4,5-Bis-(5-chloro-pentylsulfanyl)-[1,3]dithiol-2-one | 193148-65-1

• 分子结构分类: 有机化合物 - 有机硫化合物 - 硫醚类
• 英文名称: 4,5-Bis-(5-chloro-pentylsulfanyl)-[1,3]dithiol-2-one
• 英文别名: 4,5-Bis(5-chloropentylsulfanyl)-1,3-dithiol-2-one
• CAS: 193148-65-1
• 化学式: C₁₃H₂₀Cl₂OS₄
• 分子量: 391.471
• InChiKey: MQICNGUMBTZPBA-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.1
• 重原子数：
  20
• 可旋转键数：
  12
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.77
• 拓扑面积：
  118
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  4,5-Bis-(5-chloro-pentylsulfanyl)-[1,3]dithiol-2-one 在 sodium iodide 、 亚磷酸三乙酯 作用下， 以 四氢呋喃 、 1,4-二氧六环 、 丙酮 、 苯 为溶剂， 反应 80.0h， 生成 2,7:3,6-bis[2'-thioxo-1',3'-dithiole-4',5'-diylbis(pentane-1,5-diyldithio)]-1,4,5,8-tetrathiafulvalene
  参考文献：
  名称：

  Syntheses, Unique Strained Molecular Structures, and Unusual Transannular Electronic Interactions of a Series of Crisscross-Overlapped Tetrathiafulvalenophanes

  摘要：

  A series of novel tetrathiafulvalenophanes has been synthesized, in which two tetrathiafulvalenes (TTF) are linked in a crisscross-overlapped arrangement by four alkylenedithio bridges. Their molecular structures were elucidated by X-ray crystal analyses, being characterized by the bent TTF skeletons as well as the unique stacking mode. The degree of the bend largely depends on both the length and conformational rigidity of the alkylenedithio chains. The short and rigid chains induce severe bending, which brings about a hypsochromical effect in the electronic absorption spectra. On the other hand, the long and flexible chains reduce the strain and make an inside cavity large enough to include a guest molecule. In addition, the less strained compounds can effect an intramolecular transannular Coulombic interaction between their two TTF units in solution, as demonstrated by multistage redox waves in the cyclic voltammograms. All the radical cation salts formed from these tetrathiafulvalenophanes have conductivities of the same order of 10(-6)-10(-7) S cm(-1), which are apparently independent of the donor and the counterion species.

  DOI：

  10.1021/jo962239x
• 作为产物：
  描述：

  1-溴-5-氯戊烷 在 mercury(II) diacetate 作用下， 以 氯仿 、 溶剂黄146 、 丙酮 为溶剂， 反应 50.0h， 生成 4,5-Bis-(5-chloro-pentylsulfanyl)-[1,3]dithiol-2-one
  参考文献：
  名称：

  Syntheses, Unique Strained Molecular Structures, and Unusual Transannular Electronic Interactions of a Series of Crisscross-Overlapped Tetrathiafulvalenophanes

  摘要：

  A series of novel tetrathiafulvalenophanes has been synthesized, in which two tetrathiafulvalenes (TTF) are linked in a crisscross-overlapped arrangement by four alkylenedithio bridges. Their molecular structures were elucidated by X-ray crystal analyses, being characterized by the bent TTF skeletons as well as the unique stacking mode. The degree of the bend largely depends on both the length and conformational rigidity of the alkylenedithio chains. The short and rigid chains induce severe bending, which brings about a hypsochromical effect in the electronic absorption spectra. On the other hand, the long and flexible chains reduce the strain and make an inside cavity large enough to include a guest molecule. In addition, the less strained compounds can effect an intramolecular transannular Coulombic interaction between their two TTF units in solution, as demonstrated by multistage redox waves in the cyclic voltammograms. All the radical cation salts formed from these tetrathiafulvalenophanes have conductivities of the same order of 10(-6)-10(-7) S cm(-1), which are apparently independent of the donor and the counterion species.

  DOI：

  10.1021/jo962239x

文献信息

• Syntheses, Unique Strained Molecular Structures, and Unusual Transannular Electronic Interactions of a Series of Crisscross-Overlapped Tetrathiafulvalenophanes
  作者：Kazuo Takimiya、Koichi Imamura、Youji Shibata、Yoshio Aso、Fumio Ogura、Tetsuo Otsubo

  DOI：10.1021/jo962239x

  日期：1997.8.1

  A series of novel tetrathiafulvalenophanes has been synthesized, in which two tetrathiafulvalenes (TTF) are linked in a crisscross-overlapped arrangement by four alkylenedithio bridges. Their molecular structures were elucidated by X-ray crystal analyses, being characterized by the bent TTF skeletons as well as the unique stacking mode. The degree of the bend largely depends on both the length and conformational rigidity of the alkylenedithio chains. The short and rigid chains induce severe bending, which brings about a hypsochromical effect in the electronic absorption spectra. On the other hand, the long and flexible chains reduce the strain and make an inside cavity large enough to include a guest molecule. In addition, the less strained compounds can effect an intramolecular transannular Coulombic interaction between their two TTF units in solution, as demonstrated by multistage redox waves in the cyclic voltammograms. All the radical cation salts formed from these tetrathiafulvalenophanes have conductivities of the same order of 10(-6)-10(-7) S cm(-1), which are apparently independent of the donor and the counterion species.