38.0h， 生成 4-[2-[8-[2-(4-Hydroxyphenyl)ethynyl]-2,6-diphenyl-3,5-dihydroimidazo[4,5-f]benzimidazol-4-yl]ethynyl]phenol
  参考文献：
  名称：

  Benzobisimidazole Cruciform Fluorophores

  摘要：

  A series of 11 cross-conjugated cruciform fluorophores based on a benzobisimidazole nucleus has been synthesized and characterized. Like in their previously reported benzobisoxazole counterparts, the HOMOs of these new fluorophores are localized along the vertical bisethynylbenzene axes, while their LUMOs remain relatively delocalized across the molecule, except in cruciforms substituted with electron, withdrawing groups along the vertical axis. Benzobisimidazole cruciforms exhibit a pronounced response to deprotonation in their UV/vis absorption and emission spectra, but their response to protonation is significantly attenuated.

  DOI：

  10.1021/acs.joc.5b00616
• 作为产物：
  描述：

  1,2,4,5-benzenetetraamine tetrahydrochloride 在 bis-triphenylphosphine-palladium(II) chloride 、 N-溴代丁二酰亚胺(NBS) 、 copper(l) iodide 、 四丁基氟化铵 、 二异丙胺 作用下， 以 四氢呋喃 、 N,N-二甲基甲酰胺 为溶剂， 反应 44.0h， 生成 4,8-diethynyl-2,6-diphenyl-1,5-dihydrobenzo-[1,2-d:4,5-d′]diimidazole
  参考文献：
  名称：

  Benzobisimidazole Cruciform Fluorophores

  摘要：

  A series of 11 cross-conjugated cruciform fluorophores based on a benzobisimidazole nucleus has been synthesized and characterized. Like in their previously reported benzobisoxazole counterparts, the HOMOs of these new fluorophores are localized along the vertical bisethynylbenzene axes, while their LUMOs remain relatively delocalized across the molecule, except in cruciforms substituted with electron, withdrawing groups along the vertical axis. Benzobisimidazole cruciforms exhibit a pronounced response to deprotonation in their UV/vis absorption and emission spectra, but their response to protonation is significantly attenuated.

  DOI：

  10.1021/acs.joc.5b00616