[D10]-6,6'-bis(bromomethyl)-2,2'-bipyridine-N,N-dioxide | 1252676-98-4

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡啶及其衍生物
• 英文名称: [D10]-6,6'-bis(bromomethyl)-2,2'-bipyridine-N,N-dioxide
• 英文别名: [D₁₀]-6,6-bis(bromomethyl)-2,2’-bipyridine；2-[Bromo(dideuterio)methyl]-6-[6-[bromo(dideuterio)methyl]-3,4,5-trideuteriopyridin-2-yl]-3,4,5-trideuteriopyridine；2-[bromo(dideuterio)methyl]-6-[6-[bromo(dideuterio)methyl]-3,4,5-trideuteriopyridin-2-yl]-3,4,5-trideuteriopyridine
• CAS: 1252676-98-4
• 化学式: C₁₂H₁₀Br₂N₂
• 分子量: 351.953
• InChiKey: NFQNNYSVIFMWGU-WHUVPORUSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.7
• 重原子数：
  16
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.17
• 拓扑面积：
  25.8
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  [D10]-6,6'-bis(bromomethyl)-2,2'-bipyridine-N,N-dioxide 在 乌洛托品 、 氢溴酸 作用下， 以 氯仿 、 乙醇 、 水 为溶剂， 反应 3.0h， 以56%的产率得到[D₁₀]-6,6’-bis(aminomethyl)-2,2’-bipyridine trihydrobromide
  参考文献：
  名称：

  Quantification of C−H Quenching in Near-IR Luminescent Ytterbium and Neodymium Cryptates

  摘要：

  Two series of selectively deuterated cryptates with the lanthanoids Yb and Nd have been synthesized, and the luminescence lifetimes for the corresponding near-IR emission bands have been measured. Global fitting of these lifetime data combined with structural analysis allows for the accurate quantification of the contributions of individual C-H oscillators groups in the ligand to the nonradiative deactivation rates of the emissive lanthanoid states.

  DOI：

  10.1021/ja105768w
• 作为产物：
  描述：

  ([2,2'-bipyridine]-6,6'-diyl-d6)bis(methan-d2-ol) 在 三溴化磷 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 20.0h， 以98%的产率得到[D10]-6,6'-bis(bromomethyl)-2,2'-bipyridine-N,N-dioxide
  参考文献：
  名称：

  Quantification of C−H Quenching in Near-IR Luminescent Ytterbium and Neodymium Cryptates

  摘要：

  Two series of selectively deuterated cryptates with the lanthanoids Yb and Nd have been synthesized, and the luminescence lifetimes for the corresponding near-IR emission bands have been measured. Global fitting of these lifetime data combined with structural analysis allows for the accurate quantification of the contributions of individual C-H oscillators groups in the ligand to the nonradiative deactivation rates of the emissive lanthanoid states.

  DOI：

  10.1021/ja105768w

文献信息

• Rigid, Perdeuterated Lanthanoid Cryptates: Extraordinarily Bright Near-IR Luminophores.
  作者：Christine Doffek、Nicola Alzakhem、Mariusz Molon、Michael Seitz

  DOI：10.1021/ic202376k

  日期：2012.4.16

  Near-IR emissive lanthanoid cryptates have been developed with the lanthanoids Yb, Nd, Er, and Pr by designing a fully deuterated ligand environment that greatly suppresses multiphonon nonradiative deactivation pathways through avoidance of high-energy oscillators and rigidification of the ligand backbone. Strong luminescence is observed in CD3CN for all four lanthanoids. Luminescence lifetimes in CD3CN are among the highest values for molecular complexes in solution reported so far (Yb, tau(obs) = 79 mu s; Nd, tau(obs) = 3.3 mu s). For the ytterbium cryptate, the highest luminescence lifetime can be obtained using CD3OD (tau(obs) = 91 mu s) and even in nondeuterated CH3CN the lifetime is still unusually high (tau(obs) = 53 mu s). X-ray crystallography and H-1 NMR analysis of the corresponding nondeuterated lutetium cryptate suggest that the inner coordination sphere in solution is completely saturated by the octadentate cryptand and one chloride counterion. All lanthanoid cryptates remarkably show complete stability during reversed-phase HPLC measurements under strongly acidic conditions.
• Anomalous Reversal of C–H and C–D Quenching Efficiencies in Luminescent Praseodymium Cryptates
  作者：Julia Scholten、Geraldine A. Rosser、Jessica Wahsner、Nicola Alzakhem、Caroline Bischof、Felix Stog、Andrew Beeby、Michael Seitz

  DOI：10.1021/ja306052u

  日期：2012.8.29

  A series of selectively deuterated praseodymium cryptates has been synthesized. Their luminescence lifetimes in solution range from 150 to 595 ns for the (1)D(2) → (3)F(4) transition. Global fitting of the nonradiative deactivation rate differences of the isotopologic C-(H/D) oscillators revealed that aromatic C-D overtones anomalously quench the luminescence more than C-H vibrations. This is explained by the dominance of Franck-Condon overlap factors that greatly favor C-D oscillators, which are in almost ideal resonance with the relevant energy gap (1)D(2)-(1)G(4) of praseodymium.
• Quantification of C−H Quenching in Near-IR Luminescent Ytterbium and Neodymium Cryptates
  作者：Caroline Bischof、Jessica Wahsner、Julia Scholten、Simon Trosien、Michael Seitz

  DOI：10.1021/ja105768w

  日期：2010.10.20

  Two series of selectively deuterated cryptates with the lanthanoids Yb and Nd have been synthesized, and the luminescence lifetimes for the corresponding near-IR emission bands have been measured. Global fitting of these lifetime data combined with structural analysis allows for the accurate quantification of the contributions of individual C-H oscillators groups in the ligand to the nonradiative deactivation rates of the emissive lanthanoid states.