S,S'-bis(2-quinolylmethyl)-1,2-ethanedithiol | 607352-66-9

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 喹啉及其衍生物
• 英文名称: S,S'-bis(2-quinolylmethyl)-1,2-ethanedithiol
• 英文别名: S,S'-bis(2-quinolylmethyl)ethane-1,2-dithiol；1,6-bis(2'-quinolyl)-2,5-dithiahexane；BQET；2-[2-(Quinolin-2-ylmethylsulfanyl)ethylsulfanylmethyl]quinoline
• CAS: 607352-66-9
• 化学式: C₂₂H₂₀N₂S₂
• 分子量: 376.546
• InChiKey: USVDVUBVBYYMCB-UHFFFAOYSA-N

物化性质

• 沸点：
  560.7±40.0 °C(Predicted)
• 密度：
  1.261±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  5.3
• 重原子数：
  26
• 可旋转键数：
  7
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.18
• 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：

  tetrakis(acetonitrile)copper(I) perchlorate 、 S,S'-bis(2-quinolylmethyl)-1,2-ethanedithiol 以 乙腈 为溶剂， 以92%的产率得到[Cu(I)(1,6-bis(2'-quinolyl)-2,5-dithiahexane)]ClO4
  参考文献：
  名称：

  Bistable Copper Complexes of Bis-thia-bis-quinoline Ligands

  摘要：

  The new ligands R,R-trans-S,S-bis[methyl(2'-quinolyl)]-1,2-dithiacyclohexane, cis-S,S-bis[methyl(2'-quinolyl)]-1,2-dithiacyclohexane, and 1,6-bis(2'-quinolyl)-2,5-dithiahexane have been synthesized and their complexes with Cu-I and Cu-II prepared. The ligand/metal systems are bistable, as the complexes with copper in both its oxidation states are stable under the same conditions as solids and in solution. The crystal and molecular structure of [Cu-I(1,6-bis(2'-quinolyl)-2,5-dithiahexane)]ClO4 has been determined by X-ray diffraction and reveals that the complex is monomeric, with the ligand folding around the Cu+ cation, imparting to it a tetrahedral coordination. UV-vis, MS-ESI, and NMR data indicate that the same is found for the Cu-I complexes of all three ligands. Also, the Cu-II complexes are monomeric, but with a square arrangement of the ligands around Cu2+. On changing the oxidation state, the change in the geometrical arrangement is fast and complete in less than 80 ms, as demonstrated by cyclic voltammetry experiments. In the CV profiles, the oxidation and reduction events take place at separated E, and E-red values, with no return wave even at the fastest scan rates. In the E-ox-E-red interval (which ranges from 450 to 650 mV, depending on the ligand), the ligand/copper system can thus exist in one of its two states, depending on its history, and thus display electrochemical hysteretical behavior. The electrochemical cycle leading from the tetrahedral [Cu-I(ligand)](+) to the square [Cu-II(ligand)](2+) complex (and vice versa) is reversible and repeatable without degradation, as checked by coupled UV-vis-controlled potential coulometry experiments.

  DOI：

  10.1021/ic025690h
• 作为产物：
  描述：

  2-(氯甲基)喹啉 、 1,2-乙二硫醇 在 potassium carbonate 、 potassium iodide 作用下， 以 乙腈 为溶剂， 反应 48.0h， 生成 S,S'-bis(2-quinolylmethyl)-1,2-ethanedithiol
  参考文献：
  名称：

  硫醚连接的双喹啉对 Hg2+ 和 Fe3+ 离子的关断、比率和开-关荧光响应

  摘要：

  已制备了 15 种带有硫醚接头的双喹啉衍生物，并研究了它们的 Hg2+- 和 Fe3+-特异性荧光响应。添加 Hg2+ 离子后，未取代的 2-喹啉甲基衍生物 1a-1c 表现出荧光增强（关-开）响应。另一方面，对于芳香环上分别具有单甲氧基 (2a-2c) 和三甲氧基 (3a-3c) 取代基的衍生物，实现了比率和荧光猝灭（开-关）响应。8-喹啉甲基衍生物 4a-4c 和 5a-5c 表现出与 1 和 2 相似的响应模式，具有增强的 Hg2+ 离子选择性。通过连接链的延伸增加硫原子的数量也提高了 Hg2+ 离子的选择性。

  DOI：

  10.1002/ejic.201500220

文献信息

• Thioether-tethered bisquinoline derivatives as fluorescent probes for mercury(ii) and iron(iii) ions
  作者：Yuji Mikata、Fumie Nakagaki、Kaori Nakanishi

  DOI：10.1039/c3nj00233k

  日期：——

  Three ethanedithiol-linked bisquinoline derivatives with a different number of methoxy substituents on the aromatic ring exhibit a significant fluorescent response toward mercury(II) and iron(III) ions. Fluorescence enhancement (OFF–ON), ratiometric and fluorescence quenching (ON–OFF) responses were achieved with the same molecular skeleton, by changing the methoxy substitution pattern.

  在芳香环上具有不同数量的甲氧基取代基的三种乙二硫醇连接的双喹啉衍生物对汞离子（II）和铁离子（III）表现出显着的荧光响应。通过改变甲氧基取代模式，可以在相同的分子骨架上实现荧光增强（OFF-ON），比例和荧光猝灭（ON-OFF）响应。
• Bistable Copper Complexes of Bis-thia-bis-quinoline Ligands
  作者：Valeria Amendola、Carlo Mangano、Piersandro Pallavicini、Michele Zema

  DOI：10.1021/ic025690h

  日期：2003.9.1

  The new ligands R,R-trans-S,S-bis[methyl(2'-quinolyl)]-1,2-dithiacyclohexane, cis-S,S-bis[methyl(2'-quinolyl)]-1,2-dithiacyclohexane, and 1,6-bis(2'-quinolyl)-2,5-dithiahexane have been synthesized and their complexes with Cu-I and Cu-II prepared. The ligand/metal systems are bistable, as the complexes with copper in both its oxidation states are stable under the same conditions as solids and in solution. The crystal and molecular structure of [Cu-I(1,6-bis(2'-quinolyl)-2,5-dithiahexane)]ClO4 has been determined by X-ray diffraction and reveals that the complex is monomeric, with the ligand folding around the Cu+ cation, imparting to it a tetrahedral coordination. UV-vis, MS-ESI, and NMR data indicate that the same is found for the Cu-I complexes of all three ligands. Also, the Cu-II complexes are monomeric, but with a square arrangement of the ligands around Cu2+. On changing the oxidation state, the change in the geometrical arrangement is fast and complete in less than 80 ms, as demonstrated by cyclic voltammetry experiments. In the CV profiles, the oxidation and reduction events take place at separated E, and E-red values, with no return wave even at the fastest scan rates. In the E-ox-E-red interval (which ranges from 450 to 650 mV, depending on the ligand), the ligand/copper system can thus exist in one of its two states, depending on its history, and thus display electrochemical hysteretical behavior. The electrochemical cycle leading from the tetrahedral [Cu-I(ligand)](+) to the square [Cu-II(ligand)](2+) complex (and vice versa) is reversible and repeatable without degradation, as checked by coupled UV-vis-controlled potential coulometry experiments.
• Off–On, Ratiometric, and On–Off Fluorescence Responses of Thioether‐Linked Bisquinolines toward Hg ²⁺ and Fe ³⁺ Ions
  作者：Yuji Mikata、Kaori Nakanishi、Fumie Nakagaki、Asako Kizu、Hideo Konno

  DOI：10.1002/ejic.201500220

  日期：2015.8

  Fifteen bisquinoline derivatives with a thioether linker have been prepared, and their Hg2+- and Fe3+-specific fluorescence responses have been investigated. Upon the addition of Hg2+ ions, unsubstituted 2-quinolylmethyl derivatives 1a–1c exhibit a fluorescence enhancement (off–on) response. On the other hand, ratiometric and fluorescence quenching (on–off) responses are accomplished for derivatives

  已制备了 15 种带有硫醚接头的双喹啉衍生物，并研究了它们的 Hg2+- 和 Fe3+-特异性荧光响应。添加 Hg2+ 离子后，未取代的 2-喹啉甲基衍生物 1a-1c 表现出荧光增强（关-开）响应。另一方面，对于芳香环上分别具有单甲氧基 (2a-2c) 和三甲氧基 (3a-3c) 取代基的衍生物，实现了比率和荧光猝灭（开-关）响应。8-喹啉甲基衍生物 4a-4c 和 5a-5c 表现出与 1 和 2 相似的响应模式，具有增强的 Hg2+ 离子选择性。通过连接链的延伸增加硫原子的数量也提高了 Hg2+ 离子的选择性。