6-chloro-N,N'-bis(3-pyrazol-1-ylphenyl)-1,3,5-triazine-2,4-diamine

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑类
• 英文名称: 6-chloro-N,N'-bis(3-pyrazol-1-ylphenyl)-1,3,5-triazine-2,4-diamine
• 英文别名: 6-chloro-2,4-bis-(3-pyrazol-1-ylphenylamine)-1,3,5-triazine；2-chloro-4,6-bis(3-pyrazol-1-ylphenylamino)-1,3,5-triazine；6-chloro-2-N,4-N-bis(3-pyrazol-1-ylphenyl)-1,3,5-triazine-2,4-diamine
• 化学式: C₂₁H₁₆ClN₉
• 分子量: 429.871
• InChiKey: KYYWVPCUWIVBTM-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.6
• 重原子数：
  31
• 可旋转键数：
  6
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  98.4
• 氢给体数：
  2
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  6-chloro-N,N'-bis(3-pyrazol-1-ylphenyl)-1,3,5-triazine-2,4-diamine 在 N,N-二异丙基乙胺 作用下， 以 二甲基亚砜 为溶剂， 140.0~170.0 ℃ 、101.33 kPa 条件下， 反应 0.5h， 生成 N-[4,6-bis(3-pyrazol-1-ylphenylamino)-1,3,5-triazin-2-yl]-N'-[4,6-bis(4-pyrazol-1-ylphenylamino)-1,3,5-triazin-2-yl]-m-phenylenediamine
  参考文献：
  名称：

  Microwave-Assisted Selective Synthesis of Mono- and Bistriazines with π-Conjugated Spacers and Study of the Optoelectronic Properties

  摘要：

  A series of mono- and bistriazine derivatives were selectively prepared in high yields using microwave irradiation. Donor substituents were attached on the triazine ring, including pyrazolyl-substituted anilines and o-, m-, and p-phenylenediamine as pi-conjugated spacers. This method was used to build sigma-pi-sigma-A-sigma-D systems for monotriazines and D-sigma-A-sigma-pi-sigma-A-sigma-D systems for bistriazines. A study of the optoelectronic properties was performed by UV-vis and fluorescence spectroscopy and cyclic voltammetry. The monotriazines do not show any emission, but the bistriazines are blue emitters and show an interesting solvatochromic effect with large Stokes shifts of more than 10 000 cm(-1) in some cases and quantum yields up to 23%. The optoelectronic properties depend on the conjugation and the position and donor character of the substituents and spacers. Cyclic voltammetry was used to determine the energy levels (HOMO and LUMO) in the bistriazines. An increase in the energy of the HOMO and a decrease in the energy of the LUMO were observed upon extending the conjugation. The title compounds showed interesting properties for use in optoelectronic devices, especially as blue emitters.

  DOI：

  10.1021/jo500480r
• 作为产物：
  描述：

  三聚氯氰 、 3-吡唑-1-苯胺 在 N,N-二异丙基乙胺 作用下， 以 四氢呋喃 为溶剂， 反应 26.0h， 以47%的产率得到6-chloro-N,N'-bis(3-pyrazol-1-ylphenyl)-1,3,5-triazine-2,4-diamine
  参考文献：
  名称：

  2-氯-4,6-双（吡唑基氨基）-1,3,5-三嗪的合成，结构测定和动力学行为。

  摘要：

  制备了一系列2-氯-4,6-双（吡唑基氨基）-1,3,5-三嗪及其在晶体工程中的应用。在低温下，已经检测到两种或三种异构体的存在，并且在与模型化合物比较的基础上将它们分配给4,6-二氨基-1,3,5-三嗪结构。在各种溶剂和不同温度下的2D交换光谱研究已用于确定平衡常数和绕氨基三嗪键旋转受限的活化自由能。活化自由能与温度的关系图显示出良好的线性相关性，并证实在研究的所有化合物中都存在相同的过程。与模型化合物的比较还证实了旋转受限和4,6-二氨基-1,3的出现，5-三嗪互变异构用于溶液中的三嗪1-4。化合物1的结构已经通过X射线晶体学测定为固态，并且由通过内和分子间氢键稳定的4,6-二氨基-1,3,5-三嗪结构组成。

  DOI：

  10.1039/b310693d

文献信息

• Solvent-free microwave-assisted synthesis of new 2,4-dimethoxybenzylaminotriazines
  作者：Antonio de la Hoz、Ana Sánchez-Migallón、Beatriz T. Pelado、José R. Ramírez

  DOI：10.3998/ark.5550190.p008.245

  日期：——

  An efficient and green synthesis of 2,4-dimethoxybenzyaminotriazines is described, by reaction of disubstituted triazines with 2,4-dimethoxybenzylamine under microwave irradiation and in solvent-free conditions. NMR spectroscopy has been used to determine the free energy of activation of the restricted rotation of the ArylN-triazine bond that is a slow process at room temperature. Contrarily, the benzylN-triazine

  通过在微波辐射和无溶剂条件下双取代三嗪与 2,4-二甲氧基苄胺反应，描述了 2,4-二甲氧基苄氨基三嗪的高效绿色合成。核磁共振光谱已被用于确定在室温下是一个缓慢过程的芳基 N-三嗪键的受限旋转的活化自由能。相反，苄基N-三嗪键在室温下显示出快速旋转。
• Synthesis, structural determination and dynamic behavior of 2-chloro-4,6-bis(pyrazolylamino)-1,3,5-triazines
  作者：Angel Díaz-Ortiz、José Elguero、Concepción Foces-Foces、Antonio de la Hoz、Andrés Moreno、Sergio Moreno、Ana Sánchez-Migallón、Gema Valiente

  DOI：10.1039/b310693d

  日期：——

  and the activation free energies of the restricted rotation about the amino-triazine bond. A plot of the activation free energy versus temperature showed a good linear correlation and confirmed that the same process is present in all of the compounds under investigation. Comparison with model compounds also confirmed both the occurrence of the restricted rotation and the 4,6-diamino-1,3,5-triazine tautomerism

  制备了一系列2-氯-4,6-双（吡唑基氨基）-1,3,5-三嗪及其在晶体工程中的应用。在低温下，已经检测到两种或三种异构体的存在，并且在与模型化合物比较的基础上将它们分配给4,6-二氨基-1,3,5-三嗪结构。在各种溶剂和不同温度下的2D交换光谱研究已用于确定平衡常数和绕氨基三嗪键旋转受限的活化自由能。活化自由能与温度的关系图显示出良好的线性相关性，并证实在研究的所有化合物中都存在相同的过程。与模型化合物的比较还证实了旋转受限和4,6-二氨基-1,3的出现，5-三嗪互变异构用于溶液中的三嗪1-4。化合物1的结构已经通过X射线晶体学测定为固态，并且由通过内和分子间氢键稳定的4,6-二氨基-1,3,5-三嗪结构组成。
• Microwave-Assisted Selective Synthesis of Mono- and Bistriazines with π-Conjugated Spacers and Study of the Optoelectronic Properties
  作者：A. Ruiz-Carretero、O. Noguez、T. Herrera、J. R. Ramírez、A. Sánchez-Migallón、A. de la Hoz

  DOI：10.1021/jo500480r

  日期：2014.6.6

  A series of mono- and bistriazine derivatives were selectively prepared in high yields using microwave irradiation. Donor substituents were attached on the triazine ring, including pyrazolyl-substituted anilines and o-, m-, and p-phenylenediamine as pi-conjugated spacers. This method was used to build sigma-pi-sigma-A-sigma-D systems for monotriazines and D-sigma-A-sigma-pi-sigma-A-sigma-D systems for bistriazines. A study of the optoelectronic properties was performed by UV-vis and fluorescence spectroscopy and cyclic voltammetry. The monotriazines do not show any emission, but the bistriazines are blue emitters and show an interesting solvatochromic effect with large Stokes shifts of more than 10 000 cm(-1) in some cases and quantum yields up to 23%. The optoelectronic properties depend on the conjugation and the position and donor character of the substituents and spacers. Cyclic voltammetry was used to determine the energy levels (HOMO and LUMO) in the bistriazines. An increase in the energy of the HOMO and a decrease in the energy of the LUMO were observed upon extending the conjugation. The title compounds showed interesting properties for use in optoelectronic devices, especially as blue emitters.