N,N-dimethyl-4-(3-methyl-3H-imidazo[4,5-b]pyridin-2-yl)-benzenamine | 1449135-36-7

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑类
• 英文名称: N,N-dimethyl-4-(3-methyl-3H-imidazo[4,5-b]pyridin-2-yl)-benzenamine
• 英文别名: 1-methyl-2-(4'-(N,N-dimetylaminophenyl))-imidazo[4,5-b]pyridine
• CAS: 1449135-36-7
• 化学式: C₁₅H₁₆N₄
• 分子量: 252.319
• InChiKey: CHMAMCMVUCLWHO-UHFFFAOYSA-N

反应信息

• 作为产物：
  描述：

  4-(3H-imidazo[4,5-b]pyridin-2-yl)-N,N-dimethylaniline 、 碘甲烷 在 potassium hydroxide 作用下， 以 四氢呋喃 、 N,N-二甲基甲酰胺 为溶剂， 反应 24.0h， 生成 N,N-dimethyl-4-(3-methyl-3H-imidazo[4,5-b]pyridin-2-yl)-benzenamine
  参考文献：
  名称：

  Double Proton Transfer Induced Twisted Intramolecular Charge Transfer Emission in 2-(4′-N,N-Dimethylaminophenyl)imidazo[4,5-b]pyridine

  摘要：

  The spectral characteristics of N,N-dimethyl-4-(4-methyl-4H-imidazo[4,5-b]pyridin-2-yl)benzenamine (PyN-Me), 1-methyl-2-(4'-(N,N-dimethylaminophenyl)imidazo[4,5-b]pyridine (ImNH-Me), and 2-phenylimidazo[4,5-b]pyridine (PIP) are investigated to understand the mechanism of protic solvent induced dual fluorescence of 2-(4'-N,N-dimethylaminophenyl)imidazo[4,5-b]pyridine (DMAPIP-b). No dual emission is observed from PyN-Me where pyridyl nitrogen blocked from hydrogen bonding with protic solvents confirms the importance of hydrogen bonding of protic solvents with the pyridyl nitrogen in dual emission of DMAPIP-b. Like DMAPIP-b, ImNH-Me also exhibits weak emission and has a shorter fluorescence lifetime in methanol. However, single emission is observed from ImNH-Me in all solvents including protic solvents. This suggests that the imidazole >NH hydrogen also plays a role in the dual emission process. The longer wavelength emission of DMAPIP-b in water increases with increase in pH of the solution owing to deprotonation of the imidazole >NH group. On the basis of these results, the mechanism for the dual emission of DMAPIP-b is proposed.

  DOI：

  10.1021/jp404472b