N-(2-hydroxyphenyl)-9-anthrylamide | 342777-02-0

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 英文名称: N-(2-hydroxyphenyl)-9-anthrylamide
• CAS: 342777-02-0
• 化学式: C₂₁H₁₅NO₂
• 分子量: 313.356
• InChiKey: ZRVQPZKHWNTXOA-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.95
• 重原子数：
  24.0
• 可旋转键数：
  2.0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  49.33
• 氢给体数：
  2.0
• 氢受体数：
  2.0

反应信息

• 作为反应物：
  描述：

  四乙二醇二对甲苯磺酸酯 、 N-(2-hydroxyphenyl)-9-anthrylamide 在 potassium tert-butylate 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 12.0h， 生成 N,N'-[Oxybis(3-oxapentamethyleneoxy)-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
• 作为产物：
  描述：

  9-蒽甲酸 在 氯化亚砜 作用下， 以 四氢呋喃 为溶剂， 反应 25.5h， 生成 N-(2-hydroxyphenyl)-9-anthrylamide
  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

• Discriminating Detection between Mg²⁺ and Ca²⁺ by Fluorescent Signal from Anthracene Aromatic Amide Moiety
  作者：Jeongsik Kim、Tatsuya Morozumi、Hiroshi Nakamura

  DOI：10.1021/ol701976x

  日期：2007.10.1

  fluorescent reagents 1 and 2 were synthesized. In the absence of metal ions, the fluorescence emissions of these compounds were quite weak, but their intensities were much greater in the presence of alkaline earth metal ions. The peak shape and maximum wavelength of the emission of the complex with Mg2+ differed from those of Ca2+ and other alkaline earth metal ions. The peak wavelength difference was 30 nm.

  合成了新型荧光试剂1和2。在没有金属离子的情况下，这些化合物的荧光发射非常弱，但是在碱土金属离子的存在下它们的强度要大得多。与Mg2 +形成的络合物的发射峰形和最大波长不同于Ca2 +和其他碱土金属离子的发射峰形和最大波长。峰值波长差为30nm。
• Novel chemosensor for alkaline earth metal ion based on 9-anthryl aromatic amide using a naphthalene as a TICT control site and intramolecular energy transfer donor
  作者：Jeongsik Kim、Tatsuya Morozumi、Namiko Kurumatani、Hiroshi Nakamura

  DOI：10.1016/j.tetlet.2008.01.085

  日期：2008.3

  2 with two different fluorophores (naphthalene and anthracene) at the both ends of polyether was synthesized. These compounds based on 9-anthryl aromatic amide adopted a naphthalene as a TICT controller and an intramolecular energy transfer source. Compound 1 shows high fluorescence efficiency upon complexation with metal ion, and the fluorescence efficiency of 2 is regulated by metal ionic size.

  合成了在聚醚两端带有两个不同荧光团（萘和蒽）的新型荧光化学传感器1和2。这些基于9-氨基芳族酰胺的化合物采用萘作为TICT控制剂和分子内能量转移源。化合物1与金属离子络合后显示出高荧光效率，而2的荧光效率受金属离子尺寸调节。