4-ethynyl-4'-nitroazobenzene | 306763-46-2

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 偶氮苯
• 英文名称: 4-ethynyl-4'-nitroazobenzene
• 英文别名: (E)-4,4'-HCCC6H4N=NC6H4NO2；(E)-4,4'-HCCC6H4NNC6H4NO2
• CAS: 306763-46-2
• 化学式: C₁₄H₉N₃O₂
• 分子量: 251.244
• InChiKey: LLMHIGKVNLUMKO-FOCLMDBBSA-N

物化性质

• 沸点：
  430.0±30.0 °C(Predicted)
• 密度：
  1.16±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.99
• 重原子数：
  19.0
• 可旋转键数：
  3.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  67.86
• 氢给体数：
  0.0
• 氢受体数：
  4.0

反应信息

• 作为反应物：
  描述：

  chloro(cyclopentadienyl)(triphenylphosphine)nickel(II) 、 4-ethynyl-4'-nitroazobenzene 在 CuI 、 (CH₃CH₂)3N 作用下， 以 further solvent(s) 为溶剂， 以42%的产率得到[(4-ethynyl,4'-nitroazobenzene(-H))Ni(η5-C5H5)(PPh3)]
  参考文献：
  名称：

  Organometallic complexes for nonlinear optics. 41: Syntheses and quadratic NLO properties of 4-{4-(4-nitrophenyl)diazophenyl}ethynylphenylethynyl complexes

  摘要：

  The syntheses of [Au(C C-4-C(6)H(4)C C-4-C(6)H(4)N=N-4-C(6)H(4)NO(2))(PPh(3))] (3), trans-[Ru(C C-4-C(6)H(4)-C C-4-C(6)H(4)N=N-4-C(6)H(4)NO(2))Cl(dppm)(2)] (4), [Ru(C C-4-C(6)H(4)C C-4-C(6)H(4)N=N-4-C(6)H(4)NO(2))(dppe)(eta-C(5)Me(5))] (5), and [Ni(C C-4-C(6)H(4)N=N-4-C(6)H(4)NO(2))(PPh(3))(eta-C(5)H(5))] (6) are reported, together with a single-crystal X-ray diffraction study of 4. Quadratic nonlinearities for 3-6 and [Ru(C C-4-C(6)H(4)NO(2))(dppe)(eta-C(5)Me(5))] (7) have been determined at 1.064 mu m and 1.300 mu m by the hyper-Rayleigh scattering (HRS) technique, comparison to related complexes revealing that beta values increase on introduction of azo group and pi-system lengthening. (C) 2007 Elsevier B.V. All rights reserved.

  DOI：

  10.1016/j.jorganchem.2007.11.004
• 作为产物：
  描述：

  (E)-1-(4-iodophenyl)-2-(4-nitrophenyl)diazene 在 bis-triphenylphosphine-palladium(II) chloride 、 copper(l) iodide 四丁基氟化铵 、 三乙胺 作用下， 以 四氢呋喃 为溶剂， 反应 1.08h， 生成 4-ethynyl-4'-nitroazobenzene
  参考文献：
  名称：

  Organometallic complexes for nonlinear optics

  摘要：

  The syntheses of the alkyne (E)-4,4'-HC drop CC6H4N=NC6H4NO2 (1) and alkynyl complexes LnM{(E)-4,4'-C drop CC6H4N=NC6H4NO2} [LnM: = trans-[RuCl(dppm)(2)] (2), Ru(PPh3)(2)(eta-C5H5) (3), Au(PPh3) (4)] are reported. A structural study of 2 reveals E stereochemistry about the azo- linkage. Electrochemical data for the ruthenium complexes reveal that the azo-linkage in complexes 2 and 3 perturbs the metal-centred oxidation potential compared to all other alkynyl complexes of similar composition. Quadratic optical nonlinearities by hyper-Rayleigh scattering (HRS) at 1064 nm are very large for 2 and 3, but resonance-enhanced. Comparison of HRS data for 4 with those of Au{(E)-4,4'-C drop CC6H4X=CHC6H4NO2}(PPh3) (X = CH, N) reveals that complex 4 has a significantly larger quadratic nonlinearity than its ene- or imino-linked analogues. (C) 2000 Elsevier Science S.A. All rights reserved.

  DOI：

  10.1016/s0022-328x(00)00311-9