8-benzyloxy-5-[9,9-bis-(2-ethyl-hexyl)-7-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)-9H-fluoren-2-yl]-quinoline | 911679-96-4

• 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-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)-9H-fluoren-2-yl]-quinoline
• CAS: 911679-96-4
• 化学式: C₅₁H₆₄BNO₃
• 分子量: 749.885
• InChiKey: PNSLEOZZNRMLEQ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  13.26
• 重原子数：
  56.0
• 可旋转键数：
  17.0
• 环数：
  7.0
• sp3杂化的碳原子比例：
  0.47
• 拓扑面积：
  40.58
• 氢给体数：
  0.0
• 氢受体数：
  4.0

反应信息

• 作为反应物：
  描述：

  [7-Bromo-9,9-bis(2-ethylhexyl)fluoren-2-yl]-trimethylsilane 、 8-benzyloxy-5-[9,9-bis-(2-ethyl-hexyl)-7-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)-9H-fluoren-2-yl]-quinoline 在 tris(dibenzylideneacetone)dipalladium (0) 、 三(邻甲基苯基)磷 四乙基氢氧化铵 作用下， 以 甲醇 、 甲苯 为溶剂， 以93%的产率得到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：

  [7-Bromo-9,9-bis(2-ethylhexyl)fluoren-2-yl]-trimethylsilane 在 tris(dibenzylideneacetone)dipalladium (0) 、 三(邻甲基苯基)磷 (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride 、 一氯化碘 、 四乙基氢氧化铵 作用下， 以 四氢呋喃 、 甲醇 、 二氯甲烷 、 甲苯 为溶剂， 反应 48.0h， 生成 8-benzyloxy-5-[9,9-bis-(2-ethyl-hexyl)-7-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)-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

• Hydroxyquinolines with extended fluorophores: arrays for turn-on and ratiometric sensing of cations
  作者：Manuel A. Palacios、Zhuo Wang、Victor A. Montes、Grigory V. Zyryanov、Bethany J. Hausch、Karolina Jursíková、Pavel Anzenbacher Jr.

  DOI：10.1039/b705392d

  日期：——

  8-Hydroxyquinoline-based ligands with extended conjugated fluorophores were designed to provide turn-on and ratiometric signal output optimized for use in fluorescence-based sensor arrays, where the changes in blue and green channels of the RGB signal are used to distinguish between cationic analytes.

  我们设计了具有扩展共轭荧光团的 8-羟基喹啉基配体，以提供开通和比率计量信号输出，优化了基于荧光的传感器阵列的使用，其中 RGB 信号的蓝色和绿色通道的变化用于区分阳离子分析物。