2-{4-[2,5-bis(bromomethyl)phenoxy]phenyl}-5-{4-[(3,7-dimethyloctyl)oxy]phenyl}-1,3,4-oxadiazole | 676331-56-9

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: 2-{4-[2,5-bis(bromomethyl)phenoxy]phenyl}-5-{4-[(3,7-dimethyloctyl)oxy]phenyl}-1,3,4-oxadiazole
• 英文别名: 2-[4-[2,5-Bis(bromomethyl)phenoxy]phenyl]-5-[4-(3,7-dimethyloctoxy)phenyl]-1,3,4-oxadiazole；2-[4-[2,5-bis(bromomethyl)phenoxy]phenyl]-5-[4-(3,7-dimethyloctoxy)phenyl]-1,3,4-oxadiazole
• CAS: 676331-56-9
• 化学式: C₃₂H₃₆Br₂N₂O₃
• 分子量: 656.457
• InChiKey: RNAOTUCBNDAGEN-UHFFFAOYSA-N

物化性质

• 沸点：
  672.7±65.0 °C(Predicted)
• 密度：
  1.333±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  9.8
• 重原子数：
  39
• 可旋转键数：
  14
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.38
• 拓扑面积：
  57.4
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为产物：
  描述：

  对氟苯甲酸乙酯 在 N-溴代丁二酰亚胺(NBS) 、 氯化亚砜 、 potassium tert-butylate 、 一水合肼 、 三乙胺 、 过氧化苯甲酰 作用下， 以 乙醇 、 二氯甲烷 、 N,N-二甲基甲酰胺 、 苯 为溶剂， 反应 35.0h， 生成 2-{4-[2,5-bis(bromomethyl)phenoxy]phenyl}-5-{4-[(3,7-dimethyloctyl)oxy]phenyl}-1,3,4-oxadiazole
  参考文献：
  名称：

  High-Efficiency Poly(p-phenylenevinylene)-Based Copolymers Containing an Oxadiazole Pendant Group for Light-Emitting Diodes

  摘要：

  yA new series of high brightness and luminance efficient poly(p-phenylenevinylene) (PPV)-based electroluminescent (EL) polymers, poly[2-{4-[5-(4-(3,7-dimethyloctyloxy)phenyl)-1,3,4-oxadiazole-2-yl]phenyloxyl-1,4-phenylenevinylene] (Oxa-PPV), poly[2-{2-((3,7-dimethyloctyl)oxy)phenoxyl-1,4-phenylenevinylene] (DMOP-PPV), and their corresponding random copolymers, poly{[2-14-[5-(4-(3,7-dimethyloctyloxy)phenyl)-1,3,4-oxadiazole-2-yl]phenyloxyl-1,4-phenylenevinylene]-co-[2-{2-((3,7-dimethyloctyl)oxy) phenoxyl},4-phenylenevinylene] (Oxa-PPV-co-DMOP-PPV), with an electron-deficient 1,3,4-oxadiazole unit on the side groups, were synthesized through the Gilch polymerization method. The newly designed and synthesized asymmetric molecular structures of Oxa-PPV, DMOP-PPV, and Oxa-PPV-co-DMOP-PPV were completely soluble in common organic solvents, and defect-free optical thin film was easily spin-coated onto the indium tin oxide (ITO) substrate. Oxa-PPV shows a high glass transition temperature (T-g), which might be an advantage for long time operation of polymer light-emitting diodes (PLEDs). Double-layer LEDs with an ITO/PEDOT/polymer/Al configuration were fabricated by using those polymers. Electrooptical properties and device performance could be adjusted by introducing the Oxa-PPV content in the copolymers. The emission colors could be tuned from green to yellowish-orange via intramolecular energy transfer. The improved device performance of Oxa-PPV over DMOP-PPV and Oxa-PPV-co-DMOP-PPV may be due to better electron injection and charge balance between holes and electrons and also efficient intramolecular energy transfer from 1,3,4-oxadiazole units to PPV backbones. The maximum brightness and the luminance efficiency of Oxa-PPV were up to 19395 cd/m(2) at 14 V and 21.1 cd/A at 5930 cd/m(2). The maximum luminance efficiency of Oxa-PPV is ranked the highest value among the PPV derivatives to date.

  DOI：

  10.1021/ja036955+

文献信息

• High-Efficiency Poly(<i>p</i>-phenylenevinylene)-Based Copolymers Containing an Oxadiazole Pendant Group for Light-Emitting Diodes
  作者：Sung-Ho Jin、Mock-Yeon Kim、Jin Young Kim、Kwanghee Lee、Yeong-Soon Gal

  DOI：10.1021/ja036955+

  日期：2004.3.3

  yA new series of high brightness and luminance efficient poly(p-phenylenevinylene) (PPV)-based electroluminescent (EL) polymers, poly[2-4-[5-(4-(3,7-dimethyloctyloxy)phenyl)-1,3,4-oxadiazole-2-yl]phenyloxyl-1,4-phenylenevinylene] (Oxa-PPV), poly[2-2-((3,7-dimethyloctyl)oxy)phenoxyl-1,4-phenylenevinylene] (DMOP-PPV), and their corresponding random copolymers, poly[2-14-[5-(4-(3,7-dimethyloctyloxy)phenyl)-1,3,4-oxadiazole-2-yl]phenyloxyl-1,4-phenylenevinylene]-co-[2-2-((3,7-dimethyloctyl)oxy) phenoxyl},4-phenylenevinylene] (Oxa-PPV-co-DMOP-PPV), with an electron-deficient 1,3,4-oxadiazole unit on the side groups, were synthesized through the Gilch polymerization method. The newly designed and synthesized asymmetric molecular structures of Oxa-PPV, DMOP-PPV, and Oxa-PPV-co-DMOP-PPV were completely soluble in common organic solvents, and defect-free optical thin film was easily spin-coated onto the indium tin oxide (ITO) substrate. Oxa-PPV shows a high glass transition temperature (T-g), which might be an advantage for long time operation of polymer light-emitting diodes (PLEDs). Double-layer LEDs with an ITO/PEDOT/polymer/Al configuration were fabricated by using those polymers. Electrooptical properties and device performance could be adjusted by introducing the Oxa-PPV content in the copolymers. The emission colors could be tuned from green to yellowish-orange via intramolecular energy transfer. The improved device performance of Oxa-PPV over DMOP-PPV and Oxa-PPV-co-DMOP-PPV may be due to better electron injection and charge balance between holes and electrons and also efficient intramolecular energy transfer from 1,3,4-oxadiazole units to PPV backbones. The maximum brightness and the luminance efficiency of Oxa-PPV were up to 19395 cd/m(2) at 14 V and 21.1 cd/A at 5930 cd/m(2). The maximum luminance efficiency of Oxa-PPV is ranked the highest value among the PPV derivatives to date.