3',4'-dibutyl-5-formyl-2,2':5',2''-terthiophene | 950526-26-8

• 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: 3',4'-dibutyl-5-formyl-2,2':5',2''-terthiophene
• 英文别名: 5-(3,4-Dibutyl-5-thiophen-2-ylthiophen-2-yl)thiophene-2-carbaldehyde；5-(3,4-dibutyl-5-thiophen-2-ylthiophen-2-yl)thiophene-2-carbaldehyde
• CAS: 950526-26-8
• 化学式: C₂₁H₂₄OS₃
• 分子量: 388.619
• InChiKey: TXWNSSCPCKZKOM-UHFFFAOYSA-N

物化性质

• 沸点：
  505.6±50.0 °C(Predicted)
• 密度：
  1.171±0.06 g/cm3(Temp: 20 °C; Press: 760 Torr)(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  6.2
• 重原子数：
  25
• 可旋转键数：
  9
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.38
• 拓扑面积：
  74.6
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  3',4'-dibutyl-5-formyl-2,2':5',2''-terthiophene 在 氢氧化钾 、 一水合肼 作用下， 以 正丁醇 为溶剂， 反应 3.5h， 以97%的产率得到3',4'-dibutyl-5-methyl-2,2':5',2''-terthiophene
  参考文献：
  名称：

  Reverse Selectivity in m-CPBA Oxidation of Oligothiophenes to Sulfones

  摘要：

  Oligothiophene sulfones of up to six rings can be conveniently prepared by the direct oxidation of butyl-substituted thiophene oligomers with m-CPBA in dichloromethane. Reverse selectivity of oxidized rings is observed relative to previously reported systems without beta-substitution. The selectivity in the trimer and hexamer is confirmed with single-crystal X-ray structure data. The sulfones possess red-shifted absorptions and increased electron affinities relative to the parent oligomers.

  DOI：

  10.1021/ol071369x
• 作为产物：
  描述：

  N,N-二甲基甲酰胺 、 3,4-二丁基-2,5-二噻吩-2-基噻吩 在 三氯氧磷 作用下， 以 1,2-二氯乙烷 为溶剂， 反应 5.5h， 以88%的产率得到3',4'-dibutyl-5-formyl-2,2':5',2''-terthiophene
  参考文献：
  名称：

  Reverse Selectivity in m-CPBA Oxidation of Oligothiophenes to Sulfones

  摘要：

  Oligothiophene sulfones of up to six rings can be conveniently prepared by the direct oxidation of butyl-substituted thiophene oligomers with m-CPBA in dichloromethane. Reverse selectivity of oxidized rings is observed relative to previously reported systems without beta-substitution. The selectivity in the trimer and hexamer is confirmed with single-crystal X-ray structure data. The sulfones possess red-shifted absorptions and increased electron affinities relative to the parent oligomers.

  DOI：

  10.1021/ol071369x

文献信息

• Oligothiophene Tetracyanobutadienes: Alternative Donor−Acceptor Architectures for Molecular and Polymeric Materials
  作者：Ted M. Pappenfus、Deborah K. Schneiderman、Juan Casado、Juan T. López Navarrete、M. Carmen Ruiz Delgado、Gianni Zotti、Barbara Vercelli、Matthew D. Lovander、Lindsay M. Hinkle、Jon N. Bohnsack、Kent R. Mann

  DOI：10.1021/cm102128g

  日期：2011.2.8

  bis(terthienyl)-substituted TCBD molecule (3T-TCBD-3T) yields a conducting polymer exhibiting balanced ambipolar redox conduction with similar values for the oxidized and reduced states of the polymer (1 × 10−3 S cm−1). Raman spectra of the asymmetric donor−acceptor materials are characterized by two intense bands characteristic of the aromatic and quinoidal regions in the conjugated π-system of the oligothiophene

  低聚噻吩取代的1,1,4,4-四氰基丁二烯（TCBD）是通过四氰基乙烯与低聚噻吩炔烃之间的[2 + 2]环加成反应合成的。将TCBD部分与连接到二丁基对噻吩的其他电子受体（包括双氰基乙烯基（DCV）和三氰基乙烯基（TCV））进行比较。这些供体-受体分子（TCBD-3T，DCV-3T和TCV-3T）显示出由于分子内电荷转移（ICT）相对于未取代的寡噻吩的红移吸收光谱。带有电子受体的单取代的噻吩具有循环伏安法表征的氧化和还原过程。密度泛函理论（DFT）计算用于解释材料的电子和氧化还原特性。对双（叔噻吩基）取代的TCBD分子（3T-TCBD-3T）进行电化学氧化，可得到表现出平衡双极性氧化还原传导性的导电聚合物，该聚合物的氧化态和还原态值相似（1×10 -3 S cm -1）。非对称供体-受体材料的拉曼光谱的特征是，在低聚噻吩的共轭π系统中，芳族和醌型区域具有两个强带特征。
• Reverse Selectivity in <i>m</i>-CPBA Oxidation of Oligothiophenes to Sulfones
  作者：Ted M. Pappenfus、Jacob H. Melby、Brent B. Hansen、Devin M. Sumption、Scott A. Hubers、Daron E. Janzen、Paul C. Ewbank、Kari A. McGee、Michael W. Burand、Kent R. Mann

  DOI：10.1021/ol071369x

  日期：2007.9.1

  Oligothiophene sulfones of up to six rings can be conveniently prepared by the direct oxidation of butyl-substituted thiophene oligomers with m-CPBA in dichloromethane. Reverse selectivity of oxidized rings is observed relative to previously reported systems without beta-substitution. The selectivity in the trimer and hexamer is confirmed with single-crystal X-ray structure data. The sulfones possess red-shifted absorptions and increased electron affinities relative to the parent oligomers.