1,4,7-tris[ethyl(2-methylphosphinic acid)]-10-[N-(2-methyl-4-quinolyl)carbamoylmethyl]-1,4,7,10-tetraazacyclododecane | 204587-09-7

• 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-tris[ethyl(2-methylphosphinic acid)]-10-[N-(2-methyl-4-quinolyl)carbamoylmethyl]-1,4,7,10-tetraazacyclododecane
• 英文别名: [4,7-Bis[[hydroxy(methyl)phosphoryl]methyl]-10-[2-[(2-methylquinolin-4-yl)amino]-2-oxoethyl]-1,4,7,10-tetrazacyclododec-1-yl]methyl-methylphosphinic acid；[4,7-bis[[hydroxy(methyl)phosphoryl]methyl]-10-[2-[(2-methylquinolin-4-yl)amino]-2-oxoethyl]-1,4,7,10-tetrazacyclododec-1-yl]methyl-methylphosphinic acid
• CAS: 204587-09-7
• 化学式: C₂₆H₄₅N₆O₇P₃
• 分子量: 646.601
• InChiKey: UHRMFOUUWNMOPE-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -8.8
• 重原子数：
  42
• 可旋转键数：
  9
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.62
• 拓扑面积：
  167
• 氢给体数：
  4
• 氢受体数：
  12

反应信息

• 作为反应物：
  描述：

  europium(III) trifluoromethanesulfonate 、 1,4,7-tris[ethyl(2-methylphosphinic acid)]-10-[N-(2-methyl-4-quinolyl)carbamoylmethyl]-1,4,7,10-tetraazacyclododecane 以 乙醇 、 乙腈 为溶剂， 以50%的产率得到europium(III) 1,4,7-tris[ethyl(2-methylphosphinato)]-10-[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
• 作为产物：
  描述：

  1-[N-(2-methyl-4-quinolyl)carbamoylmethyl]-1,4,7,10-tetraazacyclododecane 在 氘氧化钾 、 重水 作用下， 以 四氢呋喃 为溶剂， 反应 24.33h， 生成 1,4,7-tris[ethyl(2-methylphosphinic acid)]-10-[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