1,5-bis(2'-ethylhexyloxy)-2,4-dibromobenzene | 502470-16-8

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯酚醚
• 英文名称: 1,5-bis(2'-ethylhexyloxy)-2,4-dibromobenzene
• 英文别名: 1,5-Dibromo-2,4-bis(2-ethylhexoxy)benzene
• CAS: 502470-16-8
• 化学式: C₂₂H₃₆Br₂O₂
• 分子量: 492.335
• InChiKey: INBDVLPZJPFTBF-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  9.5
• 重原子数：
  26
• 可旋转键数：
  14
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.73
• 拓扑面积：
  18.5
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  1,5-bis(2'-ethylhexyloxy)-2,4-dibromobenzene 在 N-溴代丁二酰亚胺(NBS) 、 四(三苯基膦)钯 、 氯化亚砜 、 偶氮二异丁腈 、 sodium carbonate 作用下， 以 四氢呋喃 、 苯 为溶剂， 反应 48.0h， 生成 1,4-bis(chloromethyl)-2-((2',4'-bis(2''-ethylhexyloxy)-5'-phenyl)phenyl)benzene
  参考文献：
  名称：

  New Phenyl-Substituted PPV Derivatives for Polymer Light-emitting Diodes−Synthesis, Characterization and Structure−Property Relationship Study

  摘要：

  Three new PPV derivatives with dialkoxyphenyl substituents, BEH2P-PPV, BEH3P-PPV, and BEH4P-PPV have been synthesized. The polymers were characterized by FT-IR, H-1 NMR, and elemental analysis. The polymers possess excellent solubility, high molecular weights, high photoluminescence efficiencies and good thermal stability. The influence of substitution pattern on the formation of structural defects has been investigated by measuring the signal due to tolane-bisbenzyl moieties (TBB) in the proton NMR spectra. BEH2P-PPV with a steric phenyl group at the ortho-position on the side phenyl ring shows the lowest amount of TBB, which indicates suitable steric hindrance can be applied to suppress the formation of irregular head-to-head and tail-to-tail linkage in the polymer chains. In addition, the polarity of solvents used for the Gilch polymerization will also affect the amount of irregular structure in the polymers. Polar solvents such as THF will result in polymers with low TBB content. Energy level measurement from cyclic voltammetry revealed that the influences of the substitution pattern on the HOMOs and LUMOs are different. The three polymers possess similar HOMO energy levels while the LUMO of BEH4P-PPV is much higher than that of the other two polymers. Polymer light-emitting diodes fabricated from BEH2P-PPV, BEH3P-PPV, and BEH4P-PPV with the configuration of ITO/PEDOT/polymer/Ba/Al, emitted bright blue-green to green light with the maximum peaks at 496, 488, and 525 nm, respectively. The turn-on electric field and maximum external quantum efficiencies of the diodes are 0.30, 0.50, and 0.42 MV/cm and 0.37%, 0.66%, and 0.25% respectively. The quantum efficiency is mainly determined by the electron injection from the cathode. With the highest luminance, lowest turn-on electric field, and good quantum efficiency as well as negligible structural defects, BEH2P-PPV is the most promising material among the three polymers for polymer light-emitting diodes.

  DOI：

  10.1021/ma021221n
• 作为产物：
  描述：

  1,3-bis((2-ethylhexyl)oxy)benzene 在 溴 、 溶剂黄146 作用下， 以 甲醇 、 氯仿 为溶剂， 反应 2.0h， 以93%的产率得到1,5-bis(2'-ethylhexyloxy)-2,4-dibromobenzene
  参考文献：
  名称：

  New Phenyl-Substituted PPV Derivatives for Polymer Light-emitting Diodes−Synthesis, Characterization and Structure−Property Relationship Study

  摘要：

  Three new PPV derivatives with dialkoxyphenyl substituents, BEH2P-PPV, BEH3P-PPV, and BEH4P-PPV have been synthesized. The polymers were characterized by FT-IR, H-1 NMR, and elemental analysis. The polymers possess excellent solubility, high molecular weights, high photoluminescence efficiencies and good thermal stability. The influence of substitution pattern on the formation of structural defects has been investigated by measuring the signal due to tolane-bisbenzyl moieties (TBB) in the proton NMR spectra. BEH2P-PPV with a steric phenyl group at the ortho-position on the side phenyl ring shows the lowest amount of TBB, which indicates suitable steric hindrance can be applied to suppress the formation of irregular head-to-head and tail-to-tail linkage in the polymer chains. In addition, the polarity of solvents used for the Gilch polymerization will also affect the amount of irregular structure in the polymers. Polar solvents such as THF will result in polymers with low TBB content. Energy level measurement from cyclic voltammetry revealed that the influences of the substitution pattern on the HOMOs and LUMOs are different. The three polymers possess similar HOMO energy levels while the LUMO of BEH4P-PPV is much higher than that of the other two polymers. Polymer light-emitting diodes fabricated from BEH2P-PPV, BEH3P-PPV, and BEH4P-PPV with the configuration of ITO/PEDOT/polymer/Ba/Al, emitted bright blue-green to green light with the maximum peaks at 496, 488, and 525 nm, respectively. The turn-on electric field and maximum external quantum efficiencies of the diodes are 0.30, 0.50, and 0.42 MV/cm and 0.37%, 0.66%, and 0.25% respectively. The quantum efficiency is mainly determined by the electron injection from the cathode. With the highest luminance, lowest turn-on electric field, and good quantum efficiency as well as negligible structural defects, BEH2P-PPV is the most promising material among the three polymers for polymer light-emitting diodes.

  DOI：

  10.1021/ma021221n