1,4,7,10-tetrakis[N-(2-methyl-4-quinolyl)carbamoylmethyl]-1,4,7,10-tetraazacyclododecane | 204587-05-3

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 英文名称: 1,4,7,10-tetrakis[N-(2-methyl-4-quinolyl)carbamoylmethyl]-1,4,7,10-tetraazacyclododecane
• 英文别名: N-(2-methylquinolin-4-yl)-2-[4,7,10-tris[2-[(2-methylquinolin-4-yl)amino]-2-oxoethyl]-1,4,7,10-tetrazacyclododec-1-yl]acetamide
• CAS: 204587-05-3
• 化学式: C₅₆H₆₀N₁₂O₄
• 分子量: 965.17
• InChiKey: BEBSADKDQSGKKR-UHFFFAOYSA-N

物化性质

• 密度：
  1.294±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  6.4
• 重原子数：
  72
• 可旋转键数：
  12
• 环数：
  9.0
• sp3杂化的碳原子比例：
  0.29
• 拓扑面积：
  181
• 氢给体数：
  4
• 氢受体数：
  12

反应信息

• 作为反应物：
  描述：

  1,4,7,10-tetrakis[N-(2-methyl-4-quinolyl)carbamoylmethyl]-1,4,7,10-tetraazacyclododecane 、 ytterbium(III) triflate 以 乙腈 为溶剂， 生成 ytterbium(III) 1,4,7,10-tetrakis[N-(2-methyl-4-quinolyl)carbamoylmethyl]-1,4,7,10-tetraazacyclododecane tri(trifluoromethylsulfonate)
  参考文献：
  名称：

  Lanthanide Macrocyclic Quinolyl Conjugates as Luminescent Molecular-Level Devices

  摘要：

  The Eu(III) tetraazamacrocyclic complexes [Eu.1] and [Eu.2], and the Tb(III) and Yb(III) complexes [Tb.1] and [Yb.2], have been synthesized as luminescent molecular-level devices. The Eu complexes exhibit unique dual pH switching behavior in water under ambient conditions. The delayed Eu emission is reversibly switched on in acid, with an enhancement factor of several hundred for [Eu-1]. These observations are consistent with the protonation of the quinoline aryl nitrogen moiety (pK(a) approximate to 5.9 for [Eu.1]). The fluorescence emission spectra of these complexes are unaffected by acid, but pronounced changes occur in alkaline solution due to the deprotonation of the aryl amide nitrogen (pK(a) approximate to 9.4 for [Eu.1]). [Tb.1] shows a more intriguing pH dependence; Tb emission is switched "on" only in the presence of HI and in the absence of molecular oxygen, whereas the fluorescence emission properties are similar to those observed with [Eu-1]. This behavior can be conveniently described as a molecular-level logic gate, corresponding to a two-input INHIBIT function, A boolean AND B'. The analogous [Yb.2] complex shows no such pH or O-2 dependence.

  DOI：

  10.1021/ja004316i
• 作为产物：
  描述：

  4-氨基喹哪啶 在 caesium carbonate 、 三乙胺 、 potassium iodide 作用下， 以 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， 反应 27.0h， 生成 1,4,7,10-tetrakis[N-(2-methyl-4-quinolyl)carbamoylmethyl]-1,4,7,10-tetraazacyclododecane
  参考文献：
  名称：

  Lanthanide Macrocyclic Quinolyl Conjugates as Luminescent Molecular-Level Devices

  摘要：

  The Eu(III) tetraazamacrocyclic complexes [Eu.1] and [Eu.2], and the Tb(III) and Yb(III) complexes [Tb.1] and [Yb.2], have been synthesized as luminescent molecular-level devices. The Eu complexes exhibit unique dual pH switching behavior in water under ambient conditions. The delayed Eu emission is reversibly switched on in acid, with an enhancement factor of several hundred for [Eu-1]. These observations are consistent with the protonation of the quinoline aryl nitrogen moiety (pK(a) approximate to 5.9 for [Eu.1]). The fluorescence emission spectra of these complexes are unaffected by acid, but pronounced changes occur in alkaline solution due to the deprotonation of the aryl amide nitrogen (pK(a) approximate to 9.4 for [Eu.1]). [Tb.1] shows a more intriguing pH dependence; Tb emission is switched "on" only in the presence of HI and in the absence of molecular oxygen, whereas the fluorescence emission properties are similar to those observed with [Eu-1]. This behavior can be conveniently described as a molecular-level logic gate, corresponding to a two-input INHIBIT function, A boolean AND B'. The analogous [Yb.2] complex shows no such pH or O-2 dependence.

  DOI：

  10.1021/ja004316i

文献信息

• Luminescent europium tetraazamacrocyclic complexes with wide range pH sensitivity
  作者：Thorfinnur Gunnlaugsson

  DOI：10.1039/a708342d

  日期：——

  The complexes [EuL1]3+ and [EuL2] function as luminescent pH sensors over an extended pH range; two distinguishable pH switching ranges are observed: the delayed europium emission is switched on in acidic solution, whereas the fluorescence emission spectra show a pronounced pH dependence only in alkaline media.

  [EuL1]3+和[EuL2]复合物可在较宽的 pH 值范围内发挥 pH 值发光传感器的功能；可观察到两个不同的 pH 值切换范围：延迟铕发射在酸性溶液中开启，而荧光发射光谱仅在碱性介质中显示出明显的 pH 值依赖性。