7-(diphenylamino)-4-hydroxy-2H-chromen-2-one | 1312889-76-1

• 分子结构分类: 有机化合物 - 有机氮化合物
• 英文名称: 7-(diphenylamino)-4-hydroxy-2H-chromen-2-one
• 英文别名: 4-hydroxy-7-(N-phenylanilino)chromen-2-one
• CAS: 1312889-76-1
• 化学式: C₂₁H₁₅NO₃
• 分子量: 329.355
• InChiKey: PJZYWGMTWKARIA-UHFFFAOYSA-N

物化性质

• 沸点：
  551.5±50.0 °C(Predicted)
• 密度：
  1.354±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4.97
• 重原子数：
  25.0
• 可旋转键数：
  3.0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  53.68
• 氢给体数：
  1.0
• 氢受体数：
  4.0

反应信息

• 作为反应物：
  描述：

  7-(diphenylamino)-4-hydroxy-2H-chromen-2-one 在 H-NMP*HSO₄ 作用下， 以 甲苯 为溶剂， 生成
  参考文献：
  名称：

  Deep red emitting triphenylamine based coumarin-rhodamine hybrids with large Stokes shift and viscosity sensing: Synthesis, photophysical properties and DFT studies of their spirocyclic and open forms

  摘要：

  We designed and synthesized triphenylamine based and coumarin fused rhodamine hybrid dyes and characterized using H-1,C-13 NMR and HR-LCMS analysis. Both the newly synthesized hybrid dyes were found to show red shifted absorption as well as emissions and large Stokes shift (40-68 nm) as compared to the small Stokes shift (25-30 nm) of reported dyes Rhodamine B and 101. Photophysical properties of these dyes were studied in different solvents and according to the solvents acidity or basicity they preferred to remain in their spirocyclic or open form in different ratio. We studied the spirocyclic as well as open form derivatives of these dyes for their viscosity sensitivity in three different mixture of solvents i.e. polar-protic [EtOH-PEG 400], polar-aprotic [toluene-PEG 400] and non-polaraprotic [toluene-paraffin]. They are found to show very high viscosity sensitivity in polar-protic mixture of solvents [EtOH-PEG 400] and hence concluded that both polarity as well as viscosity factor worked together for the higher emission enhancement rather than only viscosity factor. As these dyes showed very high viscosity sensitivity in their spirocyclic as well as open form, they can be utilized as viscosity sensors in visible as well as deep red region. We also correlated our experimental finding theoretically by using Density Functional theory computations. (C) 2016 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.dyepig.2016.11.010
• 作为产物：
  描述：

  二苯胺 在 potassium tert-butylate 、 palladium diacetate 、 三溴化硼 、 tri tert-butylphosphoniumtetrafluoroborate 作用下， 以 甲苯 为溶剂， 反应 36.0h， 生成 7-(diphenylamino)-4-hydroxy-2H-chromen-2-one
  参考文献：
  名称：

  通过电子配体-OMe取代基引起的意外的蓝移颜色调整效果来获得高性能的深蓝色OLED发射器

  摘要：

  合成了一系列在苯氧基亚基上带有-CF 3，-OMe或-N（Me）2取代基的7-（二苯基氨基）-4-苯氧基香豆素蓝色发射衍生物。尽管‐CF 3和‐N（Me）2发现修饰会触发红移的荧光，证明OMe取代会对深蓝色区域产生意想不到的蓝移颜色调整效果。原因是给电子的中度OMe基团可以使香豆素具有不变的HOMO，但提高了LUMO的能级。此外，发现OMe取代有利于这些香豆素的热稳定性。因此，三甲氧基取代的目标化合物可以充当高性能的深蓝色有机发光二极管（OLED）发射器，并且基于它的OLED发出的深蓝色光的CIE坐标为（0.148，0.084），最大亮度的7800 cd m -2，最大外部量子效率为5.1％。这些结果不仅揭示了通过色彩调节实现高性能深蓝色OLED发射器的分子设计策略，而且还展示了香豆素衍生物作为深蓝色OLED发射器的观点。

  DOI：

  10.1002/chem.201800974

文献信息

• Rational design of coumarin fluorophore with solvatochromism, AIE and mechanofluorochromic enhancement properties
  作者：Kaiming Zhang、Jun Shu、Wendao Chu、Xiaoqiang Liu、Bin Xu、Weidong Jiang

  DOI：10.1016/j.dyepig.2020.108898

  日期：2021.2

  wavelength (from 436 nm to 553 nm) and a decrease in the quantum yield (from 81.1% to 2.8%), indicating solvatochromic effect. Also, the AIE behaviors were observed in CH3CN/water and THF/water mixture systems. For example, the PL intensity increased 6 times in mixed solvent (CH3CN: water = 10 : 90) compared to that in pure CH3CN. Moreover, the emission of original powder samples was red-shifted (from 438 nm

  通过结合大体积的二苯胺电子给体和新戊酸酯电子，合理设计合成了新的具有溶剂致变色，聚集诱导发射（AIE）和机械荧光致变色（MFC）增强特性的7-（二苯基氨基）香豆素-4-基新戊酸酯（DPACP）。 -香豆素的受体。随着溶剂极性从正己烷到乙腈的增加，该分子在发射波长（从436 nm到553 nm）显示出红移，量子产率降低（从81.1％到2.8％），表明溶剂变色效应。同样，在CH 3 CN /水和THF /水混合物系统中观察到AIE行为。例如，在混合溶剂（CH 3与纯CH 3 CN相比，CN：水= 10:90）。此外，研磨后原始粉末样品的发射因荧光增强（固态量子产率从19％增加到28％）而红移（从438 nm到483 nm），并且研磨粉末样品的发射行为可以通过用正己烷润湿可以恢复到原始状态。此外，通过单晶衍射分析研究了分子结构，分子间相互作用和发射性质之间的关系。磷酸钙由于来自二苯胺和新戊酸酯基
• Novel Efficient Blue Fluorophors with Small Singlet-Triplet Splitting: Hosts for Highly Efficient Fluorescence and Phosphorescence Hybrid WOLEDs with Simplified Structure
  作者：Cai-Jun Zheng、Jing Wang、Jun Ye、Ming-Fai Lo、Xiao-Ke Liu、Man-Keung Fung、Xiao-Hong Zhang、Chun-Sing Lee

  DOI：10.1002/adma.201204724

  日期：2013.4.18

  The exact hosts for F‐P hybrid WOLEDs have been first demonstrated following a new design strategy for blue fluorophors with small singlet‐triplet splitting. Two novel compounds DPMC and DAPSF exhibit efficient blue fluorescence, high triplet energies and good conductivities. These merits allow us to use new simplified device designs to achieve high efficiency, slow efficiency roll‐off and stable emission

  F-P混合WOLED的确切宿主首先遵循具有小单峰-三重态分裂的蓝色荧光团的新设计策略进行了演示。两种新型化合物DPMC和DAPSF表现出有效的蓝色荧光，高三线态能量和良好的电导率。这些优点使我们能够使用新的简化设备设计来实现高效率，慢速滚降和稳定的发射颜色。