4,6-Diacetyl-2-phenylpyrimidine | 325685-74-3

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 4,6-Diacetyl-2-phenylpyrimidine
• 英文别名: 2-phenyl-4,6-diacetylpyrimidine；2-phenyl-4,6-bis(acetyl)-pyrimidine；1,1'-(2-phenylpyrimidine-4,6-diyl)bis(ethan-1-one)；1-(6-acetyl-2-phenylpyrimidin-4-yl)ethanone
• CAS: 325685-74-3
• 化学式: C₁₄H₁₂N₂O₂
• 分子量: 240.261
• InChiKey: HERZQPCKJCMHSJ-UHFFFAOYSA-N

物化性质

• 沸点：
  334.4±40.0 °C(Predicted)
• 密度：
  1.176±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.3
• 重原子数：
  18
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.14
• 拓扑面积：
  59.9
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  4,6-Diacetyl-2-phenylpyrimidine 在 ammonium acetate 、 碘 作用下， 以 甲醇 为溶剂， 反应 24.0h， 生成 6',6''''-(2-phenylpyrimidine-4,6-diyl)di-3,2':4',3''-terpyridine
  参考文献：
  名称：

  Influence of regioisomerism in bis(terpyridine) based exciplexes with delayed fluorescence

  摘要：

  研究了不同BTP的结构多样性与TCTA在复合物中的作用，以提高它们在TADF OLED中的性能。

  DOI：

  10.1039/d2tc00800a
• 作为产物：
  描述：

  苯 在 copper(I) oxide 、 tris-(dibenzylideneacetone)dipalladium(0) 、 三苯基膦 、 亚硝酸异戊酯 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 48.5h， 生成 4,6-Diacetyl-2-phenylpyrimidine
  参考文献：
  名称：

  Influence of regioisomerism in bis(terpyridine) based exciplexes with delayed fluorescence

  摘要：

  研究了不同BTP的结构多样性与TCTA在复合物中的作用，以提高它们在TADF OLED中的性能。

  DOI：

  10.1039/d2tc00800a

文献信息

• Optically Functionalized Grid-Type Complexes by a Post-Assembly Strategy
  作者：Berend Eggers、Ulrich Ziener

  DOI：10.1002/chem.201800834

  日期：2018.10.9

  Bisterpyridine‐based grid complexes can serve as supramolecular three‐dimensional scaffolds for the construction of larger molecular assemblies. Through functionalization of the ligand with azide groups, followed by self‐assembly and metal‐free Huisgen reactions, eight pyrene molecules can be attached to the grid structure in a single reaction step. The orientation and proximity provided by the scaffold

  基于Bisterpyridine的网格复合体可作为超分子三维支架，用于构建更大的分子组件。通过将具有叠氮基团的配体官能化，然后进行自组装和无金属惠斯根反应，可以在一个反应​​步骤中将八个pyr分子连接至网格结构。支架提供的取向和接近度允许调节染料分子的荧光性质。
• Enforced Helicity: Efficient Access to Self-Organized Helical Molecular Strands by the Imine Route
  作者：Kevin M. Gardinier、Richard G. Khoury、Jean-Marie Lehn

  DOI：10.1002/1521-3765(20001117)6:22<4124::aid-chem4124>3.0.co;2-m

  日期：2000.11.17

  These molecular strands are shown to adopt helical conformations of 1.5 and 2.5 turns, respectively. The helical shape of 1 has been confirmed and structurally characterized by X-ray crystallography. The results indicate that the pyrimidine-hydrazone unit is a satisfatory helicity codon, so that the facile hydrazone formation provides an efficient procedure for generating helical structures. This

  两个低聚杂环醛 8 和 16 与双肼 17 缩合得到双腙1 和 2。显示这些分子链分别采用 1.5 和 2.5 圈的螺旋构象。1 的螺旋形状已被 X 射线晶体学证实并在结构上表征。结果表明嘧啶-腙单元是一个令人满意的螺旋密码子，因此容易的腙形成为产生螺旋结构提供了有效的方法。这极大地拓宽了基于设计的杂环序列来增强分子链螺旋性的方法的范围，并为各种衍生结构开辟了有趣的途径。
• Revealing the Origin of Fast Delayed Fluorescence in a Donor Functionalized Bisterpyridine
  作者：Felix D. Goll、Andreas Schelhorn、Džiugas Litvinas、Francisco Tenopala‐Carmona、Lev Kazak、Fedor Jelezko、Christoph Lambert、Malte C. Gather、Alexander J. C. Kuehne、Ulrich Ziener

  DOI：10.1002/chem.202303067

  日期：2024.1.8

  A new carbazole‐substituted bisterpyridine with pronounced delayed fluorescence is presented. While the molecular donor‐acceptor‐donor design suggests the origin of this to be thermally activated delayed fluorescence (TADF), results from various photophysical characterizations, OLED characteristics, temperature‐dependent NMR spectroscopy, and DFT calculations all point against the involvement of triplet states. The molecule exhibits blue emission at about 440 nm with two or more fast decay channels in the lower nanosecond range in both solution and thin films. The delayed emission is proposed to be caused by rotational vibrational modes. We suggest that these results are generally applicable, especially for more complex molecules, and should be considered as alternative or competitive emissive relaxation pathways in the field of organic light emitting materials.

  摘要 本文介绍了一种具有明显延迟荧光的新型咔唑取代双isterpyridine。虽然分子的供体-受体-供体设计表明这种延迟荧光起源于热激活延迟荧光（TADF），但各种光物理特性、有机发光二极管特性、温度依赖性核磁共振光谱和 DFT 计算的结果都表明这种延迟荧光与三重态无关。在溶液和薄膜中，该分子在约 440 纳米波长处显示出蓝色发射，在纳秒级较低的范围内有两个或多个快速衰减通道。延迟发射是由旋转振动模式引起的。我们认为这些结果具有普遍适用性，尤其适用于更复杂的分子，并应被视为有机发光材料领域的替代或竞争性发射弛豫途径。
• Supramolecular Assemblies of a Bis(terpyridine) Ligand and of its [2×2] Grid-type ZnII and CoII Complexes on Highly Ordered Pyrolytic Graphite
  作者：Ulrich Ziener、Jean-Marie Lehn、Ahmed Mourran、Martin Möller

  DOI：10.1002/1521-3765(20020215)8:4<951::aid-chem951>3.0.co;2-9

  日期：2002.2.15

  The synthesis and characterisation of bis(terpyridine)-derived ligands which are capable of forming [2 x 2] grid-like complexes is presented. Additional pyridine substituents on these ligands do not interfere with the complexation process. Adsorbing one of the pure ligands on highly ordered pyrolytic graphite (HOPG) shows a highly ordered structure stabilised by additional weak intermolecular C-H... N hydrogen bonds partially through the extra-pyridines as could be shown by scanning tunneling microscopy (STM) investigations. Similar adsorption experiments with one of the corresponding [2 x 2] Co-11 grid- type complexes on graphite, led also to a well-organised structure with interdigitation of the extra-pyridine moieties.