2-(4-pyridyl)-N,N,4-triphenyl-5-thiazolamine

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑类
• 英文名称: 2-(4-pyridyl)-N,N,4-triphenyl-5-thiazolamine
• 英文别名: N,N,4-triphenyl-2-pyridin-4-yl-1,3-thiazol-5-amine
• 化学式: C₂₆H₁₉N₃S
• 分子量: 405.523
• InChiKey: AOXNDEMWFRQAIZ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.8
• 重原子数：
  30
• 可旋转键数：
  5
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  57.3
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  2-(4-pyridyl)-N,N,4-triphenyl-5-thiazolamine 在 间氯过氧苯甲酸 作用下， 以 氯仿 为溶剂， 反应 72.0h， 以23%的产率得到
  参考文献：
  名称：

  5-Amino-2-thiazolylpyridine N-Oxides: Synthesis and Properties

  摘要：

  5-Amino-2-thiazolylpyridine N-oxides were prepared in low to moderate yields by the oxidation of 2-pyridyl-5-aminothiazoles with m-CPBA. The molecular structures of the resulting N-oxides were unequivocally determined by X-ray analyses. The N-oxides exhibited the absorption maxima at around 415 +/- 20 nm in a CHCl3 solution, while the emission spectra were observed in the range of 505 to 604 nm. The red -shift of the emission was attributed to the methoxy groups attached to the para-position of an aromatic group on the nitrogen atom at the 5-position. The N-oxides exhibited halochromism with the addition of B(C6F5)(3). The change in absorption implied the formation of a 1:1 complex between N-oxide and B(C6F5)(3). The emission wavelengths of the N-oxides were observed at 510 +/- 25 nm in a solid state. Interestingly, one of the N-oxides having methoxy groups exhibited mechanofluorochromism. The solid-state emission of the N-oxide at 527 nm shifted to a longer wavelength (599 nm) when it was subjected to grinding.

  DOI：

  10.3987/com-19-s(f)51
• 作为产物：
  描述：

  N,N-二苯基硫代甲酰胺 在 碘 作用下， 以 四氢呋喃 为溶剂， 生成 2-(4-pyridyl)-N,N,4-triphenyl-5-thiazolamine
  参考文献：
  名称：

  5-Amino-2-thiazolylpyridine N-Oxides: Synthesis and Properties

  摘要：

  5-Amino-2-thiazolylpyridine N-oxides were prepared in low to moderate yields by the oxidation of 2-pyridyl-5-aminothiazoles with m-CPBA. The molecular structures of the resulting N-oxides were unequivocally determined by X-ray analyses. The N-oxides exhibited the absorption maxima at around 415 +/- 20 nm in a CHCl3 solution, while the emission spectra were observed in the range of 505 to 604 nm. The red -shift of the emission was attributed to the methoxy groups attached to the para-position of an aromatic group on the nitrogen atom at the 5-position. The N-oxides exhibited halochromism with the addition of B(C6F5)(3). The change in absorption implied the formation of a 1:1 complex between N-oxide and B(C6F5)(3). The emission wavelengths of the N-oxides were observed at 510 +/- 25 nm in a solid state. Interestingly, one of the N-oxides having methoxy groups exhibited mechanofluorochromism. The solid-state emission of the N-oxide at 527 nm shifted to a longer wavelength (599 nm) when it was subjected to grinding.

  DOI：

  10.3987/com-19-s(f)51

文献信息

• 5-N-Arylaminothiazoles as Highly Twisted Fluorescent Monocyclic Heterocycles: Synthesis and Characterization
  作者：Kirara Yamaguchi、Toshiaki Murai、Saki Hasegawa、Yohei Miwa、Shoichi Kutsumizu、Toshifumi Maruyama、Takahiro Sasamori、Norihiro Tokitoh

  DOI：10.1021/acs.joc.5b01963

  日期：2015.11.6

  adopt structures that are highly twisted from planar conformations. Their orientations were tuned by the steric and/or electronic interactions of the substituents at their 2-, 4-, and 5-positions. The 5-aminothiazoles exhibited a range of fluorescent emissions, from blue to orange. Although the absorption spectra were independent of the polarity of the solvent, fluorescent emissions were influenced

  通过使衍生自仲硫代酰胺的硫代酰胺二阴离子与硫代甲酰胺反应，然后依次用碘进行氧化，可以制备一系列5-N-芳基氨基噻唑。X射线分析表明，它们采用了与平面构象高度扭曲的结构。它们的取向通过在其2-，4-和5-位上的取代基的空间和/或电子相互作用来调节。5-氨基噻唑显示出从蓝色到橙色的一系列荧光发射。尽管吸收光谱与溶剂的极性无关，但荧光发射受溶剂的极性影响：在极性更大的溶剂中，发射发生红移。根据Lippert-Mataga图以及基态和激发态之间的偶极矩变化对这些现象进行了检验。它们还表现出固态发光，再次从蓝色到橙色。5-氨基噻唑的循环伏安法显示单电子氧化的可逆波。通过将电子给体基团引入到5-位氮原子上的苯基上，可以降低氧化的半电位。进行了DFT计算以确定HOMO和LUMO的能级。最后，TG-DTA的结果表明它们是热稳定的。进行了DFT计算以确定HOMO和LUMO的能级。最后，TG-DTA的结果表明
• Pyridinium 5-aminothiazoles: specific photophysical properties and vapochromism in halogenated solvents
  作者：Kirara Yamaguchi、Toshiaki Murai、Yuki Tsuchiya、Yohei Miwa、Shoichi Kutsumizu、Takahiro Sasamori、Norihiro Tokitoh

  DOI：10.1039/c7ra01896g

  日期：——

  Treatment of pyridyl-5-aminothiazoles (1–4) with alkyl triflates or benzyl iodide afforded the corresponding pyridinium 5-aminothiazoles (5–10), which exhibited bathochromically shifted absorption and fluorescence spectra relative to those of 1–4. Moreover, the vapochromic properties of 5 specific to halogenated solvents were examined by powder X-ray diffraction analysis. Pmma films containing 5 can

  用烷基三氟甲磺酸酯或苄基碘处理吡啶基-5-氨基噻唑（1-4）可得到相应的吡啶鎓5-氨基噻唑（5-10），相对于1-4，吡啶鎓显示出红移的吸收光谱和荧光光谱。此外，通过粉末X射线衍射分析检查了5种特定于卤化溶剂的蒸气致变色性质。因此，包含5的Pmma膜可用于检测卤化溶剂，尤其是CH 2 Cl 2。
• Acid-Responsive Absorption and Emission of 5-<i>N</i> -Arylaminothiazoles: Emission of White Light from a Single Fluorescent Dye and a Lewis Acid
  作者：Kirara Yamaguchi、Toshiaki Murai、Jing-Dong Guo、Takahiro Sasamori、Norihiro Tokitoh

  DOI：10.1002/open.201600059

  日期：2016.10

  shifts of the absorption and emission bands. DFT calculations suggested that the spectral changes arise from the protonation of the pyridyl group of the thiazoles in Et2O. Single‐crystal X‐ray diffraction analysis of a thiazole and its protonated form revealed the change of the conformation around the thiazole ring. The emission of white light was accomplished from a single fluorescent dye by adjusting

  含有吡啶基的 5- N-芳基氨基噻唑溶液在添加布朗斯台德酸和路易斯酸后表现出明显的卤代变色和卤代荧光。将三氟甲磺酸添加到 5- N-芳基氨基噻唑的 Et 2 O 溶液中会引起吸收带和发射带的红移。DFT 计算表明，光谱变化是由噻唑吡啶基在 Et 2 O 中的质子化引起的。噻唑及其质子化形式的单晶 X 射线衍射分析揭示了噻唑环周围构象的变化。通过调整染料与B(C 6 F 5 ) 3 的比例，由单一荧光染料实现白光发射，国际照明委员会坐标显示从蓝色到橙色的线性变化。
• 5-Amino-2-thiazolylpyridine N-Oxides: Synthesis and Properties
  作者：Toshiaki Murai、Yuuta Nakatsu、Yuki Tsuchiya、Kirara Yamaguchi、Toshifumi Maruyama、Yohei Miwa、Shoichi Kutsumizu

  DOI：10.3987/com-19-s(f)51

  日期：——

  5-Amino-2-thiazolylpyridine N-oxides were prepared in low to moderate yields by the oxidation of 2-pyridyl-5-aminothiazoles with m-CPBA. The molecular structures of the resulting N-oxides were unequivocally determined by X-ray analyses. The N-oxides exhibited the absorption maxima at around 415 +/- 20 nm in a CHCl3 solution, while the emission spectra were observed in the range of 505 to 604 nm. The red -shift of the emission was attributed to the methoxy groups attached to the para-position of an aromatic group on the nitrogen atom at the 5-position. The N-oxides exhibited halochromism with the addition of B(C6F5)(3). The change in absorption implied the formation of a 1:1 complex between N-oxide and B(C6F5)(3). The emission wavelengths of the N-oxides were observed at 510 +/- 25 nm in a solid state. Interestingly, one of the N-oxides having methoxy groups exhibited mechanofluorochromism. The solid-state emission of the N-oxide at 527 nm shifted to a longer wavelength (599 nm) when it was subjected to grinding.