1,3,6,8-tetrakis((9,9-diethyl-9H-fluoren-2-yl)-ethynyl)pyrene | 1369762-94-6

• 分子结构分类: 有机化合物 - 苯类化合物 - 芘
• 英文名称: 1,3,6,8-tetrakis((9,9-diethyl-9H-fluoren-2-yl)-ethynyl)pyrene
• 英文别名: 1,3,6,8-Tetrakis[2-(9,9-diethylfluoren-2-yl)ethynyl]pyrene
• CAS: 1369762-94-6
• 化学式: C₉₂H₇₄
• 分子量: 1179.6
• InChiKey: KERYOPGJQQYCEM-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  27.4
• 重原子数：
  92
• 可旋转键数：
  16
• 环数：
  16.0
• sp3杂化的碳原子比例：
  0.22
• 拓扑面积：
  0
• 氢给体数：
  0
• 氢受体数：
  0

反应信息

• 作为产物：
  描述：

  1,3,6,8-四溴芘 、 9,9-diethyl-2-ethynyl-9H-fluorene 在 bis-triphenylphosphine-palladium(II) chloride 、 copper(l) iodide 、 三苯基膦 作用下， 以 三乙胺 为溶剂， 反应 24.0h， 以87%的产率得到1,3,6,8-tetrakis((9,9-diethyl-9H-fluoren-2-yl)-ethynyl)pyrene
  参考文献：
  名称：

  Pyrene-Fluorene Hybrids Containing Acetylene Linkage as Color-Tunable Emitting Materials for Organic Light-Emitting Diodes

  摘要：

  New blue- to yellow-emitting materials have been developed by incorporating fluorene-based chromophores on pyrene core with acetylene linkage and using multifold palladium-catalyzed cross-coupling reactions. Both mono- and tetrasubstituted derivatives have been synthesized and characterized. The tetrasubstituted derivatives displayed red-shifted emission when compared to the monosubstituted derivative indicative of an extended conjugation in the former. End-capping with a diphenylamine unit further red-shifted the absorption and emission profiles and imparted a weak dipolar character to the molecules. Amine-containing derivatives displayed positive solvatochromism in the fluorescence spectra indicating a more polar excited state due to an efficient charge migration from the diphenylamine donor to the pyrene pi-acceptor. All of the derivatives were tested as emitting dopants with host material 4,4'-bis(9H-carbazol-9-yl)biphenyl (CBP) in a multilayered OLED and found to exhibit bright blue or yellow electroluminescence. The device utilizing 1,3,6,8-tetrasubstituted pyrene derivative as a dopant emitter displayed highest maximum luminescence 4630 cd/m(2) with power efficiency 3.8 lm/W and current efficiency 7.1 cd/A at 100 cd/m(2) attributable to the proper alignment of energy levels that led to the efficient harvesting of excitons. All of the devices exhibited color purity over a wide range of operating voltages.

  DOI：

  10.1021/jo300285v

文献信息

• Pyrene-Fluorene Hybrids Containing Acetylene Linkage as Color-Tunable Emitting Materials for Organic Light-Emitting Diodes
  作者：K. R. Justin Thomas、Neha Kapoor、M. N. K. Prasad Bolisetty、Jwo-Huei Jou、Yu-Lin Chen、Yung-Cheng Jou

  DOI：10.1021/jo300285v

  日期：2012.4.20

  New blue- to yellow-emitting materials have been developed by incorporating fluorene-based chromophores on pyrene core with acetylene linkage and using multifold palladium-catalyzed cross-coupling reactions. Both mono- and tetrasubstituted derivatives have been synthesized and characterized. The tetrasubstituted derivatives displayed red-shifted emission when compared to the monosubstituted derivative indicative of an extended conjugation in the former. End-capping with a diphenylamine unit further red-shifted the absorption and emission profiles and imparted a weak dipolar character to the molecules. Amine-containing derivatives displayed positive solvatochromism in the fluorescence spectra indicating a more polar excited state due to an efficient charge migration from the diphenylamine donor to the pyrene pi-acceptor. All of the derivatives were tested as emitting dopants with host material 4,4'-bis(9H-carbazol-9-yl)biphenyl (CBP) in a multilayered OLED and found to exhibit bright blue or yellow electroluminescence. The device utilizing 1,3,6,8-tetrasubstituted pyrene derivative as a dopant emitter displayed highest maximum luminescence 4630 cd/m(2) with power efficiency 3.8 lm/W and current efficiency 7.1 cd/A at 100 cd/m(2) attributable to the proper alignment of energy levels that led to the efficient harvesting of excitons. All of the devices exhibited color purity over a wide range of operating voltages.