2-(3,'4'-ethylenedioxythien-2'-yl)-3-(8,12-dioxa-9,11-dioxo-1-thitetradecyl)thiophene | 528870-87-3

• 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-(8,12-dioxa-9,11-dioxo-1-thitetradecyl)thiophene
• 英文别名: 3-O-[6-[2-(2,3-dihydrothieno[3,4-b][1,4]dioxin-5-yl)thiophen-3-yl]sulfanylhexyl] 1-O-ethyl propanedioate
• CAS: 528870-87-3
• 化学式: C₂₁H₂₆O₆S₃
• 分子量: 470.632
• InChiKey: OMTOBQZCPDDRFA-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.9
• 重原子数：
  30
• 可旋转键数：
  14
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.52
• 拓扑面积：
  153
• 氢给体数：
  0
• 氢受体数：
  9

反应信息

• 作为反应物：
  描述：

  足球烯 、 2-(3,'4'-ethylenedioxythien-2'-yl)-3-(8,12-dioxa-9,11-dioxo-1-thitetradecyl)thiophene 在 碘 、 1,8-二氮杂双环[5.4.0]十一碳-7-烯 作用下， 以 甲苯 为溶剂， 反应 12.0h， 以21%的产率得到
  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：

  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-(8,12-dioxa-9,11-dioxo-1-thitetradecyl)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

文献信息

• 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.