N-(4-(5-phenyl-1,3,4-oxadiazol-2-yl)phenyl)-di(pyridin-2-yl)amine

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: N-(4-(5-phenyl-1,3,4-oxadiazol-2-yl)phenyl)-di(pyridin-2-yl)amine
• 英文别名: N-[4-(5-phenyl-1,3,4-oxadiazol-2-yl)phenyl]-N-pyridin-2-ylpyridin-2-amine
• 化学式: C₂₄H₁₇N₅O
• 分子量: 391.432
• InChiKey: QUSRLZPADUSLDH-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.8
• 重原子数：
  30
• 可旋转键数：
  5
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  67.9
• 氢给体数：
  0
• 氢受体数：
  6

反应信息

• 作为产物：
  描述：

  2,2'-二吡啶胺 、 2-(4-溴苯基)-5-苯基-1,3,4-恶二唑 在 potassium carbonate 、 copper(II) sulfate 作用下， 反应 6.0h， 以60%的产率得到N-(4-(5-phenyl-1,3,4-oxadiazol-2-yl)phenyl)-di(pyridin-2-yl)amine
  参考文献：
  名称：

  New ligands in the 2,2′-dipyridylamine series and their Re(i) complexes; synthesis, structures and luminescence properties

  摘要：

  一系列新型二(2-吡啶基)胺配体已经被制备出来，具有通用公式 (py)2NR，其中 R 代表一系列广泛的不同基团，包括萘基、芘基、苯并-18-冠-6、芘基、噁唑基和溴联苯基。所有的配体都具有发光性，发射峰在370至520纳米之间，且在流动溶液中量子产率高达0.74。这些配体与 Re(CO)5Cl 反应后得到类型为 [Re(CO)3ClL] 的配合物，其中二(2-吡啶基)胺配体通过两个吡啶单元以 N,N-双齿螯合形式结合；五种这样的配合物结构已经得到了表征。除了一个例外，这些配合物基本不具备发光性，我们将其归因于金属基的 d-d 激发态能有效地猝灭任何 MLCT 或配体中心的激发态。例外的是 [Re(CO)3Cl(tppd)] [其中 tppd = N,N,N',N'-四(2-吡啶基)-对苯二胺]，在这个化合物中一个二(2-吡啶基)胺位点被一个 {Re(CO)3Cl} 单位占据，而另一个位点则是空的；这个化合物在流动溶液中在516纳米处发光（量子产率=0.04，寿命=42纳秒）。

  DOI：

  10.1039/b312647a

文献信息

• New ligands in the 2,2′-dipyridylamine series and their Re(<scp>i</scp>) complexes; synthesis, structures and luminescence properties
  作者：Nail M. Shavaleev、Andrea Barbieri、Zöe R. Bell、Michael D. Ward、Francesco Barigelletti

  DOI：10.1039/b312647a

  日期：——

  A series of new derivatives of the di(2-pyridyl)amine ligand has been prepared, having the general formula (py)2NR, where R is one of a wide range of groups including naphthyl, pyrenyl, benzo-18-crown-6, pyrenyl, oxazolyl and bromo-biphenyl. All ligands are luminescent, with emission maxima between 370 and 520 nm, and with quantum yields in fluid solution of up to 0.74. Reaction of these ligands with Re(CO)5Cl afforded complexes of the type [Re(CO)3ClL] in which the di(2-pyridyl)amine ligand binds as an N,N-bidentate chelate via the two pyridyl units; five such complexes have been structurally characterised. With one exception the complexes are essentially non-luminescent, which we ascribe to the energetic availability of metal-based d-d excited states which can quench any MLCT or ligand-centred excited states. The exception is [Re(CO)3Cl(tppd)] [where tppd = N,N,N′,N′-tetrakis(2-pyridyl)-p-phenylenediamine] in which one di(2-pyridyl)amine site is occupied by a Re(CO)3Cl} unit but the other is vacant; this luminesces in fluid solution at 516 nm (ϕ = 0.04, τ = 42 ns).

  一系列新型二(2-吡啶基)胺配体已经被制备出来，具有通用公式 (py)2NR，其中 R 代表一系列广泛的不同基团，包括萘基、芘基、苯并-18-冠-6、芘基、噁唑基和溴联苯基。所有的配体都具有发光性，发射峰在370至520纳米之间，且在流动溶液中量子产率高达0.74。这些配体与 Re(CO)5Cl 反应后得到类型为 [Re(CO)3ClL] 的配合物，其中二(2-吡啶基)胺配体通过两个吡啶单元以 N,N-双齿螯合形式结合；五种这样的配合物结构已经得到了表征。除了一个例外，这些配合物基本不具备发光性，我们将其归因于金属基的 d-d 激发态能有效地猝灭任何 MLCT 或配体中心的激发态。例外的是 [Re(CO)3Cl(tppd)] [其中 tppd = N,N,N',N'-四(2-吡啶基)-对苯二胺]，在这个化合物中一个二(2-吡啶基)胺位点被一个 Re(CO)3Cl} 单位占据，而另一个位点则是空的；这个化合物在流动溶液中在516纳米处发光（量子产率=0.04，寿命=42纳秒）。
• Synthesis and photoluminescence properties of four rhenium(I) complexes based on diimine ligands with oxadiazole/carbazole moiety
  作者：Jing Wu、Hong-Yan Li、Ling-Chen Kang、Dong-Ping Li、Huan-Rong Li、Xin-Hui Zhou、Yan Sui、You-Xuan Zheng、Jing-Lin Zuo、Xiao-Zeng You

  DOI：10.1016/j.jphotochem.2010.02.010

  日期：2010.4

  By introducing two carrier-transporting moieties (oxadiazole and carbazole) into two diimine ligands (2-(2-pyridine)-benzimidazole and 2,2'-dipyridylamine), respectively, four novel ligands (L1-L4) and their corresponding rhenium(I) complexes (1-4) have been synthesized and characterized by elemental analysis, H-1 NMR and IR spectra. Their photophysical properties, thermal analysis, along with the X-ray crystal structure analysis of 14 and corresponding complex 4 are also described. In absorption spectra, the 2-(2-pyridine)benzimidazole containing complexes 1,2 show the intraligand charge-transfer (pi -> pi* (L)) bands and metal-to-ligand charge-transfer d pi(Re) -> pi* MLCT bands, while the 2,2'-dipyridylamine containing complexes 3,4 only show the pi -> pi* bands. In the excitation spectra, all the complexes show strong M La bands. After excitation of pi -> pi* or MLCT bands, all the four Re(I) complexes exhibit broad bands around 550-560 nm due to the Re(I)-based (MLCT)-M-3 emission. The two complexes 1 (with oxadiazole moiety) and 2 (with carbazole moiety) show the photoluminescence quantum efficiency of 2.0% and 7.5% in solid state, respectively, indicating that the carbazole unit is the better chromophore to enhance the luminescence efficiency of diimine Re(I) complexes than the oxadiazole moiety. (C) 2010 Elsevier B.V. All rights reserved.