2,8-dithia[9](2,9)-1,10-phenanthrolinophane | 403819-60-3

• 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: 2,8-dithia[9](2,9)-1,10-phenanthrolinophane
• 英文别名: 3,9-Dithia-20,23-diazatetracyclo[9.8.4.014,22.017,21]tricosa-1(20),11(23),12,14(22),15,17(21),18-heptaene
• CAS: 403819-60-3
• 化学式: C₁₉H₂₀N₂S₂
• 分子量: 340.513
• InChiKey: LKNSWZYTXVJDSX-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.3
• 重原子数：
  23
• 可旋转键数：
  0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.37
• 拓扑面积：
  76.4
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  mercury (II) perchlorate trihydrate 、 2,8-dithia[9](2,9)-1,10-phenanthrolinophane 以 甲醇 为溶剂， 以47%的产率得到Hg(2,8-dithia[9](2,9)-1,10-phenanthrolinophane) perchlorate
  参考文献：
  名称：

  Fluorometric Chemosensors. Interaction of Toxic Heavy Metal Ions Pb^II, Cd^II, and Hg^II with Novel Mixed-Donor Phenanthroline-Containing Macrocycles:  Spectrofluorometric, Conductometric, and Crystallographic Studies

  摘要：

  The macrocycles L-1-L-3 incorporating N2S3-, N2S2O-, and N2S2-donor sets, respectively, and containing the 1,10-phenanthroline unit interact in acetonitrile solution with heavy metal ions such as Pb-II, Cd-II, and Hg-II to give 1:1 ML, 1:2 ML2, and 2:1 M2L complex species, which specifically modulate the photochemical properties of the ligands. The stoichiometry of the complex species formed during spectrofluorometric titrations and their formation constants in MeCN at 25 degreesC were determined from fluorescence vs M-II/L molar ratio data. The complexes [Pb(L-1)][ClO4](2)1/2H(2)O (1), [Pb(L-2)][ClO4](2).MeNO2 (1a), [Pb(L-3)(2)][ClO4](2).2MeCN (1b), and [Cd(L-3)][NO3](2) (2b) were also characterized by X-ray diffraction studies. The conformation adopted by L-1-L-3 in these species reveals the aliphatic portion of the rings folded over the plane containing the heteroaromatic moiety with the ligands trying to encapsulate the metal center within their cavity, In 1, 1a, and 2b the metal ion completes the coordination sphere by interacting with counteranion units and solvent molecules. On the contrary, the 1:2 complex 1b shows Pb-II sandwiched between two symmetry-related molecules of L-3 reaching an overall [4N + 4S] eight-coordination.

  DOI：

  10.1021/ic020270d

文献信息

• Complexes of CuII with mixed-donor phenanthroline-containing macrocycles: analysis of their structural, redox and spectral properties in the context of Type-1 blue copper proteins biomimetic models
  作者：Massimiliano Arca、Gholamhassan Azimi、Francesco Demartin、Francesco A. Devillanova、Lluis Escriche、Alessandra Garau、Francesco Isaia、Raikko Kivekas、Vito Lippolis、Vicent Muns、Alessandro Perra、Mojtaba Shamsipur、Luigi Sportelli、Abdollah Yari

  DOI：10.1016/j.ica.2005.01.014

  日期：2005.4

  The macrocycles L-1-L-3 having N2S2O-, N2S2-, and N2S3-donor sets, respectively, and incorporating the 1,10-phenanthroline unit interact in EtOH and MeCN solutions with Cu-II to give 1:1 [M(L)](2+) complex species. The compounds [Cu(L-1)(ClO4)]ClO4 (1), [Cu(L-2)(ClO4)]ClO4 center dot 1/2H(2)O (2) and [Cu(L-3)](ClO4)(2) (3) were isolated at the solid state and the first two also characterised by X-ray diffraction studies. The conformation adopted by L-1 and L 2 in the cation complexes reveals the aliphatic portion of the rings folded over the plane containing the heteroaromatic moiety with the ligands encapsulating the metal centre within their cavity by imposing. respectively, a square-based pyramidal and a square planar geometry. In both complexes, the metal ion completes its coordination sphere by interacting with a ClO4- ligand. The compound [Cu(L-3)(2)](PF6)(2) (4) containing a 1:2 cation complex was also isolated at the solid state: EPR spectroscopy measurements suggest the presence of a CuN4 chromophore in this complex. The EPR and electronic spectral features of 1-4 have been studied and their redox properties examined in comparison with those observed for Type-1 blue copper proteins.The reactivity of L-1-L-3 has also been tested toward stoichiometric amounts of the Cut salt [CuCl(PPh3)(3)], (c) 2005 Elsevier B.V. All rights reserved.