6,6'-bis(p-methoxyphenyl)-4,4'-bipyrimidine | 868548-64-5

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 二嗪类
• 英文名称: 6,6'-bis(p-methoxyphenyl)-4,4'-bipyrimidine
• 英文别名: 6,6'-di(p-methoxyphenyl)-4,4'-bipyrimidine；dmpb；4-(4-Methoxyphenyl)-6-[6-(4-methoxyphenyl)pyrimidin-4-yl]pyrimidine
• CAS: 868548-64-5
• 化学式: C₂₂H₁₈N₄O₂
• 分子量: 370.411
• InChiKey: ACACZNKATTXXHI-UHFFFAOYSA-N

物化性质

• 熔点：
  209-211 °C(Solv: methanol (67-56-1))
• 沸点：
  590.7±50.0 °C(Predicted)
• 密度：
  1.209±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.4
• 重原子数：
  28
• 可旋转键数：
  5
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.09
• 拓扑面积：
  70
• 氢给体数：
  0
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  6,6'-bis(p-methoxyphenyl)-4,4'-bipyrimidine 、 五羰基氯铼(I) 以 甲苯 为溶剂， 以84%的产率得到Re(6,6'-bis(p-methoxyphenyl)-4,4'-bipyrimidine)(CO)3Cl
  参考文献：
  名称：

  Synthesis and properties of Re(I) tricarbonyl complexes of 6,6′-disubstituted-4,4′-bipyrimidines with high energy excited states suitable for incorporation into polynuclear arrays

  摘要：

  A series of complexes [(N-N)Re(CO)(3)X](n) (N-N = 6,6'-diaryl-4,4-bipyrimidine, axial ligand X = Cl, MeCN, 4-phenyl-pyridine, or t-Bu-pyridine) have been synthesized and characterized. The substituent aryl on the bipyrimidine, as well as the axial ligand X, has important effects on the properties of these complexes. The co-planarity of the 4,4'-bipyrimidine core and its substituents contributes to the extent of pi-electron delocalization and, hence, to the redox and spectroscopic properties of the complexes. The complexes exhibit Re-to-bpm metal-to-ligand charge transfer absorptions in the range of 379-464 nm, which are red-shifted with the increase in the delocalization in the substituted bpm ligand and the increase in the donor character of the axial ligand. The electrochemical data support metal-based oxidations (from +1.07 to +1.40 V) and ligand-based reductions (from -0.62 to -0.75 V) and correlate well with those obtained by UV-Vis spectroscopy. The X-ray crystal structures of two of the complexes have also been investigated. (c) 2005 Elsevier B.V. All rights reserved.

  DOI：

  10.1016/j.ica.2005.09.042
• 作为产物：
  描述：

  对甲氧基苯乙酮 在 sodium ethanolate 、 sodium 作用下， 以 四氢呋喃 、 乙醇 为溶剂， 反应 59.0h， 生成 6,6'-bis(p-methoxyphenyl)-4,4'-bipyrimidine
  参考文献：
  名称：

  通过自由基阴离子偶联合成一系列新型 6,6'-二取代 4,4'-双嘧啶：用于配位化学的新型 π 受体配体

  摘要：

  一个新的 6,6'-二取代 4,4'-联嘧啶配体家族已被制备和表征。通过循环伏安法测定的新配体的还原电位表明，这些新配体是比普遍存在的 2,2'-联吡啶配体更好的 π-受体，甚至优于未取代的母体 4,4'-联嘧啶配体。4,4'-联嘧啶的 6,6' 位置的取代基也会导致整个 UV 区域的 ππ* 和 nπ* 吸收发生红移。双嘧啶家族成员的 X 射线晶体结构表明，芳基取代基在固态时可以与嘧啶环共面。嘧啶环上的芳基取代基提供的额外电子离域作用有助于这些化合物更好的接受 π 能力。(© Wiley-VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2005)

  DOI：

  10.1002/ejoc.200500335

文献信息

• Spectroscopy and electrochemistry of new 6,6′-disubstituted-4,4′-bipyrimidine molybdenum(0) and tungsten(0) tetracarbonyl complexes
  作者：Elena Ioachim、Garry S Hanan

  DOI：10.1139/v05-127

  日期：2005.8.1

  new family of tetracarbonyl molybdenum(0) and tungsten(0) complexes based on new 6,6′-disubstituted-4,4′-bipyrimidine ligands was synthesized and characterized. The visible region of the absorption spectrum of each complex is dominated by a metal-to-ligand charge transfer band significantly lower in energy than the corresponding transition in 2,2′-bipyridine tetracarbonyl metal complexes. The 6,6′-substituents

  合成并表征了基于新的 6,6'-二取代-4,4'-联嘧啶配体的新系列四羰基钼 (0) 和钨 (0) 配合物。每个配合物的吸收光谱的可见区由金属到配体的电荷转移带支配，其能量显着低于 2,2'-联吡啶四羰基金属配合物的相应跃迁。6,6'-取代基在取代的双嘧啶中产生更大的 π-电子系统，因此是比母体 4,4'-双嘧啶更好的 π 受体。吸收带随着溶剂极性的降低而向红移。关键词：钼和钨，氮配体，四羰基金属配合物，吸收光谱，电化学。
• Synthesis and properties of red emitter Ru(II) complexes based on 6,6′-disubstituted-4,4′-bipyrimidine
  作者：Elena Ioachim、Elaine A. Medlycott、Garry S. Hanan、Frédérique Loiseau、Sebastiano Campagna

  DOI：10.1016/j.ica.2005.03.057

  日期：2006.2

  Heteroleptic complexes [Ru(bpy)(2)(R(2)bpm)](2+), where bpy = 2,2'-bipyridine and R(2)bpm = 6,6'-diaryl-4,4'-bipyrimidine, have been synthesized and characterized, together with the homoleptic complex [Ru(R(2)bPM)3](2+), in which R(2)bpm = 6,6'-diphenyl-4,4'-bipyrimidine. The substituent aryl on the bipyrimidine has significant effects on the properties of these complexes as compared to the parent [Ru(bpy)(2)(bpM)](2+) complex. The complexes exhibit Ru-to-bpm charge transfer (CT) absorptions centered at about 540 nm and Ru-to-bpy CT absorptions centered at about 435 nm. The assignment of the low energy absorptions is supported by the relative ease of the reduction of the new complexes as compared to [Ru(bpy)3](2+). The new complexes exhibit a relatively intense emission at room temperature, with lifetimes in the 10-50 ns range, with the homoleptic species exhibiting the higher-energy (maximum at 724 nm) and the longest-lived (tau = 48 ns) emission among the complexes. Luminescence lifetimes and quantum yields are governed by the energy gap law, indicating that direct deactivation to the ground state is the dominant relaxation pathway for 1-6, while thermally activated processes are inefficient. (c) 2005 Elsevier B.V. All rights reserved.
• Synthesis and properties of Re(I) tricarbonyl complexes of 6,6′-disubstituted-4,4′-bipyrimidines with high energy excited states suitable for incorporation into polynuclear arrays
  作者：Elena Ioachim、Elaine A. Medlycott、Garry S. Hanan

  DOI：10.1016/j.ica.2005.09.042

  日期：2006.6

  A series of complexes [(N-N)Re(CO)(3)X](n) (N-N = 6,6'-diaryl-4,4-bipyrimidine, axial ligand X = Cl, MeCN, 4-phenyl-pyridine, or t-Bu-pyridine) have been synthesized and characterized. The substituent aryl on the bipyrimidine, as well as the axial ligand X, has important effects on the properties of these complexes. The co-planarity of the 4,4'-bipyrimidine core and its substituents contributes to the extent of pi-electron delocalization and, hence, to the redox and spectroscopic properties of the complexes. The complexes exhibit Re-to-bpm metal-to-ligand charge transfer absorptions in the range of 379-464 nm, which are red-shifted with the increase in the delocalization in the substituted bpm ligand and the increase in the donor character of the axial ligand. The electrochemical data support metal-based oxidations (from +1.07 to +1.40 V) and ligand-based reductions (from -0.62 to -0.75 V) and correlate well with those obtained by UV-Vis spectroscopy. The X-ray crystal structures of two of the complexes have also been investigated. (c) 2005 Elsevier B.V. All rights reserved.
• Synthesis of a Novel Series of 6,6'-Disubstituted 4,4'-Bipyrimidines by Radical Anion Coupling: New π-Accepting Ligands for Coordination Chemistry
  作者：Elena Ioachim、Elaine A. Medlycott、Matthew I. J. Polson、Garry S. Hanan

  DOI：10.1002/ejoc.200500335

  日期：2005.9

  A new family of 6,6'-disubstituted 4,4'-bipyrimidine ligands has been prepared and characterized. The reduction potentials of the new ligands, as determined by cyclic voltammetry, indicate that these new ligands are considerably better π-acceptors than the ubiquitous 2,2'-bipyridine ligand, and are even superior to the parent unsubstituted 4,4'-bipyrimidine ligand. The substituents in 6,6' positions

  一个新的 6,6'-二取代 4,4'-联嘧啶配体家族已被制备和表征。通过循环伏安法测定的新配体的还原电位表明，这些新配体是比普遍存在的 2,2'-联吡啶配体更好的 π-受体，甚至优于未取代的母体 4,4'-联嘧啶配体。4,4'-联嘧啶的 6,6' 位置的取代基也会导致整个 UV 区域的 ππ* 和 nπ* 吸收发生红移。双嘧啶家族成员的 X 射线晶体结构表明，芳基取代基在固态时可以与嘧啶环共面。嘧啶环上的芳基取代基提供的额外电子离域作用有助于这些化合物更好的接受 π 能力。(© Wiley-VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2005)