6-dimethylamino-2,2':6',2''-terpyridine

• 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: 6-dimethylamino-2,2':6',2''-terpyridine
• 英文别名: N,N-dimethyl-6-(6-pyridin-2-ylpyridin-2-yl)pyridin-2-amine
• 化学式: C₁₇H₁₆N₄
• 分子量: 276.341
• InChiKey: AZVWJNGEGPDTFP-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.6
• 重原子数：
  21
• 可旋转键数：
  3
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.12
• 拓扑面积：
  41.9
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  六甲基磷酰三胺 、 6-溴-2,2':6',2''-三联吡啶 反应 17.0h， 以65%的产率得到6-dimethylamino-2,2':6',2''-terpyridine
  参考文献：
  名称：

  6-Amino-2,2′:6′,2″-terpyridines as highly fluorescent compounds—effect of the number of pyridine rings on fluorescence properties

  摘要：

  研究发现，2,2â²:6â²,2â³-三吡啶（thyy）在有机溶液中被 6-氨基（2，δ "fl = 384 nm，δ = 0.70，二氯甲烷）和 6,6â³-二氨基（3，δ "fl = 386 nm，δ = 0.48，二氯甲烷）基团取代后，会表现出显著的高效荧光。随着溶剂极性的增加，6-氨基 tpys 的荧光最大值向更长波长移动，而吸收最大值则几乎不受影响。在质子溶剂中，荧光在很大程度上被淬灭。2 和 3 的吸收带和荧光带与 6-氨基-2,2â²-联吡啶的吸收带和荧光带位于同一区域，但与 2-氨基吡啶相比，波长要长得多。这些结果以及对吸收光谱和荧光光谱的详细分析揭示，噻哌噻嗪的光物理特性可以解释为噻哌噻嗪结构中的两个共用中心吡啶环的双吡啶基单元的贡献；6-氨基双吡啶基单元似乎是 2 和 3 的荧光发色团。半经验分子轨道计算支持上述结论。

  DOI：

  10.1039/b201911f

文献信息

• Preparation of a series of novel fluorophores, N-substituted 6-amino and 6,6″-diamino-2,2′:6′,2″-terpyridine by palladium-catalyzed amination
  作者：Jin-Dong Cheon、Toshiki Mutai、Koji Araki

  DOI：10.1016/j.tetlet.2006.05.073

  日期：2006.7

  A new series of N-substituted 6-amino- and 6,6"-diamino-2,2':6,2"-terpyridine (6-amino- and 6,6"-diamino-tpy) was conveniently synthesized in one-step by Pd-catalyzed amination of bromo-substituted tpys with various amines. For highly coordinating tpy substrates, use of appropriate chelating phosphine ligand was critical to achieve moderate to satisfactory yield. The prepared N-substituted 6-amino- and 6,6"-diamino-tpys exhibited moderate to intense fluorescence in dichloromethane with fine-tuned fluorescence maxima ranging from 385 to 455 nm. (c) 2006 Elsevier Ltd. All rights reserved.
• 6-Amino-2,2′:6′,2″-terpyridines as highly fluorescent compounds—effect of the number of pyridine rings on fluorescence properties
  作者：Toshiki Mutai、Jin-Dong Cheon、Gaku Tsuchiya、Koji Araki

  DOI：10.1039/b201911f

  日期：2002.4.29

  2,2′:6′,2″-Terpyridine (tpy) was found to exhibit remarkably efficient fluorescence in organic solutions when substituted by 6-amino (2, λfl = 384 nm, Φ = 0.70, dichloromethane) and 6,6″-diamino (3, λfl = 386 nm, Φ = 0.48, dichloromethane) groups. The fluorescence maxima of 6-amino tpys were shifted to longer wavelengths as the solvent polarity increased, whereas the absorption maxima were little affected. In protic solvents, the fluorescence was largely quenched. The absorption and fluorescence bands of 2 and 3 were observed in the same region as those of 6-amino-2,2′-bipyridine, but at much longer wavelengths compared to 2-aminopyridine. These results and detailed analysis of the absorption and fluorescence spectra reveal that the photophysical properties of tpys could be interpreted as resulting from a contribution of the two bipyridyl units within the tpy structures that share the center pyridyl ring; the 6-aminobipyridyl unit appeared to be the fluorescent chromophore of 2 and 3. Semi-empirical molecular orbital calculations supported the above conclusion.

  研究发现，2,2â²:6â²,2â³-三吡啶（thyy）在有机溶液中被 6-氨基（2，δ "fl = 384 nm，δ = 0.70，二氯甲烷）和 6,6â³-二氨基（3，δ "fl = 386 nm，δ = 0.48，二氯甲烷）基团取代后，会表现出显著的高效荧光。随着溶剂极性的增加，6-氨基 tpys 的荧光最大值向更长波长移动，而吸收最大值则几乎不受影响。在质子溶剂中，荧光在很大程度上被淬灭。2 和 3 的吸收带和荧光带与 6-氨基-2,2â²-联吡啶的吸收带和荧光带位于同一区域，但与 2-氨基吡啶相比，波长要长得多。这些结果以及对吸收光谱和荧光光谱的详细分析揭示，噻哌噻嗪的光物理特性可以解释为噻哌噻嗪结构中的两个共用中心吡啶环的双吡啶基单元的贡献；6-氨基双吡啶基单元似乎是 2 和 3 的荧光发色团。半经验分子轨道计算支持上述结论。