N,N'-[ethylenedioxybis(3-oxaoctamethyleneoxy)-2-phenyl]bis(9-anthracenencarbonamide)

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 英文名称: N,N'-[ethylenedioxybis(3-oxaoctamethyleneoxy)-2-phenyl]bis(9-anthracenencarbonamide)
• 英文别名: N-[2-[2-[2-[2-[2-[2-[2-(anthracene-9-carbonylamino)phenoxy]ethoxy]ethoxy]ethoxy]ethoxy]ethoxy]phenyl]anthracene-9-carboxamide
• 化学式: C₅₂H₄₈N₂O₈
• 分子量: 828.962
• InChiKey: JULDEHCBGVCPHP-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  9.6
• 重原子数：
  62
• 可旋转键数：
  21
• 环数：
  8.0
• sp3杂化的碳原子比例：
  0.19
• 拓扑面积：
  114
• 氢给体数：
  2
• 氢受体数：
  8

反应信息

• 作为产物：
  描述：

  9-蒽甲酸 在 氯化亚砜 、 potassium tert-butylate 作用下， 以 四氢呋喃 、 N,N-二甲基甲酰胺 为溶剂， 反应 37.5h， 生成 N,N'-[ethylenedioxybis(3-oxaoctamethyleneoxy)-2-phenyl]bis(9-anthracenencarbonamide)
  参考文献：
  名称：

  New Fluorescent “Off−On” Behavior of 9-Anthryl Aromatic Amides through Controlling the Twisted Intramolecular Charge Transfer Relaxation Process by Complexation with Metal Ions

  摘要：

  New fluorophores based on linear polyether N,N '-[oxybis(3-oxapentamethylenoxy)-2-phenyl]bis(9-anthracene- carbonamide) (3) and its analogues (2 and 4) have been synthesized, and their complexation properties with Various alkali-metal and alkaline-earth-metal ions were investigated by fluorescence, UV, and H-1 NMR spectroscopies. in the absence of metal ion, 2-4 showed almost no fluorescence emission (fluorescence quantum yield Phi = 0.0003, fluorescence "off" State) since twisted intramolecular charge transfer (TICT) occurred through the amide bond. However, 2-4 demonstrated a significant increase in fluorescence intensity around 430 nm upon complexation with alkaline-earth-metal ions. In the case of 4.Ca2+, a large enhancement effect on the fluorescence quantum yield (Phi = 0.014, [Ca2+]/[4] = 5, Phi (2+)(4.Ca)/Phi (free4) = 42, fluorescence "on" state) was observed. This "off-on" fluorescence characteristic was originated from the cooperative strong binding mode between the carbonyl group and the ethylenoxy moiety for alkaline-earth-metal ions, resulting in effective inhibition of photoinduced TICT relaxation. Fluorophores 2-4 formed a 1:1 complex (the order of the complex formation constants was Ca2+ > Sr2+ approximate to Ba2+) and showed no considerable spectral changes upon complexation with alkali-metal ions and Mg2+. The H-1 NMR study on 2-4 and their complexes indicated that free 2-4 formed a helical structure. After complexation, the conformational change of 2 from a helical structure to a semicircular structure was observed. The pseudocyclic form was supported as the complex structure of 3, whereas the large conformational change of 4 was not observed after the addition of metal ions.

  DOI：

  10.1021/jp0030600

文献信息

• New Fluorescent “Off−On” Behavior of 9-Anthryl Aromatic Amides through Controlling the Twisted Intramolecular Charge Transfer Relaxation Process by Complexation with Metal Ions
  作者：Tatsuya Morozumi、Takahisa Anada、Hiroshi Nakamura

  DOI：10.1021/jp0030600

  日期：2001.4.1

  New fluorophores based on linear polyether N,N '-[oxybis(3-oxapentamethylenoxy)-2-phenyl]bis(9-anthracene- carbonamide) (3) and its analogues (2 and 4) have been synthesized, and their complexation properties with Various alkali-metal and alkaline-earth-metal ions were investigated by fluorescence, UV, and H-1 NMR spectroscopies. in the absence of metal ion, 2-4 showed almost no fluorescence emission (fluorescence quantum yield Phi = 0.0003, fluorescence "off" State) since twisted intramolecular charge transfer (TICT) occurred through the amide bond. However, 2-4 demonstrated a significant increase in fluorescence intensity around 430 nm upon complexation with alkaline-earth-metal ions. In the case of 4.Ca2+, a large enhancement effect on the fluorescence quantum yield (Phi = 0.014, [Ca2+]/[4] = 5, Phi (2+)(4.Ca)/Phi (free4) = 42, fluorescence "on" state) was observed. This "off-on" fluorescence characteristic was originated from the cooperative strong binding mode between the carbonyl group and the ethylenoxy moiety for alkaline-earth-metal ions, resulting in effective inhibition of photoinduced TICT relaxation. Fluorophores 2-4 formed a 1:1 complex (the order of the complex formation constants was Ca2+ > Sr2+ approximate to Ba2+) and showed no considerable spectral changes upon complexation with alkali-metal ions and Mg2+. The H-1 NMR study on 2-4 and their complexes indicated that free 2-4 formed a helical structure. After complexation, the conformational change of 2 from a helical structure to a semicircular structure was observed. The pseudocyclic form was supported as the complex structure of 3, whereas the large conformational change of 4 was not observed after the addition of metal ions.