2,4,6,8-tetraphenyl-1,9-anthrazoline | 1301749-59-6

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 二芳基庚烷
• 英文名称: 2,4,6,8-tetraphenyl-1,9-anthrazoline
• 英文别名: 2,4,6,8-Tetraphenylpyrido[3,2-g]quinoline；2,4,6,8-tetraphenylpyrido[3,2-g]quinoline
• CAS: 1301749-59-6
• 化学式: C₃₆H₂₄N₂
• 分子量: 484.6
• InChiKey: IORZVALPRVRAOY-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  9
• 重原子数：
  38
• 可旋转键数：
  4
• 环数：
  7.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  25.8
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为产物：
  描述：

  均苯四甲酸二酐 在 aluminum (III) chloride 、 ammonium hydroxide 、 sodium hypochlorite 、 氯化亚砜 、 间甲酚 、 potassium hydroxide 作用下， 以 N-甲基吡咯烷酮 、 水 、 N,N-二甲基甲酰胺 为溶剂， 反应 60.0h， 生成 2,4,6,8-tetraphenyl-1,9-anthrazoline
  参考文献：
  名称：

  The synthesis, crystal structures and photophysical properties of a series of novel 4,6-diphenyl-1,9-anthrazolines

  摘要：

  The synthesis and properties of a:series of nine new 4,6-diphenyl-1,9-anthrazolines molecules 1a-1i are reported. Compounds 1a-1i were synthesized by Friedlander condensation of 4,6-dibenzoyl-1,3-phenylenediamines and acetyl-functionalized compounds in the presence of polyphosphoric acid as catalyst, in yields ranging from 60% to 94%. The 4,6-diphenyl-1,9-anthrazolines are thermally robust with high decomposition temperatures (>371.0 degrees C) and high melt transitions (215.1-322.8 degrees C). Compounds la and if crystallized in the triclinic system with the space groups P-1. All of them show the lowest energy absorption bands (lambda(Abs)(max): 397-454 nm), revealing low optical band gaps (2.55-3.00 eV). The compounds emit blue fluorescence with lambda(Em)(max) ranging from 432 to 493 nm in dilute toluene solution. 4,6-Diphenyl-1,9-anthrazolines 1a-1i have a formal reduction potential in the range -1.02 to -1.19 V (versus SCE) and estimated electron affinities (LUMO levels) of 3.21-3.38 eV. These results demonstrate that the new 4,6-diphenyl-1,9-anthrazolines are promising thermally stable n-type semiconductors for organic electronics. (C) 2011 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.dyepig.2011.02.011

文献信息

• The synthesis, crystal structures and photophysical properties of a series of novel 4,6-diphenyl-1,9-anthrazolines
  作者：Qin Zhang、Peng Jiang、Kunyan Wang、Guangliang Song、Hongjun Zhu

  DOI：10.1016/j.dyepig.2011.02.011

  日期：2011.10

  The synthesis and properties of a:series of nine new 4,6-diphenyl-1,9-anthrazolines molecules 1a-1i are reported. Compounds 1a-1i were synthesized by Friedlander condensation of 4,6-dibenzoyl-1,3-phenylenediamines and acetyl-functionalized compounds in the presence of polyphosphoric acid as catalyst, in yields ranging from 60% to 94%. The 4,6-diphenyl-1,9-anthrazolines are thermally robust with high decomposition temperatures (>371.0 degrees C) and high melt transitions (215.1-322.8 degrees C). Compounds la and if crystallized in the triclinic system with the space groups P-1. All of them show the lowest energy absorption bands (lambda(Abs)(max): 397-454 nm), revealing low optical band gaps (2.55-3.00 eV). The compounds emit blue fluorescence with lambda(Em)(max) ranging from 432 to 493 nm in dilute toluene solution. 4,6-Diphenyl-1,9-anthrazolines 1a-1i have a formal reduction potential in the range -1.02 to -1.19 V (versus SCE) and estimated electron affinities (LUMO levels) of 3.21-3.38 eV. These results demonstrate that the new 4,6-diphenyl-1,9-anthrazolines are promising thermally stable n-type semiconductors for organic electronics. (C) 2011 Elsevier Ltd. All rights reserved.