3,4-bis(4-bromophenyl)-1-ethyl-2,5-bis(naphthalen-2-yl)-1H-pyrrole | 944344-69-8

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡咯
• 英文名称: 3,4-bis(4-bromophenyl)-1-ethyl-2,5-bis(naphthalen-2-yl)-1H-pyrrole
• 英文别名: 3,4-Bis(4-bromophenyl)-1-ethyl-2,5-dinaphthalen-2-ylpyrrole；3,4-bis(4-bromophenyl)-1-ethyl-2,5-dinaphthalen-2-ylpyrrole
• CAS: 944344-69-8
• 化学式: C₃₈H₂₇Br₂N
• 分子量: 657.447
• InChiKey: WNKUGLWKZHHQDH-UHFFFAOYSA-N

物化性质

• 沸点：
  637.1±55.0 °C(predicted)
• 密度：
  1.37±0.1 g/cm3(Temp: 20 °C; Press: 760 Torr)(predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  11.4
• 重原子数：
  41
• 可旋转键数：
  5
• 环数：
  7.0
• sp3杂化的碳原子比例：
  0.05
• 拓扑面积：
  4.9
• 氢给体数：
  0
• 氢受体数：
  0

反应信息

• 作为反应物：
  描述：

  3,4-bis(4-bromophenyl)-1-ethyl-2,5-bis(naphthalen-2-yl)-1H-pyrrole 、 N-苯基-1-萘胺 在 palladium diacetate 三叔丁基膦 、 sodium t-butanolate 作用下， 以 甲苯 为溶剂， 反应 24.0h， 以73%的产率得到1-ethyl-3,4-bis[4-N-(1-naphthyl)anilinophenyl]-2,5-bis(naphthalen-2-yl)-1H-pyrrole
  参考文献：
  名称：

  Peripheral aryl-substituted pyrrole fluorophores for glassy blue-light-emitting diodes

  摘要：

  In this work, a series of aryl-substituted pyrrole analogues were synthesized. These pyrrole analogues emit violet to blue light. Fluorescence and amorphous glassy properties of these pyrrole analogues were induced by manipulating the peripheral aryl groups. These crowded peripheral aryl groups would effectively prevent the fluorophores from aggregation, resulting in higher quantum efficiency and a stable emission spectrum in the solid state. One of the aryl-substituted pyrrole analogues, namely NPANPy can be used as hole-transporting material or hole-transporting/emitting material. The devices would emit blue light when the fluorophore NPANPy acts as the hole-transporting/ emitting material. Their CIE coordinate is around (0.16, 0.14), whereas the maximum brightness can reach 4300-5000 cd m(-2). Apart from that, when the fluorophore was used only as the hole-transporting material, better device performances, especially in low current density, were found, as compared with the standard device. (C) 2007 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2007.05.032
• 作为产物：
  描述：

  2,3-bis(4-bromophenyl)-1,4-bis(naphthalen-2-yl)butane-1,4-dione 在 乙酸铵 、 sodium hydride 、 溶剂黄146 作用下， 以 正己烷 、 N,N-二甲基乙酰胺 为溶剂， 反应 28.0h， 生成 3,4-bis(4-bromophenyl)-1-ethyl-2,5-bis(naphthalen-2-yl)-1H-pyrrole
  参考文献：
  名称：

  Peripheral aryl-substituted pyrrole fluorophores for glassy blue-light-emitting diodes

  摘要：

  In this work, a series of aryl-substituted pyrrole analogues were synthesized. These pyrrole analogues emit violet to blue light. Fluorescence and amorphous glassy properties of these pyrrole analogues were induced by manipulating the peripheral aryl groups. These crowded peripheral aryl groups would effectively prevent the fluorophores from aggregation, resulting in higher quantum efficiency and a stable emission spectrum in the solid state. One of the aryl-substituted pyrrole analogues, namely NPANPy can be used as hole-transporting material or hole-transporting/emitting material. The devices would emit blue light when the fluorophore NPANPy acts as the hole-transporting/ emitting material. Their CIE coordinate is around (0.16, 0.14), whereas the maximum brightness can reach 4300-5000 cd m(-2). Apart from that, when the fluorophore was used only as the hole-transporting material, better device performances, especially in low current density, were found, as compared with the standard device. (C) 2007 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2007.05.032

文献信息

• Peripheral aryl-substituted pyrrole fluorophores for glassy blue-light-emitting diodes
  作者：Wen-Jang Kuo、Ying-Hsiao Chen、Ru-Jong Jeng、Li-Hsin Chan、Wen-Peng Lin、Zhe-Ming Yang

  DOI：10.1016/j.tet.2007.05.032

  日期：2007.7

  In this work, a series of aryl-substituted pyrrole analogues were synthesized. These pyrrole analogues emit violet to blue light. Fluorescence and amorphous glassy properties of these pyrrole analogues were induced by manipulating the peripheral aryl groups. These crowded peripheral aryl groups would effectively prevent the fluorophores from aggregation, resulting in higher quantum efficiency and a stable emission spectrum in the solid state. One of the aryl-substituted pyrrole analogues, namely NPANPy can be used as hole-transporting material or hole-transporting/emitting material. The devices would emit blue light when the fluorophore NPANPy acts as the hole-transporting/ emitting material. Their CIE coordinate is around (0.16, 0.14), whereas the maximum brightness can reach 4300-5000 cd m(-2). Apart from that, when the fluorophore was used only as the hole-transporting material, better device performances, especially in low current density, were found, as compared with the standard device. (C) 2007 Elsevier Ltd. All rights reserved.