2-(4-N,N'-diphenylaminophenyl)-5-(4-formalphenyl)-1,3,4-oxadiazole | 758119-08-3

• 分子结构分类: 有机化合物 - 有机氮化合物
• 英文名称: 2-(4-N,N'-diphenylaminophenyl)-5-(4-formalphenyl)-1,3,4-oxadiazole
• 英文别名: 4-(5-(4-(diphenylamino)phenyl)-1,3,4-oxadiazol-2-yl)benzaldehyde；4-[5-[4-(N-phenylanilino)phenyl]-1,3,4-oxadiazol-2-yl]benzaldehyde
• CAS: 758119-08-3
• 化学式: C₂₇H₁₉N₃O₂
• 分子量: 417.467
• InChiKey: OYPCWXYETXLRRU-UHFFFAOYSA-N

物化性质

• 沸点：
  614.7±65.0 °C(Predicted)
• 密度：
  1.257±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  5.8
• 重原子数：
  32
• 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：
  59.2
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  1,10-邻二氮杂菲-5,6-二酮 、 2-(4-N,N'-diphenylaminophenyl)-5-(4-formalphenyl)-1,3,4-oxadiazole 在 乙酸铵 、 溶剂黄146 作用下， 以80%的产率得到2-(4-(5-(4-N,N'-diphenylaminophenyl)-1,3,4-oxadiazol-2-yl)phenyl)imidazo[4,5-f] phenanthroline
  参考文献：
  名称：

  Synthesis of efficient blue and red light emitting phenanthroline derivatives containing both hole and electron transporting properties

  摘要：

  Two phenanthroline derivatives containing a hole transporting triphenylamine and an electron transporting 1,3,4-oxadiazole unit have been prepared with high yield. UV-vis absorption and fluorescence measurement indicated they are high efficient light-emitting materials. The compounds are 6-(5-(4-N,N'-diphenylaminophenyl)-1,3,4-oxadiazol-2-yl) quinoxalino[2,3-f] phenanthroline (9, lambda(max)=635nm, 40% quantum yield), and 1-ethyl-2-(4-(5-(4-N,N'-diphenylaminophenyl)-1,3,4-oxadiazol-2-yl)phenyl)imidazo[4,5-f]phenanthroline (14, lambda(max)=461 nm, 78% quantum yield). Preliminary study on electroluminescence for the two fluorescent dyes prepared from vacuum evaporation resulted in blue and red light emitting organic light emitting diodes (OLED). (C) 2004 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2004.06.087
• 作为产物：
  描述：

  4-二苯氨基苯甲腈 在 吡啶 、 sodium azide 、 氯化铵 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 42.0h， 生成 2-(4-N,N'-diphenylaminophenyl)-5-(4-formalphenyl)-1,3,4-oxadiazole
  参考文献：
  名称：

  D-A-π-A organic dyes for dye-sensitized solar cells: effect of π-bridge length between two acceptors on photovoltaic properties

  摘要：

  We report synthesis, photophysical and photovoltaic properties of organic dyes with D-A-pi-A backbone having 1,3,4-oxadiazole moiety as an auxiliary acceptor, triphenylamine as donor with varying pi-bridges and acceptors. The effect of increased distance between the auxiliary acceptor and main acceptor on their photovoltaic properties is studied with the help of optical and electrochemical spectroscopy, quantum chemical calculations, current-voltage (I-V) measurements, incident photon-to-current conversion efficiency (IPCE) and electrochemical impedance spectroscopy (EIS). The length of the pi-bridge of the studied dyes has significant effect on the photophysical and photovoltaic properties. Dye OD3 with the longest pi-bridge has superior performance in dye-sensitized solar cells compared to other dyes. (C) 2015 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2015.08.068

文献信息

• Synthesis of efficient blue and red light emitting phenanthroline derivatives containing both hole and electron transporting properties
  作者：Yuan Ji Bing、Louis M. Leung、Gong Menglian

  DOI：10.1016/j.tetlet.2004.06.087

  日期：2004.8

  Two phenanthroline derivatives containing a hole transporting triphenylamine and an electron transporting 1,3,4-oxadiazole unit have been prepared with high yield. UV-vis absorption and fluorescence measurement indicated they are high efficient light-emitting materials. The compounds are 6-(5-(4-N,N'-diphenylaminophenyl)-1,3,4-oxadiazol-2-yl) quinoxalino[2,3-f] phenanthroline (9, lambda(max)=635nm, 40% quantum yield), and 1-ethyl-2-(4-(5-(4-N,N'-diphenylaminophenyl)-1,3,4-oxadiazol-2-yl)phenyl)imidazo[4,5-f]phenanthroline (14, lambda(max)=461 nm, 78% quantum yield). Preliminary study on electroluminescence for the two fluorescent dyes prepared from vacuum evaporation resulted in blue and red light emitting organic light emitting diodes (OLED). (C) 2004 Elsevier Ltd. All rights reserved.
• D-A-π-A organic dyes for dye-sensitized solar cells: effect of π-bridge length between two acceptors on photovoltaic properties
  作者：Sandeep B. Mane、Chih-Fu Cheng、Albertus Adrian Sutanto、Amitabha Datta、Amitava Dutta、Chen-Hsiung Hung

  DOI：10.1016/j.tet.2015.08.068

  日期：2015.10

  We report synthesis, photophysical and photovoltaic properties of organic dyes with D-A-pi-A backbone having 1,3,4-oxadiazole moiety as an auxiliary acceptor, triphenylamine as donor with varying pi-bridges and acceptors. The effect of increased distance between the auxiliary acceptor and main acceptor on their photovoltaic properties is studied with the help of optical and electrochemical spectroscopy, quantum chemical calculations, current-voltage (I-V) measurements, incident photon-to-current conversion efficiency (IPCE) and electrochemical impedance spectroscopy (EIS). The length of the pi-bridge of the studied dyes has significant effect on the photophysical and photovoltaic properties. Dye OD3 with the longest pi-bridge has superior performance in dye-sensitized solar cells compared to other dyes. (C) 2015 Elsevier Ltd. All rights reserved.