2-(3,'4'-ethylenedioxythien-2'-yl)-3-(2-cyanoethylsulfanyl)thiophene | 528870-91-9

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 双噻吩和低聚噻吩
• 英文名称: 2-(3,'4'-ethylenedioxythien-2'-yl)-3-(2-cyanoethylsulfanyl)thiophene
• 英文别名: 2-(3,4-ethylenedioxythienyl)-3-(2-cyanoethylsulfanyl)thiophene；3-[2-(2,3-Dihydrothieno[3,4-b][1,4]dioxin-5-yl)thiophen-3-yl]sulfanylpropanenitrile
• CAS: 528870-91-9
• 化学式: C₁₃H₁₁NO₂S₃
• 分子量: 309.434
• InChiKey: YMLNOKUADNYVLB-UHFFFAOYSA-N

物化性质

• 熔点：
  79-80 °C(Solv: dichloromethane (75-09-2); ligroine (8032-32-4))
• 沸点：
  499.5±45.0 °C(Predicted)
• 密度：
  1.45±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.9
• 重原子数：
  19
• 可旋转键数：
  4
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.31
• 拓扑面积：
  124
• 氢给体数：
  0
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  2-(3,'4'-ethylenedioxythien-2'-yl)-3-(2-cyanoethylsulfanyl)thiophene 在 吡啶 、 cesium hydroxide 作用下， 以 甲醇 、 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， 反应 16.0h， 生成 2-(3,'4'-ethylenedioxythien-2'-yl)-3-(4,8-dioxa-5,7-dioxo-1-thiadecyl)thiophene
  参考文献：
  名称：

  Electrochemical Synthesis of C₆₀-Derivatized Poly(thiophene)s from Tailored Precursors

  摘要：

  New series of C-60-derivatized bithiophenic precursors with low oxidation potential have been synthesized using the thiolate deprotection chemistry. The analysis of the electropolymerization of these compounds shows that the use of two-site precursors leads to polymers combining enhanced conjugation length, faster switching time, and improved stability under redox cycling. The unsuccessful attempts to identify the optical signature of the reduced forms of the attached C-60 by spectroelectrochemistry suggest that the PT backbone is unstable in the presence of the C-60 anion radical. Preliminary photoelectrochemical experiments on films deposited on platinum electrode reveal a significant enhancement of the photocurrent for the C-60-derivatized polymer when compared to a nonsubstituted reference polymer, indicating that these new materials are potentially useful for photovoltaic energy conversion.

  DOI：

  10.1021/ma034047r
• 作为产物：
  描述：

  3-[(2-cyanoethyl)sulfanyl]thiophene 在 N-溴代丁二酰亚胺(NBS) 、 正丁基锂 作用下， 以 四氢呋喃 、 N,N-二甲基甲酰胺 为溶剂， 生成 2-(3,'4'-ethylenedioxythien-2'-yl)-3-(2-cyanoethylsulfanyl)thiophene
  参考文献：
  名称：

  Electrogenerated poly(thiophenes) derivatized by bipyridine ligands and metal complexes

  摘要：

  The synthesis of a series of bithiophenic precursors of electrogenerated conjugated polymers functionalized by bipyridine ligands is described. The precursor structure involves two polymerizable groups attached at both ends of a bipyridine ligand and fixed at an internal beta-position of thiophene via an alkylsulfanyl or alkoxy spacer. Electrochemical and optical data show that the low polymerization potential resulting from the association of 3,4-ethylenedioxythiophene (EDOT) and alkylsulfanyl or alkoxy thiophene combined with the multi-site polymerization approach allows a straightforward electrosynthesis of extensively conjugated and stable functionalized polymers. On the basis of these results, iron and ruthenium complexes of these precursors have been synthesized and electropolymerized. The analysis of the electrochemical behavior of the resulting polymers shows that they exhibit the typical electrochemical signature of both the conjugated polythiophene backbone and the immobilized metal complex.

  DOI：

  10.1039/b313291a

文献信息

• Internally referenced analysis of charge-transfer reactions in a new ferrocenyl bithiophenic conducting polymer through cyclic voltammetry
  作者：Chuang Peng、Xiaohang Zhou、George Z. Chen、Fabrice Moggia、Frédéric Fages、Hugues Brisset、Jean Roncali

  DOI：10.1039/b817101g

  日期：——

  A new ferrocenyl bithiophenic polymer has enabled the first demonstration of internally referenced quantitative analysis of charge-transfer reactions, which may enable better understanding and applications of conducting polymers in e.g. supercapacitors.

  一种新型二茂铁基二噻吩聚合物首次展示了电荷转移反应的内部参考定量分析，这有助于更好地理解导电聚合物在超级电容器等领域的应用。
• Electrochemical Synthesis of C₆₀-Derivatized Poly(thiophene)s from Tailored Precursors
  作者：Bruno Jousselme、Philippe Blanchard、Eric Levillain、Rémi de Bettignies、Jean Roncali

  DOI：10.1021/ma034047r

  日期：2003.5.1

  New series of C-60-derivatized bithiophenic precursors with low oxidation potential have been synthesized using the thiolate deprotection chemistry. The analysis of the electropolymerization of these compounds shows that the use of two-site precursors leads to polymers combining enhanced conjugation length, faster switching time, and improved stability under redox cycling. The unsuccessful attempts to identify the optical signature of the reduced forms of the attached C-60 by spectroelectrochemistry suggest that the PT backbone is unstable in the presence of the C-60 anion radical. Preliminary photoelectrochemical experiments on films deposited on platinum electrode reveal a significant enhancement of the photocurrent for the C-60-derivatized polymer when compared to a nonsubstituted reference polymer, indicating that these new materials are potentially useful for photovoltaic energy conversion.
• Electrogenerated poly(thiophenes) derivatized by bipyridine ligands and metal complexes
  作者：Bruno Jousselme、Philippe Blanchard、Maïtena Oçafrain、Magali Allain、Eric Levillain、Jean Roncali

  DOI：10.1039/b313291a

  日期：——

  The synthesis of a series of bithiophenic precursors of electrogenerated conjugated polymers functionalized by bipyridine ligands is described. The precursor structure involves two polymerizable groups attached at both ends of a bipyridine ligand and fixed at an internal beta-position of thiophene via an alkylsulfanyl or alkoxy spacer. Electrochemical and optical data show that the low polymerization potential resulting from the association of 3,4-ethylenedioxythiophene (EDOT) and alkylsulfanyl or alkoxy thiophene combined with the multi-site polymerization approach allows a straightforward electrosynthesis of extensively conjugated and stable functionalized polymers. On the basis of these results, iron and ruthenium complexes of these precursors have been synthesized and electropolymerized. The analysis of the electrochemical behavior of the resulting polymers shows that they exhibit the typical electrochemical signature of both the conjugated polythiophene backbone and the immobilized metal complex.