N-2-aminophenyl-N',N"-bis(3-pyrazol-1-ylphenyl)-1,3,5-triazine-2,4,6-triamine | 1607446-27-4

• 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-2-aminophenyl-N',N"-bis(3-pyrazol-1-ylphenyl)-1,3,5-triazine-2,4,6-triamine
• CAS: 1607446-27-4
• 化学式: C₂₇H₂₃N₁₁
• 分子量: 501.553
• InChiKey: FGVWBDUPYGDBQC-UHFFFAOYSA-N

反应信息

• 作为反应物：
  描述：

  N-2-aminophenyl-N',N"-bis(3-pyrazol-1-ylphenyl)-1,3,5-triazine-2,4,6-triamine 、 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， 170.0 ℃ 、101.33 kPa 条件下， 反应 0.5h， 以94%的产率得到N,N'-bis[4,6-bis(3-pyrazol-1-ylphenylamino)-1,3,5-triazin-2-yl]-o-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：

  邻苯二胺 、 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 ℃ 、101.33 kPa 条件下， 反应 0.33h， 以98%的产率得到N-2-aminophenyl-N',N"-bis(3-pyrazol-1-ylphenyl)-1,3,5-triazine-2,4,6-triamine
  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