4-(5-bromo-1,3-thiazol-2-yl)-N,N-diphenylaniline | 1451736-90-5

• 分子结构分类: 有机化合物 - 有机氮化合物
• 英文名称: 4-(5-bromo-1,3-thiazol-2-yl)-N,N-diphenylaniline
• CAS: 1451736-90-5
• 化学式: C₂₁H₁₅BrN₂S
• 分子量: 407.333
• InChiKey: JOBOQSGLHXXKHG-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.9
• 重原子数：
  25
• 可旋转键数：
  4
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  44.4
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  4-(5-bromo-1,3-thiazol-2-yl)-N,N-diphenylaniline 在 四(三苯基膦)钯 、 caesium carbonate 、 联硼酸频那醇酯 作用下， 以 1,4-二氧六环 、 水 为溶剂， 反应 10.0h， 以78%的产率得到N,N-diphenyl-4-[5-[2-[4-(N-phenylanilino)phenyl]-1,3-thiazol-5-yl]-1,3-thiazol-2-yl]aniline
  参考文献：
  名称：

  Asymmetrical/Symmetrical D−π–A/D−π–D Thiazole-Containing Aromatic Heterocyclic Fluorescent Compounds Having the Same Triphenylamino Chromophores

  摘要：

  A family of linear asymmetrical D-pi-A and symmetrical D-pi-D types of thiazole-based aromatic heterocyclic fluorescent compounds bearing various electron-donating and electron-withdrawing tails (bromo, triphenylamino, pyridyl, thienyl and benzoic acid) have been designed and prepared successfully. Synthetic, structural, thermal, spectral and computational comparisons have been carried out for related compounds because of their adjustable electronic properties. It is interesting to mention that compound 2 can be prepared from 5-bromothiazole by one-pot Suzuki-Miyaura coupling and subsequent C-H activation reactions via a 5-TPA-substituted thiazole intermediate 1. X-ray single-crystal structures of six compounds indicate that they all crystallize in the triclinic P (1) over bar space group and the thiazole core exhibits different dihedral angles with its adjacent benzene ring of the triphenylamino group (3.6(3)-40.8(3)degrees). The photophysical and electrochemical results demonstrate that compound 7 exhibits high electrochemical activity with a green fluorescence emission. Meanwhile, compounds 1, 2, and 6 show high luminescence quantum yields, and compound 8 exhibits excellent thermal stability (T-d10 = 503 degrees C).

  DOI：

  10.1021/jo401384g
• 作为产物：
  描述：

  2,5-二溴噻唑 、 4-硼酸三苯胺 在 四(三苯基膦)钯 、 caesium carbonate 作用下， 以 水 、 甲苯 为溶剂， 反应 48.0h， 以67%的产率得到4-(5-bromo-1,3-thiazol-2-yl)-N,N-diphenylaniline
  参考文献：
  名称：

  Asymmetrical/Symmetrical D−π–A/D−π–D Thiazole-Containing Aromatic Heterocyclic Fluorescent Compounds Having the Same Triphenylamino Chromophores

  摘要：

  A family of linear asymmetrical D-pi-A and symmetrical D-pi-D types of thiazole-based aromatic heterocyclic fluorescent compounds bearing various electron-donating and electron-withdrawing tails (bromo, triphenylamino, pyridyl, thienyl and benzoic acid) have been designed and prepared successfully. Synthetic, structural, thermal, spectral and computational comparisons have been carried out for related compounds because of their adjustable electronic properties. It is interesting to mention that compound 2 can be prepared from 5-bromothiazole by one-pot Suzuki-Miyaura coupling and subsequent C-H activation reactions via a 5-TPA-substituted thiazole intermediate 1. X-ray single-crystal structures of six compounds indicate that they all crystallize in the triclinic P (1) over bar space group and the thiazole core exhibits different dihedral angles with its adjacent benzene ring of the triphenylamino group (3.6(3)-40.8(3)degrees). The photophysical and electrochemical results demonstrate that compound 7 exhibits high electrochemical activity with a green fluorescence emission. Meanwhile, compounds 1, 2, and 6 show high luminescence quantum yields, and compound 8 exhibits excellent thermal stability (T-d10 = 503 degrees C).

  DOI：

  10.1021/jo401384g

文献信息

• Asymmetrical/Symmetrical D−π–A/D−π–D Thiazole-Containing Aromatic Heterocyclic Fluorescent Compounds Having the Same Triphenylamino Chromophores
  作者：Tao Tao、Bin-Bin Ma、Yu-Xin Peng、Xiao-Xu Wang、Wei Huang、Xiao-Zeng You

  DOI：10.1021/jo401384g

  日期：2013.9.6

  A family of linear asymmetrical D-pi-A and symmetrical D-pi-D types of thiazole-based aromatic heterocyclic fluorescent compounds bearing various electron-donating and electron-withdrawing tails (bromo, triphenylamino, pyridyl, thienyl and benzoic acid) have been designed and prepared successfully. Synthetic, structural, thermal, spectral and computational comparisons have been carried out for related compounds because of their adjustable electronic properties. It is interesting to mention that compound 2 can be prepared from 5-bromothiazole by one-pot Suzuki-Miyaura coupling and subsequent C-H activation reactions via a 5-TPA-substituted thiazole intermediate 1. X-ray single-crystal structures of six compounds indicate that they all crystallize in the triclinic P (1) over bar space group and the thiazole core exhibits different dihedral angles with its adjacent benzene ring of the triphenylamino group (3.6(3)-40.8(3)degrees). The photophysical and electrochemical results demonstrate that compound 7 exhibits high electrochemical activity with a green fluorescence emission. Meanwhile, compounds 1, 2, and 6 show high luminescence quantum yields, and compound 8 exhibits excellent thermal stability (T-d10 = 503 degrees C).