3-(N-苯基-N-(芘-1-基)氨基)苯甲醛 | 840531-06-8

• 分子结构分类: 有机化合物 - 苯类化合物 - 芘
• 中文名称: 3-(N-苯基-N-(芘-1-基)氨基)苯甲醛
• 英文名称: 3-(N-phenyl-N-(pyren-1-yl)amino)benzaldehyde
• 英文别名: 3-(phenyl(pyren-1-yl)amino)benzaldehyde；3-(N-pyren-1-ylanilino)benzaldehyde
• CAS: 840531-06-8
• 化学式: C₂₉H₁₉NO
• 分子量: 397.476
• InChiKey: CGCOZPQVRWOETA-UHFFFAOYSA-N

物化性质

• 沸点：
  616.1±38.0 °C(Predicted)
• 密度：
  1.304±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  7.87
• 重原子数：
  31.0
• 可旋转键数：
  4.0
• 环数：
  6.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  20.31
• 氢给体数：
  0.0
• 氢受体数：
  2.0

反应信息

• 作为反应物：
  描述：

  3-(N-苯基-N-(芘-1-基)氨基)苯甲醛 在 sodium tetrahydroborate 作用下， 以 四氢呋喃 、 甲醇 为溶剂， 以96%的产率得到N-(3-(hydroxymethyl)phenyl)-N-phenylpyren-1-amine
  参考文献：
  名称：

  Energy and Electron Transfer in Bifunctional Non-Conjugated Dendrimers

  摘要：

  \Nonconjugated dendrimers, which are capable of funneling energy from the periphery to the core followed by a charge-transfer process from the core to the periphery, have been synthesized. The energy and electron donors involve a diarylaminopyrene unit and are incorporated at the periphery of these dendrimers. The energy and electron acceptor is at the core of the dendrimer, which involves a chromophore based on a benzthiadiazole moiety. The backbone of the dendrimers is benzyl ether based. A direct electron-transfer quenching of the excited state of the periphery or a sequential energy transfer-electron-transfer pathway are the two limiting mechanisms of the observed photophysical properties. We find that the latter mechanism is prevalent in these dendrimers. The energy transfer occurs on a picosecond time scale, while the charge-transfer process occurs on a nanosecond time scale. The lifetime of the charge separated species was found to be in the range of microseconds. Energy transfer efficiencies ranging from 80% to 90% were determined using both steady-state and time-resolved measurements, while charge-transfer efficiencies ranging from 70% to 80% were deduced from fluorescence quenching of the core chromophore. The dependence of the energy and charge-transfer processes on dendrimer generation is analyzed in terms of the backfolding of the flexible benzyl ether backbone, which leads to a weaker dependence of the energy and charge-transfer efficiencies on dendrimer size than would be expected for a rigid system.

  DOI：

  10.1021/ja044778m
• 作为产物：
  描述：

  2-(3-溴苯基)-1,3-二氧烷 在 三叔丁基膦 、 溶剂黄146 、 bis(dibenzylideneacetone)-palladium⁽⁰⁾ 作用下， 以 甲苯 为溶剂， 反应 11.0h， 生成 3-(N-苯基-N-(芘-1-基)氨基)苯甲醛
  参考文献：
  名称：

  Energy and Electron Transfer in Bifunctional Non-Conjugated Dendrimers

  摘要：

  \Nonconjugated dendrimers, which are capable of funneling energy from the periphery to the core followed by a charge-transfer process from the core to the periphery, have been synthesized. The energy and electron donors involve a diarylaminopyrene unit and are incorporated at the periphery of these dendrimers. The energy and electron acceptor is at the core of the dendrimer, which involves a chromophore based on a benzthiadiazole moiety. The backbone of the dendrimers is benzyl ether based. A direct electron-transfer quenching of the excited state of the periphery or a sequential energy transfer-electron-transfer pathway are the two limiting mechanisms of the observed photophysical properties. We find that the latter mechanism is prevalent in these dendrimers. The energy transfer occurs on a picosecond time scale, while the charge-transfer process occurs on a nanosecond time scale. The lifetime of the charge separated species was found to be in the range of microseconds. Energy transfer efficiencies ranging from 80% to 90% were determined using both steady-state and time-resolved measurements, while charge-transfer efficiencies ranging from 70% to 80% were deduced from fluorescence quenching of the core chromophore. The dependence of the energy and charge-transfer processes on dendrimer generation is analyzed in terms of the backfolding of the flexible benzyl ether backbone, which leads to a weaker dependence of the energy and charge-transfer efficiencies on dendrimer size than would be expected for a rigid system.

  DOI：

  10.1021/ja044778m

文献信息

• Deep-blue emitting pyrene–benzimidazole conjugates for solution processed organic light-emitting diodes
  作者：Durai Karthik、K. R. Justin Thomas、Jwo-Huei Jou、Sudhir Kumar、Yu-Lin Chen、Yung-Cheng Jou

  DOI：10.1039/c4ra11043a

  日期：——

  the triarylamine donor to pyrene acceptor in the excited state. All derivatives were used as emitting dopants in multilayered organic light-emitting diodes exhibiting deep blue electroluminescence. The solution processed device fabricated by utilizing 1-phenyl-2-(pyren-1-yl)-1H-benzo[d]imidazole as an emitter displayed promising deep blue emission characteristics with a maximum luminance of 714 cd m−2

  合成了新的pyr-苯并咪唑共轭物，其中包含不同的π-连接基，例如苯基，噻吩和三芳基胺，并通过光物理，电化学，热和电致发光研究对其进行了表征。含三芳基胺的染料由于在激发态下从三芳基胺供体到pyr受体的明显分子内电荷转移（ICT），显示出红移的吸收光谱和发射光谱中的正溶剂溶变色。所有衍生物均用作呈现深蓝色电致发光的多层有机发光二极管中的发射掺杂剂。利用1-苯基-2-（吡喃-1-基）-1 H-苯并[ d]制得的溶液加工装置作为发射体的咪唑显示出有希望的深蓝色发射特性，其最大亮度为714 cd m -2，外部量子效率为1.5％，在100 cd m -2时的CIE坐标为（0.16，0.05），色彩饱和度为100％。