4'-hydroxymethyl-6-6''-bis(bromomethyl)-2,2':6',2''-terpyridine | 1363597-57-2

• 英文名称: 4'-hydroxymethyl-6-6''-bis(bromomethyl)-2,2':6',2''-terpyridine
• CAS: 1363597-57-2
• 化学式: C₁₈H₁₅Br₂N₃O
• 分子量: 449.145
• InChiKey: BROKNUXYZWXZQQ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.49
• 重原子数：
  24.0
• 可旋转键数：
  5.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.17
• 拓扑面积：
  58.9
• 氢给体数：
  1.0
• 氢受体数：
  4.0

反应信息

• 作为反应物：
  描述：

  4'-hydroxymethyl-6-6''-bis(bromomethyl)-2,2':6',2''-terpyridine 在 三溴化磷 、 sodium hydride 作用下， 以 四氢呋喃 、 乙腈 为溶剂， 反应 3.0h， 生成 tetraethyl (4′-bromomethyl-2,2′:6′,2′-terpyridine-6,6′-diyl)bis(methylenenitrilo)tetrakis(acetate)
  参考文献：
  名称：

  A Ratiometric Luminescence Probe for Highly Reactive Oxygen Species Based on Lanthanide Complexes

  摘要：

  Reactive oxygen species (ROS) are important mediators in a variety of pathological events, but the oxidative stress owing to excessive generation of ROS is implicated in many human diseases. In this work, we designed and synthesized a novel dual-functional chelating ligand, [4'-(p-aminophenoxy)methylene-2,2':6',2 ''-terpyridine-6,6 ''-diyl]bis(tnethylenenitrilo)tetrakis(acetic acid) (AMTTA), that can strongly coordinate with both Eu3+ and Tb3+ in aqueous solutions for the recognition and time-gated luminescence detection of highly ROS (hROS), hydroxyl radical ((OH)-O-center dot), and hypochlorite (ClO-). The complexes AMTTA-Ln(3+) (Ln = Eu and Tb) are almost nonluminescent because of the photoinduced electron transfer from the electron-rich aminophenyl group to the terpyridine-Ln(3+) moiety but can rapidly react with hROS to afford highly luminescent complexes (4'-hydroxymethyl-2,2':6',2 ''-terpyridine-6,6 ''-diyl)bis(methylenenitrilo)tetrakis(acetate)- Ln(3+) (HTTA-Ln(3+)). Interestingly, when the AMTTA-Eu3+/Tb3+ mixture (AMTTA/Eu3+/Tb3+ = 2/1/1) was reacted with hROS, the intensity ratio of its Tb3+ emission at 540 nm to its Eu3+ emission at 610 nm, I-540/I-610, showed a ratiometric response toward hROS, and the dose-dependent increase of the ratio displayed a double-exponential correlation to the concentration of hROS. This unique luminescence response allowed the AMTTA-Eu3+/Tb3+ mixture to be used as a ratiometric probe for the time-gated luminescence detection of hROS.

  DOI：

  10.1021/ic202195a
• 作为产物：
  描述：

  6,6''-二(溴甲基)-[2,2':6',2''-三联吡啶]-4'-羧酸乙酯 在 lithium aluminium tetrahydride 作用下， 以 四氢呋喃 为溶剂， 反应 2.5h， 以25%的产率得到4'-hydroxymethyl-6-6''-bis(bromomethyl)-2,2':6',2''-terpyridine
  参考文献：
  名称：

  A Ratiometric Luminescence Probe for Highly Reactive Oxygen Species Based on Lanthanide Complexes

  摘要：

  Reactive oxygen species (ROS) are important mediators in a variety of pathological events, but the oxidative stress owing to excessive generation of ROS is implicated in many human diseases. In this work, we designed and synthesized a novel dual-functional chelating ligand, [4'-(p-aminophenoxy)methylene-2,2':6',2 ''-terpyridine-6,6 ''-diyl]bis(tnethylenenitrilo)tetrakis(acetic acid) (AMTTA), that can strongly coordinate with both Eu3+ and Tb3+ in aqueous solutions for the recognition and time-gated luminescence detection of highly ROS (hROS), hydroxyl radical ((OH)-O-center dot), and hypochlorite (ClO-). The complexes AMTTA-Ln(3+) (Ln = Eu and Tb) are almost nonluminescent because of the photoinduced electron transfer from the electron-rich aminophenyl group to the terpyridine-Ln(3+) moiety but can rapidly react with hROS to afford highly luminescent complexes (4'-hydroxymethyl-2,2':6',2 ''-terpyridine-6,6 ''-diyl)bis(methylenenitrilo)tetrakis(acetate)- Ln(3+) (HTTA-Ln(3+)). Interestingly, when the AMTTA-Eu3+/Tb3+ mixture (AMTTA/Eu3+/Tb3+ = 2/1/1) was reacted with hROS, the intensity ratio of its Tb3+ emission at 540 nm to its Eu3+ emission at 610 nm, I-540/I-610, showed a ratiometric response toward hROS, and the dose-dependent increase of the ratio displayed a double-exponential correlation to the concentration of hROS. This unique luminescence response allowed the AMTTA-Eu3+/Tb3+ mixture to be used as a ratiometric probe for the time-gated luminescence detection of hROS.

  DOI：

  10.1021/ic202195a