8-benzyloxy-5-[9,9-bis-(2-ethyl-hexyl)-7-iodo-9H-fluoren-2-yl]-quinoline | 911679-95-3

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 喹啉及其衍生物
• 英文名称: 8-benzyloxy-5-[9,9-bis-(2-ethyl-hexyl)-7-iodo-9H-fluoren-2-yl]-quinoline
• CAS: 911679-95-3
• 化学式: C₄₅H₅₂INO
• 分子量: 749.818
• InChiKey: VANSATZLCDJRMA-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  13.56
• 重原子数：
  48.0
• 可旋转键数：
  16.0
• 环数：
  6.0
• sp3杂化的碳原子比例：
  0.4
• 拓扑面积：
  22.12
• 氢给体数：
  0.0
• 氢受体数：
  2.0

反应信息

• 作为反应物：
  描述：

  8-benzyloxy-5-[9,9-bis-(2-ethyl-hexyl)-7-iodo-9H-fluoren-2-yl]-quinoline 在 tris(dibenzylideneacetone)dipalladium (0) 、 三(邻甲基苯基)磷 (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride 、 四乙基氢氧化铵 作用下， 以 四氢呋喃 、 甲醇 、 甲苯 为溶剂， 反应 48.0h， 生成 8-benzyloxy-5-[9,9,9',9'-tetrakis-(2-ethyl-hexyl)-7'-trimethylsilanyl-9H,9'H-[2,2']bifluorenyl-7-yl]-quinoline
  参考文献：
  名称：

  Molecular-Wire Behavior of OLED Materials:  Exciton Dynamics in Multichromophoric Alq₃-Oligofluorene-Pt(II)porphyrin Triads

  摘要：

  Donor-bridge-acceptor triads consisting of the Alq3 complex, oligofluorene bridge, and PtII tetraphenylporphyrin (PtTPP) were synthesized. The triads were designed to study the energy level/distance-dependence in energy transfer both in a solution and in solid state. The materials show effective singlet transfer from the Alq3-fluorene fluorophore to the porphyrin, while the triplet energy transfer, owing to the shorter delocalization of triplet excitons, appears to take place via a triplet energy cascade. Using femtosecond transient spectroscopy, the rate of the singlet-singlet energy transfer was determined. The exponential dependence of the donor-acceptor distance and the respective energy transfer rates of 7.1 x 1010 to 1.0 x 109 s-1 with the attenuation factor â of 0.21 +/- 0.02 A-1 suggest that the energy transfer proceeds via a mixed incohererent wire/superexchange mechanism. In the OLEDs fabricated using the Alq3-oligofluorene-PtTPP triads with better triplet level alignment, the order of a magnitude increase in efficacy appears to be due to facile triplet energy transfer. The devices, where the triplet-triplet energy transfer is of paramount importance, showed high color purity emission (CIE X,Y: 0.706, 0.277), which is almost identical to the emission from thin films. Most importantly, we believe that the design principles demonstrated above are general and may be used to prepare OLED materials with enhanced quantum efficacy at lowered operational potentials, being crucial for improved lifespan of OLEDs.

  DOI：

  10.1021/ja064471i
• 作为产物：
  描述：

  8-benzyloxy-5-[9,9-bis-(2-ethyl-hexyl)-7-trimethylsilanyl-9H-fluoren-2-yl]-quinoline 在 一氯化碘 作用下， 以 二氯甲烷 为溶剂， 以92%的产率得到8-benzyloxy-5-[9,9-bis-(2-ethyl-hexyl)-7-iodo-9H-fluoren-2-yl]-quinoline
  参考文献：
  名称：

  Molecular-Wire Behavior of OLED Materials:  Exciton Dynamics in Multichromophoric Alq₃-Oligofluorene-Pt(II)porphyrin Triads

  摘要：

  Donor-bridge-acceptor triads consisting of the Alq3 complex, oligofluorene bridge, and PtII tetraphenylporphyrin (PtTPP) were synthesized. The triads were designed to study the energy level/distance-dependence in energy transfer both in a solution and in solid state. The materials show effective singlet transfer from the Alq3-fluorene fluorophore to the porphyrin, while the triplet energy transfer, owing to the shorter delocalization of triplet excitons, appears to take place via a triplet energy cascade. Using femtosecond transient spectroscopy, the rate of the singlet-singlet energy transfer was determined. The exponential dependence of the donor-acceptor distance and the respective energy transfer rates of 7.1 x 1010 to 1.0 x 109 s-1 with the attenuation factor â of 0.21 +/- 0.02 A-1 suggest that the energy transfer proceeds via a mixed incohererent wire/superexchange mechanism. In the OLEDs fabricated using the Alq3-oligofluorene-PtTPP triads with better triplet level alignment, the order of a magnitude increase in efficacy appears to be due to facile triplet energy transfer. The devices, where the triplet-triplet energy transfer is of paramount importance, showed high color purity emission (CIE X,Y: 0.706, 0.277), which is almost identical to the emission from thin films. Most importantly, we believe that the design principles demonstrated above are general and may be used to prepare OLED materials with enhanced quantum efficacy at lowered operational potentials, being crucial for improved lifespan of OLEDs.

  DOI：

  10.1021/ja064471i

文献信息

• Ultrafast Dynamics of Triplet Excitons in Alq₃-Bridge-Pt(II)porphyrin Electroluminescent Materials
  作者：Victor A. Montes、César Pérez-Bolívar、Leandro A. Estrada、Joseph Shinar、Pavel Anzenbacher

  DOI：10.1021/ja073491x

  日期：2007.10.1

  it is important to harvest the energy of triplets in light-emitting processes. Self-assembled multichromophore electroluminescent materials consisting of a trisquinolinolate aluminum(III) (Alq3) donor, fluorene-based conjugated oligomers as a bridge, and Pt(II)tetraphenylporphyrin as an acceptor and phosphorescent emitter are described. In these materials, the energy of singlet as well as triplet states

  激发态动力学对于最大化有机发光二极管 (OLED) 的性能至关重要。因为电子-空穴复合以 3:1 的比例产生单重态和三重态激发态，所以在发光过程中收集三重态的能量很重要。描述了自组装多发色团电致发光材料，包括三羟基喹啉铝 (III) (Alq3) 供体、芴基共轭低聚物作为桥梁和 Pt (II) 四苯基卟啉作为受体和磷光发射体。在这些材料中，单线态和三线态的能量被收集并作为红色磷光从卟啉受体发射。注意力集中在三重态激子动力学上，通过超快瞬态光谱研究，并将观察结果与薄膜中的磷光和来自 OLED 的电致发光进行比较。发现正向 Alq3 到芴桥三重态转移的放热性似乎更小……