5-(diphenylamino)-2-hydroxybenzaldehyde | 209914-59-0

• 分子结构分类: 有机化合物 - 有机氮化合物
• 英文名称: 5-(diphenylamino)-2-hydroxybenzaldehyde
• 英文别名: 2-hydroxy-5-(N-phenylanilino)benzaldehyde；5-(Diphenylamino)-2-hydroxybenzaldehyde
• CAS: 209914-59-0
• 化学式: C₁₉H₁₅NO₂
• 分子量: 289.334
• InChiKey: IIXFERSYOUWBLC-UHFFFAOYSA-N

物化性质

• 沸点：
  459.5±35.0 °C(Predicted)
• 密度：
  1.254±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4.8
• 重原子数：
  22
• 可旋转键数：
  4
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  40.5
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  5-(diphenylamino)-2-hydroxybenzaldehyde 在 肼 作用下， 以 乙醇 、 水 为溶剂， 以27 %的产率得到(1E)-2-hydroxy-5-(N-phenylanilino)benzaldehyde hydrazone
  参考文献：
  名称：

  取代基对水杨醛腙衍生物性能的影响

  摘要：

  本研究调查了在两个选定位置（即对位）取代水杨醛腙的影响-关于形成氢桥的质子供给和质子接受中心的位置。对通过理论方法和 X 射线实验获得的结构数据以及原始共振哈米特常数的详细分析表明，可以通过用化学物质取代母体分子系统来选择性地调节水杨醛腙中存在的分子内氢键的强度一组已知的 π 给电子或受电子特性。我们的研究结果为规划水杨醛腙物种的合成途径和预测其氢键和相关物理和化学性质的结果提供了见解。

  DOI：

  10.1021/acs.joc.2c02547
• 作为产物：
  描述：

  4-甲氧基三苯胺 在 溴乙烷 、 碘 、 三溴化硼 、 magnesium 作用下， 以 四氢呋喃 、 二氯甲烷 、 甲苯 为溶剂， 反应 24.5h， 生成 5-(diphenylamino)-2-hydroxybenzaldehyde
  参考文献：
  名称：

  SalenZn-bridged D-π-A Dyes For Dye-Sensitized Solar Cells

  摘要：

  AbstractA series of SalenZn based dyes with triphenylamine derivatives as the donor, benzoic acid as the acceptor, and coplanar Salen complexes as the spacer have been designed and synthesized for dye‐sensitized solar cells. The absorption, electrochemical, and photovoltaic properties for all sensitizers have been systematically investigated. When the tail length of the alkyl substituents is increased from C‐0 to C‐8 on the donor part, the efficiency of its DSSC augments evidently. It is found that the incorporation of bis‐carboxyl groups instead of the single carboxyl group as anchoring groups induces a remarkable enhancement of the electron injection efficiency from the excited dyes to the TiO2 semiconductor and generates higher electron density and voltage.

  DOI：

  10.1002/cjoc.201300924

文献信息

• Strongly Luminescent Tungsten Emitters with Emission Quantum Yields of up to 84 %: TADF and High‐Efficiency Molecular Tungsten OLEDs
  作者：Kaai‐Tung Chan、Tsz‐Lung Lam、Daohong Yu、Lili Du、David Lee Phillips、Chun‐Lam Kwong、Glenna So Ming Tong、Gang Cheng、Chi‐Ming Che

  DOI：10.1002/anie.201906698

  日期：2019.10.14

  ligand that exhibit high emission quantum yields of up to 56 % in solutions and 84 % in thin-film (5 wt % in 1,3-bis(N-carbazolyl)benzene, mCP) at room temperature. Femtosecond time-resolved emission (fs-TRE) spectroscopy and DFT calculations were undertaken to decipher the TADF properties. Solution-processed OLEDs fabricated with the W-TADF emitter demonstrated external quantum efficiency (EQE) and luminance

  金属-TADF（热激活延迟荧光）发射器在开发用于显示和照明应用的下一代发光材料方面很有前途，然而，其中的例子主要限于CuI发射器，而最近仅限于AuI，AgI和AuIII发射器。本文介绍了一种空前类型的金属-TADF发射极的设计策略，该发射极基于廉价的金属与Schiff碱配体螯合，在溶液中显示出高达56％的高发射量子产率，在薄膜中显示出84％的高发射量子产率（5wt％ 1,3-双（N-咔唑基）苯，mCP）在室温下。飞秒时间分辨发射（fs-TRE）光谱和DFT计算用于破译TADF特性。使用W-TADF发射器制造的溶液处理的OLED表现出外部量子效率（EQE）和高达15的亮度。
• Unsymmetric chiral salen Schiff bases: A new chiral ligand pool from bis-schiff bases containing two different salicylaldehyde units
  作者：Jose Lopez、Sidney Liang、Xiu R. Bu

  DOI：10.1016/s0040-4039(98)00784-9

  日期：1998.6

  An efficient and facile synthesis of a new class of novel chiral Salen Schiff base ligands has been developed via a stepwise approach. An important feature of these new Salen ligands is that they possess two different salicylaldehyde units, therefore, while steric factor or electronic factor can be fixed on one side, electronic or/and steric factors can be tuned from the other side with different substituents. (C) 1998 Elsevier Science Ltd. All rights reserved.
• SalenZn-bridged D-π-A Dyes For Dye-Sensitized Solar Cells
  作者：Yongjian Jia、Faliang Gou、Ran Fang、Huanwang Jing、Zhenping Zhu

  DOI：10.1002/cjoc.201300924

  日期：2014.6

  AbstractA series of SalenZn based dyes with triphenylamine derivatives as the donor, benzoic acid as the acceptor, and coplanar Salen complexes as the spacer have been designed and synthesized for dye‐sensitized solar cells. The absorption, electrochemical, and photovoltaic properties for all sensitizers have been systematically investigated. When the tail length of the alkyl substituents is increased from C‐0 to C‐8 on the donor part, the efficiency of its DSSC augments evidently. It is found that the incorporation of bis‐carboxyl groups instead of the single carboxyl group as anchoring groups induces a remarkable enhancement of the electron injection efficiency from the excited dyes to the TiO2 semiconductor and generates higher electron density and voltage.
• Effect of a Substituent on the Properties of Salicylaldehyde Hydrazone Derivatives
  作者：Marta Hoelm、Justyna Adamczyk、Kinga Wzgarda-Raj、Marcin Palusiak

  DOI：10.1021/acs.joc.2c02547

  日期：2023.2.17

  the strength of the intramolecular hydrogen bonding present in salicylaldehyde hydrazones can be selectively modulated by substitution of the parent molecular system with the chemical group of known π-electron-donating or -accepting properties. Our findings provide an insight into planning synthesis pathways for salicylaldehyde hydrazone species and predicting their result with regard to their H-bonding

  本研究调查了在两个选定位置（即对位）取代水杨醛腙的影响-关于形成氢桥的质子供给和质子接受中心的位置。对通过理论方法和 X 射线实验获得的结构数据以及原始共振哈米特常数的详细分析表明，可以通过用化学物质取代母体分子系统来选择性地调节水杨醛腙中存在的分子内氢键的强度一组已知的 π 给电子或受电子特性。我们的研究结果为规划水杨醛腙物种的合成途径和预测其氢键和相关物理和化学性质的结果提供了见解。