1-(benzimidazol-2-ylmethyl)-1,4, 8,11-tetraazacyclotetradecane | 1293912-04-5

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 苯并咪唑类
• 英文名称: 1-(benzimidazol-2-ylmethyl)-1,4, 8,11-tetraazacyclotetradecane
• 英文别名: 1-(benzimidazol-2-ylmethyl)-1,4,8,11-tetraazacyclotetradecane；2-(1,4,8,11-tetrazacyclotetradec-1-ylmethyl)-1H-benzimidazole
• CAS: 1293912-04-5
• 化学式: C₁₈H₃₀N₆
• 分子量: 330.476
• InChiKey: QVDYCSKBANORCF-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.6
• 重原子数：
  24
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.61
• 拓扑面积：
  68
• 氢给体数：
  4
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  zinc(II) nitrate 、 1-(benzimidazol-2-ylmethyl)-1,4, 8,11-tetraazacyclotetradecane 以 甲醇 为溶剂， 以85%的产率得到[Zn(1-(benzimidazol-2-ylmethyl)-1,4,8,11-tetraazacyclotetradecane)](NO3)2*H2O
  参考文献：
  名称：

  Cyclam-methylbenzimidazole: a Selective OFF-ON Fluorescent Sensor for Zinc

  摘要：

  The coordination properties and the photophysical response of a new cyclam fluorescent probe for Zn(II), [L1H: 1-(benzimidazol-2-ylmethyl]-1,4, 8,11-tetraazacyclotetradecane] toward Cu(II), Zn(II), and Cd(II) are reported. The stability constants of the corresponding complexes were determined by means of potentiometric measurements in aqueous solution. The fluorescence of L1H was quenched by the presence of Cu(II), and L1H behaves as an OFF ON sensor for Zn(II) even in the presence of a wide range of biological divalent cations. Furthermore, on addition of successive amounts of Zn(II), the fluorescence emission of L1H increases linearly by a factor of 12. This can be correlated to the efficient Zn(II) binding of L1H and to the participation of all the amine functions in the metal coordination which prevents the photoincluced electron transfer (PET) effect and promotes a good chelation-enhanced fluorescence (CHEF) effect; this confers to the cyclam probe better sensing properties than the cyclen ionophore.

  DOI：

  10.1021/ic102521g
• 作为产物：
  描述：

  在 一水合肼 作用下， 反应 9.0h， 以1.93 g的产率得到1-(benzimidazol-2-ylmethyl)-1,4, 8,11-tetraazacyclotetradecane
  参考文献：
  名称：

  Cyclam-methylbenzimidazole: a Selective OFF-ON Fluorescent Sensor for Zinc

  摘要：

  The coordination properties and the photophysical response of a new cyclam fluorescent probe for Zn(II), [L1H: 1-(benzimidazol-2-ylmethyl]-1,4, 8,11-tetraazacyclotetradecane] toward Cu(II), Zn(II), and Cd(II) are reported. The stability constants of the corresponding complexes were determined by means of potentiometric measurements in aqueous solution. The fluorescence of L1H was quenched by the presence of Cu(II), and L1H behaves as an OFF ON sensor for Zn(II) even in the presence of a wide range of biological divalent cations. Furthermore, on addition of successive amounts of Zn(II), the fluorescence emission of L1H increases linearly by a factor of 12. This can be correlated to the efficient Zn(II) binding of L1H and to the participation of all the amine functions in the metal coordination which prevents the photoincluced electron transfer (PET) effect and promotes a good chelation-enhanced fluorescence (CHEF) effect; this confers to the cyclam probe better sensing properties than the cyclen ionophore.

  DOI：

  10.1021/ic102521g

文献信息

• Cyclam-methylbenzimidazole: a Selective OFF-ON Fluorescent Sensor for Zinc
  作者：Abir El Majzoub、Cyril Cadiou、Isabelle Déchamps-Olivier、Bernard Tinant、Françoise Chuburu

  DOI：10.1021/ic102521g

  日期：2011.5.2

  The coordination properties and the photophysical response of a new cyclam fluorescent probe for Zn(II), [L1H: 1-(benzimidazol-2-ylmethyl]-1,4, 8,11-tetraazacyclotetradecane] toward Cu(II), Zn(II), and Cd(II) are reported. The stability constants of the corresponding complexes were determined by means of potentiometric measurements in aqueous solution. The fluorescence of L1H was quenched by the presence of Cu(II), and L1H behaves as an OFF ON sensor for Zn(II) even in the presence of a wide range of biological divalent cations. Furthermore, on addition of successive amounts of Zn(II), the fluorescence emission of L1H increases linearly by a factor of 12. This can be correlated to the efficient Zn(II) binding of L1H and to the participation of all the amine functions in the metal coordination which prevents the photoincluced electron transfer (PET) effect and promotes a good chelation-enhanced fluorescence (CHEF) effect; this confers to the cyclam probe better sensing properties than the cyclen ionophore.