1-cyano-1,2-bis(2-thienylene)vinylene | 10569-39-8

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 杂芳族化合物
• 英文名称: 1-cyano-1,2-bis(2-thienylene)vinylene
• 英文别名: (2E)-2,3-di-thienylprop-2-enenitrile；(E)-2,3-di(thiophen-2-yl)acrylonitrile；trans-α,β-Di-<2>thienyl-acrylonitril；2,3c-di-[2]thienyl-acrylonitrile；2,3-Di(2-thienyl)acrylonitrile；(E)-2,3-dithiophen-2-ylprop-2-enenitrile
• CAS: 10569-39-8
• 化学式: C₁₁H₇NS₂
• 分子量: 217.315
• InChiKey: OXJZQVOOGYHIQG-VQHVLOKHSA-N

物化性质

• 沸点：
  350.2±37.0 °C(Predicted)
• 密度：
  1.318±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.1
• 重原子数：
  14
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  80.3
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  1-cyano-1,2-bis(2-thienylene)vinylene 、 氯仿 生成 alkaline earth salt of/the/ methylsulfuric acid
  参考文献：
  名称：

  Badger et al., Australian Journal of Chemistry, 1966, vol. 19, p. 1243,1248

  摘要：

  DOI：
• 作为产物：
  描述：

  2-氯甲基噻吩 在 氢氧化钾 、 水 、 丙酮 作用下， 生成 1-cyano-1,2-bis(2-thienylene)vinylene
  参考文献：
  名称：

  Cagniant, Bulletin de la Societe Chimique de France, 1949, p. 847,851

  摘要：

  DOI：

文献信息

• Direct C-S Bond Functionalization of Benzyl Mercaptan
  作者：Khokan Choudhuri、Milan Pramanik、Prasenjit Mal

  DOI：10.1002/ejoc.202000521

  日期：2020.7.7

  Using 1,10‐phenanthroline as organocatalyst and t BuOK as base, cascaded activation of three different bonds: C(sp3)–H, benzylic C–S, and aryl–halide could be achievable in one pot.

  以1,10-菲咯啉为有机催化剂，以t BuOK为碱，可以在一锅中实现三个不同键的级联活化：C（sp 3）–H，苄基C–S和芳基–卤化物。
• Synthesis, chemical polymerization and electrochemical properties of low band gap conducting polymers for use in supercapacitors
  作者：Patrick Soudan、Philippe Lucas、Hoang Ang Ho、Donald Jobin、Livain Breau、Daniel Bélanger

  DOI：10.1039/b006577n

  日期：——

  A set of nine monomers derived from diaryl-cyanovinylene, -carboxyvinylene and -cyanobutadiene were synthesized as were the corresponding polymers resulting from the chemical polymerization of the monomers in the presence of an almost quantitative amount of FeCl3 in chloroform. The aim of this work was to investigate the effect of the chemical structure of the polymers on their charge capacitance and stability upon galvanostatic charge/discharge cycling. The electrochemical performances of composite electrodes based on polymer, acetylene black and PTFE have been investigated in acetonitrile containing 1 M Et4NBF4 using cyclic voltammetry and galvanostatic charge/discharge cycling experiments. The best performances in terms of charge capacitance for both the p- and n-doping processes were demonstrated with poly(7) (2E,4E)-2,5-di-2-thienylpenta-2,4-dienenitrile and poly(9) (2E)-3-(2,2′-bithienyl-5-yl)-2-(2-thienyl)prop-2-enenitrile since values as high as 245 C g−1 were obtained with poly(7) in its n-doped state and 325 C g−1 with p-doped poly(9). The energy density (68 Wh kg−1) and power density (24 kW kg−1) delivered by a poly(9) capacitor are in good agreement with those expected from cyclic voltammetry and galvanostatic charge/discharge experiments performed with single electrodes. Unfortunately, a capacitance loss was observed upon cycling and was ascribed exclusively to the n-doping process occurring at the negative electrode since the capacitance of the positive electrode remained almost unchanged during these experiments.

  一组来自二芳基氰烯烃、氰基乙烯和氰基丁二烯的九种单体被合成，相应的聚合物也在氯仿中几乎定量的FeCl3存在下进行化学聚合。此次研究的目的是探讨聚合物化学结构对其电荷电容和在恒电流充放电循环中的稳定性的影响。基于聚合物、乙炔黑和聚四氟乙烯的复合电极在含有1 M Et4NBF4的乙腈中进行了循环伏安法和恒电流充放电循环实验。无论是在p掺杂还是n掺杂过程中，聚(7) (2E,4E)-2,5-二(2-噻吩基)戊-2,4-二烯腈和聚(9) (2E)-3-(2,2'-二噻吩基-5-基)-2-(2-噻吩基)丙-2-烯腈在电荷电容方面表现出最佳性能，其中聚(7)在其n掺杂状态下获得高达245 C g−1的值，而p掺杂的聚(9)则达到325 C g−1。聚(9)电容器提供的能量密度（68 Wh kg−1）和功率密度（24 kW kg−1）与在单电极上进行的循环伏安法和恒电流充放电实验所预期的结果良好吻合。不幸的是，在充放电循环中观察到电容损失，这被完全归因于在负极发生的n掺杂过程，因为在这些实验中正极的电容几乎保持不变。
• Electrogenerated small bandgap π-conjugated polymers derived from substituted dithienylethylenes
  作者：Hoang Anh Ho、Hugues Brisset、Pierre Frère、Jean Roncali

  DOI：10.1039/c39950002309

  日期：——

  Electropolymerization of E-1,2-(2,2′-dithienylethylene) bearing a cyano group at the ethylene linkage leads to new small bandgap π-conjugated polymers.

  E-1,2-(2,2'-二噻吩乙烯) 在乙烯链接处带有氰基的电聚合反应生成了新的小带隙 π-共轭聚合物。
• Nucleophilic Cyanation of Enones and Imines with Formamide as the Cyano Source
  作者：Lei Luo、Hong Dai、Ming‐Qing Yang、Luo Yang

  DOI：10.1002/adsc.202400482

  日期：——

  Conflict of Interests The authors declare no competing financial interest.

  利益冲突 作者声明不存在竞争性经济利益。
• Donor-Mediated Band Gap Reduction in a Homologous Series of Conjugated Polymers
  作者：Christopher A. Thomas、Kyukwan Zong、Khalil A. Abboud、Peter J. Steel、John R. Reynolds

  DOI：10.1021/ja048637w

  日期：2004.12.1

  A family of six donor-acceptor-donor monomers was synthesized using combinations of thiophene, 3,4-ethylenedioxythiophene and 3,4-ethylenedioxypyrrole as donor moieties, and cyanovinylene as the acceptor moiety, to understand the effects of modified donor ability on the optoelectronic and redox properties of the resulting electropolymerized materials. Spectroelectrochemistry, differential pulse voltammetry, and cyclic voltammetry results indicate band gaps ranging from 1.1 to 1.6 eV and suggest that these polymers can be both p-type and n-type doped at accessible potentials. In situ conductivity results indicate that the n-type conductivity magnitude is modest, and the conductivity profile indicates a redox conductivity mechanism as opposed to a delocalized electronic band mechanism as observed for p-type doping.