2-formyl-(3’,4’-ethylenedioxy)-5,2’:5’,2’’-terthiophene | 872177-33-8

• 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-formyl-(3’,4’-ethylenedioxy)-5,2’:5’,2’’-terthiophene
• 英文别名: 5-(7-Thiophen-2-yl-2,3-dihydrothieno[3,4-b][1,4]dioxin-5-yl)thiophene-2-carbaldehyde；5-(7-thiophen-2-yl-2,3-dihydrothieno[3,4-b][1,4]dioxin-5-yl)thiophene-2-carbaldehyde
• CAS: 872177-33-8
• 化学式: C₁₅H₁₀O₃S₃
• 分子量: 334.441
• InChiKey: KGRZUSGGXMPKNV-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.2
• 重原子数：
  21
• 可旋转键数：
  3
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.13
• 拓扑面积：
  93
• 氢给体数：
  0
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  2-乙酰基吡啶 、 2-formyl-(3’,4’-ethylenedioxy)-5,2’:5’,2’’-terthiophene 在 氨 、 potassium hydroxide 作用下， 以 四氢呋喃 、 乙醇 、 水 为溶剂， 反应 48.0h， 以61%的产率得到4'-(3',4'-ethylenedioxy-5,2',5',2''-terthiophen-2-yl)-2,2':6',2''-terpyridine
  参考文献：
  名称：

  Synthesis of π-Conjugated 2,2:6′,2″-Terpyridine-Substituted Oligomers Based on 3,4-Ethylenedioxythiophene

  摘要：

  Dissymmetric pi-conjugated monomers and oligomers incorporating 3,4-ethylenedioxythiophene (EDOT) units and bearing terpyridine end groups were synthesized in good yields through Vilsmeyer-Haak formylation followed by a reaction with 2-acetylpyridine in basic media or, for the longest oligomers, direct C H bond arylation. They have a low HOMO-UMO gap and are easily oxidized at low potentials. Upon complexation with cobalt(II) and iron(II) they yield new hybrid materials that can be used in various applications ranging from photovoltaics to spintronics.

  DOI：

  10.1021/ol303512f
• 作为产物：
  描述：

  3',4'-ethylenedioxy-2,2':5',2''-terthiophene 、 N,N-二甲基甲酰胺 在 三氯氧磷 、 水 、 sodium acetate 作用下， 以 1,2-二氯乙烷 为溶剂， 反应 20.0h， 以91%的产率得到2-formyl-(3’,4’-ethylenedioxy)-5,2’:5’,2’’-terthiophene
  参考文献：
  名称：

  Synthesis of π-Conjugated 2,2:6′,2″-Terpyridine-Substituted Oligomers Based on 3,4-Ethylenedioxythiophene

  摘要：

  Dissymmetric pi-conjugated monomers and oligomers incorporating 3,4-ethylenedioxythiophene (EDOT) units and bearing terpyridine end groups were synthesized in good yields through Vilsmeyer-Haak formylation followed by a reaction with 2-acetylpyridine in basic media or, for the longest oligomers, direct C H bond arylation. They have a low HOMO-UMO gap and are easily oxidized at low potentials. Upon complexation with cobalt(II) and iron(II) they yield new hybrid materials that can be used in various applications ranging from photovoltaics to spintronics.

  DOI：

  10.1021/ol303512f

文献信息

• Synthesis of π-Conjugated 2,2:6′,2″-Terpyridine-Substituted Oligomers Based on 3,4-Ethylenedioxythiophene
  作者：Laure Fillaud、Gaëlle Trippé-Allard、Jean Christophe Lacroix

  DOI：10.1021/ol303512f

  日期：2013.3.1

  Dissymmetric pi-conjugated monomers and oligomers incorporating 3,4-ethylenedioxythiophene (EDOT) units and bearing terpyridine end groups were synthesized in good yields through Vilsmeyer-Haak formylation followed by a reaction with 2-acetylpyridine in basic media or, for the longest oligomers, direct C H bond arylation. They have a low HOMO-UMO gap and are easily oxidized at low potentials. Upon complexation with cobalt(II) and iron(II) they yield new hybrid materials that can be used in various applications ranging from photovoltaics to spintronics.