pseudo-4,6-dibenzoylisophthaloyl chloride | 52496-56-7

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮
• 英文名称: pseudo-4,6-dibenzoylisophthaloyl chloride
• 英文别名: 1,7-Dichloro-1,7-diphenylfuro[3,4-f][2]benzofuran-3,5-dione
• CAS: 52496-56-7
• 化学式: C₂₂H₁₂Cl₂O₄
• 分子量: 411.241
• InChiKey: GLMAVIURQZRNFE-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.2
• 重原子数：
  28
• 可旋转键数：
  2
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.09
• 拓扑面积：
  52.6
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  pseudo-4,6-dibenzoylisophthaloyl chloride 在 ammonium hydroxide 、 sodium hypochlorite 、 间甲酚 、 potassium hydroxide 作用下， 以 N-甲基吡咯烷酮 、 水 为溶剂， 反应 54.0h， 生成 2,8-bis(2-flourenyl)-4,6-diphenyl-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
• 作为产物：
  描述：

  均苯四甲酸二酐 在 aluminum (III) chloride 、 氯化亚砜 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 6.0h， 生成 pseudo-4,6-dibenzoylisophthaloyl chloride
  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

• SALAZKIN S. N.; MELEXINA G. N.; KOMAROVA L. I.; KORSHAK V. V.; VINOGRADOV+, IN-T EHLEMENTOORGANICHESKIX SOEDINENIJ AN CCCP. M., 1976. 25 S., IL., BIB+
  作者：SALAZKIN S. N.、 MELEXINA G. N.、 KOMAROVA L. I.、 KORSHAK V. V.、 VINOGRADOV+

  DOI：——

  日期：——
• FAWCETT N. C.; CASSIDY P. E.; LIN J. C., J. ORG. CHEM. <JOCE-AH>, 1977, 42, NO 17, 2929-2930
  作者：FAWCETT N. C.、 CASSIDY P. E.、 LIN J. C.

  DOI：——

  日期：——