3,4,7,8-tetrachloro-1,10-phenanthroline | 143661-56-7

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 菲咯啉
• 英文名称: 3,4,7,8-tetrachloro-1,10-phenanthroline
• 英文别名: 3,4,7,8-Tetrachlorophenanthroline
• CAS: 143661-56-7
• 化学式: C₁₂H₄Cl₄N₂
• 分子量: 317.989
• InChiKey: ZUOFJJUHJJXFIJ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5
• 重原子数：
  18
• 可旋转键数：
  0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  25.8
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  iron perchlorate hexahydrate 、 3,4,7,8-tetrachloro-1,10-phenanthroline 以 甲醇 、 二氯甲烷 为溶剂， 以30%的产率得到[Fe2O(Cl4phen)4(H2O)2][ClO4]4
  参考文献：
  名称：

  New phenanthroline iron complexes: Synthesis and catalytic activity in alkane oxidation with hydrogen peroxide

  摘要：

  New binuclear iron complexes with labile coordination sites, [Fe2OL4(H2O)(2)](ClO4)(4) where L stands for hydrophobic phenanthroline (phen) bearing electronegative and lipophilic substituents (Cl, Br, C2H5, C6H5, C6H13), are synthesized. The stereospecificity, alcohol/ketone ratio, regioselectivity, and substituent effect in the hydroxylation of alkanes (cyclohexane, adamantane, cis-1,2-dimethylcyclohexane) with hydrogen peroxide catalyzed by these complexes are studied. The said parameters, as well as a decrease in the alkane oxidation regioselectivity with increasing hydrogen peroxide concentration, are similar to the respective parameters for mononuclear iron complexes of tetradentate ligands. The results confirm that regardless of the nature of chelating ligands, the same mechanism operates in both cases, namely, the transfer of an oxygen atom with the participation of ferryl intermediates.

  DOI：

  10.1134/s0036023607010159
• 作为产物：
  描述：

  1,10-菲罗啉 在 五氯化磷 作用下， 以 三氯氧磷 为溶剂， 反应 72.0h， 以94%的产率得到3,4,7,8-tetrachloro-1,10-phenanthroline
  参考文献：
  名称：

  五氯化磷在氯化磷中氧化氯化1,10-菲咯啉及其衍生物

  摘要：

  1,10-菲咯啉及其衍生物1,10-丙酰桥连1,10-菲咯啉-2,9(1H,10H)-二酮的部分芳香氢被氯原子和过量的五氯化磷氧化取代在磷酰氯中得到多氯化产物。

  DOI：

  10.1246/bcsj.65.2007

文献信息

• Tuning the LUMO energy of 1,10-phenanthroline in α-diimine–dithiolate Ni(II) complex and enhancement of nonlinear optical properties
  作者：Luca Pilia、Maddalena Pizzotti、Francesca Tessore、Neil Robertson

  DOI：10.1016/j.ica.2015.03.002

  日期：2015.5

  The synthesis, characterization, nonlinear optical properties and DFT calculations for a new Ni-diiminedithiolate complex [Ni(Cl-4-phen)(mi-5edt)] (Cl-4-phen = 3,4,7,8-tetrachloro-1,10-phenanthroline; mi-5edt = 1-(N-methylindol-5-yl)-ethene-1,2-dithiolate), are reported. The UV-Vis spectrum shows a solvatochromic absorption at 700 nm in DMF (epsilon = 5520 mol(-1) dm(3) cm(-1)) due to a charge-transfer (CT) highest occupied molecular orbital (HOMO)-lowest unoccupied molecular orbital (LUMO) transition, typical of push-pull complexes. The CT character of this electronic transition is confirmed by DFT calculations with the HOMO mainly centered on the mi-5edt moiety and the LUMO on the Cl-4-phen ligand. By comparison with the unsubstituted analogue compound, computational studies confirm the role of the chlorination enhancing the optical properties of this complex. The second order nonlinear optical properties were measured by EFISH technique (at 1.907 mu m), giving values of -2030 and -810 x 10(-48) esu for mu beta(1.907) and mu beta(0), respectively. These values are among the highest reported so far for the class of d(8) square-planar push-pull compounds. (C) 2015 Elsevier B.V. All rights reserved.