1-(4-bromophenyl)-3-hexyloxy-1H-pyrazole-4-carbaldehyde | 1224881-13-3

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑类
• 英文名称: 1-(4-bromophenyl)-3-hexyloxy-1H-pyrazole-4-carbaldehyde
• CAS: 1224881-13-3
• 化学式: C₁₆H₁₉BrN₂O₂
• 分子量: 351.243
• InChiKey: MPEKNISZCASOEF-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.41
• 重原子数：
  21.0
• 可旋转键数：
  8.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.38
• 拓扑面积：
  44.12
• 氢给体数：
  0.0
• 氢受体数：
  4.0

反应信息

• 作为反应物：
  描述：

  1-(4-bromophenyl)-3-hexyloxy-1H-pyrazole-4-carbaldehyde 、 苯硼酸 在 potassium phosphate 、 四(三苯基膦)钯 作用下， 以 1,4-二氧六环 为溶剂， 反应 3.0h， 以94%的产率得到1-(biphenyl-4-yl)-3-hexyloxy-1H-pyrazole-4-carbaldehyde
  参考文献：
  名称：

  Pyrazolyl-substituted polyconjugated molecules for optoelectronic applications

  摘要：

  Pyrazolyl-substituted diethylene derivative and its analogue containing additional cyano groups were synthesized and investigated as potential multifunctional materials for organic light emitting diodes. The influence of the electron affinitive cyano groups on the ionization potential (I-p) of the films as well as on the photoluminescence (PL) spectrum, PL quantum yield (eta) and PL decay time of the dilute solutions and thin films of the pyrazole derivatives was studied. PL measurements revealed that highly luminescent (eta = 0.88) cyano-free pyrazole derivative in solution became non-emissive (eta = 0.01) by attaching cyano groups as a result of these groups-induced torsional deactivation. However in the solid state, the steric and electrostatic effects of the bulky and polar cyano groups prevented tight packing of the pyrazole derivative molecules, thus significantly reducing migration-induced quenching of the excitons at the defects. Incorporation of the cyano groups resulted in the two-fold enhancement of the PL quantum yield in the film of the pyrazole derivative as compared to that of the cyano-free film. The I-p of 5.90 eV estimated for the cyano groups-containing compound was found to be higher as compared to the I-p of 5.46 eV for cyano-free analogue, what in conjunction with the PL data for the films indicates increased electron affinity in the pyrazole derivative with additional cyano groups. (C) 2009 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.dyepig.2009.10.007
• 作为产物：
  描述：

  4-bromo-1-(4-bromophenyl)-3-hexyloxy-1H-pyrazole 、 N,N-二甲基甲酰胺 在 正丁基锂 、 水 作用下， 以 四氢呋喃 、 正己烷 为溶剂， 以50%的产率得到1-(4-bromophenyl)-3-hexyloxy-1H-pyrazole-4-carbaldehyde
  参考文献：
  名称：

  Pyrazolyl-substituted polyconjugated molecules for optoelectronic applications

  摘要：

  Pyrazolyl-substituted diethylene derivative and its analogue containing additional cyano groups were synthesized and investigated as potential multifunctional materials for organic light emitting diodes. The influence of the electron affinitive cyano groups on the ionization potential (I-p) of the films as well as on the photoluminescence (PL) spectrum, PL quantum yield (eta) and PL decay time of the dilute solutions and thin films of the pyrazole derivatives was studied. PL measurements revealed that highly luminescent (eta = 0.88) cyano-free pyrazole derivative in solution became non-emissive (eta = 0.01) by attaching cyano groups as a result of these groups-induced torsional deactivation. However in the solid state, the steric and electrostatic effects of the bulky and polar cyano groups prevented tight packing of the pyrazole derivative molecules, thus significantly reducing migration-induced quenching of the excitons at the defects. Incorporation of the cyano groups resulted in the two-fold enhancement of the PL quantum yield in the film of the pyrazole derivative as compared to that of the cyano-free film. The I-p of 5.90 eV estimated for the cyano groups-containing compound was found to be higher as compared to the I-p of 5.46 eV for cyano-free analogue, what in conjunction with the PL data for the films indicates increased electron affinity in the pyrazole derivative with additional cyano groups. (C) 2009 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.dyepig.2009.10.007