4,5-(phenyl-ethylenedithio)-1,3-dithiole-2-thione | 111082-47-4

• 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-(phenyl-ethylenedithio)-1,3-dithiole-2-thione
• 英文别名: 1,3-Dithiolo[4,5-b][1,4]dithiin-2-thione, 5,6-dihydro-5-phenyl-；5-phenyl-5,6-dihydro-[1,3]dithiolo[4,5-b][1,4]dithiine-2-thione
• CAS: 111082-47-4
• 化学式: C₁₁H₈S₅
• 分子量: 300.515
• InChiKey: KAZNFIJVLOEIFR-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.7
• 重原子数：
  16
• 可旋转键数：
  1
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.18
• 拓扑面积：
  133
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  4,5-(phenyl-ethylenedithio)-1,3-dithiole-2-thione 在 sodium ethanolate 作用下， 以 乙醚 、 乙醇 为溶剂， 生成 sodium 5,6-dihydro-5-phenyl-2,3-dithiolate
  参考文献：
  名称：

  Underhill, Allan E.; Clark, R. Andrew; Varma, K. Sukumar, Phosphorus, Sulfur and Silicon and the Related Elements, 1989, vol. 43, # 1-2, p. 111 - 128

  摘要：

  DOI：
• 作为产物：
  描述：

  4,5-双(苯甲酰硫基)-1,3-二硫杂环戊烯-2-硫酮 、 1,2-二溴乙基苯 在 sodium ethanolate 作用下， 生成 4,5-(phenyl-ethylenedithio)-1,3-dithiole-2-thione
  参考文献：
  名称：

  Fourier transform Raman spectroscopy of 1,3-dithiole-2-thione and related compounds

  摘要：

  The Raman spectra of 1,3-dithiole-2-thione and a series of related compounds were recorded on a fourier transform Raman spectrometer using near-infrared laser excitation. The spectra proved, with limited exception, to be of high quality. With the help of measured depolarisation ratios it has proved possible to make assignments for the stronger peaks in the spectrum of 1,3-dithiole-2-thione, thereby resolving ambiguities and disagreements in the results of previous workers. These assignments have been used to aid in the interpretation of the very characteristic spectra of substituted thiones. The value of these spectra for analytical purposes is discussed.

  DOI：

  10.1016/0584-8539(91)80209-2

文献信息

• Semiconducting Langmuir–Blodgett films of ethylenedithiotetrathiafulvalene (EDT–TTF) derivatives bearing charged and uncharged aromatic substituents
  作者：Leonid M. Goldenberg、James Y. Becker、Ofra Paz-Tal Levi、Vladimir Yu. Khodorkovsky、Lev M. Shapiro、Martin R. Bryce、John P. Cresswell、Michael C. Petty

  DOI：10.1039/a606831f

  日期：——

  Ethylenedithiotetrathiafulvalene (EDT–TTF) derivatives1–4 functionalised with a single aromatic ring have been synthesised and their Langmuir–Blodgett (LB) films have been assembled utilising only 25% molar ratio of fatty acid. For compounds 1, 3 and 4, predominantly Y-type deposition onto solid supports was observed with a transfer ratio close to unity. After doping with iodine vapour, the maximum in-plane conductivity values obtained were σ rt =10 -3 S cm -1 for 1 and 3, and 10 -5 S cm -1 for 4. LB deposition of 2 was not uniform and the conductivity value after doping was low. UV–VIS spectra of the LB films reveal the appearance of a charge-transfer (CT) band at λ max =ca. 900 nm for 1 and 4 after iodine doping. A solution of compound 3 exhibited a weak absorption band at ca. 665 nm which is assigned to an intramolecular CT band; the intensity of this band increases on exposure of the solution to light. This band is not observed in LB films of 3, neither as-deposited nor after doping. Molecular orbital calculations indicate that in the minimum energy conformation of 3, the pyridinium moiety is practically orthogonal to the TTF unit and this conformation may be obtained in solution, enabling charge-transfer to occur. A more linear conformation of 3 in the LB films may prevent intramolecular charge-transfer from occurring. Monolayers of 1, 3 and 4 were characterised by cyclic voltammetry which revealed two redox steps consistent with the formation of the EDT–TTF cation radical and dication, respectively.

  我们合成了具有单个芳香环功能的亚乙基二硫代四硫杂戊烯（EDTâTTF）衍生物1â4，并利用仅 25% 摩尔比的脂肪酸组装了它们的朗缪尔-布洛杰特（LB）薄膜。 对于化合物 1、3 和 4，在固体支撑物上观察到的主要是 Y 型沉积，转移比接近于一。在掺入碘蒸气后，1 和 3 获得的最大面内电导率值为 Ï rt =10 -3 S cm -1 ，4 为 10 -5 S cm -1 。2 的枸杞沉积不均匀，掺杂后的电导率值较低。枸杞薄膜的紫外可见光谱显示，1 和 4 在δ" max =ca.900 nm 处出现电荷转移（CT）带。化合物 3 的溶液在约 665 纳米波长处显示出一条微弱的吸收带。该吸收带的强度在溶液暴露于光线时会增加。在 3 的枸杞薄膜中，无论是沉积时还是掺杂后，都没有观察到这条带。分子轨道计算表明，在 3 的最小能量构象中，吡啶鎓分子实际上与 TTF 单元正交，这种构象可以在溶液中获得，从而实现电荷转移。通过循环伏安法对 1、3 和 4 的单层膜进行了表征，发现其中有两个氧化还原步骤分别与 EDTâTTF 阳离子自由基和二阳离子的形成相一致。
• Bis(phenylethylenedithio)tetrathiafulvalene (BPhEDT-TTF)
  作者：K. S. Varma、J. Evans、S. Edge、A. E. Underhill、G. Bojesen、J. Becher

  DOI：10.1039/c39890000257

  日期：——

  The title compound, synthesized from (±)-4,5-phenylethylenedithio-1,3-dithiole-2-thione via triethyl phosphite coupling, has been prepared and characterized; some electrochemically prepared salts of this new π-donor are described.

  经亚磷酸三乙酯偶联，由（±）-4,5-苯基亚乙基二硫-1,3-二硫基-2-硫酮合成了标题化合物，并进行了表征。描述了这种新的π-给体的一些电化学制备的盐。
• New synthesis of phenyl-substituted 2,3-dihydro-1,3-dithiolo[4,5-e][1,4]dithiin-6-thione
  作者：Dong-Youn Noh、Ha-Jin Lee、Jongki Hong、Allan E Underhill

  DOI：10.1016/0040-4039(96)01672-3

  日期：1996.10

  The facile synthesis of 4 and (±)-6 was carried out via a Diels-Alder type [2+4] cycloaddition reaction of oligomeric dien 8 with styrene or t-stilbene, respectively, as a dienophile by a thermal reaction and/or photoreaction. (±)-6 crystallized as a racemic compound composed of (2R,3R) and (2S,3S) enantiomers.

  的简便合成4和（±） - 6进行经由狄尔斯-阿尔德型[2 + 4]的低聚二烯的环加成反应8与苯乙烯或吨通过热反应分别芪，作为亲双烯体和/或光反应。（±）-6结晶为由（2R，3R）和（2S，3S）对映异构体组成的外消旋化合物。
• Structure of inorganic–organic hybrid polymer assembled by mercury(II) iodide and sulfur-rich compound
  作者：Jie Dai、Xin Wang、Guo-Qing Bian、Jia-Sheng Zhang、Lin Guo、Megumu Munakata

  DOI：10.1016/j.molstruc.2003.11.020

  日期：2004.3

  [Hg2I4(PEDT)]∞ (1), PEDT=4,5-(phenyl-ethylenedithio)-1,3-dithiole-2-thione, has been synthesized and characterized by single crystal X-ray diffraction. It is found to be an unusual organic–inorganic hybrid structure. The inorganic layer is composed of chains of Hg with bridging I, in one case doubly bridged and in the other singly, interconnected by further bridging I to complete the two dimensional connectivity

  摘要 合成了金属配合物 [Hg2I4(PEDT)]∞ (1), PEDT=4,5-(phenyl-ethylenedithio)-1,3-dithiole-2-thione, 并通过单晶 X 射线衍射表征. 它被发现是一种不寻常的有机-无机杂化结构。无机层由带桥接 I 的 Hg 链组成，一种情况下双桥连，另一种情况下单独桥接，通过进一步桥接 I 相互连接以完成二维连接。有机层包含成对的中心对称相关，因此头对尾，面对面的分子。这种对中的每个分子都参与了与中心对称相关的相邻分子对中的一个分子形成短 S⋯S 接触的过程，从而形成了分子链。有机层内的连接由链之间的 C–H⋯π 接触完成。
• Larsen, Sine; Thorsteinsson, Thorstein; Boewadt, Soeren, Acta Chemica Scandinavica, 1991, vol. 45, # 7, p. 709 - 715
  作者：Larsen, Sine、Thorsteinsson, Thorstein、Boewadt, Soeren、Hansen, Thomas K.、Varma, Karikath S.、et al.

  DOI：——

  日期：——