3-perilenylmetilen-4′-ethylaniline | 1265554-71-9

• 分子结构分类: 有机化合物 - 苯类化合物 - 菲及其衍生物
• 英文名称: 3-perilenylmetilen-4′-ethylaniline
• 英文别名: (3-perylenylmethylidene)-4'-ethylaniline；N-(4-ethylphenyl)-1-perylen-3-ylmethanimine
• CAS: 1265554-71-9
• 化学式: C₂₉H₂₁N
• 分子量: 383.492
• InChiKey: UWAFQLZMUYBKHZ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  7.8
• 重原子数：
  30
• 可旋转键数：
  3
• 环数：
  6.0
• sp3杂化的碳原子比例：
  0.07
• 拓扑面积：
  12.4
• 氢给体数：
  0
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  (2-methylallyl)platinum chloride dimer 、 3-perilenylmetilen-4′-ethylaniline 以 甲醇 为溶剂， 反应 24.0h， 以86%的产率得到
  参考文献：
  名称：

  与per（ii）或钯（ii）类似物相比，per亚胺的 铂（iv）正金属化络合物的荧光更高†

  摘要：

  3- perylenylmethylen -4'-乙基苯胺（反应1）与[PT 2我4（μ-SMe的2）2 ]（和随后加入的PPH 3）或用[PT 2（η 3 -C 4 ħ 7）2（μ-Cl）2 ]分别生成环金属化的Pt II配合物[Pt（C ^ N）Me（PPh 3）]（2）和[Pt 2（C ^ N）2（μ-Cl）2 ]（3）（HC ^ N = 3-C 20 H 11 CH NC 6ħ 4 - p -C 2 ħ 5），有Pt结合到邻位的苝片段的位点。由3个单核络合物[Pt（C ^ N）L 2 ]（L 2 = acac（4）; S 2 COMe（5）; S 2 CNEt 2（6）容易形成。 -planar的Pt II络合物2，4，和6得到相应的金属化Pt IV化合物[铂（C ^ N）L- 2将MeI] 7，8和9。的X射线结构4，6，和7显示，苝片段保持在基本平坦的4和6以及在稍扭曲7。这些Pt

  DOI：

  10.1039/c5dt02572a
• 作为产物：
  描述：

  3-甲酰基芘 、 4-乙基苯胺 在 对甲苯磺酸 作用下， 以 甲苯 为溶剂， 以67%的产率得到3-perilenylmetilen-4′-ethylaniline
  参考文献：
  名称：

  Cyclopalladated Complexes of Perylene Imine: Formation of Acetato-Bridged Dinuclear Complexes with 6,6- and 5,6-Membered Metallacycles

  摘要：

  Perylene-3-carbaldehyde (1) was condensed with 4-ethylaniline to give 3-perilenylmetilen-4'-ethylaniline (2). The metalation reaction of 2 with palladium acetate, in toluene at 60 degrees C, produced a mixture of palladium complexes where the two major components, 3 and 4, have been characterized as acetate-bridged dimers. Complex 3 is made of two identical six-membered endo cyclometalated Pd(C boolean AND N) moieties, in which the palladium is bound to the peri site with anti arrangement. Compound 4 is the first example combining six- and five-membered metallacycles in a dinuclear compound and adopts an unusual syn arrangement of metal ligands. The X-ray structures of 3 and 4 show pi-pi stacking of perylenyl rings, intermolecular for 3 and intramolecular for 4. The intramolecular pi-pi stacking in 4 has a detrimental effect on luminescence. The imine 2 and all the palladium complexes exhibit fluorescence associated with the perylene fragment, with emission quantum yields, in solution at room temperature, in the range 0.04-0.13 (and emission lifetimes similar to 5 ns). The similarity of the luminescence spectral pattern of the imine and their metalated complexes to that of perylene, although red-shifted, strongly suggests a perylene-dominated intraligand pi-pi* emissive state, metal-perturbed by interaction of the palladium fragment.

  DOI：

  10.1021/om1010929

文献信息

• Higher fluorescence in platinum(<scp>iv</scp>) orthometallated complexes of perylene imine compared with their platinum(<scp>ii</scp>) or palladium(<scp>ii</scp>) analogues
  作者：J. Emilio Expósito、Marta Álvarez-Paíno、Gabriel Aullón、Jesús A. Miguel、Pablo Espinet

  DOI：10.1039/c5dt02572a

  日期：——

  reaction of 3-perylenylmethylen-4′-ethylaniline (1) with [Pt2Me4(μ-SMe2)2] (and subsequent addition of PPh3) or with [Pt2(η3-C4H7)2(μ-Cl)2] produced cyclometallated PtII complexes [Pt(C^N)Me(PPh3)] (2) and, respectively, [Pt2(C^N)2(μ-Cl)2] (3) (HC^N = 3-C20H11CHNC6H4-p-C2H5), with Pt bound to the ortho site of the perylenyl fragment. From 3 the mononuclear complexes [Pt(C^N)L2] (L2 = acac (4); S2COMe (5);

  3- perylenylmethylen -4'-乙基苯胺（反应1）与[PT 2我4（μ-SMe的2）2 ]（和随后加入的PPH 3）或用[PT 2（η 3 -C 4 ħ 7）2（μ-Cl）2 ]分别生成环金属化的Pt II配合物[Pt（C ^ N）Me（PPh 3）]（2）和[Pt 2（C ^ N）2（μ-Cl）2 ]（3）（HC ^ N = 3-C 20 H 11 CH NC 6ħ 4 - p -C 2 ħ 5），有Pt结合到邻位的苝片段的位点。由3个单核络合物[Pt（C ^ N）L 2 ]（L 2 = acac（4）; S 2 COMe（5）; S 2 CNEt 2（6）容易形成。 -planar的Pt II络合物2，4，和6得到相应的金属化Pt IV化合物[铂（C ^ N）L- 2将MeI] 7，8和9。的X射线结构4，6，和7显示，苝片段保持在基本平坦的4和6以及在稍扭曲7。这些Pt
• Cyclopalladated Complexes of Perylene Imine: Formation of Acetato-Bridged Dinuclear Complexes with 6,6- and 5,6-Membered Metallacycles
  作者：Sergio Lentijo、Jesús A. Miguel、Pablo Espinet

  DOI：10.1021/om1010929

  日期：2011.3.14

  Perylene-3-carbaldehyde (1) was condensed with 4-ethylaniline to give 3-perilenylmetilen-4'-ethylaniline (2). The metalation reaction of 2 with palladium acetate, in toluene at 60 degrees C, produced a mixture of palladium complexes where the two major components, 3 and 4, have been characterized as acetate-bridged dimers. Complex 3 is made of two identical six-membered endo cyclometalated Pd(C boolean AND N) moieties, in which the palladium is bound to the peri site with anti arrangement. Compound 4 is the first example combining six- and five-membered metallacycles in a dinuclear compound and adopts an unusual syn arrangement of metal ligands. The X-ray structures of 3 and 4 show pi-pi stacking of perylenyl rings, intermolecular for 3 and intramolecular for 4. The intramolecular pi-pi stacking in 4 has a detrimental effect on luminescence. The imine 2 and all the palladium complexes exhibit fluorescence associated with the perylene fragment, with emission quantum yields, in solution at room temperature, in the range 0.04-0.13 (and emission lifetimes similar to 5 ns). The similarity of the luminescence spectral pattern of the imine and their metalated complexes to that of perylene, although red-shifted, strongly suggests a perylene-dominated intraligand pi-pi* emissive state, metal-perturbed by interaction of the palladium fragment.