4,5-bis(octylthio)-1,3-dithiole-2-thione | 106920-24-5

• 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(octylthio)-1,3-dithiole-2-thione
• 英文别名: 4,5-Bis(octylsulfanyl)-1,3-dithiole-2-thione
• CAS: 106920-24-5
• 化学式: C₁₉H₃₄S₅
• 分子量: 422.809
• InChiKey: PSIFLQLLERUSRM-UHFFFAOYSA-N

物化性质

• 沸点：
  499.0±55.0 °C(Predicted)
• 密度：
  1.12±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  10.3
• 重原子数：
  24
• 可旋转键数：
  16
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.84
• 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-bis(octylthio)-1,3-dithiole-2-thione 以80%的产率得到
  参考文献：
  名称：

  WU, PEIJI;SAITO, GUNZI;IMAEDA, KENICHI;SHI, ZURONG;MORI, TAKEHIKO;ENOKI, +, CHEM. LETT., 1986, N 4, 441-444

  摘要：

  DOI：
• 作为产物：
  描述：

  1-碘辛烷 、 bis(tetraethylammonium)bis(1,3-dithiole-4,5-dithiolate)zincate 以 丙酮 为溶剂， 以64%的产率得到4,5-bis(octylthio)-1,3-dithiole-2-thione
  参考文献：
  名称：

  Selective and Reversible Noncovalent Functionalization of Single-Walled Carbon Nanotubes by a pH-Responsive Vinylogous Tetrathiafulvalene–Fluorene Copolymer

  摘要：

  A vinylogous tetrathiafulvalene (TTFV) monomer was prepared and copolymerized with fluorene to give a conformationally switchable conjugated copolymer. This copolymer was shown to undergo a conformational change upon protonation with trifluoroacetic acid (TFA). When mixed with single-walled carbon nanotubes (SWNTs), this TTFV-fluorene copolymer exhibited strong interactions with the SWNT surface, leading to stable, concentrated,nanotube dispersions in toluene. Photoluminescence excitation mapping indicated that the copolymer selectively disperses low-diameter SWNTs, as would be expected from its ability to form a tightly coiled conformation on the nanotube surface. Addition of TFA to the copolymer SWNT dispersion resulted in a rapid conformational change and desorption of the polymer from the SWNT surface, resulting in precipitation of pure SWNTs that were completely free of polymer. Importantly, the nanotubes isolated after dispersion and release by the TTFV fluorene copolymer were more pure than the original SWNTs that were initially dispersed.

  DOI：

  10.1021/ja409918n

文献信息

• Appending Diverse π-Extended Acceptors with Tetrathiafulvalene/Dithiafulvalene Donors: Multistate Redox Properties, Radical Ion Generation, and Mid-IR-Absorbing Mixed-Valence States
  作者：Sudhir Kumar Keshri、Deepak Asthana、Sonam Chorol、Yogendra Kumar、Pritam Mukhopadhyay

  DOI：10.1002/chem.201704604

  日期：2018.2.6

  orbitals and influence the optoelectronic properties. The D moieties allow the formation of radical cations (D.+) and the π‐extended A moieties aid the formation of radical anions (A.−) by oxidation/reduction under ambient conditions. The molecules revealed UV/Vis/near‐IR absorption, fluorescence extending into the near‐IR region, and amphoteric electrochemical properties. Chromophores 10 and 12 show solvatochromism

  通过亚磷酸酯介导的交叉偶联反应合成了三类供体-受体（D–A）π扩展发色团（1 – 12），其中酸酐或酰亚胺基π-As和四硫富瓦烯（TTF）的数目）/二硫富瓦烯（DTF）Ds被系统地改变了。大的π环，例如苯并ylene和co烯，首次被整合到TTF / DTF单元中，以克服它们的高不溶性。π受体中的酸酐和酰亚胺基团可显着改变边界轨道并影响光电性能。D部分允许形成自由基阳离子（D。+），而π扩展的A部分帮助形成自由基阴离子（A .-）通过在环境条件下进行氧化/还原。这些分子显示出UV / Vis /近红外吸收，荧光延伸到近红外区域以及两性电化学性质。发色团10和12在多种溶剂中均表现出溶剂变色现象。相对于酰亚胺基团，具有酸酐官能团的π-A使得电子吸收更容易，而D TTF / DTF单元数目的增加使它们易于氧化。有趣的是，反式-TTF稠合的分子（1，6，和11）在中红外区域显示出混合价态（ = 5
• Regulation of dithiafulvene-based molecular shape and aggregation on TiO₂ for high efficiency dye-sensitized solar cells
  作者：Yuezhen Wu、Quande Zhang、Jie Li、Xia Tian、Da Li、Xiaoqing Lu、Bingshe Xu、Yucheng Wu、Kunpeng Guo

  DOI：10.1039/c8tc06109b

  日期：——

  shape and aggregation of donor–π–acceptor (D–π–A) organic dyes is of great significance for realizing the principle of maximizing the performance of dye-sensitized solar cells (DSCs). To this end, two dithiafulvene-based organic sensitizers with different molecular shapes were synthesized, and the influence of their aggregation on TiO2 on the various performance parameters of DSCs was investigated. It was

  供体-π-受体（D-π-A）有机染料的分子形状与聚集之间的良好匹配关系对于实现最大化染料敏化太阳能电池（DSC）性能的原理具有重要意义。为此，合成了两种分子形状不同的二硫富富烯类有机增感剂，研究了它们的聚集对TiO 2的影响。发现在分子结构中供体和受体之间的扩口角为150.6°的V形DTF-C5倾向于在TiO 2的表面上形成致密的聚集体，而不会损失吸附的染料，从而得到更高的短路密度（J sc）为14.92 mA cm -2，功率转换效率（PCE）为7.39％；这些值分别比具有CDCA共吸附剂的DSC高1.48倍和1.53倍。另一方面，DTF-C6具有典型的V型构型，耀斑角为120.6°，需要与CDCA共同吸附以填充TiO 2表面染料聚集体之间的空位，目的是：减少电流损耗并抑制电子复合。相比于用原始的DSC DTF-C6聚合，基于共吸附系统上的示例显着提高了PCE从5.50％至9.04％，由于该改进的Ĵ
• Varied nanostructures from a single multifunctional molecular material
  作者：David Canevet、Ángel Pérez del Pino、David B. Amabilino、Marc Sallé

  DOI：10.1039/c0jm02302g

  日期：——

  The control of the morphology of nanostructures formed from a single component molecular material incorporating electron accepting and donating moieties is shown, from both solution and gel states. The compound comprises one tetrathiafulvalene (TTF) and two pyrene units which act as the π-electron rich and deficient units, respectively, and which are united by amide-containing linkers whose additional role is to aide aggregation by hydrogen bonding. This role was demonstrated by IR and NMR spectroscopy. The gels were deposited onto surfaces and the solvent allowed to evaporate, leaving films formed by meshes of fibres with different morphologies in accord with the different solvents used to form the materials. Doping of these xerogels with iodine vapour afforded conducting films whose characteristics were probed with current sensing atomic force microscopy (CS-AFM), providing current maps and I–V curves which show how dramatically the processing solvent can influence the electronic properties of these xerogel-derived materials.

  展示了来自单一组分分子材料的纳米结构形态的控制，这些材料包含电子受体和供体部分，适用于溶液和凝胶状态。该化合物由一个四硫杂富瓦烯（TTF）和两个芘单元组成，分别充当π-电子丰富和匮乏的单元，并通过含酰胺的链接剂结合在一起，这些链接剂的额外作用是通过氢键促进聚集。通过红外光谱（IR）和核磁共振（NMR）光谱证明了这一作用。这些凝胶被沉积在表面上，溶剂允许蒸发，留下由不同形态纤维网形成的薄膜，具体取决于用于制备材料的不同溶剂。用碘蒸气掺杂这些干凝胶产生的导电薄膜的特性通过电流传感原子力显微镜（CS-AFM）进行了探测，提供了电流图和I–V曲线，显示加工溶剂可以显著影响这些干凝胶衍生材料的电子特性。
• Highly conjugated donor-acceptor dyad based on monotetrathiafulvalene covalently attached to a magnesium norphthalocyanine unit
  作者：Ruibin Hou、Li Wang、Fuzhi Wei、Yan Xia、Dongfeng Li

  DOI：10.1016/j.molstruc.2020.127890

  日期：2020.5

  characterized. Ultraviolet–visible spectroscopy and electron paramagnetic resonance data reveal that 1 forms an electron transfer complex with 2,3,5,6-tetrafluoro-7,7,8,8-tetra-cyanoquinodimethane (F4TCNQ). Detailed electrochemical investigations show one irreversible one-electron oxidation wave, two quasi-reversible one-electron oxidation waves, and two irreversible one-electron reduction waves, indicating

  摘要 一种新型的高度共轭供体 - 受体二元组由共价连接到镁去酞菁 (NPc) 单元 (1) 上的四硫富瓦烯 (TTF) 部分组成并得到充分表征。紫外-可见光谱和电子顺磁共振数据显示 1 与 2,3,5,6-四氟-7,7,8,8-四氰基醌二甲烷 (F4TCNQ) 形成电子转移复合物。详细的电化学研究显示有一个不可逆的单电子氧化波、两个准可逆的单电子氧化波和两个不可逆的单电子还原波，表明 1 是一个很好的 π 电子供体。化合物 1 显示出从四硫富瓦烯片段到去甲酞菁核的明显分子内电荷转移 (ICT) 相互作用。这种现象可以用密度泛函理论（DFT）来解释。
• UNCAPPED ALKYLTHIO SUBSTITUTED TETRATHIAFULVALENES (TTC_n-TTF) AND THEIR CHARGE TRANSFER COMPLEXES
  作者：Peiji Wu、Gunzi Saito、Kenichi Imaeda、Zurong Shi、Takehiko Mori、Toshiaki Enoki、Hiroo Inokuchi

  DOI：10.1246/cl.1986.441

  日期：1986.4.5

  A series of tetraalkylthio substituted tetrathiafulvalenes (TTCn-TTF) was prepared. The syntheses, molecular and crystal structures, and physical properties of TTCn-TTF reveal marked differences from those of BEDT-TTF. The conformational change of TTC1-TTF molecule on the formation of charge transfer complexes and the mode of the S…S contacts are described in connection with those of BEDT-TTF compounds

  制备了一系列四烷硫基取代的四硫富瓦烯 (TTCn-TTF)。TTCn-TTF 的合成、分子和晶体结构以及物理性质显示出与 BEDT-TTF 的显着差异。TTC1-TTF 分子在形成电荷转移复合物时的构象变化和 S…S 接触的模式与 BEDT-TTF 化合物的结构变化有关。