3,3'-(thiophene-3,4-diylbis(sulfanediyl))dipropanenitrile | 437711-56-3

• 分子结构分类: 有机化合物 - 有机硫化合物 - 硫醚类
• 英文名称: 3,3'-(thiophene-3,4-diylbis(sulfanediyl))dipropanenitrile
• 英文别名: 3,4-bis(2-cyanoethylsulfanyl)thiophene；3-[4-(2-Cyanoethylsulfanyl)thiophen-3-yl]sulfanylpropanenitrile
• CAS: 437711-56-3
• 化学式: C₁₀H₁₀N₂S₃
• 分子量: 254.401
• InChiKey: RCGPBXAEJSVRIZ-UHFFFAOYSA-N

物化性质

• 熔点：
  61-64 °C
• 沸点：
  459.4±45.0 °C(Predicted)
• 密度：
  1.31±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2
• 重原子数：
  15
• 可旋转键数：
  6
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.4
• 拓扑面积：
  126
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  3,3'-(thiophene-3,4-diylbis(sulfanediyl))dipropanenitrile 在 cesium hydroxide 作用下， 以 甲醇 为溶剂， 反应 4.25h， 生成 3-(n-butylsulfanyl)-4-(methylsulfanyl)thiophene
  参考文献：
  名称：

  3- and 3,4-Bis(2-cyanoethylsulfanyl)thiophenes as Building Blocks for Functionalized Thiophene-Based π-Conjugated Systems

  摘要：

  The facile access to 3- and 3,4-bis(2-cyanoethyl-sulfanyl)thiophenes allows the straightforward synthesis of 3-alkylsulfanyl and symmetrical or unsymmetrical 3,4-dialkylsulfanylthiophenes by using a methodology based on a highly efficient sequence of deprotection/alkylation reactions of thiolate group(s).

  DOI：

  10.1021/jo025627+
• 作为产物：
  描述：

  3,4-二溴噻吩 、 3-溴丙腈 在 1,2,3,4,5,6,7,8-八硫杂环辛烷 、 叔丁基锂 作用下， 以 乙醚 、 正戊烷 为溶剂， 以3.43 g的产率得到3,3'-(thiophene-3,4-diylbis(sulfanediyl))dipropanenitrile
  参考文献：
  名称：

  3- and 3,4-Bis(2-cyanoethylsulfanyl)thiophenes as Building Blocks for Functionalized Thiophene-Based π-Conjugated Systems

  摘要：

  The facile access to 3- and 3,4-bis(2-cyanoethyl-sulfanyl)thiophenes allows the straightforward synthesis of 3-alkylsulfanyl and symmetrical or unsymmetrical 3,4-dialkylsulfanylthiophenes by using a methodology based on a highly efficient sequence of deprotection/alkylation reactions of thiolate group(s).

  DOI：

  10.1021/jo025627+

文献信息

• Synthesis and characterisation of new diindenodithienothiophene (DITT) based materials
  作者：Irina Afonina、Peter J. Skabara、Filipe Vilela、Alexander L. Kanibolotsky、John C. Forgie、Ashu K. Bansal、Graham A. Turnbull、Ifor D. W. Samuel、John G. Labram、Thomas D. Anthopoulos、Simon J. Coles、Michael B. Hursthouse

  DOI：10.1039/b919574b

  日期：——

  Three new diindenodithienothiophene (DITT) based materials were synthesised and their electrochemical properties investigated. The HOMO–LUMO gaps were observed to be 3.33, 3.48 and 2.81 eV, respectively. Cyclic voltammetry results indicate increased stability for the alkylated derivatives. The dioxide exhibits strong photoluminescence, giving a photoluminescence quantum yield of 0.72 in solution and 0.14 in the solid state. Hole mobility measurements were carried out on the non-alkylated derivative and the corresponding values were ∼10−4 cm2 V−1 s−1.

  研究人员合成了三种基于二茚二噻吩（DITT）的新材料，并对其电化学特性进行了研究。观察到的 HOMO-LUMO 间隙分别为 3.33、3.48 和 2.81 eV。循环伏安法结果表明，烷基化衍生物的稳定性增强。二氧化物具有很强的光致发光性能，在溶液中的光致发光量子产率为 0.72，在固态中为 0.14。对非烷基化衍生物进行了空穴迁移率测量，其相应值为 ∼10-4 cm2 V-1 s-1。
• Effect of Structural Factor on the Electropolymerization of Bithiophenic Precursors Containing a 3,4-Ethylenedisulfanylthiophene Unit
  作者：Mathieu Turbiez、Pierre Frère、Magali Allain、Nuria Gallego-Planas、Jean Roncali

  DOI：10.1021/ma050655q

  日期：2005.8.1

  steric hindrance to coplanarity is counterbalanced by the development of intramolecular S···S and S···O interactions. Dramatic structural change from twisted to planar conformation of bis(3,4-ethylenedisulfanylthiophene) is observed when the dimer is associated with TCNQ. The electronic properties of the dimers, analyzed by UV−vis spectroscopy, cyclic voltammetry, and theoretical calculations, are discussed

  合成了一系列基于双（3,4-亚烷基二硫基噻吩）和将3,4-亚乙基二硫基噻吩（EDST）与噻吩或3,4-亚乙基二氧噻吩（EDOT）部分关联的杂化体系的噻吩。这些系统的分子结构通过X射线衍射和理论上的几何优化来表征。尽管双（亚烷基硫基噻吩）在噻吩循环之间存在较大的二面角，但对于杂化系统，共平面性的空间位阻通过分子内S··S和S··O相互作用的发展得以抵消。当二聚体与TCNQ缔合时，观察到双（3,4-亚乙基二硫基噻吩）从扭曲构型到平面构型的剧烈结构变化。通过紫外可见光谱，循环伏安法分析二聚体的电子性质，结合联噻吩的分子结构讨论了理论和理论计算。最后，对电生成聚合物的分析证实了电子和自结构效应对于增强共轭体系的平面性和控制聚合物间隙的关键作用。因此，结合了EDST和EDOT单元的前体显示出最低的氧化电势，并且导致聚合物呈现出比源自纯EDOT或EDST二聚体的两种聚合物更低的带隙。
• 3- and 3,4-Bis(2-cyanoethylsulfanyl)thiophenes as Building Blocks for Functionalized Thiophene-Based π-Conjugated Systems
  作者：Philippe Blanchard、Bruno Jousselme、Pierre Frère、Jean Roncali

  DOI：10.1021/jo025627+

  日期：2002.5.1

  The facile access to 3- and 3,4-bis(2-cyanoethyl-sulfanyl)thiophenes allows the straightforward synthesis of 3-alkylsulfanyl and symmetrical or unsymmetrical 3,4-dialkylsulfanylthiophenes by using a methodology based on a highly efficient sequence of deprotection/alkylation reactions of thiolate group(s).